Welcome to Winning Farm of Winchester —an award-winning 55+ community and one of Winchester’s most sought-after addresses for effortless, elevated living. This meticulously maintained and lightly lived-in 3-bedroom, 2.5-bath townhome offers 2,306 sq ft of thoughtfully designed living, showcasing fine craftsmanship & timeless finishes throughout. Sun-drenched interiors highlight gorgeous hardwood floors, soaring ceilings, & an open-concept first floor ideal for both everyday living & entertaining. The main-level primary suite provides convenience & privacy, creating a seamless single-level living option, while additional bedrooms and flexible spaces upstairs offer room for guests, a home office, or hobbies. The home’s inviting layout is complemented by abundant natural light and a warm, welcoming feel in every room. Set within a beautifully maintained community known for its charm and lifestyle, residents enjoy a peaceful setting with close proximity to shops, dining, and major routes.
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| Year | Land | Building | Total | Change |
|---|---|---|---|---|
| FY2026 | $0 | $1,735,100 | $1,735,100 | — |
| Date | Price | Book/Page |
|---|---|---|
| Jul 1, 2024 | $2,125,000 | 82957/220 |
| May 30, 2024 | $1,670,000 | 82826/356 |
| Oct 2, 2023 | $2,150,000 | 82054/482 |
| May 19, 2023 | $1,950,000 | 81552/554 |
| Apr 13, 2023 | $1,799,000 | 81421/289 |
| Sep 29, 2022 | $1,754,200 | 80773/260 |
| Jul 21, 2022 | $1,625,000 | 80465/448 |
| Apr 8, 2022 | $1,475,000 | 79949/102 |
| Sep 16, 2021 | $1,732,500 | 78709/533 |
| Aug 31, 2021 | $1,590,000 | 78597/442 |
Permit history not yet available for this municipality.
Discrepancies found between MLS and assessor records.
| Field | Assessor | MLS | Match |
|---|---|---|---|
| Sqft | 4,460 | 2,306 | ✗ |
| Year built | 2,019 | 2,019 | ✓ |
2 Gershon Way # 2, Winchester MA 01890
Winchester, MA 01890
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 04/19/2026 | 📋 Status: Active under contract | - | - | - | Active → Active Under Contract |
| 04/14/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 04/07/2026 | 🏠 Listed for Sale | $1,899,000 | - | - | Original listing |
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