January 8, 2025

John A. Carroll
Chief Executive Officer
Winchester Bancorp, Inc.
661 Main Street
Winchester, MA 01890

       Re: Winchester Bancorp, Inc.
           Registration Statement on Form S-1
           Filed December 12, 2024
           File No. 333-283752
Dear John A. Carroll:

       We have reviewed your registration statement and have the following
comments.

        Please respond to this letter by amending your registration statement
and providing
the requested information. If you do not believe a comment applies to your
facts and
circumstances or do not believe an amendment is appropriate, please tell us why
in your
response.

       After reviewing any amendment to your registration statement and the
information
you provide in response to this letter, we may have additional comments.

Form S-1 filed December 12, 2024
Summary, page 1

1.     We note that your risk factors exceed 15 pages. In the forepart of the
prospectus,
       please include a series of concise, bulleted or numbered statements,
that is no more
       than two pages, summarizing the principal factors that make an
investment in
       the registrant or offering speculative or risky. Refer to Item 105(b) of
Regulation S-K.
Our Officers, Directors and Employees Will Receive Additional Benefits and
Compensation
After the Offering
Employee Stock Ownership Plan, page 14

2.     We note your disclosure that you anticipate your employee stock
ownership plan will
       purchase 8.0% of the aggregate of the number of shares sold in the
offering and
       contributed to the charitable foundation with the proceeds of a loan to
be made by
       Winchester Bancorp, Inc. to the plan. Please file the plan as an exhibit
to this
 January 8, 2025
Page 2

       registration statement or advise.
Risk Factors
The geographic concentration of our loan portfolio and lending activities makes
us vulnerable
to a downturn in our local market area, page 19

3.     Revise this risk factor to discuss, as appropriate, the factors that
impact your market
       area. For instance, discuss any changes in occupancy for office,
industrial or retail real
       estate. Further, discuss the extent to which the ability to compete in
this area is
       dependent on existing relationships, or advise.
Management's Discussion and Analysis of Financial Condition and Results of
Operations
Liquidity and Capital Resources, page 69

4.     We note that you monitor your liquidity position on a daily basis.
Please revise to
       discuss in more detail any liquidity policy guidelines and metrics you
use to manage
       your liquidity, such as coverage ratios or specific thresholds as
applicable and whether
       you complied with your internal guidelines with respect to these metrics
, for the
       periods presented in your financial statements.
Business of Winchester Savings Bank
Loan Underwriting Risks
Commercial Real Estate Loans and Multi-Family Real Estate Loans, page 76

5.     We note that you intend to expand your lending activities to make more
multi-family
       loans. Please tell us, with a view towards enhanced disclosure, whether
the properties
       that provide collateral for of your current multi-family loans are
subject to rent control
       regulation. Similarly, if management expects to expand lending into
areas where rent
       control regulation might impact the ability of borrowers to maintain
rents in line with
       the current market, please clarify.
Loan Approval Procedures and Authority, page 77

6.     We note your disclosure, both on this page and in the risk factor on
page 18, that your
       loan to one borrower limit will increase as a result of this offering.
Revise your
       disclosure, in an appropriate portion, to discuss the amount that this
limit might
       increase at the minimum, mid-point or maximum offering amount.
Sources of Funds
Deposits, page 85

7.     We note your disclosure on page 86 that all of your deposits are fully
insured due to
       the additional insurance provided to a Massachusetts savings bank and
you expect that
       coverage under the DIF will continue after consummation of the
reorganization and
       offering. Please address the following items:
           revise your disclosure on page 32, or where most appropriate to
discuss and
           identify the thresholds used to determine when a Massachusetts
savings bank
           becomes too large to qualify (or other possible reasons for
disqualification) for
           participation in the Depositors Insurance Fund;
           revise here, or where most appropriate, to discuss other scenarios
and related risks
 January 8, 2025
Page 3

           in which a Massachusetts savings bank may no longer be qualified to
participate
           in the Depositors Insurance Fund; and
             clarify whether the Depositors Insurance Fund insures deposits
from out of state
           depositors, including brokered deposits.

        We remind you that the company and its management are responsible for
the accuracy
and adequacy of their disclosures, notwithstanding any review, comments, action
or absence
of action by the staff.

       Refer to Rules 460 and 461 regarding requests for acceleration. Please
allow adequate
time for us to review any amendment prior to the requested effective date of
the registration
statement.

       Please contact Victor Cecco at 202-551-2064 or Lory Empie at
202-551-3714 if you
have questions regarding comments on the financial statements and related
matters. Please
contact Aisha Adegbuyi at 202-551-8754 or Christian Windsor at 202-551-3419
with any
other questions.



                                                           Sincerely,

                                                           Division of
Corporation Finance
                                                           Office of Finance
cc:   Ned Quint, Esq.