WINCHESTER BANCORP, INC. Up to 3,532,143 Shares (subject to increase up to 4,061,964 Shares) COMMON STOCK ($0.01 Par Value) Subscription Price $10.00 Per Share AGENCY AGREEMENT [February] [•], 2025

Management Fee. A non-refundable cash fee of $25,000 (the “Management Fee”) has already been paid by the Winchester Parties to the Agent. The Management Fee will be credited against any Success Fee owed pursuant to subsection (b) below.

Success Fee. The Winchester Parties shall pay to the Agent a fee equal to the greater of (i) $400,000 or (ii) 1.15% of the aggregate purchase price of the Shares sold in the Subscription and Community Offerings (the “Success Fee”). Such fee shall be due at the closing of the Offering. No fee shall be payable for any shares of Common Stock sold to the Officers, trustees, Corporators, Employees or the immediate family of such persons (“Insiders”), or trust of or companies controlled by Insiders, and qualified and non-qualified employee benefit plans or contributed to the Foundation. “Immediate family” for purposes of this Agreement includes the spouse, parents, siblings and children who live in the same house as the Officer, trustee, Corporator or Employee. The Management Fee set forth in Section 2(a) above will be credited against the Success Fee.

Syndicated Community Offering. In the event the Winchester Parties elect to pursue a Syndicated Community Offering, the Winchester Parties shall pay to the Agent, in addition to (and not in lieu of) the Success Fee, a commission not to exceed six percent (6.0%) of the aggregate purchase price of the Shares sold in the Syndicated Community Offering. The Agent, as sole book running manager, may seek to form a syndicate of registered dealers to assist in the sale of such common stock on a best efforts basis, subject to the terms and conditions set forth in a selected dealers agreement to be entered into between the Winchester Parties and the Agent. The Agent will endeavor to distribute the Common Stock among dealers, if any, in a fashion that best meets the distribution objectives of the Winchester Parties and the requirements of the Plan, which may result in limiting the allocation of stock to certain selected dealers. It is understood that in no event shall the Agent be obligated to take or purchase any Shares.

Records Agent Fee. The Agent shall also receive a non-refundable cash fee of $25,000 for certain records agent services set forth in the Engagement Letter, all of which shall be payable to the Agent upon the mailing of subscription documents with respect to the Offering.

Expenses. The Winchester Parties will pay all of the fees, disbursements and expenses in connection with the Offering customarily borne by issuers, including without limitation (a) costs of obtaining all securities and bank regulatory approvals, including any required SEC or Financial Industry Regulatory Authority (“FINRA”) filing fees; (b) costs of printing and distributing the materials used in connection with the Offering; (c) costs to qualify or register the Shares for sale with required state securities agencies (“Blue Sky filings”); (d) Nasdaq Stock Market listing fees or OTC Markets Group fees; (e) DTCC clearing eligibility fees; (f) fees and disbursements of the Winchester Parties’ counsel, accountants and other advisors; (g) operational expenses for the Stock Information Center (e.g. postage, telephones, supplies, temporary employees, etc.); and (h) Syndicated Community Offering expenses associated with the Offering. In the event the Agent incurs any such fees and expenses on behalf of the Winchester Parties, the Winchester Parties will reimburse the Agent for such fees and expenses whether or not the Offering is consummated.

The Registration Statement, which was prepared by the Mid-Tier Holding Company and filed with the SEC, has been declared effective by the SEC, no stop order has been issued with respect thereto and no proceedings therefor have been initiated or, to the knowledge of the Winchester Parties, threatened by the SEC. At the time the Registration Statement became effective, at the Applicable Time (as defined in Section 4(c) hereof) and at the Closing Date, the Registration Statement complied and will comply in all material respects as to form with the requirements of the 1933 Act and the 1933 Act Regulations and the Registration Statement did not and will not contain an untrue statement of a material fact or omit or will omit to state a material fact required to be stated therein or necessary to make the statements therein not misleading, and at the time any Rule 424(b) Prospectus is filed with the SEC and at the Closing Date referred to in Section 2 hereof, the Prospectus (including any amendment or supplement thereto) and any information regarding the Winchester Parties contained in Sales Information (as such term is defined in Section 9 hereof) authorized by the Winchester Parties for use in connection with the Offering will not contain an untrue statement of a material fact or omit to state a material fact necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading; provided, however, that the representations and warranties in this Section 4(a) shall not apply to statements or omissions made in reliance upon and in conformity with written information furnished to the Winchester Parties by the Agent or its counsel expressly regarding the Agent for use in the Prospectus set forth in the second paragraph under the caption “The Reorganization and Offering—Plan of Distribution; Selling Agent Compensation—Subscription and Community Offerings” and the first sentence of the paragraph under “The Reorganization and Offering—Plan of Distribution; Selling Agent Compensation—Syndicated Offering” (the “Agent Information”).

No Winchester Party has directly or indirectly distributed or otherwise used and will not directly or indirectly distribute or otherwise use any prospectus, any “free writing prospectus” (as defined in Rule 405 of the 1933 Act Regulations) or other offering material (including, without limitation, content on the party’s website that may be deemed to be a prospectus, free writing prospectus or other offering material) in connection with the offering and sale of the Shares other than any Permitted Free Writing Prospectus (as defined in Section 4(c) hereof) or the Prospectus or other materials permitted by the 1933 Act and the 1933 Act Regulations distributed by the Winchester Parties and reviewed and approved in advance for distribution by the Agent. No Winchester Party has, directly or indirectly, prepared or used and will not directly or indirectly, prepare or use, any Permitted Free Writing Prospectus except in compliance with the filing and other requirements of Rules 164 and 433 of the 1933 Act Regulations; assuming that such Permitted Free Writing Prospectus is so sent or given after the Registration Statement was filed with the SEC (and after such Permitted Free Writing Prospectus was, if required pursuant to Rule 433(d) of the 1933 Act Regulations, filed with the SEC), the sending or giving, by the Agent, of any Permitted Free Writing Prospectus will satisfy the provisions of Rules 164 and 433 of the 1933 Act Regulations (without reliance on subsections (b),

As of the Applicable Time (as defined below), neither (i) the Issuer-Represented General Free Writing Prospectus(es) issued at or prior to the Applicable Time and the Statutory Prospectus, all considered together (collectively, the “General Disclosure Package”), nor (ii) any individual Issuer-Represented Limited-Use Free Writing Prospectus, when considered together with the General Disclosure Package, included any untrue statement of a material fact or omitted to state any material fact necessary in order to make the statements therein, in the light of the circumstances under which they were made, not misleading. The preceding sentence does not apply to statements in or omissions from any Prospectus included in the Registration Statement relating to the offered Shares or any Issuer-Represented Free Writing Prospectus based upon and in conformity with written information furnished to the Mid-Tier Holding Company by the Agent specifically for use therein, it being understood and agreed that the only information furnished by the Agent consists of the Agent Information. As used in this paragraph and elsewhere in this Agreement:

“Applicable Time” means each and every date when a potential purchaser submitted a subscription or otherwise committed to purchase Shares.

“Statutory Prospectus,” as of any time, means the Prospectus relating to the offered Shares that is included in the Registration Statement relating to the offered Shares immediately prior to the Applicable Time, including any document incorporated by reference therein.

“Issuer-Represented Free Writing Prospectus” means any “issuer free writing prospectus,” as defined in Rule 433(h) of the 1933 Act Regulations, relating to the offered Shares in the form filed or required or, if not required to be filed, in the form retained in the Mid-Tier Holding Company’s records pursuant to Rule 433(g) under the 1933 Act Regulations. The term does not include any writing exempted from the definition of prospectus pursuant to clause (a) of Section 2(a)(10) of the 1933 Act, without regard to Rule 172 or Rule 173 of the 1933 Act Regulations.

“Issuer-Represented General Free Writing Prospectus” means any Issuer-Represented Free Writing Prospectus that is intended for general distribution to prospective investors.

“Issuer-Represented Limited-Use Free Writing Prospectus” means any Issuer-Represented Free Writing Prospectus that is not an Issuer-Represented General Free Writing Prospectus. The term Issuer-Represented Limited-Use Free Writing Prospectus also includes any “bona fide electronic road show,” as defined in Rule 433 of the 1933 Act Regulations, that is made available without restriction pursuant to Rule 433(d)(8)(ii) of the 1933 Act Regulations or otherwise, even though not required to be filed with the SEC.

“Permitted Free Writing Prospectus” means any free writing prospectus as defined in Rule 405 of the 1933 Act Regulations that is consented to by the Mid-Tier Holding Company, the Bank and the Agent.

Each Issuer-Represented Free Writing Prospectus, as of its date of first use and at all subsequent times through the completion of the Offering and sale of the Shares or until any earlier date that the Mid-Tier Holding Company notified or notifies the Agent (as described in the next sentence), did not, does not and will not include any information that conflicted, conflicts or will conflict with the information contained in the Registration Statement, including any document incorporated by reference therein that has not been superseded or modified. If at any time following the date of first use of an Issuer-Represented Free Writing Prospectus, there occurred or occurs an event or development as a result of which such Issuer-Represented Free Writing Prospectus conflicted or would conflict with the information contained in the Registration Statement relating to the Shares or included or would include an untrue statement of a material fact or omitted or would omit to state a material fact necessary in order to make the statements therein, in the light of the circumstances prevailing at that subsequent time, not misleading, the Mid-Tier Holding Company has notified or will notify promptly the Agent so that any use of such Issuer-Represented Free-Writing Prospectus may cease until it is amended or supplemented and the Mid-Tier Holding Company has promptly amended or will promptly amend or supplement such Issuer-Represented Free Writing Prospectus to eliminate or correct such conflict, untrue statement or omission. The first sentence of this Section 4(d) does not apply to statements in or omissions from any Issuer-Represented Free Writing Prospectus based upon and in conformity with written information furnished to the Mid-Tier Holding Company by the Agent specifically for use therein.

The Prospectus and each Issuer-Represented Free Writing Prospectus when filed, if filed by electronic transmission, pursuant to ▇▇▇▇▇ (except as may be permitted by Regulation S-T under the 1933 Act), was identical to the copy thereof delivered to the Agent for use in connection with the offering of the Shares.

The Bank has filed the Massachusetts Reorganization Application with the Division and has published notice of such filing and the Massachusetts Reorganization Application is accurate and complete in all material respects. The Bank has received written notice from the Division of its approval of the various applications comprising the Massachusetts Reorganization Application including the approval of the Information Statement, the Prospectus, the order form and the marketing materials for use in the Offering, such approval remains in full force and effect and no order has been issued by the Division suspending or revoking such approval and no proceedings therefor have been initiated or, to the knowledge of the Winchester Parties, threatened by the Division. At the Closing Time, the Bank will have received written notice from the Division of its approval of the Plan, and no order will have been issued by the Division suspending or revoking such

The Mid-Tier Holding Company and the MHC have filed the Holding Company Application with the FRB and have published notice of such filing and the Holding Company Application is accurate and complete in all material respects. The FRB has conditionally approved the Holding Company Application, such approval remains in full force and effect and no order has been issued by the FRB suspending or revoking such approval and no proceedings therefor have been initiated or, to the knowledge of the Winchester Parties, threatened by the FRB. At the date of such approval and as of the Closing Date referred to in Section 2, the Holding Company Application complied and will comply in all material respects with the applicable requirements of BHCA and the Control Act Regulations, except as the FRB has expressly waived such regulations in writing.

