For sale

$749,900

255 High Street Hill Rd, Windsor, MA 01270

5beds

3,744sqft

$4,802/mo

Get pre-qualified

Single Family Residence

Built in 1987

3.24 Acres Lot

$729,400 Zestimate^®

$200/sqft

$-- HOA

What's special

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 a 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.

35 days

574

27

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 5
Bathrooms: 4
Full bathrooms: 3
1/2 bathrooms: 1

Primary bedroom

Level: Second

Bedroom

Description: In-Law Suite
Level: Second

Bedroom 2

Level: Second

Bedroom 3

Level: Second

Bedroom 4

Description: In-Law Suite
Level: First

Primary bathroom

Level: Second

Half bathroom

Description: With Laundry
Level: First

Full bathroom

Level: Second

Full bathroom

Description: In-Law Suite
Level: First

Dining room

Level: First

Family room

Level: First

Foyer

Level: First

Great room

Level: Third

Kitchen

Level: First

Kitchen

Description: In-Law Suite
Level: First

Living room

Level: First

Living room

Description: In-Law Suite
Level: First

Heating

Oil, Hot Water, Fireplace(s)

Appliances

Included: Dryer, Range, Refrigerator, Washer

Features

Interior Balcony, Radon Mitigation System
Flooring: Carpet, Ceramic Tile, Laminate, Wood
Windows: Skylight(s)
Basement: Radon Remed Sys,Garage Access,Full,Concrete
Has fireplace: Yes

Interior area

Total structure area: 3,744
Total interior livable area: 3,744 sqft

Property

Parking

Total spaces: 2
Parking features: Garaged & Off-Street
Attached garage spaces: 2
Details: Garaged & Off-Street

Accessibility

Accessibility features: Accessible Bedroom, Accessible Full Bath

Features

Patio & porch: Deck
Exterior features: Privacy, Landscaped
Has view: Yes
View description: Hill/Mountain

Lot

Size: 3.24 Acres
Dimensions: 228x697

Details

Parcel number: M 14 L 115
Zoning description: Residential

Construction

Type & style

Home type: SingleFamily
Architectural style: Salt Box,Contemporary
Property subtype: Single Family Residence

Materials

Roof: Asphalt Shingles

Condition

Year built: 1987

Utilities & green energy

Electric: 200 Amp, Circuit Breakers
Sewer: Private Sewer
Water: Well
Utilities for property: Fiber Optic Availabl

Green energy

Energy generation: Solar, Solar Panels Owned

Community & HOA

Location

Region: Windsor

Financial & listing details

Price per square foot: $200/sqft
Tax assessed value: $464,100
Annual tax amount: $5,263
Date on market: 7/8/2026

Estimated market value

$729,400

$693,000 - $766,000

$3,339/mo

Price history

Date	Event	Price
7/8/2026	Listed for sale	$749,900+226%$200/sqft
Source: BCMLS #250133 Report a problem
10/15/1999	Sold	$230,000$61/sqft
Source: Public Record Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$5,263 +2.4%	$464,100 +4.2%
2024	$5,138 +4.1%	$445,200 +18.3%
2023	$4,935 -0.1%	$376,400 +0.2%
2022	$4,940 +2.4%	$375,700 +1.6%
2021	$4,826 +2.3%	$369,800 +10.4%
2020	$4,718 +0%	$335,100 -5.4%
2019	$4,717 -18.2%	$354,400 -17.2%
2018	$5,764 +9.6%	$428,200 +10.6%
2017	$5,258 +0.1%	$387,200 -1.3%
2016	$5,254 -3.3%	$392,400 -3.8%
2015	$5,432 +0.5%	$408,100 -0.7%
2014	$5,406 +0.5%	$410,800 -3.9%
2013	$5,381 +3.2%	$427,400 -4.7%
2012	$5,214 -2.9%	$448,700 +7.8%
2011	$5,368 +4.4%	$416,100 -10%
2010	$5,141 -0.3%	$462,300 -6.4%
2009	$5,156 +14.5%	$493,900 +17.1%
2008	$4,504 -2.5%	$421,700 +17.8%
2007	$4,618 +3.6%	$358,000 +2.8%
2006	$4,456 +9.2%	$348,100 +22.7%
2005	$4,081 +7.2%	$283,800
2004	$3,806 +2.4%	$283,800
2003	$3,718 +8.6%	$283,800 +8.7%
2002	$3,424	$261,000