<SEC-DOCUMENT>0001437749-25-017190.txt : 20250515
<SEC-HEADER>0001437749-25-017190.hdr.sgml : 20250515
<ACCEPTANCE-DATETIME>20250515161507
ACCESSION NUMBER:		0001437749-25-017190
CONFORMED SUBMISSION TYPE:	4
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20250514
FILED AS OF DATE:		20250515
DATE AS OF CHANGE:		20250515

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Hood William Preston
		CENTRAL INDEX KEY:			0002066176
		ORGANIZATION NAME:           	

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-42627
		FILM NUMBER:		25953276

	MAIL ADDRESS:	
		STREET 1:		661 MAIN STREET
		CITY:			WINCHESTER
		STATE:			MA
		ZIP:			01890

ISSUER:		

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			Winchester Bancorp, Inc./MD/
		CENTRAL INDEX KEY:			0002047235
		STANDARD INDUSTRIAL CLASSIFICATION:	SAVINGS INSTITUTIONS, NOT FEDERALLY CHARTERED [6036]
		ORGANIZATION NAME:           	02 Finance
		EIN:				000000000
		STATE OF INCORPORATION:			MD
		FISCAL YEAR END:			0630

	BUSINESS ADDRESS:	
		STREET 1:		661 MAIN STREET
		CITY:			WINCHESTER
		STATE:			MA
		ZIP:			01890
		BUSINESS PHONE:		(781) 729-2130

	MAIL ADDRESS:	
		STREET 1:		661 MAIN STREET
		CITY:			WINCHESTER
		STATE:			MA
		ZIP:			01890
</SEC-HEADER>
<DOCUMENT>
<TYPE>4
<SEQUENCE>1
<FILENAME>rdgdoc.xml
<DESCRIPTION>FORM 4
<TEXT>
<XML>
<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0508</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2025-05-14</periodOfReport>

    <issuer>
        <issuerCik>0002047235</issuerCik>
        <issuerName>Winchester Bancorp, Inc./MD/</issuerName>
        <issuerTradingSymbol>WSBK</issuerTradingSymbol>
    </issuer>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0002066176</rptOwnerCik>
            <rptOwnerName>Hood William Preston</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>661 MAIN STREET</rptOwnerStreet1>
            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>WINCHESTER</rptOwnerCity>
            <rptOwnerState>MA</rptOwnerState>
            <rptOwnerZipCode>01890</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>1</isDirector>
        </reportingOwnerRelationship>
    </reportingOwner>

    <aff10b5One>0</aff10b5One>

    <nonDerivativeTable>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2025-05-14</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>3900</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>9.5818</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>48900</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2025-05-14</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>300</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>9.59</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>49200</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2025-05-14</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>800</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>9.60</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>50000</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
    </nonDerivativeTable>

    <ownerSignature>
        <signatureName>/s/ Ned A. Quint, pursuant to power of attorney</signatureName>
        <signatureDate>2025-05-15</signatureDate>
    </ownerSignature>
</ownershipDocument>
</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