The Winchester Parties have filed the Prospectus and the Sales Information (as defined in Section 9(a)) with the SEC, the Division and the FDIC. The Prospectus and the Sales Information, as of the date the Registration Statement became effective and on the Closing Date referred to in Section 2, complied and will comply in all material respects with the applicable requirements of the 1933 Act Regulations, the Massachusetts Regulations and Conversion and Related Regulations and, at or prior to the time of their first use, will have received all required authorizations of the SEC, the Division and the FDIC and any other applicable regulatory authority for use in final form. No approval of any other regulatory or supervisory or other public authority is required in connection with the distribution of the Prospectus or any Sales Information that has not been obtained and a copy of which has been delivered to the Agent. The Winchester Parties have not distributed any offering material in connection with the Offering except for the Prospectus and any Sales Information that has been filed with the Registration Statement, the Massachusetts Reorganization Application, the FDIC Notice and authorized for use by the SEC, the Division and the FDIC or any other applicable regulatory authority. The information contained in the Sales Information filed as an exhibit to the Registration Statement, the Massachusetts Reorganization Application and the FDIC Notice does not

The Plan has been approved and adopted by the Boards of Directors or Trustees, as applicable, of the Winchester Parties and such approval and adoption have not been rescinded or revoked, and the offer and sale of the Shares, and the contribution of the Foundation Shares will have been conducted in all material respects in accordance with the Plan, the Massachusetts Regulations and the Conversion and Related Regulations (except to the extent waived or otherwise approved in writing by the Division and/or the FDIC), and all other applicable laws, regulations, decisions and orders, including all terms, conditions, requirements and provisions precedent to the Offering imposed upon the Winchester Parties by the SEC, the Division, the FDIC, the FRB or any other regulatory authority, except to the extent waived or otherwise approved by such regulatory authority, and, in all material respects, in the manner described in the Prospectus. To the knowledge of the Winchester Parties, no person has sought to obtain review of the final action of the Division in approving the Plan or the Reorganization, the FDIC in not objecting to the FDIC Notice, or the FRB in approving the Holding Company Application.

The Bank has been duly organized and is validly existing as a Massachusetts-chartered savings bank in mutual form and upon completion of the Reorganization and the interim bank merger, Stock Bank will be duly organized and validly existing as a Massachusetts-chartered savings bank in stock form, in both instances duly authorized to conduct its business and own its property as described in the Registration Statement, the Prospectus and the General Disclosure Package; upon completion of the Reorganization, the Stock Bank, as successor to the Bank, will have full corporate power and authority to own, lease and operate its properties and to conduct its business as described in the Registration Statement, Prospectus and General Disclosure Package; the Bank has obtained all licenses, permits, easements, convents, and other governmental authorizations (“Permits”) currently required for the conduct of its business, except those that individually or in the aggregate would not have a material adverse effect on the conduct of the business, financial condition, results of operations, capital, properties, management, affairs or prospects of the Winchester Parties and the Subsidiaries (as hereinafter defined), taken as a whole (a “Material Adverse Effect”); all such Permits are in full force and effect and the Bank has not and the Stock Bank, as successor thereto, will not have received notice of any proceeding or action relating to the revocation or

The Mid-Tier Holding Company is a stock corporation duly organized and validly existing as a corporation under the laws of the State of Maryland with full corporate power and authority to own, lease and operate its properties and to conduct its business as described in the Registration Statement, the Prospectus and the General Disclosure Package, and the Mid-Tier Holding Company is, and at the Closing Date will be, qualified to do business as a foreign corporation in each jurisdiction in which the conduct of its business requires such qualification, except where the failure to so qualify would not have a Material Adverse Effect. The Mid-Tier Holding Company has obtained all Permits required for the conduct of its business except those that individually or in the aggregate would not have a Material Adverse Effect; all such Permits are in full force and effect, and the Mid-Tier Holding Company has in all material respects complied with all statutes, laws, rules, regulations, decisions, directives, and orders applicable to the operation of its business, except where failure to be in compliance would not have a Material Adverse Effect. There are not any outstanding warrants or options to purchase any securities of the Mid-Tier Holding Company. Upon completion of the Reorganization, the Mid-Tier Holding Company will be a registered bank holding company under the BHCA.

As of the Closing Date, the MHC will be a mutual holding company, duly organized, validly existing and in good standing as a mutual holding company organized under the laws of Massachusetts with full corporate power and authority to own and operate its properties and to conduct its business as described in the Registration Statement and the Prospectus and, at the Closing Date, will be duly qualified to do business as a foreign corporation in each jurisdiction in which the conduct of its business requires such qualification, except where the failure to so qualify would not have a Material Adverse Effect. As of the Closing Date, the MHC will have obtained all Permits currently required for the conduct of its business except those that individually or in the aggregate would not have a Material Adverse Effect. Upon completion of the Reorganization, the MHC will be a registered bank holding company under the BHCA.

The authorized capital stock of the Mid-Tier Holding Company consists of twenty million (20,000,000) shares of Common Stock and five million (5,000,000) shares of preferred stock, par value $0.01 per share (the “Company Preferred Stock”). No shares of Common Stock and no shares of Company Preferred Stock are issued and outstanding as of the date hereof. As of the date hereof, no shares of Bank Common Stock and no shares of Bank Preferred Stock are issued and outstanding. The MHC has no authorized capital stock. No additional shares of Common Stock, or Bank Common Stock, and no shares of Company Preferred Stock or Bank Preferred Stock will be issued prior to the Closing Date. At the time of the Reorganization, the Shares and the Foundation Shares will have been duly authorized for issuance and, when issued and delivered by the Mid-Tier Holding Company pursuant to the Plan against payment of the consideration calculated as set forth in the Plan and stated on the cover page of the Prospectus, will be duly and validly issued and fully paid and nonassessable. The terms and provisions of the Common Stock conform in all material respects with the requirements of applicable federal and Maryland law and to all statements relating thereto contained in the Prospectus.

Except as described in the Prospectus there are no encumbrances or restrictions or requirements or material legal restrictions or requirements required to be described therein, on the ability of any of the Winchester Parties, (i) to pay dividends or make any other distributions on its capital stock or to pay any indebtedness owed to another party, (ii) to make any loans or advances to, or investments in, another party or (iii) to transfer any of its property or assets to another party.

The Bank has properly administered all accounts for which it acts as a fiduciary, including but not limited to accounts for which it serves as a trustee, agent, custodian, personal representative, guardian, conservator or investment advisor, in accordance with the terms of the governing documents and applicable state and federal law and regulation, except where the failure to do so would not have a Material Adverse Effect. Neither the Bank, nor any of its officers or employees has committed any material breach of trust with respect to any such fiduciary account, and the accountings for each such fiduciary account are true and correct in all material respects and accurately reflect the assets of such fiduciary account in all material respects.

The Bank is a member of the Federal Home Loan Bank of Boston (“FHLB-Boston”). The deposit accounts of the Bank are, and at the Closing Date the deposit accounts of the Stock Bank will be, insured by the FDIC up to the applicable limits and the deposit accounts of the Bank are, and at the Closing Date, the deposit accounts of the Stock Bank will be, insured in excess of the FDIC limits by the DIF, and no proceedings for the termination or revocation of such insurance are pending or, to the knowledge of the Winchester Parties, threatened.

At the Closing Date, the Mid-Tier Holding Company will have no direct subsidiaries other than the Stock Bank. The Bank has the subsidiaries as set forth on Exhibit C hereto (the “Subsidiaries”), which Subsidiaries shall become the Subsidiaries of the Stock Bank in connection with the completion of the Reorganization. Each Subsidiary is duly organized, validly existing in good standing under the laws of the jurisdiction of its incorporation, has full power and authority to own, lease and operate its properties and to conduct its business as described in the Registration Statement and the Prospectus; has obtained all Permits currently required for the conduct of its business except those that individually or in the aggregate would not have a Material Adverse Effect; all such Permits are in full force and effect, and the Subsidiary is in all material respects complying therewith and with all statutes, laws, rules, regulations, decisions, directives, and orders applicable to the operation of its business; and is duly qualified to do business as a foreign corporation in each jurisdiction in which the conduct its business requires such qualification, except where the failure to so qualify would not have a Material Adverse Effect; the activities of each Subsidiary are permitted to subsidiaries of a Massachusetts-chartered savings bank by the regulations of the FRB, the Division and the FDIC; all of the issued and outstanding capital stock or ownership interests of each Subsidiary has been duly authorized and validly issued, is fully paid and nonassessable and is owned by the Bank as of the Closing Date, will be owned by the Stock Bank, free and clear of any security interest, mortgage, pledge, lien, encumbrance or legal or equitable claim. No Winchester Party owns equity securities or any equity interest in any other business enterprise except as otherwise described in the Registration Statement and Prospectus or as are immaterial in amount and are not required to be described in the Registration Statement and the Prospectus.

The Winchester Parties have good and marketable title to all real property owned by them and good title to all other properties owned by them, in each case, free and clear of all mortgages, pledges, liens, security interests, claims, restrictions or encumbrances of any kind except such as (a) are described in the Prospectus or (b) would not, singly or in the aggregate, result in a Material Adverse Effect; and all of the leases and subleases material to the business of the Winchester Parties, considered as one enterprise, and under which the Winchester Parties holds properties, including those described in the Prospectus, are in full force and effect, and no Winchester Party has received any written or, to the knowledge of the Winchester Parties, oral notice of any material claim of any sort that has been asserted by anyone adverse to the rights of such Winchester Party under any such leases or subleases.

The Winchester Parties have received an opinion of its special counsel, ▇▇▇▇ ▇▇▇▇▇▇, PC (“▇▇▇▇ ▇▇▇▇▇▇”), with respect to the federal income tax consequences of the Reorganization and an opinion of its tax advisor, Wolf & Company, P.C. with respect to the Commonwealth of Massachusetts income tax consequences of the Reorganization, and such opinions are accurately summarized, in all material respects, in the Registration Statement and the Prospectus. The Winchester Parties represent and warrant that the facts upon which such opinions are based are truthful, accurate and complete in all material respects. None of the Winchester Parties will take any action inconsistent therewith.

Each of the Winchester Parties has all such power, authority, authorizations, approvals and orders as may be required to enter into this Agreement, to carry out the provisions and conditions hereof and to issue and sell the Shares and to contribute the Foundation Shares as provided herein and as described in the Prospectus, subject to approval or confirmation by the Division and the FDIC of the final Appraisal as may be required. The execution, delivery and performance of this Agreement and the consummation of the transactions herein contemplated have been duly and validly authorized by all necessary corporate action on the part of each of the Winchester Parties. This Agreement has been validly executed and delivered by each of the Winchester Parties and, assuming due execution and delivery by the Agent, is the valid, legal and binding agreement of each of the Winchester Parties enforceable in accordance with its terms (except as the enforceability thereof may be limited by bankruptcy, insolvency, moratorium, reorganization or similar laws relating to or affecting the enforcement of creditors’ rights generally or the rights of creditors of bank holding companies, the accounts of whose subsidiaries are insured by the FDIC and the DIF, or by general equity principles, regardless of whether such enforceability is considered in a proceeding in equity or at law, and except to the extent, if any, that the provisions of Sections 9 and 10 hereof may be unenforceable as against public policy or pursuant to applicable Federal law and the rules and regulations of the Division, the FDIC, the FRB and the SEC).

