155 Highland Ave, Winchester MA 01890
About this home
Charming turn-of-the-century 5-bedroom Gambrel-style home in move-in condition, blending classic character with modern updates. This spacious residence features a beautifully updated interior with central air, a stunning primary suite with private bath, custom closet system, and generous living spaces throughout. The detached 2-car garage adds convenience, while the location offers unbeatable lifestyle perks—just a short stroll to the 2,600-acre Middlesex Fells Reservation. Enjoy easy access to Winchester Center’s shops, restaurants, top-rated schools, and public transportation, including the commuter rail to Boston. Quick access to Rt. 93 puts downtown Boston just minutes away. Basement features small home office with direct access to Beacon Hill style back yard.
Sale Statistics
This property sold for 12.8% above the original asking price, indicating strong buyer demand.
With only 7 days on market, this was a quick sale compared to typical market conditions.
Facts & Features
Property Overview
Interior Features
Exterior & Structure
Lot & Land
Parking & Garage
Utilities & Systems
Community & HOA
Financial & Tax Information
Additional Details
Location
Neighborhood
155 Highland Ave, Winchester MA 01890
Winchester, MA 01890
Walkability
Schools
Monthly Payment Calculator
Payment Breakdown
Property History
Market Insights
Property Timeline
Sold
Sep 2, 2025Listed for Sale
Aug 11, 2025| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 09/02/2025 | ✓ Sold | $1,510,000 | - | - | Property sold |
| 08/11/2025 | 🏠 Listed for Sale | $1,339,000 | - | - | Original listing |