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Winchester Bancorp is like a **Bank of America**, but focused on specific local communities in Massachusetts.

Think of it as a **Wells Fargo** that primarily serves a smaller, concentrated community rather than a national footprint.

It's a community bank, operating similarly to the retail arm of a **JPMorgan Chase**, but without the national scale or extensive corporate operations.

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• Deposit Services: These include various checking, savings, money market, and certificate of deposit accounts for individuals and businesses to store and manage their funds.
• Residential Mortgage Loans: The bank provides financing to individuals for the purchase, construction, or refinancing of owner-occupied residential properties.
• Commercial Real Estate Loans: Lending services are offered to businesses for the acquisition, development, and refinancing of commercial and multi-family real estate properties.
• Commercial & Industrial Loans: These loans provide capital to businesses for a range of purposes including working capital, equipment financing, and other operational needs.
• Consumer Loans: This category encompasses personal loans, home equity loans, and lines of credit offered to individuals for various personal financial needs.

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Winchester Bancorp (WSBK), through its subsidiary Winchester Savings Bank, operates as a community bank primarily serving individuals and businesses within its local market. Therefore, its major customers fall into the following categories:

• Individual Customers (Retail Banking): This category includes households and consumers who utilize personal checking and savings accounts, certificates of deposit, residential mortgage loans, home equity loans, and various other consumer loans.

• Small to Medium-sized Business Customers (Commercial Banking): This category encompasses local businesses, including small commercial enterprises, professional practices, and real estate investors, which rely on the bank for commercial real estate loans, business lines of credit, term loans, business deposit accounts, and cash management services.

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RSM US LLP

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John A. Carroll President and Chief Executive Officer

Mr. Carroll joined Winchester Savings Bank in January 2022. Before that, he was employed by East Boston Savings Bank from 2012 to December 2021, where he served as Executive Vice President and Chief Operating Officer. East Boston Savings Bank was sold to Rockland Trust Company in 2021. Mr. Carroll has over 20 years of experience in the banking industry.

Elda Heller Executive Vice President, Chief Financial Officer and Treasurer

Ms. Heller has held this position since April 2022. She joined Winchester Savings Bank in 2014. Prior to that, she spent a decade in the credit union industry, holding roles of increasing responsibility, including Vice President of Finance at Metro Credit Union.

Paul V. Cheremka Senior Vice President and Senior Lender

Mr. Cheremka joined Winchester Savings Bank in July 2022. He previously served as a Vice President and Commercial Lender at North Shore Bank, Reading Cooperative Bank, East Boston Savings Bank, and Bank of New England.

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The key risks to Winchester Bancorp's (WSBK) business operations are primarily concentrated in its lending practices, exposure to interest rate fluctuations, and operational vulnerabilities.

1. Credit Risk and Real Estate Loan Concentration: Winchester Bancorp's business model heavily emphasizes real estate loans, which exposes it to significant credit risk. A decline in real estate values, particularly in its primary operating area of eastern Massachusetts where it focuses on residential and commercial real estate lending, could impair the value of the collateral securing these loans and adversely affect the company's financial condition. The company reported a substantial increase in its provision for credit losses and net charge-offs in 2025 compared to 2024, indicating potential asset quality concerns.
2. Interest Rate Risk: Changes in market interest rates pose a significant risk to Winchester Bancorp's operating results and asset values. Rising interest rates can increase the cost of funds for the bank and negatively impact the ability of borrowers to repay their loans. While the company utilizes simulation models to monitor interest rate risk, a substantial and unexpected shift in market rates could still have a material adverse effect on its financial condition and results of operations.
3. Operational and Cybersecurity Risks: Winchester Bancorp relies on technology and third-party vendors for its operations. This reliance exposes the company to operational disruptions and cybersecurity threats, which could have adverse effects on its financial condition and results of operations.

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The clearest emerging threat for Winchester Bancorp, like many traditional regional banks, is the rapid rise and adoption of Fintech companies and digital-only banks (neobanks). These entities leverage technology to offer streamlined, often lower-cost, and highly convenient banking services (e.g., mobile-first accounts, rapid loan approvals, user-friendly budgeting tools). They threaten WSBK's traditional business model by:

• Attracting younger demographics who prefer digital interactions and are less tied to physical branches.
• Eroding deposit bases through competitive interest rates or fee structures.
• Challenging lending markets for mortgages, personal loans, and small business loans by offering faster approval processes and more tailored products.
• Increasing pressure on traditional banks to continually invest in their digital platforms and user experience to remain competitive.

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1. Continued Loan Growth in Key Segments: Winchester Bancorp anticipates sustained growth in its loan portfolio, particularly in construction and commercial real estate. Net loans increased by 5.6% or $42.0 million in the quarter ended September 30, 2025, primarily driven by these categories, along with multi-family and residential real estate loans. The year ended June 30, 2025, also saw a 10.2% increase in net loans, with multi-family, residential real estate, and commercial real estate as main contributors.
2. Expansion of Deposit Base through Municipal Deposits: The company has launched a new deposit channel specifically targeting municipal deposits, which is expected to continue contributing to strong deposit growth. This strategy has already yielded results, with municipal customer deposits increasing by $38.9 million in the quarter ended September 30, 2025. Overall deposits grew by 5.5% in the same quarter.
3. Net Interest Margin Expansion: Growth in net interest income is expected to be driven by an expanding net interest margin. The company has seen its net interest margin increase due to higher yields on investment securities and a decrease in average rates on interest-bearing deposit accounts. The net interest margin expanded by nine basis points for the quarter ended September 30, 2025, and 65 basis points compared to the same quarter last year.
4. Prudent Growth of Customer Base and Market Share Acquisition: Management has expressed a clear intention to "continue to gain market share as we prudently grow our customer base." This strategic focus on expanding its customer base within its existing markets in southeastern New Hampshire and portions of north-central Massachusetts is a key driver for future revenue.

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Share Repurchases

• In the year ended June 30, 2025, Winchester Bancorp used $3.3 million for the purchase of 334,633 shares of common stock by its Employee Stock Ownership Plan ("ESOP") in connection with the initial public offering.
• The company's S-1 IPO registration in 2024 indicated that a portion of the net proceeds from the offering might be used to repurchase shares of common stock in the future.

Share Issuance

• Winchester Bancorp, Inc. completed its initial public offering (IPO) on April 30, 2025, selling 3,997,012 shares of common stock at $10.00 per share, raising gross proceeds of $39,970,120.
• As part of the reorganization and IPO, the company issued 5,112,457 shares of common stock to Winchester Bancorp, MHC, and 185,907 shares to the Winchester Savings Bank Charitable Foundation, Inc.
• Net proceeds from the stock offering contributed $37.8 million to shareholders' equity for the year ended June 30, 2025.

Inbound Investments

• The company's initial public offering in April 2025 resulted in $39.97 million in gross proceeds from the sale of common stock to public investors.

Outbound Investments

• Winchester Bancorp, Inc. stated in its S-1 IPO registration that it may use a portion of the net proceeds from the offering to finance the possible acquisition of other financial institutions or other financial services businesses.

Capital Expenditures

• In 2024, Winchester Savings Bank celebrated the grand opening of its fifth branch office in Danvers.
• The company intends to continue seeking opportunities to expand its branch network in communities that could benefit from its services.