As of the date hereof and as of the Closing Date, neither the Winchester Parties nor any of the Subsidiaries are subject to and have not been advised by the Division, the FDIC, the FRB or any other federal or state governmental authorities that it is considering issuing or requesting, any cease and desist order, written agreement, directive, memorandum of understanding or other regulatory enforcement actions, proceeding or order, commitment letter or similar undertaking (other than orders or directives applicable to the banking industry as a whole), supervisory letter or adoption of board resolutions. None of the Winchester Parties is in violation of any directive received from the Division, the FDIC, the FRB, the SEC, or any other agency to make any material change in the method of conducting its business so as to comply in all material respects with all applicable statutes and regulations (including, without limitation, regulations, decisions, directives and orders of the Division, the FDIC, the FRB and the SEC).

Except as described in the General Disclosure Package and the Prospectus, no suit or proceeding, charge, investigation or action before or by any court, regulatory authority or governmental agency or body is or will be pending or, to the knowledge of the Winchester Parties, threatened, which might materially and adversely affect the performance by the Winchester Parties of their obligations under this Agreement or the consummation of the transactions contemplated in the Plan and as described in the Prospectus, or which might result in a Material Adverse Effect or which is required to be disclosed in the Registration Statement, the Prospectus, or any Permitted Free Writing Prospectus and is not so disclosed. No Winchester Party has failed to file with applicable regulatory authorities any statement, report, information or form required by any applicable law, regulation or order, except where the failure to be so in compliance would not, individually or in the aggregate, have a Material Adverse Effect, all such filings were in material compliance with applicable laws when filed and no material deficiencies have been asserted by any regulatory commission, agency or authority with respect to any such filings or submissions.

The consolidated financial statements, schedules and notes related thereto which are included in the Registration Statement, the General Disclosure Package and the Prospectus fairly present the balance sheet, statement of net income, statement of comprehensive income (loss), statement of changes in surplus and statement of cash flows of the Bank on a consolidated basis at the respective dates indicated and for the respective periods covered thereby and comply as to form in all material respects with the applicable accounting requirements of the 1933 Act Regulations, the Massachusetts Regulations and the Conversion and Related Regulations. Such financial statements, schedules and notes related thereto have been prepared in accordance with generally accepted accounting principles (“GAAP”) consistently applied through the periods involved, present fairly in all material respects the information required to be stated therein and are consistent with the most recent financial statements and other reports filed by the Winchester Parties with the FDIC and the Division, and any other applicable regulatory authority, except that accounting principles employed in such regulatory filings conform to the requirements of such authorities and not necessarily to GAAP. The other financial, statistical and pro forma information and related notes included in the Prospectus and the General Disclosure Package present fairly the information shown therein on a basis consistent with the audited and unaudited consolidated financial statements of the Bank included in the Prospectus, and as to the pro forma adjustments, the adjustments made therein have been properly applied on the basis described therein.

The Winchester Parties and the Subsidiaries carry, or are covered by, insurance in such amounts and covering such risks as is adequate for the conduct of their respective businesses and the value of their respective properties and as is customary for companies engaged in similar industries. All policies of insurance insuring the Winchester Parties and the Subsidiaries or any of their respective businesses, assets, employees, officers and directors are in full force and effect, and the Winchester Parties and the Subsidiaries are in compliance with the terms of such policies in all material respects. No Winchester Party or Subsidiary has been refused any insurance coverage sought or applied for during the last four years; and no Winchester Party or Subsidiary has any reason to believe that

Since the respective dates as of which information is given in the Registration Statement, including the Prospectus and except as disclosed in the General Disclosure Package and the Prospectus: (i) no event resulting in a Material Adverse Effect has occurred, whether or not arising in the ordinary course of business; (ii) there has not been any material increase in the long-term debt of any of the Winchester Parties or in the principal amount of the Winchester Parties’ consolidated assets which are classified by any of such entities as substandard, doubtful or loss or in loans past due 90 days or more or real estate acquired by foreclosure, by deed-in-lieu of foreclosure or deemed in-substance foreclosure or any material decrease in equity capital or total assets of any of the Winchester Parties; nor have any of the Winchester Parties issued any securities or incurred any liability or obligation, direct or contingent, for borrowed money, except borrowings from the same or similar sources indicated in the Prospectus in the ordinary course of business; (iii) there have not been any material transactions entered into by the Winchester Parties; (iv) there has not been any material adverse change in the aggregate dollar amount of the Winchester Parties deposits or its capital accounts; (v) there has been no material adverse change in any of the Winchester Parties’ or Subsidiaries’ relationship with its insurance carriers, including, without limitation, cancellation or other termination of any of the Winchester Parties’ fidelity bond or any other type of insurance coverage; (vi) there has been no material change in management of any of the Winchester Parties or Subsidiaries; (vii) none of the Winchester Parties has sustained any material loss or interference with its respective business or properties from fire, flood, windstorm, earthquake, accident or other calamity, whether or not covered by insurance; (viii) none of the Winchester Parties has defaulted in the payment of principal or interest on any outstanding debt obligations; (ix) the capitalization, liabilities, assets, properties and business of the Winchester Parties conform in all material respects to the descriptions thereof contained in the General Disclosure Package and the Prospectus; and (x) none of the Winchester Parties has any material liabilities, contingent or otherwise, except as set forth in the Prospectus.

None of the Winchester Parties is in material violation of their respective articles of incorporation, charters or bylaws (and none of the Winchester Parties will be in material violation of its articles of incorporation, charter or bylaws upon completion of the Reorganization). The execution and delivery of this Agreement and the consummation of the transactions herein contemplated will not: (i) conflict with or constitute a breach of, or default (or an event which, with notice or lapse of time, or both, would constitute a breach or default) under, or result in the creation of any lien, charge or encumbrance upon any of the assets of any of the Winchester Parties pursuant to the respective articles

All documents made available or delivered by, or to be made available to or delivered by the Winchester Parties or their representatives in connection with the issuance and sale of the Shares and the contributions of the Foundation Shares, or in connection with the Agent’s exercise of due diligence, except for those documents which were prepared by parties other than the Winchester Parties or their representatives were on the dates on which they were delivered, or will be on the dates on which they are to be delivered, true, complete and correct in all material respects. The records used by the Winchester Parties to determine the identities of Eligible Account Holders, Employees, Officers, trustees and Corporators are accurate and complete in all material respects.

Upon consummation of the Reorganization and the contribution of Foundation Shares, the authorized, issued and outstanding equity capital of the Mid-Tier Holding Company will be within the range set forth in the General Disclosure Package and the Prospectus under the caption “Capitalization,” and no Shares or Foundation Shares have been or will be issued and outstanding prior to the Closing Date; the Shares and the Foundation Shares will have been duly and validly authorized for issuance and, when issued and delivered by the Mid-Tier Holding Company pursuant to the Plan and, with respect to the Shares, against payment of the consideration calculated as set forth in the Plan and in the Prospectus, will be duly and validly issued, fully paid and non-assessable and with respect to the Foundation Shares, when contributed by the Mid-Tier Company pursuant to the Plan, will be duly and validly issued and fully paid and non-assessable; except to the extent that subscription rights and priorities pursuant thereto exist pursuant to the Plan, no preemptive rights exist with respect to the Shares or the Foundation Shares; and the terms and provisions of the Shares and the Foundation Shares will conform in all material respects to the description thereof contained in the Registration Statement and the Prospectus. Upon the issuance of the Shares and the Foundation Shares, good title to the Shares and the Foundation Shares will be transferred from the Mid-Tier Holding Company to the purchasers thereof or the Foundation, as applicable, against payment therefor, subject to such claims as may be asserted against the purchasers thereof or the Foundation by third-party claimants.

No default exists, and no event has occurred which, with notice or lapse of time or both, would constitute a default, on the part of any of the Winchester Parties or the Subsidiaries in the due performance and observance of any term, covenant, agreement, obligation, representation, warranty or condition of any indenture, mortgage, deed of trust, note, bank loan or credit agreement, lease, license, Permit or any other instrument or agreement to

Subsequent to the date the Registration Statement is declared effective by the SEC and prior to the Closing Date, except as otherwise may be indicated or contemplated in the Registration Statement, none of the Winchester Parties has or will have issued any securities or incurred any liability or obligation, direct or contingent, for borrowed money, except borrowings from the same or similar sources indicated in the Prospectus in the ordinary course of its business.

Except for the Winchester Savings Bank 401(k) Profit Sharing Plan, the Winchester Savings Bank Employee Stock Ownership Plan and the Winchester Savings Bank defined benefit pension plan, none of the Winchester Parties maintains any “pension plan,” as defined in the Employee Retirement Income Security Act of 1974, as amended (“ERISA”). In addition, (A) the employee benefit plans, including employee welfare benefit plans, of the Winchester Parties and the Subsidiaries (the “Employee Plans”) have been operated in compliance with the applicable provisions of ERISA, the Internal Revenue Code of 1986, as amended (the “Code”), all regulations, rulings and announcements promulgated or issued thereunder and all other applicable laws and governmental regulations, (B) no reportable event under Section 4043(c) of ERISA has occurred with respect to any Employee Plan of the Winchester Parties for which the reporting requirements have not been waived by the Pension Benefit Guaranty Corporation, (C) the Winchester Parties have not incurred and do not expect to incur liability under (i) Title IV of ERISA with respect to termination of, or withdrawal from,

No approval of any regulatory or supervisory or other public authority is required in connection with the execution and delivery of this Agreement, the issuance of the Shares or the contribution of the Foundation Shares to the Foundation, except for the approval or non-objection, as applicable, of the Division, the FDIC, the FRB and the SEC, and any necessary qualification, notification, registration or exemption under the securities or blue sky laws of the various states in which the Shares and the Foundation Shares are to be offered, and except as may be required under the rules and regulations of FINRA or the Nasdaq Stock Market LLC.

Wolf & Company, P.C., which has certified the audited consolidated financial statements of the Bank included in the Prospectus, has advised the Winchester Parties in writing that they are, with respect to the Winchester Parties, independent certified public accountants as required by the Code of Professional Ethics of the American Institute of Certified Public Accountants, the applicable rules of the Public Company Accounting Oversight Board (United States) (“PCAOB”) and the SEC, they are registered with the PCAOB and such firm is not, with respect to the Winchester Parties, in violation of the auditor independence requirements of the Sarbanes Oxley Act of 2002 and the rules and regulations promulgated in connection therewith (“▇▇▇▇▇▇▇▇-▇▇▇▇▇ Act”).

RP Financial, LC., which has prepared the Appraisal, has advised the Winchester Parties in writing that it is independent of the Winchester Parties within the meaning of the Massachusetts Regulations and the Conversion and Related Regulations and is believed by the Winchester Parties to be experienced and expert in the valuation and the appraisal of business entities, including savings institutions, and the Winchester Parties believe that RP Financial, LC. has prepared the Appraisal information set forth in the Prospectus in accordance with the requirements of the Massachusetts Regulations and the Conversion and Related Regulations.

The Winchester Parties have timely filed or extended all required federal, state and local tax returns; the Winchester Parties have paid all taxes that have become due and payable in respect of such returns, except where permitted to be extended or where such taxes may be contested in good faith, have made adequate reserves for similar future tax liabilities and no deficiency has been asserted with respect thereto by any taxing authority. The Winchester Parties have no knowledge of any tax deficiency which has been or might be assessed against any of them or the Subsidiaries which, if the subject of an unfavorable decision, ruling or finding, could have, individually or in the aggregate with other tax deficiencies, a Material Adverse Effect. All material tax liabilities have been adequately provided for in the consolidated financial statements of the Winchester Parties in accordance with GAAP. There are no transfer taxes or other similar fees or charges under Federal law or the laws of any state, or any political subdivision thereof, required to be paid in connection with the execution and delivery of this Agreement by the Mid-Tier Holding Company or with the issuance, sale by the Mid-Tier Holding Company of the Shares or the issuance of the Foundation Shares.

