Fully gutted in 2026, this exceptional Winchester home offers the perfect blend of luxury, craftsmanship, and location. Featuring a brand-new roof, upgraded 400-amp electrical service, designer kitchen, beautifully renovated baths, and HVAC systems and all-new finishes throughout. First floor featuring wide open large living & dinning area with a family room. 2nd floor featuring (3) main bedroom with full baths suites. The stunning finished lower level includes a custom wine cellar and recreation area, and flexible rooms perfect for a home office, gym, media room, or guest accommodations.. Ideally located just minutes from Winchester's highly rated schools, town center, parks, dining, and commuter routes. Move-in ready and thoughtfully redesigned for modern living—this is a rare opportunity in one of Winchester's most sought-after neighborhoods.
View in the App
Save this property, schedule tours instantly, and get alerts when the price drops
| Year | Land | Building | Total | Change |
|---|---|---|---|---|
| FY2026 | $964,300 | $585,800 | $1,553,000 | — |
| Date | Price | Book/Page |
|---|---|---|
| Aug 21, 2025 | $1,330,000 | 84518/165 |
Permit history not yet available for this municipality.
Discrepancies found between MLS and assessor records.
| Field | Assessor | MLS | Match |
|---|---|---|---|
| Sqft | 4,729 | 3,881 | ✗ |
| Year built | 1,870 | 1,870 | ✓ |
14 Hillside Ave, Winchester MA 01890
Winchester, MA 01890
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 06/24/2026 | 🏠 Listed for Sale | $2,380,000 | - | - | Original listing |
| 08/21/2025 | 🏷️ Previously Sold | $1,330,000 | - | - | MLS #73362145 |
Finding comparable properties...
Your message will be sent to BMN Boston Real Estate.
