For sale

$724,900

Est. $4,535/mo —

•

3,744

sq ft

255 High St Hill Rd, Windsor, MA 01270

About this home

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.

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 16, 2026 at 01:07pm

Redfin checked: 2 minutes ago

•Source:MLS PIN #73564933

Payment calculator

$4,535 per month

Principal and interest$4,005

Property taxes

$439

HOA dues

Home insurance

$91

Utilities

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Open houses

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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

$720K and above

75% chance or better to win

Why $720K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 46 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

Oct 12, 2026

Pending

—

Aug 19, 2026

Price Changed

$724,900

$194/sq ft

Jul 6, 2026

Listed

$749,900

$200/sq ft

+33

Public Remarks

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.

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

$687,832

$37K under list price of $725K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $323K to $790K.

SOLD JUN 12, 2026
$509,000 Last sold price
4 beds2.5 baths2,892 sq ft
268 Devonshire Dr, Cheshire, MA 01225
$18/sq ft
smaller lot
14 years older
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 FEB 9, 2026
$790,000 Last sold price
4 beds2.5 baths2,438 sq ft
20 Pleasant View Dr, Cheshire, MA 01225
$130/sq ft
larger lot
1 year newer
SOLD SEP 21, 2026
$322,500 Last sold price
4 beds2 baths2,112 sq ft
32 Valley St, Adams, MA 01220
$41/sq ft
smaller lot
87 years older
SOLD JUL 1, 2026
$715,000 Last sold price
3 beds3 baths2,078 sq ft
141 Griffin Hill Rd, Savoy, MA 01256
$150/sq ft
larger lot
11 years newer
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

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Details provided by MLS PIN and may not match the public record. Learn more.

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About this home

Payment calculator

Affordability tools

See this home in person

Around this home

Schools

Lifestyle

Offer insights

Property details

Sale and tax history for 255 High St Hill Rd

Public record

Historical weather

Sun exposure

Redfin Estimate for 255 High St Hill Rd

Early Access listings

Nearby similar homes

More real estate resources