The operations of each of the Winchester Parties are and have been conducted at all times in compliance in all material respects with the anti-money laundering statutes of applicable jurisdictions, the rules and regulations thereunder and any related or similar rules, regulations or guidelines, issued, administered or enforced by any applicable governmental agency (collectively, the “Anti-Money Laundering Laws”) and to their knowledge, no action, suit or proceeding by or before any court or governmental agency, authority or body or any arbitrator involving the Winchester Parties with respect to the Anti-Money Laundering Laws is pending or, to the knowledge of the Winchester Parties, threatened.

No labor dispute with the employees of the Winchester Parties exists or, to the knowledge of the Winchester Parties, is threatened, and, to the knowledge of the Winchester Parties, there are no existing or threatened labor disturbance by the employees of any of its or any subsidiaries’ principal customers or contractors, which, in either case, may reasonably be expected to result in a Material Adverse Effect.

No Winchester Party or any Subsidiary or any trustee, director, officer or, to the knowledge of the Winchester Parties, employee of the Winchester Parties or any Subsidiary nor, to the knowledge of the Winchester Parties, any agent, affiliate or other person associated with or acting on behalf of the Winchester Parties or any Subsidiary has (a) used any corporate funds for any unlawful contribution, gift, entertainment or other unlawful expense relating to political activity; (b) made or taken an act in furtherance of an offer, promise or authorization of any direct or indirect unlawful payment or benefit to any foreign or domestic government official or employee, including of any government-owned or controlled entity or of a public international organization, or any person acting in an official capacity for or on behalf of any of the foregoing, or any political party or party official or candidate for political office; (c) violated or is in violation of any provision of the Foreign Corrupt Practices Act of 1977, as amended, or any other applicable anti-bribery or anti-corruption law; or (d) made, offered, agreed, requested or taken an act in furtherance of any unlawful bribe or other unlawful benefit, including, without limitation, any rebate, payoff, influence payment, kickback or other unlawful or improper payment or benefit. The Bank has instituted, maintains and enforces, and the Winchester Parties, and the Stock Bank subsequent to the Reorganization, will continue to maintain and enforce policies and procedures designed to promote and ensure compliance with all applicable anti-bribery and anti-corruption laws.

None of the Winchester Parties has: (i) issued any securities within the last 18 months (except for notes to evidence bank loans and reverse repurchase agreements or other liabilities in the ordinary course of business or as described in the Prospectus); (ii) had any dealings within the 12 months prior to the date hereof with any member of FINRA or any person related to or associated with such member, other than discussions and meetings relating to the proposed Offering and routine purchases and sales of United States government and agency and other securities in the ordinary course of business; (iii) entered into a financial or management consulting agreement except as contemplated hereunder; and (iv) engaged any intermediary between the Agent and the Winchester Parties in connection with the offering of the Shares, and no person is being compensated in any manner for such service. The Winchester Parties have not relied upon the Agent or its legal counsel for any legal, tax or accounting advice in connection with the Reorganization. To the knowledge of the Winchester Parties, there are no affiliations or associations (as such terms are defined by the FINRA) between any member of FINRA and any of the Winchester Parties’ officers, directors or trustees.

The Winchester Parties and each Subsidiary own, or possess adequate rights to use, all patents, copyrights, trademarks, service marks, trade names and other rights necessary to conduct the businesses now conducted by them in all material respects or as described in the Prospectus and any Permitted Free Writing Prospectus and no Winchester Party or any Subsidiary has received any written notice or has any knowledge of infringement or conflict with asserted rights of others or of any facts or circumstances which would render invalid or inadequate to protect the rights of the Winchester Parties or the Subsidiaries with respect to any patents, copyrights, trademarks, service marks, trade names or other rights which, individually or in the aggregate, if the subject of an unfavorable decision, ruling or finding, would have a Material Adverse Effect, and, to the knowledge of the Winchester Parties, there is no basis for any such infringement or conflict which, individually or in the aggregate, if the subject of an unfavorable decision, ruling or finding, could have a Material Adverse Effect.

Except as has not had and would not reasonably be expected to have a Material Adverse Effect:

The Bank has complied in all material respects with, and all documentation in connection with the origination, processing, underwriting and credit approval of any mortgage loan originated, purchased or serviced by the Bank satisfied, (A) all applicable federal and state laws, rules and regulations with respect to the origination, insuring, purchase, sale, pooling, servicing, subservicing, or filing of claims in connection with mortgage loans, including all laws relating to real estate settlement procedures, consumer credit protection, truth in lending laws, usury limitations, fair housing, transfers of servicing, collection practices, equal credit opportunity and adjustable rate mortgages, (B) the responsibilities and obligations

No Agency, Loan Investor or Insurer has (A) notified the Bank in writing that the Bank has violated or has not complied with the applicable underwriting standards with respect to mortgage loans sold by the Bank to a Loan Investor or Agency, or with respect to any sale of mortgage servicing rights to a Loan Investor, (B) imposed in writing restrictions on the activities (including commitment authority) of the Bank or (C) indicated in writing to the Bank that it has terminated or intends to terminate its relationship with the Bank for poor performance, poor loan quality or concern with respect to the Bank compliance with laws.

None of the Winchester Parties is, and none intend to conduct business in a manner which would cause it to become, an “investment company,” an entity “controlled” by an “investment company” or an “investment adviser” within the meaning of the Investment Company Act of 1940, as amended, or the Investment Advisers Act of 1940, as amended.

None of the Winchester Parties or Subsidiaries or any properties owned or operated by any of the Winchester Parties or Subsidiaries, is in violation of or liable under any Environmental Law (as defined below), except for such violations or liabilities that, individually or in the aggregate, would not have a Material Adverse Effect. There are no actions, suits or proceedings, or demands, claims, notices or investigations (including, without limitation, notices, demand letters or requests for information from any environmental agency) instituted or pending or, to the knowledge of the Winchester

The Winchester Parties maintain a system of internal accounting controls sufficient to provide reasonable assurance that (A) transactions are executed in accordance with management’s general or specific authorizations, (B) transactions are recorded as necessary to permit preparation of financial statements in conformity with generally accepted accounting principles and to maintain accountability for assets, (C) access to assets is permitted only in accordance with management’s general or specific authorization, and (D) the recorded accounts or assets is compared with the existing assets at reasonable intervals and appropriate action is taken with respect to any differences. To the knowledge of the Winchester Parties, Wolf & Company, P.C. and the Audit Committee of the Board of Trustees (the “Audit Committee”) have been advised of: (A) any significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which could adversely affect the Mid-Tier Holding Company’s and the Bank’s ability to record, process, summarize, and report financial data; and (B) any fraud, whether or not material, that involves management or other employees who have a significant role in the Winchester Parties’ internal accounting controls.

All of the loans represented as assets of the Winchester Parties in the Prospectus meet or are exempt from all requirements of federal, state and local law pertaining to lending, including, without limitation, truth in lending (including the requirements of Regulation Z and 12 C.F.R. Parts 226 and 1026), real estate settlement procedures, consumer credit protection, equal credit opportunity and all disclosure laws applicable to such loans, except for violations which, if asserted, would not have a Material Adverse Effect. All such loans secured by dwellings constitute qualified mortgages within the meaning of 12 C.F.R. § 1026.43.

All of the information, as may have been updated or amended, provided to the Agent or to counsel for the Agent by the Winchester Parties and their respective officers and directors in connection with letters, filings or other supplemental information provided to FINRA pursuant to FINRA Rules 5110 and 5121 is true, complete and correct.

Other than as contemplated by this Agreement, there is no broker, finder or other party that is entitled to receive from the Winchester Parties any brokerage or finder’s fee or any other fee, commission or payment as a result of the transactions contemplated by this Agreement.

The statistical and market related data contained in any Permitted Free Writing Prospectus, the Prospectus and the Registration Statement are based on or derived from sources which the Winchester Parties believe were reliable and accurate at the time they were filed with the SEC. No forward-looking statement (within the meaning of Section 27A of the 1933 Act and Section 21E of the Securities Exchange Act of 1934, as amended (the “1934 Act”)) contained in the Registration Statement, the Prospectus, or any Permitted Free Writing Prospectus has been made or reaffirmed without a reasonable basis or has been disclosed other than in good faith.

To the knowledge of the Winchester Parties, with the exception of the intended loan to the Bank’s ESOP by the Mid-Tier Holding Company to enable the ESOP to purchase Shares in an amount up to 3.6% of the Common Stock that will be outstanding following the Reorganization including the contribution of the Foundation Shares, none of the Winchester Parties or their employees has made any payment of funds of the Winchester Parties as a loan for the purchase of the Common Stock. To the knowledge of the Winchester Parties, none of the Winchester Parties or their employees has made any payment of funds prohibited by law, and no funds have been set aside to be used for any payment prohibited by law.

The Mid-Tier Holding Company has submitted or will have submitted prior to the Closing Date all notices required to consummate the Reorganization and to have the Shares and the Foundation Shares listed on the Nasdaq Capital Market effective as of the Closing Date referred to in Section 2 hereof.

At or prior to the hour and date upon which the Mid-Tier Holding Company shall release for delivery all of the Securities, in accordance with the terms hereof, is herein called the “Closing Time”, the Holding Company will have filed a Form 8-A for the Shares and the Foundation Shares to be registered under Section 12(b) of the Exchange Act (the “Exchange Act Registration Statement”).

Upon the completion of the Reorganization, the Mid-Tier Holding Company will be in compliance with the applicable provisions of the ▇▇▇▇▇▇▇▇-▇▇▇▇▇ Act and the rules and regulations of the Commission thereunder and the Nasdaq Stock Market LLC corporate governance rules, to the extent applicable to the Mid-Tier Holding Company, and will use its best efforts to comply with those provisions of the ▇▇▇▇▇▇▇▇-▇▇▇▇▇ Act that will become effective in the future upon their effectiveness.

None of the Winchester Parties or any Subsidiary nor any director, trustee, officer, employee or, to the knowledge of the Winchester Parties, after due inquiry, agent or affiliate thereof is (a) currently subject to any U.S. sanctions administered by the Office of Foreign Assets Control of the U.S. Treasury Department (“OFAC”) or relevant sanctioning authority; (b) located, organized or resident in a country or territory that is the subject of such sanctions (including, without limitation, Burma/Myanmar, Cuba, Iran, North Korea, Sudan and Syria); and (c) the Holding Company will not, directly or indirectly, use the proceeds of the Offerings, or lend, contribute or otherwise make available such proceeds to any subsidiary, joint venture partner or other person or entity, for the purpose of financing the activities of any person, or engage in dealings or transactions with any person, or in any country, or territory, subject to any U.S. sanctions administered by OFAC or relevant sanctioning authority.

Neither any of the Winchester Parties nor any of their affiliates does business with the government of Cuba or with any person or affiliate located in Cuba within the meaning of Section 517.075, Florida Statutes. For purposes of this subsection, “affiliate” means a person that directly, or indirectly through one or more intermediaries, controls, is controlled by, or is under common control with the MHC, the Mid-Tier Holding Company, the Bank or the Stock Bank.

