255 High St Hill Rd Windsor — Photo 1 of 34
Recent Drop: $25,000
$724,900
255 High St Hill Rd, Windsor, MA 01270
Windsor, MA 01270
Beds
5
Baths
3.5
SqFt
3,744
Style
Single Family
Built
1987
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 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.
Market Value Analysis
* Analysis is based on 1 actively listed and recently sold comparable properties within ~5 miles of this property.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Water Heater • Range • Refrigerator • Washer • Dryer
Geography
Property History
$724,900
Was $749,900
Aug 27, 2026
MLS® 73564933
$749,900
Jul 6, 2026
MLS® 73564933
Population
1,036
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$116K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
3.9%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Berkshire County
144 housing units permitted in the last 12 months (+4% vs the prior 12 months) — 19 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 3,744 sq ft principal dwelling). Lot size: 141,134 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Listing Agent: Reciprocal Reciprocal
Listing Office: Berkshire Reciprocal
MLS® Number: 73564933
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