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For Sale

255 High St Hill Rd, Windsor MA 01270

Windsor, MA 01270

$725K
5 BD · 4 BA · 3,744 sf · 3.24 ac · Built 1987
The residence

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.

At a glance
Property type
Single Family Residence
Status
Active
Year built
1987
Lot size
3.24 acres
Living area
3,744 sf
MLS#
c8f8f63fa2c4d56682f4ea0efbaeae3b
Beds · Baths
5 · 4
Location

Windsor, MA.

Windsor, Massachusetts, is a market our advisors follow closely — its streets, housing stock and setting each shape what a residence here is worth and how it lives day to day. We are glad to walk you through the locale in detail, and how this particular address sits within it.

Estimated Monthly Payment+
$4K/mo
Approximate · principal & interest only
Display Currency
$725K

Indicative conversion — settlement always in USD.

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Listing courtesy of Berkshire Reciprocal · MLSPIN

MLS Property Information Network.The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information 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. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.

Listings updated Sep 16, 2026

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