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Two-family homes in Winchester are limited, which is exactly why opportunities like this get attention quickly. Whether you are looking for an owner-occupied property with rental income or a solid long-term investment, this one checks the boxes. The larger unit spans the second and third floors, offering three bedrooms, two full baths, and living space that feels more like a single-family home. The first-floor unit includes two bedrooms and one full bath, making it ideal for rental income, extended family, or multi-generational living. Each unit has its own garage space, something tenants and owners always appreciate, plus a long driveway with plenty of additional parking. The layout offers separation, functionality, and strong future potential. Location matters, and this property comes with access to the highly desirable Winchester Public Schools, adding even more long-term value. Investment properties in Winchester do not come along often, especially ones with this much upside.

More Info

Basic Information

  • Gross Income $72,000
  • Mls StatusActive
  • Parcel Number 897528

Basic Information

  • List Price$1,150,000
  • MLS Number73515601
  • Modification Date05/13/2026
  • Property SubType2 Family - 2 Units Up/Down

Property

  • Acreage0.12

Interior

  • Interior Features Living Room, Kitchen, Mudroom, Office/Den, Dining Room

Property Information

  • Building Area Source Public Records
  • Living Area 2,186
  • Lot Size Square Feet 5,118
  • Lot Size Units Acres
  • Square Feet2,186

Other

  • Date Listed05/09/2026
  • Farm Land Area Units Square Feet
  • View Count3

Tax Information

  • Tax Assessed Value $1,025,600
  • Tax Year 2025
  • Taxes$11,374

Rooms

  • Bathroom3
  • Bathrooms Total Decimal 3
  • Bedrooms5
  • Full Bath3

Building

  • BasementUnfinished
  • Building Area Units Square Feet
  • FoundationStone
  • Garage Spaces1
  • Levels 3
  • Rooms10
  • Stories3
  • Units2
  • Year Built1880
  • Year Built Details Approximate
  • Year Built Source Public Records

Parking

  • Covered Spaces 1
  • Garage YN Yes
  • Open Parking YN Yes
  • Parking Features Paved Drive
  • Parking Spaces9

Location

  • Address63-65 Harvard Street
  • Building Number63-65
  • CountyMiddlesex
  • StateMA
  • StreetHarvard Street
  • TownWinchester
  • Zip01890

Utilities

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

Amenities

  • Other AmenitiesBasement

Map Location

Listed by Beth Sager Group of Keller Williams Realty Boston Northwest

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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