1. Massachusetts
2. Winchester
3. 155 Highland Ave

155 Highland Ave, Winchester, MA 01890

• 5 beds |
• 3 baths |
• 1,965 sqft

Property Description

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.

Listing Status:

Active

Date Added:

August 11, 2025 at 05:00AM

Listing Office:

Advisors Living - Winchester : 978-423-5235

Listing Agent:

Pirani & Wile Group : 781-608-1805

MLS ID:

73416499

Interior

• General: OfficeMud RoomEntry Hall
• Appliances: Gas Water HeaterRangeDishwasherDisposalRefrigeratorWasherDryer
• Laundry: In Basement
• Basement: Partially FinishedWalk-Out Access
• Flooring: HardwoodLaminateFlooring - Stone/Ceramic TileFlooring - Hardwood
• A/C: Central AirWindow Unit(s)
• Heating: Forced AirNatural Gas
• Fireplace: Living RoomFireplaceFireplaces: 1
• Disability Feature: None

Exterior

Construction

Location

Lot

Utilities

Financial

This listing courtesy of Pirani & Wile Group, Advisors Living - Winchester