255 High St Hill Rd Windsor — Photo 1 of 34
Recent Drop: $25,000
$724,900
Investment Analysis — 255 High St Hill Rd
Windsor, MA 01270
Based on HUD Small Area Fair Market Rent for Amherst Town-Northampton, MA MSA, a 5-bedroom in 01270 carries an estimated $2,530/mo in gross rent — about a 2.46% cap rate and $17,811/yr in estimated NOI at the $724,900 list price. Adjust every assumption in the calculator below.
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.
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.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
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
Listing Agent: Reciprocal Reciprocal
Listing Office: Berkshire Reciprocal
MLS® Number: 73564933
