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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

Tax Information

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

School Information

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

Parking

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

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

Basic Information

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

Location

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

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

Property

  • Acreage0.3

Interior

  • Flooring Wood, Tile

Exterior

  • Exterior Features Deck - Wood
  • RoofShingle

Utilities

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

Property Information

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

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

Legal

  • ZoningRDB

Other

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

Map Location

Driving Directions

Listed by The Fenway Group of Compass

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