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Land with Home for Sale in Windsor, Massachusetts

255 High St Hill Rd, Windsor, MA 01270

$724,900
3.24 acres
Pending sale
Under contract

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.

3,744
Sq feet
5
Beds
3
Full baths
1
1/2 bath
1987
Built

Location

Street address
255 High St Hill Rd
Zip code
01270
Community
North Registry
Elevation
1,694 feet
Coordinates
42.4827, -73.0002

Directions

Route 9 to Old Route 9 to High Street Hill Road.

Property details

Acreage
3.24 acres
Zoning
Residential
MLS #
BCBOR 250133
Posted

Property taxes

2025
$5,263

Parcels

  • M 14 L 115

Details and features

Listing

Type
Residential
Franchise
RE/MAX International

Exterior

Parking
Off Street

Structure

Style
Contemporary
Basement
Concrete, Full
Water
Well
Sewer
Private Sewer
Heating
Hot Water
Materials
Wood, Wood Frame
Roof
Asphalt

Interior

Room Count
9
Rooms
Basement, Bathroom x 4, Bedroom x 5, Dining Room, Family Room, Laundry Room x 2
Flooring
Carpet, Laminate, Tile-Ceramic
Fireplaces
Yes
Appliances
Dryer, Range, Refrigerator, Washer
Features
Cedar Closet(s), Fireplace (s), Radon Mitigation System, Skylight(s)

Nearby schools

NameType
Berkshire TrailElementary
Nessacus RegionalMiddle
Wahconah RegionalHigh

Listing history

DateEventPriceChangeSource
Oct 13, 2026Under contract$724,900—BCBOR
Aug 20, 2026Price drop$724,900$25,000 -3.3%BCBOR
July 9, 2026New listing$749,900—BCBOR
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This 3.24-acre property is located at 255 High St Hill Rd in Windsor, MA 01270. The property is pending sale. It has a 3,744 square foot 5-bedroom, 3.5-bath house built in 1987.

Listed by RE/MAX Compass, (413) 568-0040

Checked 1 hour agoUpdated Source

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