For sale

$724,900

Est. $4,339/mo —

•

3,744

sq ft

255 High St Hill Rd, Windsor, MA 01270

About this home

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.

Single-familyProperty Type

1987Year Built

3.24 acresLot Size

$194Price/Sq.Ft.

2 garage spacesParking

Listed by Reciprocal Reciprocal • Berkshire Reciprocal

Listed by • Berkshire Reciprocal

Listing updated: Sep 3, 2026 at 01:49pm

Redfin checked: 2 minutes ago

•Source:MLS PIN #73564933

Payment calculator

$4,339 per month

Principal and interest$3,810

Property taxes

$439

HOA dues

Home insurance

$91

Utilities

Add

5 minutes to get started. No credit impact.

Discover your buying power

Find out if this home is within budget

Down payment assistance

View down payment assistance programs for this home

See this home in person

We'll connect you with a local agent to show you this home, answer your questions, and assist you on your buying journey.

Next available tour time: Today

Open houses

No upcoming open houses.

Nearby open houses (6)

OPEN SAT, 10AM TO 11AM
$269,900
3 beds1 bath1,593 sq ft
14 Stockbridge Ave, Dalton, MA 01226
OPEN SAT, 10AM TO 12PM
$339,000
6 beds2.5 baths2,523 sq ft
32 First St, Adams, MA 01220
OPEN SAT, 10AM TO 12PM
$339,900
4 beds1.5 baths1,488 sq ft
1981 East St, Pittsfield, MA 01201
OPEN SAT, 11AM TO 1PM
$315,000
3 beds1 bath1,152 sq ft
62 Greenridge Dr, Dalton, MA 01226
OPEN SAT, 12:30PM TO 2:30PM3D WALKTHROUGH
$399,000
2 beds2 baths1,442 sq ft
35 South Rd Ext, Peru, MA 01235
OPEN SUN, 10AM TO 11:30AM
$240,000
3 beds2 baths1,392 sq ft
53 Off South St, Hinsdale, MA 01235

Around this home

Schools

K - 12
Preschool & daycare

Craneville Elementary School

Public K-5 • Assigned • 9.1mi

7/10

Nessacus Regional Middle School

Public 6-8 • Assigned • 7.2mi

7/10

Wahconah Regional High School

Public 9-12 • Assigned • 7.2mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Offer insights

255 High St Hill Rd · $724,900

Strong offer

$725K and above

75% chance or better to win

Why $725K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 42 days.

SALE-TO-LIST

Most homes are selling 2% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
High speed internet
Insulated windows
Total of 9 rooms
Full concrete basement

Bathrooms
3 full bathrooms
1 half bathroom

Kitchen
Range
Refrigerator
Water heater

Laundry & utility
Washer
Dryer

Flooring
Wood
Tile
Carpet
Laminate

Heating & cooling
Oil baseboard heating

Sale and tax history for 255 High St Hill Rd

Sale History
Tax History

Date

Event

Price

BCMLS #250133

Aug 19, 2026

Price Changed

$724,900

$194/sq ft

Jul 6, 2026

Listed

$749,900

$200/sq ft

+29

Public Remarks

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.

MLS PIN #73564933

Aug 27, 2026

Price Changed

$724,900

$194/sq ft

Jul 6, 2026

Listed

$749,900

$200/sq ft

BCMLS #145314

Oct 15, 1999

Sold

$230,000

$61/sq ft

Jan 26, 1999

Listed

$271,000

$72/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$4,935 (−0.1%)

$36,200 + $340,200

$376,400

2022

$4,940 (+2.4%)

$35,500 + $340,200

$375,700

2021

$4,826 (+2.3%)

$35,500 + $334,300

$369,800

2020

$4,718

$34,300 + $300,800

$335,100

2019

$4,717 (−18.2%)

$34,300 + $320,100

$354,400

2018

$5,764 (+9.6%)

$35,600 + $392,600

$428,200

2017

$5,258

$38,200 + $349,000

$387,200

2016

$5,254 (−2.8%)

$43,400 + $349,000

$392,400

2014

$5,406

$53,900 + $356,900

$410,800

Public record

Beds

Baths

3.5

Stories

Lot width

—

Lot depth

—

Lot size

3.24 Acres

Year renovated

—

Finished Sq. Ft.

3,744

Unfinished Sq. Ft.

—

Total Sq. Ft.

3,744

Year built

1987

Style

Multi-Family (2-4 Unit)

County

Berkshire County

APN

3870147

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 19, 2023.

Historical weather

Windsor, MA • 01270

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

91/ 100

Exceptional sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

10 hrs

5.6 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 255 High St Hill Rd

$693,844

$31K under list price of $725K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $340K to $685K.

SOLD AUG 17, 2026
$585,000 Last sold price
3 beds3.5 baths1,776 sq ft
222 Brough Rd, Cheshire, MA 01225
$135/sq ft
smaller lot
1 year older
SOLD JUL 9, 2026
$437,000 Last sold price
3 beds1.5 baths2,523 sq ft
5 Mckinley St, Adams, MA 01220
$21/sq ft
smaller lot
37 years older
SOLD JUN 24, 2026
$417,500 Last sold price
6 beds2.5 baths3,619 sq ft
27-29 Richmond St, Cheshire, MA 01225
$79/sq ft
smaller lot
167 years older
SOLD NOV 14, 2025
$685,000 Last sold price
4 beds3.5 baths2,952 sq ft
39 North Mountain Rd, Lanesborough, MA 01237
$38/sq ft
2 years newer
SOLD AUG 24, 2026
$340,000 Last sold price
4 beds2 baths1,824 sq ft
8 Richmond St, Adams, MA 01220
$8/sq ft
smaller lot
87 years older
SOLD AUG 14, 2026
$425,000 Last sold price
4 beds2 baths2,616 sq ft
1130 Main Dalton Rd, Windsor, MA 01270
$32/sq ft
larger lot
3 years older

Tour for free, no strings attached

Takes about 5 minutes & won't affect your credit

Start an offer

Early Access listings

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

$1,950,000

4 beds4 baths2,684 sq ft

9 Richard Rd, Lexington, MA 02421