$1,339,000
155 Highland Ave
Winchester, MA, 01890
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.
Property Details
Price:
$1,339,000
MLS #:
73416499
Status:
Pending
Beds:
5
Baths:
2.5
Address:
155 Highland Ave
Type:
Single Family
Subtype:
Single Family Residence
City:
Winchester
Listed Date:
Aug 11, 2025
State:
MA
Finished Sq Ft:
1,965
Total Sq Ft:
1,965
ZIP:
01890
Lot Size:
5,001 sqft / 0.11 acres (approx)
Year Built:
1900
Schools
Elementary School:
Muraco
Middle School:
Mccall
High School:
Whs
Interior
Appliances
Gas Water Heater, Range, Dishwasher, Disposal, Refrigerator, Washer, Dryer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Window Unit(s)
Fireplaces Total
1
Flooring
Hardwood, Laminate, Flooring – Stone/ Ceramic Tile, Flooring – Hardwood
Heating
Forced Air, Natural Gas
Laundry Features
In Basement
Exterior
Architectural Style
Colonial
Community Features
Public Transportation, Shopping, Tennis Court(s), Park, Walk/ Jog Trails, Medical Facility, Highway Access, Public School, T- Station
Construction Materials
Frame
Exterior Features
Porch, Patio, Sprinkler System
Parking Features
Detached, Paved Drive
Parking Spots
2
Roof
Shingle
Financial
Tax Year
2025
Taxes
$14,404
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Courtesy of Leading Edge Real Estate. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
155 Highland Ave
Winchester, MA
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