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Tucked away on 3.24 wooded acres, this one-of-a-kind Contemporary offers 3,744 sq. ft. of living space across multiple finished levels. The main home features four bedrooms, 2.5 baths, spacious living, family and dining rooms, plus a third-floor great room and additional flex space. A separate in-law suite adds exceptional versatility with its own kitchen, living room, bedroom, full bath, deck and upper-level flex room-ideal for extended living, guests or a variety of household needs. Soaring ceilings, exposed timber beams, hardwood floors and a dramatic center chimney add character throughout, complemented by multiple wood-burning fireplaces, a pellet stove and abundant natural light. Additional highlights include an owned 9.52 kW solar system, oversized attached garage, spacious decks and generous parking, all within a short drive of Berkshire attractions and Northampton.

More Info

Basic Information

  • Bedrooms5
  • Mls StatusActive
  • Bathroom4
  • Lot Features Gentle Sloping

Basic Information

  • List Price$724,900
  • MLS Number73564933
  • Modification Date09/16/2026
  • Property SubTypeSingle Family Residence

Property

  • Acreage3.24
  • Frontage Length 228

Exterior

  • Exterior Features Deck
  • RoofShingle

Property Information

  • Square Feet3,744
  • Building Area Source Public Records
  • Living Area 3,744
  • Lot Size Square Feet 141,134
  • Lot Size Units Acres

Tax Information

  • Tax Year 2025
  • Taxes$5,263

Rooms

  • Bathrooms Total Decimal 3.5
  • Full Bath3
  • Half Baths1

Building

  • Attached Garage YN Yes
  • BasementFull, Concrete
  • Building Area Units Square Feet
  • Construction Materials Frame
  • FireplaceYes
  • Fireplaces Total 2
  • FoundationConcrete Perimeter
  • Garage Spaces2
  • Patio And Porch Features Deck
  • Property StyleContemporary, Saltbox
  • Rooms9
  • Window Features Insulated Windows
  • Year Built1987
  • Year Built Details Actual
  • Year Built Source Public Records

Other

  • Date Listed08/18/2026
  • Farm Land Area Units Square Feet
  • View Count1

Parking

  • Parking Spaces8
  • Covered Spaces 2
  • Garage YN Yes
  • Parking Features Under, Garage Door Opener, Off Street

Location

  • Address255 High St Hill Road
  • Building Number255
  • CountyBerkshire
  • StateMA
  • StreetHigh St Hill Road
  • TownWindsor
  • Zip01270

Interior

  • Flooring Wood, Tile, Carpet, Laminate
  • Interior Features High Speed Internet

Utilities

  • Electric 200+ Amp Service
  • Heat SystemYes
  • Heating Baseboard, Oil
  • Sewer Private Sewer
  • Water Source Private

Amenities

  • Appliances IncludedWater Heater, Range, Refrigerator, Washer, Dryer
  • Green Energy Generation Solar

Map Location

Listed by Reciprocal Reciprocal of Berkshire Reciprocal

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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