The Foundation will be duly incorporated and validly existing as a non-stock corporation in good standing under the laws of the State of Delaware with corporate power and authority to own, lease and operate its properties and to conduct its business as described in the Prospectus. The Foundation will be a qualified charitable organization exempt from federal and state income tax under Section 501(c)(3) of the Code and, to the knowledge of the Winchester Parties, nothing has occurred, whether by action or by failure to act, that would cause a loss of such qualification. The Foundation is not currently and will not be a bank holding company with the meaning of 12 C.F.R. Section 225.2 as a result of the issuance of the Foundation Shares to it in accordance with the terms of the Plan and in the amounts as described in the Prospectus. No approvals are required to establish the Foundation and to contribute the Foundation Shares as described in the Prospectus other than those obtained from the Division and the FDIC and the approval of the corporators of the Bank. Except as specifically disclosed in the Prospectus, there are no agreements and/or understandings, written or oral, between the Winchester Parties on the one hand and the Foundation, on the other, with respect to the control, directly or indirectly, over the voting and the acquisition or disposition of the Foundation Shares other than as required by the FRB, the Division or the FDIC. At the Closing Time, the Foundation Shares will have been duly authorized for issuance and, when issued and contributed by the Mid-Tier Holding Company pursuant to the Plan, will be duly and validly issued and fully paid and nonassessable. The issuance of the Foundation Shares to the Foundation pursuant to the Plan has been registered under the 1933 Act pursuant to the Registration Statement.

Any certificates signed by an officer of any of the Winchester Parties pursuant to the conditions of this Agreement and delivered to the Agent or their counsel that refers to this Agreement shall be deemed to be a representation and warranty by such Winchester Party to the Agent as to the matters covered thereby with the same effect as if such representation and warranty were set forth herein

The Agent is a corporation and is validly existing in good standing under the laws of the State of Florida with full power and authority to provide the services to be furnished to the Winchester Parties hereunder. The Agent is registered as a broker-dealer with the SEC and is a member of FINRA.

Any funds received by the Agent to purchase Shares in the Syndicated Community Offering will be handled in accordance with Rule 15c2-4 under the 1934 Act, to the extent applicable.

With respect to certain non-public information about the Bank’s depositors and customers (“Customer Information”) that the Agent may be provided access to in connection with providing services under this Agreement, the Agent shall: (i) use Customer Information only as necessary to perform its obligations pursuant to this Agreement or as permitted by the ▇▇▇▇▇-▇▇▇▇▇-▇▇▇▇▇▇ Act of 1999 (the “GLB Act”), and the policies of the Division and the FDIC thereunder and other applicable law, all as may be amended from time to time; (ii) not disclose Customer Information to any third party, except to other third party service providers assisting the Bank with the Offering and the Reorganization or the Agent with respect to its obligations under this Agreement, unless the Bank has consented in writing to the disclosure or the Bank has confirmed that such disclosure is permissible pursuant to applicable law; and (iii) adopt reasonably appropriate measures to protect against unauthorized access to or use of the Customer Information in its control that could result in substantial harm or inconvenience to any customer of the Bank.

Each of the Agent and its employees, agents and representatives who shall perform any of the services hereunder shall be duly authorized and empowered, and shall have all licenses, approvals and permits necessary to perform such services; and the Agent is a registered selling agent in each of the jurisdictions in which the Shares are to be offered by the Mid-Tier Holding Company in reliance upon the Agent as a registered selling agent as set forth in the blue sky memorandum prepared with respect to the Offering.

No approval of any regulatory or supervisory or other public authority is required in connection with the Agent’s execution and delivery of this Agreement, except as may have been received.

There is no suit or proceeding or charge or action pending before or by any court, regulatory authority or government agency or body or, to the knowledge of the Agent, threatened, which might materially adversely affect the Agent’s performance under this Agreement.

The execution and delivery of this Agreement by the Agent, the consummation of the transactions contemplated hereby and compliance with the terms and provisions hereof will not conflict with, or result in a breach of, any of the terms, provisions or conditions of, or constitute a default (or an event which with notice or lapse of time or both would constitute a default) under, the articles of incorporation or bylaws of the Agent or any agreement, indenture or other instrument to which the Agent is a party or by which it or its property is bound.

The execution and delivery of this Agreement and the consummation of the transactions contemplated hereby have been duly and validly authorized by all necessary action on the part of the Agent, and this Agreement has been duly and validly executed and delivered by the Agent and is a legal, valid and binding agreement of the Agent, enforceable in accordance with its terms, except as the legality, validity, binding nature and enforceability thereof may be limited by (i) bankruptcy, insolvency, moratorium, reorganization, conservatorship, receivership or other similar laws relating to or affecting the enforcement of creditors’ rights generally, and (ii) general equity principles regardless of whether such enforceability is considered in a proceeding in equity or at law.

The Winchester Parties will not, after the date of effectiveness or approval, as applicable, file any amendment or supplement to the Registration Statement, the Prospectus, the Information Statement, the Massachusetts Reorganization Application, the FDIC Applications or the Holding Company Application without written notice to the Agent of their intention to do so and providing the Agent and its counsel an opportunity to review such amendment or supplement, nor will any Winchester Party file any such amendment or supplement to which the Agent shall reasonably object.

If at any time following issuance of an Issuer-Represented Free Writing Prospectus there occurred or occurs an event or development as a result of which such Issuer Represented Free Writing Prospectus conflicted or would conflict with the information contained in the Registration Statement or included or would include an untrue statement of a material fact or omitted or would omit to state a material fact necessary in order to make the statements therein, in light of the circumstances prevailing at the subsequent time, not misleading, the Winchester Parties will notify promptly the Agent so that any use of such Issuer-Represented Free Writing Prospectus may cease until it is amended or supplemented and the Mid-Tier Holding Company will promptly amend or supplement such Issuer-Represented Free Writing Prospectus to eliminate or correct such conflict, untrue statement or omission; provided, however, that this covenant shall not apply to any statements or omissions made in reliance upon and in conformity with information furnished in writing to the Winchester Parties by the Agent expressly for use therein.

Each of the Winchester Parties represents and agrees that, unless it obtains the prior consent of the Agent, and the Agent represents and agrees that, unless it obtains the prior consent of the Winchester Parties, it has not made and will not make any offer relating to the Shares that would constitute an “issuer free writing prospectus” as defined in Rule 433 of the 1933 Act Regulations, or that would constitute a “free writing prospectus,” as defined in Rule 405 of the 1933 Act Regulations, required to be filed with the SEC. The Winchester Parties represent that they have treated or agree that they will treat each Permitted Free Writing Prospectus as an “issuer free writing prospectus,” as defined in Rule 433 of the 1933 Act Regulations, and have complied and will comply in all material respects with the requirements of Rule 433 of the 1933 Act Regulations applicable to any Permitted Free Writing Prospectus, including timely SEC filing where required, legending and record keeping. The Winchester Parties need not treat any communication as a free writing prospectus if it is exempt from the definition of prospectus pursuant to clause (a) of Section 2(a)(10) of the 1933 Act without regard to Rule 172 or 173 of the 1933 Act Regulations.

The Winchester Parties will use their best efforts to cause any post-effective amendment to the Registration Statement to be declared effective by the SEC and any post-approval amendment to the Massachusetts Reorganization Application, the FDIC Applications and/or the Holding Company Application to be approved or non-objected to, as applicable, by the Division, the FDIC or the FRB, as applicable, or any other governmental entity, and will immediately upon receipt of any information concerning the events listed below notify the Agent: (i) when the Registration Statement, as amended, has become effective; (ii) when the Massachusetts Reorganization Application, the FDIC Applications and/or the Holding Company Application have been approved or non-objected to by the Division, the FDIC or the FRB or any other governmental entity; (iii) of any comments from the SEC, the Division, the FDIC, the FRB, or any other governmental entity with respect to the Reorganization; (iv) of the request by the SEC, the Division, the FDIC, the FRB, or any other governmental entity for any amendment or supplement to the Registration Statement, the Massachusetts Reorganization Application, the FDIC Applications, the Holding Company Application, or for additional information; (v) of the issuance by the SEC, the Division, the FDIC, the FRB or any other governmental entity of any order or other action suspending the Reorganization or the use of the Registration Statement or the Prospectus or any other filing of the Winchester Parties under the Massachusetts Regulations, the Conversion and Related Regulations and the Control Act Regulations, or other applicable law, or the threat of any such action; (vi) of the issuance by the SEC or any other authority of any stop order suspending the effectiveness of the Registration Statement or of the initiation or threat of initiation or threat of any proceedings for that purpose; or (vii) of the occurrence of any event mentioned in paragraph (h) below. The Winchester Parties will make every reasonable effort (i) to prevent the issuance by the SEC, the Division, the FDIC, the FRB or any other regulatory authority of any such order and (ii) if any such order shall at any time be issued, to obtain the lifting thereof at the earliest possible time. The Winchester Parties will provide copies of the foregoing comments, requests and orders to the Agent promptly following receipt of such items.

The Winchester Parties will deliver to the Agent and to its counsel an electronic copy of the Registration Statement, the Massachusetts Reorganization Application, the FDIC Applications and the Holding Company Application, as originally filed and of each amendment or supplement thereto, including all exhibits. Further, the Winchester Parties will deliver such additional copies of the foregoing documents to counsel to the Agent as may be required for any FINRA filings. In addition, the Winchester Parties will also promptly deliver to the Agent such number of copies of the closing documents with respect to the Reorganization and the Offering as the Agent may reasonably request.

The Mid-Tier Holding Company and the Bank will furnish to the Agent, from time to time during the period when the Prospectus (or any later prospectus related to this offering) is required to be delivered under the 1933 Act or the 1934 Act, such number of copies of such Prospectus (as amended or supplemented) as the Agent may reasonably request for the purposes contemplated by the 1933 Act, the 1933 Act Regulations, the 1934 Act or the rules and regulations promulgated under the 1934 Act (the “1934 Act Regulations”), state securities laws or regulations or applicable rules of any other governmental entity. The Winchester Parties authorize the Agent to use the Prospectus (as amended or supplemented, if amended or supplemented) in any lawful manner contemplated by the Plan in connection with the sale of the Shares by the Agent.

The Winchester Parties will comply with any and all material terms, conditions, requirements and provisions with respect to the Reorganization and the Offering imposed by the SEC, the Division, the FDIC, the FRB, or any other applicable regulator, or the Massachusetts Regulations, the Conversion and Related Regulations or the Control Act Regulations, and by the 1933 Act, the 1933 Act Regulations, the 1934 Act and the 1934 Act Regulations to be complied with prior to or subsequent to the Closing Date and when the Prospectus is required to be delivered, and during such time period the Winchester Parties will comply, at their own expense, with all material requirements imposed upon them by the SEC, the Division, the FDIC, the FRB or any other applicable regulator, or the Massachusetts Regulations, the Conversion and Related Regulations or the Control Act Regulations, and by the 1933 Act, the 1933 Act Regulations, the 1934 Act and the 1934 Act Regulations, including, without limitation, Rule 10b-5 under the 1934 Act, in each case as from time to time in force, so far as necessary to permit the continuance of sales or dealing in the Shares during such period in accordance with the provisions hereof and the Prospectus. The Mid-Tier Holding Company will comply in all material respects with all undertakings contained in the Registration Statement.

