• $1,300,000List Price
  • 3Bedrooms
  • 2Bathrooms
  • 0.3Acreage
  • 1933Year Built
  • 2,006Square Feet

Nestled at the end of a coveted cul-de-sac, 3 Chesterford Terrace presents a rare opportunity to own a timeless Winchester home on a picture-perfect 12,972 SQ FT flat lot. Designed by renowned Winchester architect Jerome Bailey Foster, this charming 3+ bed, 1.5-bath residence blends classic architectural character with an exceptional setting. Surrounded by mature landscaping & set on one of Winchester's most desirable streets, the home offers endless potential for today's buyer. Enjoy the convenience of being a short stroll to Lynch Elementary School & moments from Winchester's scenic Three Ponds area, where walking trails & outdoor recreation await. Whether you're looking to restore & enhance an architectural gem or create your dream home in an unbeatable location, this property offers a truly special combination of history, charm, & opportunity. Rarely does a home with such pedigree, setting, & potential become available in Winchester. Estate Sale. Sold in as-is condition.

More Info

Basic Information

  • Bedrooms3
  • Mls StatusNew
  • Bathroom2
  • Lot Features Wooded
  • Parcel Number M:019 B:0153 L:0,899819

Basic Information

  • List Price$1,300,000
  • MLS Number73545054
  • Modification Date07/06/2026
  • Property SubTypeSingle Family Residence
  • Virtual TourView Tour

Building

  • BasementFull, Partially Finished, Bulkhead
  • Building Area Units Square Feet
  • FireplaceYes
  • Fireplaces Total 2
  • FoundationConcrete Perimeter, Irregular
  • Garage Spaces1
  • Patio And Porch Features Deck - Wood
  • Property StyleCape
  • Rooms6
  • Year Built1933
  • Year Built Details Actual
  • Year Built Source Public Records

Other

  • Date Listed07/06/2026
  • Farm Land Area Units Square Feet

Tax Information

  • Tax Assessed Value $1,469,000
  • Tax Year 2026
  • Taxes$16,176

Parking

  • Parking Spaces2
  • Covered Spaces 1
  • Garage YN Yes
  • Open Parking YN Yes
  • Parking Features Paved Drive

Location

  • Address3 Chesterford Terrace
  • Building Number3
  • CountyMiddlesex
  • StateMA
  • StreetChesterford Terrace
  • TownWinchester
  • Zip01890

Interior

  • Flooring Wood, Tile

Utilities

  • Cooling Window Unit(s)
  • Cooling YN Yes
  • Heat SystemYes
  • Heating Steam, Natural Gas
  • Sewer Public Sewer
  • Water Source Public

Amenities

  • Amenities
    • Bike Path
    • Conservation Area
    • Golf
    • Highway Access
    • House of Worship
    • Park
    • Private School
    • Public School
    • Public Transportation
    • Shopping
    • Walk/Jog Trails
  • Appliances IncludedGas Water Heater, Range, Dishwasher, Disposal, Refrigerator, Washer, Dryer

School Information

  • High School Winchester High School
  • Elementary SchoolLynch Elementry
  • Junior HighMccall Middle

Rooms

  • Bathroom 1 First
  • Bathroom 2 Second
  • Bathrooms Total Decimal 1.5
  • Bedroom 2 Second
  • Bedroom 3 Second
  • Dining Room First
  • Full Bath1
  • Half Baths1
  • Kitchen First
  • Living Room First
  • Master Bedroom Second

Property

  • Acreage0.3

Exterior

  • Exterior Features Deck - Wood
  • RoofShingle

Property Information

  • Square Feet2,006
  • Building Area Source Public Records
  • Living Area 2,006
  • Lot Size Square Feet 12,972
  • Lot Size Units Acres

Map Location

Driving Directions

Listed by The Fenway Group of Compass

Winchester, MA Demographics

There is no data available

Winchester, MA Real Estate Market Data

There is no data available

Winchester, MA Schools

School NameDistanceTypeGrades

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. The property listing data and information, and the Images, 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. MLSPIN and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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