Winchester Bancorp grants Pierce 7,500 stock options

Both awards begin vesting on November 4, 2027, at 20% per year, and the options expire November 4, 2036.

Available on EDGAR 11/06/2026 - 12:51 PM EST Accepted by SEC EDGAR 11/06/2026 - 12:51 PM EST Learn about SEC filing dates

Rhea-AI Filing Summary

Winchester Bancorp, Inc. (WSBK) director Connolly Carole Ann Pierce received 3,000 shares of restricted stock, reported at $13.64 per share, and 7,500 stock options with a $13.64 exercise price on November 4, 2026. Both awards vest at 20% per year beginning November 4, 2027; the options expire November 4, 2036. Her direct common-stock holdings following the restricted-stock award were 28,000 shares. Separate entries list 25,000 shares held indirectly by Company A and 25,000 by Company B as of November 6, 2026.

Insider Trade Summary

Grant/Award: 10,500 shares

Grant/Award 2 txns

Insider Pierce Connolly Carole Ann

Role Director

Type	Security	Shares	Price	Value
Holding	Common Stock	--	--	--
Holding	Common Stock	--	--	--
Grant/Award	Stock Options F2	7,500	$13.64	$102K
Grant/Award	Common Stock F1	3,000	$13.64	$41K

Holdings After Transaction: Stock Options — 7,500 contracts (Direct); Common Stock — 28,000 shares (Direct); Common Stock — 25,000 shares (Indirect, By Company A); Common Stock — 25,000 shares (Indirect, By Company B)

Holdings Before and After: Stock Options, 0 to 7,500 contracts (Direct); Common Stock, 25,000 to 28,000 shares (Direct)

Footnotes (2)

1. F1. Shares of restricted stock vest at a rate of 20% per year commencing November 4, 2027.
2. F2. Stock option vest at a rate of 20% per year commencing on November 4, 2027.

Key Figures

Restricted stock awarded: 3,000 shares Reported restricted-stock price: $13.64 per share Stock options awarded: 7,500 options +3 more

6 metrics

Restricted stock awarded 3,000 shares November 4, 2026

Reported restricted-stock price $13.64 per share Award dated November 4, 2026

Stock options awarded 7,500 options November 4, 2026

Option exercise price $13.64 per share Options awarded November 4, 2026

Direct common-stock holdings after award 28,000 shares Following the November 4, 2026 restricted-stock award

Annual vesting rate 20% per year Beginning November 4, 2027, for the restricted stock and stock options

Key Terms

restricted stock, Stock Options, exercise price, vest at a rate of 20% per year

4 terms

restricted stock financial

"Shares of restricted stock vest at a rate of 20% per year"

Shares granted to an individual that carry limits on transfer or sale until certain conditions are met, such as staying with the company for a set time or hitting performance targets. Think of them as a locked gift that gradually opens; for investors they matter because they affect how many shares may enter the market later, signal management incentives and potential dilution, and reveal confidence in future company performance.

Stock Options financial

"Stock option vest at a rate of 20% per year"

Stock options are agreements that give a person the right to buy or sell a company's stock at a specific price within a certain time frame. They are often used as a reward or incentive, similar to a coupon that can be used later if the stock price rises, allowing the holder to make a profit.

exercise price financial

"Stock Options with a $13.64 exercise price"

The exercise price is the fixed amount at which you can buy or sell an asset, like a stock, when using an options contract. It matters because it helps determine whether exercising the option will be profitable or not, depending on the current market price. Think of it as the set price you agree on today to buy or sell later.

vest at a rate of 20% per year financial

"vest at a rate of 20% per year commencing November 4, 2027"

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What stock awards did WSBK director Connolly Carole Ann Pierce receive?

On November 4, 2026, she received 3,000 shares of restricted stock, reported at $13.64 per share, and 7,500 stock options with a $13.64 exercise price. Her direct common-stock position after the restricted-stock award was 28,000 shares.

When do WSBK director Connolly Carole Ann Pierce's awards vest, and when do the options expire?

The restricted stock and stock options vest at a rate of 20% per year beginning November 4, 2027. The stock options expire November 4, 2036.

AI-generated analysis. How Rhea-AI works. Not financial advice.

Form 4 Insider Transactions: What Each Field Means →

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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^*

Pierce Connolly Carole Ann

(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
	Officer (give title below)		Other (specify below)

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
11/06/2026

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	11/04/2026		A		3,000(1)	A	$13.64	28,000	D
Common Stock								25,000	I	By Company A
Common Stock								25,000	I	By Company B

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
Stock Options	$13.64	11/04/2026		A		7,500(2)		11/04/2027	11/04/2036	Common Stock	7,500(2)	$13.64	7,500(2)	D

Explanation of Responses:

1. Shares of restricted stock vest at a rate of 20% per year commencing November 4, 2027.

2. Stock option vest at a rate of 20% per year commencing on November 4, 2027.

	/s/ Elda Heller, pursuant to power of attorney	11/06/2026
	** 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)