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.
255 High St Hill Rd, Windsor MA 01270
Windsor, MA 01270
- 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
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.
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Listings updated Sep 16, 2026