If, at any time during the period when the Prospectus is required to be delivered, any event relating to or affecting any of the Winchester Parties shall occur, as a result of which it is necessary or appropriate, in the opinion of counsel for the Mid-Tier Holding Company and in the reasonable opinion of the Agent’s counsel, to amend or supplement the Registration Statement or Prospectus in order to make the Registration Statement or Prospectus not misleading in light of the circumstances existing at the time the Prospectus is delivered to a purchaser, the Mid-Tier Holding Company will immediately so inform the Agent and prepare and file, at its own expense, with the SEC, the Division, the FDIC and the FRB, if applicable, and furnish to the Agent a reasonable number of copies, of an amendment or amendments of, or a supplement or supplements to, the Registration Statement or Prospectus (in form and substance reasonably satisfactory to the Agent and its counsel after a reasonable time for review) which will amend or supplement the

The Winchester Parties will take all necessary actions in cooperating with the Agent and furnish to whomever the Agent may direct such information as may be required to qualify or register the Shares and the Foundation Shares, to the extent applicable, for offering and sale or issuance by the Mid-Tier Holding Company or to exempt such Shares from registration, or to exempt the Mid-Tier Holding Company as a broker-dealer and its officers, directors and employees as broker-dealers, salesmen or agents under applicable securities or blue sky laws of such U.S. jurisdictions in which the Shares are required under the Massachusetts Regulations and the Conversion and Related Regulations to be sold or as the Agent and the Mid-Tier Holding Company may reasonably agree upon; provided, however, that the Mid-Tier Holding Company shall not be obligated to file any general consent to service of process, to qualify to do business in any jurisdiction in which it is not so qualified, or to register its directors or officers as brokers, dealers, salesmen or agents in any jurisdiction. In each jurisdiction where any of the Shares shall have been qualified or registered as above provided, the Mid-Tier Holding Company will make and file such statements and reports in each fiscal period as are or may be required by the laws of such jurisdiction.

The Mid-Tier Holding Company will not sell or issue, contract to sell or otherwise dispose of, for a period of 90 days after the Closing Date, without the Agent’s prior written consent, any of its shares of common stock, other than the Shares and the Foundation Shares or other than in connection with any plan or arrangement described in the Prospectus.

The Mid-Tier Holding Company will register its common stock under Section 12(b) of the 1934 Act. The Mid-Tier Holding Company shall maintain the effectiveness of such registration for not less than three years from the time of effectiveness. For three years, the Mid-Tier Holding Company will use its best efforts to effect and maintain the listing of the Common Stock on the Nasdaq Capital Market and, once listed on the Nasdaq Capital Market, the Mid-Tier Holding Company will comply with all applicable listing standards required by the Nasdaq Stock Market LLC.

During the period during which the Common Stock is registered under the 1934 Act or for three years from the date hereof, whichever period is greater, the Mid-Tier Holding Company will furnish to its stockholders as soon as practicable after the end of each fiscal year an annual report of the Mid-Tier Holding Company (including a consolidated balance sheet and statements of consolidated income, stockholders’ equity and cash flows of the Mid-Tier Holding Company and its subsidiaries as at the end of and for such year, certified by independent registered public accountants in accordance with Regulation S-X under the 1933 Act and the 1934 Act) and make available as soon as practicable after the end of each of the first three quarters of each fiscal year (beginning with the first fiscal quarter ending after the effective time of the Registration Statement) financial information of the Mid-Tier Holding Company and its subsidiaries for such quarter in reasonable detail.

During the period of three years from the date hereof, the Mid-Tier Holding Company will furnish to the Agent: (i) as soon as practicable after such information is publicly available, a copy of each report of the Mid-Tier Holding Company furnished to or filed with the SEC under the 1934 Act or any national securities exchange or system on which any class of securities of the Mid-Tier Holding Company is listed or quoted (including, but not limited to, reports on Forms 10-K, 10-Q and 8-K and all proxy statements and annual reports to stockholders); provided, however, that for purposes of this requirement, documents filed electronically on the SEC’s Electronic Data Gathering, Analysis and Retrieval (▇▇▇▇▇) System shall be deemed to be delivered to the Agent upon filing with the SEC: (ii) a copy of each other non-confidential report of the Mid-Tier Holding Company mailed to its stockholders or filed with the SEC, the Division, the FDIC, the FRB or any other supervisory or regulatory authority or any national securities exchange or system on which any class of securities of the Mid-Tier Holding Company is listed or quoted, each press release and material news items and additional documents and information with respect to the Mid-Tier Holding Company or the Stock Bank as the Agent may reasonably request; and (iii) from time to time, such other nonconfidential information concerning the Holding Company or the Stock Bank as the Agent may reasonably request.

The Mid-Tier Holding Company and the Stock Bank will use the net proceeds from the sale of the Shares in the manner set forth in the Prospectus under the caption “How We Intend to Use the Proceeds from the Offering.”

The Mid-Tier Holding Company will make generally available to its security holders as soon as practicable, but not later than 60 days after the close of the period covered thereby, an earning statement (in form complying with the provisions of Rule 158 of the 1933 Act Regulations) covering a twelve-month period beginning not later than the first day of the Mid-Tier Holding Company’s fiscal quarter next following the effective date (as defined in such Rule 158) of the Registration Statement.

The Mid-Tier Holding Company shall notify the Agent when funds shall have been received for the minimum number of Shares set forth in the Prospectus.

The Winchester Parties will maintain appropriate arrangements for depositing all funds received from persons mailing or delivering subscriptions for or orders to purchase Shares in the Offering with the Bank, on an interest-bearing basis at the rate described in the Prospectus until the Closing Date and satisfaction of all conditions precedent to the release of the Mid-Tier Holding Company’s or the Bank’s obligation to refund payments received from persons subscribing for or ordering Shares in the Offering in accordance with the Plan and as described in the Prospectus or until refunds of such funds have been made to the persons entitled thereto or withdrawal authorizations canceled in accordance

The Mid-Tier Holding Company will report the use of proceeds of the Offering in accordance with Rule 463 under the 1933 Act.

The Mid-Tier Holding Company and the MHC will promptly take all necessary action to each register as a bank holding company under the BHCA within the time period required by applicable law.

The Winchester Parties will take such actions and furnish such information as are reasonably requested by the Agent in order for the Agent to ensure compliance with FINRA Rules 5130 and 5131.

None of the Winchester Parties will amend the Plan without notifying the Agent and the Agent’s counsel prior thereto.

The Mid-Tier Holding Company shall assist the Agent, if necessary, in connection with the allocation of the Shares in the event of an oversubscription and shall provide the Agent with any information necessary to assist the Mid-Tier Holding Company in allocating the Shares in such event and such information shall be accurate and reliable in all material respects.

Prior to the Closing Date, the Mid-Tier Holding Company and the Bank will inform the Agent of any event or circumstances of which either is aware as a result of which the Registration Statement and/or Prospectus, as then amended or supplemented, would contain an untrue statement of a material fact or omit to state a material fact necessary in order to make the statements therein not misleading.

The Mid-Tier Holding Company will not deliver the Shares or the Foundation Shares until the Winchester Parties have satisfied or caused to be satisfied each condition set forth in Section 8 hereof, unless such condition is waived in writing by the Agent.

Subsequent to the date the Registration Statement is declared effective by the SEC and prior to the Closing Date, except as otherwise may be indicated or contemplated therein or set forth in an amendment or supplement thereto, none of the Winchester Parties will have: (i) issued any securities or incurred any liability or obligation, direct or contingent, for borrowed money, except borrowings from the same or similar sources indicated in the Prospectus in the ordinary course of its business, or (ii) entered into any transaction which is material in light of the business and properties of the Winchester Parties, taken as a whole.

Until the Closing Date, the Winchester Parties will conduct their businesses in compliance in all material respects with all applicable federal and state laws, rules, regulations, decisions, directives and orders, including all decisions, directives and orders of the SEC, the Division, the FDIC and the FRB.

The facts and representations provided to ▇▇▇▇ ▇▇▇▇▇▇ by the Winchester Parties and upon which ▇▇▇▇ ▇▇▇▇▇▇ will base its opinion under Section 8(c) are and will be truthful, accurate and complete.

Other than as permitted by the Massachusetts Regulations, the Conversion and Related Regulations, the 1933 Act, the 1933 Act Regulations and the laws of any jurisdiction in which the Shares are qualified for sale, the Winchester Parties will not distribute any offering material in connection with the Offering except for the Prospectus and the Sales Information (except for any affidavit to qualify an exemption under state securities laws) that has been filed with the Registration Statement, the Massachusetts Reorganization Application and the FDIC Notice and authorized for use by the SEC, the Division and the FDIC. The Sales Information shall not conflict in any material respect with the information contained in the Registration Statement and the Prospectus.

The Mid-Tier Holding Company will comply in all material respects with all applicable provisions of the ▇▇▇▇▇▇▇▇-▇▇▇▇▇ Act and the ▇▇▇▇-▇▇▇▇▇ ▇▇▇▇ Street Reform and Consumer Protection Act and all applicable rules, regulations, guidelines and interpretations promulgated thereunder by any governmental entity having jurisdiction over the Mid-Tier Holding Company.

The Winchester Parties will not, prior to the Closing Date, incur any liability or obligation, direct or contingent, or enter into any material transaction, other than in the ordinary course of business consistent with past practice, except as contemplated by the Prospectus.

Prior to the Closing Date, the Mid-Tier Holding Company will establish and maintain “disclosure controls and procedures” (as defined in Rule 13a-15(e) under the 1934 Act) that are designed to ensure that the information it will be required to disclose in the reports it files or submits under the 1934 Act is accumulated and communicated to the Mid-Tier Holding Company’s management (including the Mid-Tier Holding Company’s Chief Executive Officer and Chief Financial Officer) in a timely manner and recorded, processed, summarized and reported within the periods specified in the SEC’s rules and forms. The books, records and accounts and systems of internal accounting control of the Winchester Parties and its subsidiaries will comply in all material respects with the requirements of the 1934 Act.

During the period when the Prospectus is required to be delivered, the Mid-Tier Holding Company, the Bank and the Stock Bank will comply, at their own expense, with all requirements imposed upon them by the Division, the FDIC, the FRB, by the applicable Massachusetts Regulation and the Conversion and Related Regulations, as from time to time in force, the 1933 Act, the 1933 Act Regulations, the 1934 Act, and the 1934 Act Regulations, including, without limitation, Regulation M under the 1934 Act, so far as necessary to permit the continuance of sales or dealing in shares of Common Stock during such period in accordance with the provisions hereof and the Prospectus.

The Mid-Tier Holding Company authorizes the Agent and any Selected Dealer to act as agents of the Mid-Tier Holding Company in distributing the Prospectus to persons entitled to receive subscription rights and other persons to be offered ▇▇▇▇▇▇ having record addresses in the states or jurisdictions set forth in a survey of the securities or “blue sky” laws of the various jurisdictions in which the Offering will be made.

The Winchester Parties will take all necessary action, in cooperation with the Agent, to qualify the Shares for offering and sale under the applicable securities laws of such states of the United States and other jurisdictions as the Massachusetts Regulations and the Conversion and Related Regulations may require and as the Agent and the Mid-Tier Holding Company have agreed; provided, however, that none of the Winchester Parties shall be obligated to file any general consent to service of process or to qualify as a foreign corporation in any jurisdiction in which it is not so qualified. In each jurisdiction in which the Shares have been so qualified, the Mid-Tier Holding Company, the Bank and the Stock Bank will file such statements and reports as may be required by the laws of such jurisdiction to continue such qualification in effect for a period of not less than one year from the effective date of the Registration Statement.

