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255 High St Hill Rd

Windsor, MA 01270

$749,900 PRICE
5 Beds
3/1 Baths
3,744 Sqft
3.24 Acres
1987 Built

Tucked away on 3.24 private wooded acres, this one-of-a-kind Contemporary offers 3,744 sq. ft. of living space across three finished levels. Soaring ceilings, exposed timber beams, hardwood floors, and a dramatic center chimney create a warm yet impressive setting. The open floor plan is anchored by multiple wood-burning fireplaces, a pellet stove, and abundant natural light. Offering a total of five bedrooms and 3.5 baths, including a private in-law suite above the oversized attached two-car garage, this home provides exceptional flexibility for guests or extended living. Enjoy an owned 9.52 kW solar system, spacious decks, beautifully maintained grounds, and the privacy of a true Berkshire retreat just a short drive from everything the Berkshires and Northampton have to offer.

Additional Information

LOT DETAILS

HAS VIEW: Yes
LOT DESCRIPTION: Landscaped
WATER: Private, Well

EXTERIOR FEATURES

EXTERIOR FEATURES: Accessible Bedroom, Accessible Full Bath, Deck

INTERIOR FEATURES

APPLIANCES INCLUDED: Dryer, Range, Refrigerator, Washer
BEDS: 5
FLOORING: Carpet, Ceramic Tile, Laminate, Wood
FULL BATHS: 3
HEAT: Oil, Hot Water
ROOMS: 9

ADDITIONAL INFORMATION

BASEMENT DESCRIPTION: Concrete, Full
DAYS ON MARKET: 20
ELECTRICAL FEATURES: Circuit Breakers
ELEMENTARY SCHOOL: Berkshire Trail
HIGH SCHOOL: Wahconah Regional
LIVING AREA SQFT: 3744
MIDDLE SCHOOL: Nessacus Regional
ON MARKET DATE: 2026-07-08
PARKING: Off Street, Attached
SEWER: Private Sewer
STYLE: Salt Box, Contemporary
TAX YEAR: 2025
VIEW: Mountain(s)
YEAR BUILT: 1987
ZONING: Residential

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Location for 255 High St Hill Rd, Windsor, MA

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Schools for 255 High St Hill Rd, Windsor, MA

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Community

Windsor

Berkshire County, Massachusetts

The Berkshire County town of Windsor, which is home to about 830 residents throughout its 35.2 square miles, is located at the juncture of routes 9 and 88. The town, originally known as Gageborough in...

Market Stats for Windsor, Massachusetts

An exclusive report that informs you of residential real estate sales activity and trends in Windsor, Massachusetts.

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Great Barrington Brokerage
306 Main Street
Great Barrington, MA 01230
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Yes, I would like more information from Sotheby's International Realty. Please use and/or share my information with a Sotheby's International Realty agent to contact me about my real estate needs.