For sale

Street View

$749,900

255 High Street Hill Rd, Windsor, MA 01270

5beds

3,744sqft

$4,751/mo

Get pre-qualified

Single Family Residence

Built in 1987

3.24 Acres Lot

$722,100 Zestimate^®

$200/sqft

$-- HOA

What's special

Multiple wood-burning fireplacesPellet stoveDramatic center chimneyExposed timber beamsHardwood floorsBeautifully maintained groundsOpen floor plan

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.

41 days

512

30

Facts & features

Interior

Bedrooms & bathrooms

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

Heating

Baseboard, Oil

Cooling

None

Appliances

Included: Water Heater, Range, Refrigerator, Washer, Dryer

Features

High Speed Internet
Flooring: Wood, Tile, Carpet, Laminate
Windows: Insulated Windows
Basement: Full,Concrete
Number of fireplaces: 2

Interior area

Total structure area: 3,744
Total interior livable area: 3,744 sqft
Finished area above ground: 3,744

Property

Parking

Total spaces: 8
Parking features: Under, Garage Door Opener, Off Street
Attached garage spaces: 2
Uncovered spaces: 6

Features

Patio & porch: Deck
Exterior features: Deck
Frontage length: 228.00

Lot

Size: 3.24 Acres
Features: Gentle Sloping

Details

Parcel number: WINDM0140B0000L01150
Zoning: R1

Construction

Type & style

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

Materials

Frame
Foundation: Concrete Perimeter
Roof: Shingle

Condition

Year built: 1987

Utilities & green energy

Electric: 200+ Amp Service
Sewer: Private Sewer
Water: Private

Green energy

Energy generation: Solar

Community & HOA

HOA

Has HOA: No

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: 7/6/2026

Estimated market value

$722,100

$686,000 - $758,000

$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