The Winchester Parties will promptly inform the Agent upon its receipt of service with respect to any material litigation or administrative action instituted with respect to the Reorganization, the contribution of the Foundation Shares or the Offering.

The Winchester Parties will use all reasonable efforts to comply with, or cause to be complied with, the conditions precedent to the several obligations of the Agent specified in Section 8.

At Closing Time, the Shares and the Foundation Shares shall have been approved for quotation on the Nasdaq Capital Market upon notice of issuance.

The Winchester Parties shall use their best efforts to ensure that the Foundation submits within the time frames required by applicable law a request to the Internal Revenue Service to be recognized as a tax-exempt organization under Section 501(c)(3) of the Code; the Winchester Parties will take no action which may reasonably be expected to result in the possible loss of the Foundation’s tax-exempt status; and none of the Winchester Parties will contribute any additional assets to the Foundation until such time that such additional contributions will be deductible for federal and state income tax purposes.

The liquidation account required under the Plan for the benefit of Eligible Account Holders (as defined in the Plan) will be duly established and maintained in accordance with the requirements of the Massachusetts Regulations and the Conversion and Related Regulations, and such Eligible Account Holders who continue to maintain their savings accounts in the Stock Bank will have an inchoate interest in their pro rata portion of the liquidation account, which shall have a priority superior to that of the holders of the Common Stock in the event of a complete liquidation of the Mid-Tier Holding Company and the Stock Bank.

At the Closing Date, the Winchester Parties shall have conducted the Reorganization and the establishment and contribution to the Foundation of the Foundation Shares in all material respects in accordance with the Plan, the Massachusetts Regulations, the Conversion and Related Regulations and the Control Act Regulations (except to the extent waived or otherwise approved by the Division, the FDIC or the FRB), and all other applicable laws, regulations, decisions and orders, including all terms, conditions, requirements and provisions precedent to the Reorganization imposed upon them by the Division, the FDIC, the FRB or any other regulatory body to the reasonable satisfaction of Agent and its counsel.

The Registration Statement shall have been declared effective by the SEC, the Holding Company Application shall have been approved by the FRB, the Massachusetts Reorganization Application shall have been approved by the Division and the FDIC Applications shall have been approved or not been objected to, as applicable, by the FDIC, not later than 5:30 p.m. on the date of this Agreement, or with the Agent’s consent at a later time and date; and at the Closing Date, no stop order suspending the effectiveness of the Registration Statement shall have been issued under the 1933 Act or proceedings therefore initiated or, to the knowledge of the Winchester Parties, threatened by the SEC or any regulatory authority, and no order or other action suspending the authorization of the Prospectus or the consummation of the Reorganization shall have been issued or proceedings therefore initiated or, to the Winchester Parties’ knowledge,

At the Closing Date, the Agent shall have received the favorable opinion, dated as of the Closing Date and addressed to the Agent and for its benefit and upon which Agent’s counsel may rely for purposes of delivering its legal opinion pursuant to Section 8(d), of ▇▇▇▇ ▇▇▇▇▇▇, special counsel for the Winchester Parties, in form and substance satisfactory to the Agent and its counsel, as attached hereto as Exhibit B.

At the Closing Date, the Agent shall have received the favorable opinion, dated as of the Closing Date and addressed to the Agent and for its benefit, of Silver, ▇▇▇▇▇▇▇▇, ▇▇▇▇ & ▇▇▇▇▇▇▇ LLP, special counsel for the Agent, with respect to such matters as the Agent may reasonably require. Such opinion may rely upon certificates of officers and directors of the Winchester Parties delivered pursuant hereto or as such counsel shall reasonably request and the opinion of ▇▇▇▇ ▇▇▇▇▇▇ delivered pursuant to subsection (c) above.

Prior to the mailing of the Prospectus to eligible subscribers, a blue sky memorandum from ▇▇▇▇ ▇▇▇▇▇▇ relating to the Offering, including Agent’s participation therein, shall have been furnished to the Mid-Tier Holding Company with a copy thereof addressed to Agent or upon which ▇▇▇▇ ▇▇▇▇▇▇ shall state the Agent may rely. The blue sky memorandum will relate to the necessity of obtaining or confirming exemptions, qualifications or the registration of the Shares and the Foundation Shares under applicable state securities law.

At the Closing Date, the Agent shall receive a certificate of the President and the Chief Financial Officer of each of the Winchester Parties, solely in their capacities as such and without personal liability therefor, in form and substance reasonably satisfactory to the Agent’s counsel, dated as of such Closing Date, to the effect that: (i) they have carefully examined the Registration Statement, the Prospectus and the General Disclosure Package and, in their opinion, as of the effective date of the Registration Statement, and at the time the Prospectus became authorized for final use, the Registration Statement, the Prospectus and the General Disclosure Package did not contain any untrue statement of a material fact or omit to state a material fact necessary in order to make the statements therein, in light of the circumstances in which they were made, not misleading; (ii) since

None of the Winchester Parties shall have sustained, since the date of the latest financial statements included in the Registration Statement, the General Disclosure Package and Prospectus, any material loss or interference with its business from fire, explosion, flood or other calamity, whether or not covered by insurance, or from any labor dispute or court or governmental action, order or decree, otherwise than as set forth in the Registration Statement and the Prospectus, and since the respective dates as of which information is given in the Registration Statement, the Prospectus and the General Disclosure Package, there shall not have been any Material Adverse Effect that is in the Agent’s reasonable judgment sufficiently material and adverse as to make it impracticable or inadvisable to proceed with the Offering or the delivery of the Shares on the terms and in the manner contemplated in the Prospectus.

Prior to and at the Closing Date, in the reasonable opinion of the Agent, (i) there shall have been no material adverse change in the financial condition, results of operations, business, affairs or prospects of the Winchester Parties considered as one enterprise, from that as of the latest dates as of which such condition is set forth in the Prospectus, other than transactions referred to or contemplated therein; (ii) there shall have been no material transaction entered into by any Winchester Party since the latest dates as of which the financial condition of the Winchester Parties is set forth in the Prospectus, other than transactions referred to or contemplated therein or in the ordinary course of business; (iii) none of the Winchester Parties shall have received from the Division, the FDIC or the FRB any direction (oral or written) to make any material change in the method of conducting their business with which it has not complied (which direction (if permitted to be disclosed), if any, shall have been disclosed to the Agent) or which materially and adversely would affect the financial condition, results of operations or business of the Winchester Parties taken as a whole; (iv) none of the Winchester Parties shall have been in default (nor shall an event have occurred which, with notice or lapse of time or both, would constitute a default) under any provision of any agreement or instrument relating to any outstanding indebtedness; (v) no action, suit or proceeding, at law or in equity or before or by any federal or state commission, board or other administrative agency, not disclosed in the Prospectus, shall be pending or, to the knowledge of the Winchester Parties, threatened against the any of the Winchester Parties or affecting any of their properties wherein an unfavorable decision, ruling or finding would have a Material Adverse Effect; and (vi) the Shares shall have been qualified or registered for offering and sale or exempted therefrom under the securities or blue sky laws of the jurisdictions as the Agent shall have reasonably requested and as agreed to by the Winchester Parties.

Concurrently with the execution of this Agreement, the Agent shall receive a letter from Wolf & Company, P.C., dated as of the date hereof and addressed to the Agent: (i) confirming that Wolf & Company, P.C. is a firm of independent registered public accountants within the applicable rules of the SEC and the PCAOB and stating in effect that in its opinion the financial statements and related notes of the Bank as of June 30, 2024 and 2023, and for each of the years in the two-year period ended June 30, 2024, and covered by their opinion included in the Prospectus, and any other more recent unaudited financial statements included in the Prospectus, comply as to form in all material respects with the applicable accounting requirements of the 1933 Act and related published rules and regulations of the SEC; (ii) stating in effect that, on the basis of certain agreed upon procedures (but not an audit in accordance with standards of the PCAOB) consisting of a reading of the latest available consolidated financial statements of the Bank prepared by the Bank, a reading of the minutes of the meetings of the Boards of Directors or Trustees, as applicable, of each of the Winchester Parties and consultations with officers of the Bank responsible for financial and accounting matters, nothing came to their attention which caused them to believe that: (A) the audited consolidated financial statements and any unaudited interim consolidated financial statements included in the Prospectus are not in conformity with the applicable accounting requirements of the 1933 Act and related published rules and regulations of the SEC and accounting principles generally accepted in the United States of America applied on a basis substantially consistent with that of the audited consolidated financial statements included in the Prospectus; (B) during the period from the date of the latest consolidated financial statements included in the Prospectus to a specified date not more than three business days prior to the date of the Prospectus, except as has been described in the Prospectus, there was any increase in consolidated long-term or short-term debt or non-performing assets of the Bank; (C) except as set forth in said letter, there was any decrease in the total assets, total investment securities, total loans, the allowance for credit losses, total deposits, or total surplus of the Bank at the date of such letter as compared with amounts shown in the latest consolidated balance sheet included in the Prospectus; or (D) there was any decrease in total interest and dividend income, net interest income, net interest income after provision for credit losses, other income or net income or increase in interest expense, operating expense or the provision for credit losses of the Bank, in each case for the period commencing immediately after the period covered by the latest consolidated balance sheet and net income (loss) statement included in the Prospectus and ended on a specified date not more than three business days prior to the date of this Agreement as compared to the corresponding period in the preceding year; and (iii) stating that, in addition to the audit referred to in their opinion included in the Prospectus and the performance of the procedures referred to in clause (ii) of this subsection (i), they have compared with the general accounting records of the Bank, which are subject to the internal controls of the Bank, the accounting system and other data prepared by the Bank, directly from such accounting records, to the extent specified in such letter, such amounts and/or percentages set forth in the Prospectus, any Permitted Free Writing Prospectus and any prospectus supplement, as the Agent may reasonably request; and they have found such amounts and percentages to be in agreement therewith (subject to rounding).

At the Closing Date, the Agent shall receive a letter dated the Closing Date, addressed to the Agent, confirming the statements made by Wolf & Company, P.C. in the letter delivered by it pursuant to subsection (i) of this Section 8, the “specified date” referred to in clause (ii)(B) of subsection (i) to be a date specified in the letter required by this subsection (j) which for purposes of such letter shall not be more than three business days prior to the Closing Date.

At the Closing Date, the Mid-Tier Holding Company shall receive a letter from RP Financial, LC. dated the Closing Date (i) confirming that said firm is independent of the Winchester Parties and is experienced and expert in the area of corporate appraisals within the meaning of the Massachusetts Regulations and the Conversion and Related Regulations, (ii) stating in effect that the Appraisal prepared by such firm complies in all material respects with the applicable requirements of the Massachusetts Regulations and the Conversion and Related Regulations, and (iii) further stating that its opinion of the aggregate pro forma market value of the Mid-Tier Holding Company including the Bank, as most recently updated, remains in effect.

At or prior to the Closing Date, the Agent shall receive: (i) a copy of the letter from the Division approving the Massachusetts Reorganization Application, including the establishment of the Foundation; (ii) a copy of the letter from the FRB approving the Holding Company Application; (iii) a copy of the letter or letters from the FDIC approving or not objecting to, as applicable, the FDIC Applications; (iv) a copy of the order from the SEC declaring the Registration Statement effective; (v) certificates or other evidence from the FDIC and the DIF evidencing the Bank’s insurance of accounts; (v) a certificate from the FHLB-Boston evidencing the Bank’s membership therein; (vi) a certified copy of each of the Mid-Tier Holding Company’s, the Bank’s and the MHC’s articles of incorporation, charter and bylaws, as applicable; and (ix) any other documents that Agent shall reasonably request.

