[Form 4] Winchester Bancorp, Inc./MD/ Insider Trading Activity

Rhea-AI Filing Summary

Winchester Bancorp, Inc. President & CEO John A. Carroll reported an open-market purchase of 50 shares of common stock at $12.75 per share on May 21, 2026. The shares are held indirectly by his spouse as custodian for their child.

The filing also shows indirect holdings of 560 shares through an ESOP and 25,000 shares through a trust, plus 25,000 shares held directly, with a footnote stating some transactions reflected are not required Section 16 reports.

Insider Trade Summary

Net Buyer: 50 shares ($638)

Net Buy 4 txns

Insider Carroll John A

Role President & CEO

Bought 50 shs ($637.50)

Type	Security	Shares	Price	Value
Purchase	Common Stock	50	$12.75	$637.50
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 50 shares (Indirect, By Spouse as custodian for child); Common Stock — 25,000 shares (Direct, null)

Footnotes (1)

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Key Figures

Open-market purchase: 50 shares Purchase price: $12.75/share Indirect ESOP holding: 560 shares +3 more

6 metrics

Open-market purchase 50 shares Common Stock bought on May 21, 2026

Purchase price $12.75/share Open-market transaction for Common Stock

Indirect ESOP holding 560 shares Common Stock held indirectly by ESOP after transactions

Indirect trust holding 25,000 shares Common Stock held indirectly by trust after transactions

Direct holding 25,000 shares Common Stock held directly after transactions

Custodial account holding 50 shares Common Stock held by spouse as custodian for child

Key Terms

open-market purchase, ESOP, Section 16

3 terms

open-market purchase financial

"transaction_action: "open-market purchase""

An open-market purchase is when an investor or a company buys shares on a public stock exchange at the going market price, rather than through a private deal. It matters to investors because these purchases change how many shares are available, can push the stock price up or signal confidence from large buyers, and often affect per-share metrics like earnings—think of it like someone buying lots of apples off a grocery shelf, reducing supply and potentially raising the price.

ESOP financial

"nature_of_ownership: "By ESOP""

An Employee Stock Ownership Plan (ESOP) is a program that gives employees ownership shares in their company, often as part of their benefits package. It acts like a company-sponsored savings plan, allowing workers to have a stake in the company's success, which can boost motivation and loyalty. For investors, ESOPs can influence company decisions and stock value, making them an important aspect of corporate ownership and governance.

Section 16 regulatory

"Reflects transactions not required to be reported pursuant to Section 16 of the Securities Act of 1934, as amended"

Section 16 is a U.S. securities law rule that governs the trading and disclosure obligations of company insiders — typically officers, directors and large shareholders — to promote transparency and deter unfair profit-taking. It requires insiders to publicly report their stock trades and allows companies or the issuer to reclaim quick, short-term profits from certain insider trades, like a scoreboard and a refund policy that help investors see and limit possible insider advantage.

Form 4 Insider Transactions: What Each Field Means →

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Carroll John A

(Last) (First) (Middle)

661 MAIN STREET

(Street)

WINCHESTER MASSACHUSETTS 01890

(City) (State) (Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
Winchester Bancorp, Inc./MD/ [ WSBK ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	President & CEO

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/21/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	05/21/2026		P		50	A	$12.75	50	I	By Spouse as custodian for child
Common Stock								25,000	D
Common Stock								25,000	I	By Trust
Common Stock								560(1)	I	By ESOP

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

1. Reflects transactions not required to be reported pursuant to Section 16 of the Securities Act of 1934, as amended

	/s/ Edward A. Quint, pursuant to power of attorney	05/22/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

FAQ

What insider transaction did Winchester Bancorp (WSBK) report for John A. Carroll?

Winchester Bancorp reported that President & CEO John A. Carroll bought 50 common shares in an open-market transaction. The filing shows this purchase at $12.75 per share on May 21, 2026, held indirectly through his spouse for their child.

How many Winchester Bancorp (WSBK) shares did the CEO buy and at what price?

The CEO bought 50 shares of Winchester Bancorp common stock at $12.75 per share. These shares are part of his indirect holdings and are recorded as held by his spouse acting as custodian for their child according to the filing details.

How are John A. Carroll’s Winchester Bancorp (WSBK) shares held after this Form 4?

After the reported transactions, the filing lists 25,000 shares held directly, 25,000 shares held indirectly by a trust, 560 shares held indirectly via an ESOP, and 50 shares held indirectly by his spouse as custodian for their child, all in Winchester Bancorp common stock.

Does the Winchester Bancorp (WSBK) Form 4 show any insider share sales?

The Form 4 shows one open-market purchase of 50 shares and no reported sales. Other entries are holdings with “unknown” transaction codes, and the summary section indicates a net-buy position of 50 shares for the reported period in this filing.

Are there any derivative securities reported in this Winchester Bancorp (WSBK) Form 4?

The filing’s derivative section is empty, indicating no options or other derivative securities are reported in this Form 4. All positions shown relate to Winchester Bancorp common stock held directly or indirectly through an ESOP, trust, or family custodial account.

What does the Section 16 footnote in the Winchester Bancorp (WSBK) Form 4 indicate?

A footnote explains that some entries reflect transactions not required to be reported under Section 16 of the Securities Exchange Act of 1934. This clarifies that certain listed position changes fall outside mandatory insider transaction reporting rules even though they appear on the form.