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Listing broker remarks

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.— Berkshire Reciprocal

Open Houses

Key details

  • 3,744 sq ft
  • 3.24 acres
  • 5 beds
  • 3.5 baths
  • 1987 built
  • $193 / sq ft
  • $5,263 2025 taxes
MLS #
7⁠3⁠5⁠6⁠4⁠9⁠3⁠3⁠
Last updated
Address
255 High St Hill Rd
Town
Windsor, MA
ZIP
01270

Map

Neighborhood: Windsor

Pin shown at town level

National Historic Landmark

Federally designated as nationally significant — the highest U.S. historic recognition. Section 106 review applies to federal undertakings affecting the property.

National Register

Listed on the National Register of Historic Places. Owners may qualify for the 20% federal Historic Rehabilitation Tax Credit on certified rehabilitation work.

State Register

Listed on the Massachusetts State Register of Historic Places.

Local Historic District

Inside a Local Historic District. Exterior changes visible from a public way require approval from the local historic district commission.

Local Landmark

Individually designated by the town as a local landmark. Exterior alterations require commission approval.

MACRIS Inventory

Documented in MACRIS, the state historic inventory. Informational only — no regulatory constraints.

Article 85 (Boston)

Subject to Boston Article 85 demolition-delay review, which can pause demolition of buildings 50+ years old for up to 90 days.

Ch. 91 Waterways License

An active MassDEP permit for a dock, pier, seawall, or other structure on or over a Massachusetts waterway. Many older licenses are not digitized; this record is provided for reference only.

Massachusetts Great Pond

A Great Pond under M.G.L. Ch. 91 — the Commonwealth retains public rights to fish and navigate these state-designated waters. Private docks and other waterfront structures require a Waterways License from MassDEP.

Likely Great Pond

The MLS listing describes this property as being on a Great Pond, which would be a state-designated water body under M.G.L. Ch. 91. GIS data did not independently confirm the pond name — verification needed.