At the Closing Time, the Shares and the Foundation Shares shall have been approved for listing on the Nasdaq Stock Market.

Subsequent to the date hereof, there shall not have occurred any of the following; (i) a suspension or limitation in trading in securities generally on the New York Stock Exchange (the “NYSE”) or the NYSE MKT or quotations halted generally on the Nasdaq Stock Market or in the over-the-counter market or minimum or maximum prices for trading have been fixed, or maximum ranges for prices for securities have been required by the NYSE, the NYSE MKT or the Nasdaq Stock Market or in the over-the-counter market or by order of the SEC, FINRA or any other governmental authority; (ii) a general moratorium on the operations of commercial banks, or savings associations or a general moratorium on the withdrawal of deposits from commercial banks or savings associations declared by federal or state authorities; (iii) the engagement by the United States in hostilities which have resulted in the declaration, on or after the date hereof, of a national emergency or war or a material decline in the price of equity or debt securities, if the effect of such declaration or decline, in the Agent’s reasonable judgment, makes it impracticable or inadvisable to proceed with the Offering or the delivery of the Shares on the terms and in the manner contemplated in the Registration Statement and the Prospectus.

At or prior to the Closing Date, the Agent and counsel to the Agent shall have been furnished with such documents and opinions as they may reasonably require for the purpose of enabling them to pass upon the sale of the Shares and the contribution of the Foundation Shares as herein contemplated and related proceedings or in order to evidence the occurrence or completeness of any of the representations or warranties, or the fulfillment of any of the conditions, herein contained; and all proceedings taken by the Winchester Parties in connection with the sale of the Shares and the contribution of the Foundation Shares as herein contemplated shall be satisfactory in form and substance to the Agent or its counsel.

All opinions, certificates, letters and documents delivered pursuant to this Section 8 will be in compliance with the provisions hereof only if they are reasonably satisfactory in form and substance to the Agent or to counsel for the Agent. Any certificate signed by an officer of any of the Winchester Parties and delivered to the Agent or to counsel for the Agent shall be deemed a representation and warranty by such Winchester Party to the Agent as to the statements made therein.

The Winchester Parties jointly and severally agree to indemnify and hold harmless the Agent, its officers and directors, employees and agents, and each person, if any, who controls the Agent within the meaning of Section 15 of the 1933 Act or Section 20(a) of the 1934 Act, against any and all loss, liability, claim, damage or expense whatsoever (including, but not limited to, settlement expenses), joint or several, that the Agent or any of them may suffer or to which the Agent and any such persons may become subject under all applicable federal or state laws or otherwise, and to promptly reimburse the Agent and any such persons upon written demand for any expense (including all fees and disbursements of counsel) incurred by the Agent or any of them in connection with investigating, preparing or defending any actions, proceedings or claims (whether commenced or threatened) to the extent such losses, claims, damages, liabilities or actions: (i) arise out of or are based upon any untrue statement or alleged untrue statement of a material fact contained in the Registration Statement (or any amendment or supplement thereto), the General Disclosure Package, any Issuer-Represented Limited-Use Free Writing Prospectus, any Issuer Represented General Free Writing Prospectus, preliminary or final Prospectus (or any amendment or supplement thereto), the Massachusetts Reorganization Application (or any amendment or supplement thereto), the Holding Company Application (or any amendment or supplement thereto), the FDIC Notice (or any amendment or supplement thereto) or any instrument or document executed by the Winchester Parties or based upon written information supplied by the Mid-Tier Holding Company filed in any state or jurisdiction to register or qualify any or all of the Shares or the Foundation Shares or to claim an exemption therefrom or provided to any state or jurisdiction to exempt the Winchester Parties as a broker-dealer or its officers, directors and employees as broker-dealers or agents, under the securities laws thereof (collectively, the “Blue Sky Application”), or any document, advertisement, oral statement or communication, or supplemental sales material (including the supplemental sales material filed as an exhibit to the Registration Statement, the Massachusetts Reorganization

The Agent agrees to indemnify and hold harmless the Winchester Parties, their directors and officers and each person, if any, who controls the Mid-Tier Holding Company or the Bank within the meaning of Section 15 of the 1933 Act or Section 20(a) of the 1934 Act against any and all loss, liability, claim, damage or expense whatsoever (including but not limited to settlement expenses), joint or several, which they, or any of them, may suffer or to which they, or any of them may become subject under all applicable federal and state laws or otherwise, and to promptly reimburse the Winchester Parties, and any such persons upon written demand for any expenses (including reasonable fees and disbursements of counsel) incurred by them, or any of them, in connection with investigating, preparing or defending any actions, proceedings or claims (whether commenced or threatened) to the extent such losses, claims, damages, liabilities or actions: (i) arise out of or are based upon

Each indemnified party shall give prompt written notice to each indemnifying party of any action, proceeding, claim (whether commenced or threatened), or suit instituted against it in respect of which indemnity may be sought hereunder, but failure to so notify an indemnifying party shall not relieve it from any liability which it may have on account of this Section 9 or otherwise. An indemnifying party may participate at its own expense in the defense of such action. In addition, if it so elects within a reasonable time after receipt of such notice, an indemnifying party, jointly with any other indemnifying parties receiving such notice, may assume defense of such action with counsel chosen by it and approved by the indemnified parties that are defendants in such action, unless such indemnified parties reasonably object to such assumption on the ground that there may be legal defenses available to them that are different from or in addition to those available to such indemnifying party. If an indemnifying party assumes the defense of such action, the indemnifying parties shall not be liable for any fees and expenses of counsel for the indemnified parties incurred thereafter in connection with such action, proceeding or claim, other than reasonable costs of investigation. In no event shall the indemnifying parties be liable for the fees and expenses of more than one separate firm of attorneys (and any special counsel that said firm may retain) for each indemnified party in connection with any one action, proceeding or claim or separate but similar or related actions, proceedings or claims in the same jurisdiction arising out of the same general allegations or circumstances. The Winchester Parties will not, without the Agent’s prior written consent, settle, compromise, consent to the entry of any judgment in or otherwise seek to terminate any action, claim, suit or proceeding in respect of which indemnification may be sought hereunder (whether or not any indemnified person is a party thereto) unless such settlement, compromise, consent or termination does not include a statement or acknowledgment as to, or an admission of, fault, culpability or failure to act by or on behalf of any indemnified party and provides that the Agent and the other indemnified parties shall be unconditionally and irrevocably released from all liability in respect of such action, claim, suit or proceeding. No indemnified party seeking indemnification or reimbursement under this Section 9 or contribution under Section 10 will, without the indemnifying parties’ prior written consent,

In addition to, and without limiting, the provisions of Section 9(a) hereof, in the event that the Agent, any person, if any, who controls the Agent within the meaning of Section 15 of the 1933 Act or Section 20 of the 1934 Act or any of its partners, directors, officers, employees, affiliates or agents is requested or required to appear as a witness or otherwise gives testimony in any action, proceeding, investigation or inquiry brought by or on behalf of or against the Winchester Parties, the Agent or any of its affiliates or any participant in the transactions contemplated hereby in which the Agent or such person or agent is not named as a defendant, the Winchester Parties jointly and severally agree to reimburse the Agent and its partners, directors, officers, employees or agents for all reasonable and necessary out-of-pocket expenses incurred by them in connection with preparing or appearing as a witness or otherwise giving testimony and to compensate the Agent and its partners, directors, officers, employees or agents in an amount to be mutually agreed upon.

In order to provide for just and equitable contribution in circumstances in which the indemnification provided for in Section 9 is due in accordance with its terms but is for any reason held by a court to be unavailable from the Winchester Parties or the Agent, the Winchester Parties and the Agent shall contribute to the aggregate losses, claims, damages and liabilities (including any investigation, legal and other expenses incurred in connection with, and any amount paid in settlement of, any action, suit or proceeding, but after deducting any contribution received by the Winchester Parties or the Agent from persons other than the other parties thereto, who may also be liable for contribution) in such proportion so that the Agent is responsible for that portion represented by the percentage that the fees paid to the Agent pursuant to Section 2 of this Agreement (not including expenses) bears to the gross proceeds received by the Mid-Tier Holding Company from the sale of the Shares in the Offering, and the Winchester Parties shall be responsible for the balance. If, however, the allocation provided above is not permitted by applicable law, then each indemnifying party shall contribute to such amount paid or payable by such indemnified party in such proportion as is appropriate to reflect not only such relative fault of the Winchester Parties on the one hand and the Agent on the other in connection with the statements or omissions which resulted in such losses, claims, damages or liabilities (or actions, proceedings or claims in respect thereto), but also the relative benefits received by the Winchester Parties on the one hand and the Agent on the other from the Offering (before deducting expenses). The relative fault shall be determined by reference to, among other things, whether the untrue or alleged untrue statement of a material fact or the omission or alleged omission to state a material fact relates to information supplied by the Winchester Parties on the one hand or the Agent on the other and the parties’ relative intent, good faith, knowledge, access to information and opportunity to correct or prevent such statement or omission. The Winchester Parties

Neither termination nor completion of the engagement of the Agent nor any investigation made by or on behalf of the Agent shall affect the indemnification obligations of the Winchester Parties or the Agent hereunder, which shall remain and continue to be operative and in full force and effect.

If any domestic or international event or act or occurrence has materially disrupted the United States securities markets such as to make it, in the Agent’s reasonable opinion, impracticable to proceed with the offering of the Shares; or if trading on the NYSE, NYSE MKT, Nasdaq Stock Market, or over-the-counter market (“OTC”) shall have suspended (except that this shall not apply to the imposition of NYSE, NYSE MKT, Nasdaq Stock Market, or OTC trading collars imposed on program trading); or if the United States shall have become involved in a war or major hostilities or escalation thereof; or if a general banking moratorium has been declared by a state or federal authority which has a material

In the event the Mid-Tier Holding Company fails to sell the required minimum number of the Shares by the date when such sales must be completed, in accordance with the provisions of the Plan or as required by the Conversion and Related Regulations, and applicable law, this Agreement shall terminate upon refund by the Mid-Tier Holding Company to each person who has subscribed for or ordered any of the Shares the full amount which it may have received from such person, together with interest as provided in the Prospectus, and no party to this Agreement shall have any obligation to the other hereunder, except as set forth in Sections 2(a), 2(d), 2(e), 7, 9 and 10 hereof.

If any of the conditions specified in Section 8 shall not have been fulfilled when and as required by this Agreement, unless waived in writing, or by the Closing Date, this Agreement and all of the Agent’s obligations hereunder may be cancelled by the Agent by notifying the Mid-Tier Holding Company of such cancellation in writing or by electronic mail at any time at or prior to the Closing Date, and any such cancellation shall be without liability of any party to any other party except as otherwise provided in Sections 2(a), 2(d), 2(e), 7, 9 and 10 hereof.

If the Agent elects to terminate this Agreement as provided in this Section, the Winchester Parties shall be notified promptly by telephone or electronic mail, confirmed by letter.

WINCHESTER BANCORP, INC.,

a Maryland Corporation

WINCHESTER BANCORP, MHC

(IN FORMATION)

Accepted as of the date first above written

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