Winchester Bancorp grants Curtis 7,500 stock options

Both awards vest at 20% per year beginning November 4, 2027.

Available on EDGAR 11/06/2026 - 11:27 AM EST Accepted by SEC EDGAR 11/06/2026 - 11:26 AM EST Learn about SEC filing dates

Rhea-AI Filing Summary

Winchester Bancorp, Inc. director Geoffrey Adams Curtis received grant awards on November 4, 2026: 3,000 shares of restricted stock and options covering 7,500 common shares. The restricted-stock award was reported at $13.64 per share, and 8,000 common shares were held directly afterward; the options have a $13.64 exercise price.

Insider Trade Summary

Grant/Award: 10,500 shares

Grant/Award 2 txns

Insider Curtis Geoffrey Adams

Role Director

Type	Security	Shares	Price	Value
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 — 8,000 shares (Direct)

Holdings Before and After: Stock Options, 0 to 7,500 contracts (Direct); Common Stock, 5,000 to 8,000 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 Common shares underlying options: 7,500 shares Reported restricted-stock per-share amount: $13.64 per share +4 more

7 metrics

Restricted stock awarded 3,000 shares Grant dated November 4, 2026

Common shares underlying options 7,500 shares Stock-option grant dated November 4, 2026

Reported restricted-stock per-share amount $13.64 per share Restricted-stock grant dated November 4, 2026

Option exercise price $13.64 per share Stock-option grant dated November 4, 2026

Common shares held directly after restricted-stock award 8,000 shares After the November 4, 2026 award

Vesting rate 20% per year Both awards begin vesting November 4, 2027

Option expiration date November 4, 2036 Stock-option grant dated November 4, 2026

Key Terms

restricted stock, Stock option, vest at a rate of 20% per year

3 terms

restricted stock technical

"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 option technical

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

A stock option is a contract that gives you the right to buy or sell a company's stock at a specific price within a certain time frame. People use them to potentially make money if the stock's price moves favorably or to protect against losses. It's like holding a coupon that can be used to buy or sell stock at a set price later on.

vest at a rate of 20% per year technical

"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.

When do Geoffrey Adams Curtis's WSBK awards vest?

The restricted stock and stock options vest at 20% per year beginning November 4, 2027.

When do the WSBK options expire?

The options have an expiration date of November 4, 2036.

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

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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^*

Curtis Geoffrey Adams

(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	8,000	D

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)