Active
91 Days on market
255 High St Hill Rd Windsor — Photo 1 of 34

255 High St Hill Rd Windsor — Photo 1 of 34

Recent Drop: $25,000

$749,900
$724,900

$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 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.

Key facts

It was listed on July 6, 2026. The price has come down from an original $749,900 to $724,900, most recently on August 27, 2026. The annual property taxes are $5,263 (2025 tax year). It sits on a 3.24-acre (141,134 sq ft) lot.

Market Value Analysis

Not enough listings in Windsor for a city-only view.
This Property$194/sqft
Nearby Avg (5 mi)$311/sqft
38% BelowMarket Average

* Analysis is based on 1 actively listed and recently sold comparable properties within ~5 miles of this property.

Property Details

Financials

Original Price$749,900
Annual Taxes$5,263

Parking

Garage2
Off-Street8

Interior Specifications

Total Rooms9
Fireplaces2
FlooringWood, Tile, Carpet, Laminate
BasementFull, Concrete

Climate & Utilities

HeatingBaseboard, Oil
CoolingNone
WaterPrivate
SewerPrivate Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningR1

Property & Lot

Acres3.24
SqFt Lot141,134
Lot FeaturesGentle Sloping

Amenities & Appliances

Water Heater • Range • Refrigerator • Washer • Dryer

Geography

Property History

Price Drop
$724,900

Was $749,900

Aug 27, 2026

MLS® 73564933

Listed
$749,900

Jul 6, 2026

MLS® 73564933

Questions about this home

When was 255 High St Hill Rd, Windsor listed?

255 High St Hill Rd, Windsor was listed on July 6, 2026.

Has the price of 255 High St Hill Rd, Windsor changed?

The price has come down from an original $749,900 to $724,900, most recently on August 27, 2026.

What are the property taxes for 255 High St Hill Rd, Windsor?

The annual property taxes for 255 High St Hill Rd, Windsor are $5,263 (2025 tax year).

How big is the lot at 255 High St Hill Rd, Windsor?

255 High St Hill Rd, Windsor sits on a 3.24-acre (141,134 sq ft) lot.

What is the status of 255 High St Hill Rd, Windsor?

255 High St Hill Rd, Windsor is actively listed for sale.

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

146 housing units permitted in the last 12 months (+3% vs the prior 12 months) — 24 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jul '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 Provided By

Listing Agent: Reciprocal Reciprocal

Listing Office: Berkshire Reciprocal

MLS® Number: 73564933