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255 High St Hill Rd

Windsor, MA 01270

$749,900 $3,161/Mo

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Overview

Bed

Bath

3,744

Sqft

3.24

Acres(Lot)

Description

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.

Property Details

Property Type : Residential

Price : $749,900

AD Id : 87722489

MLS Id : 250133

Beds : 5

Lot Size : 3.24 Acres

Living Area Size : 3,744

Year Built : 1987

Garage : 2

County : Berkshire

Map

What's Nearby

Nearby Areas

Features

Bedroom Information

Total beds: 5

Bathroom Information

Total Baths: 4 Full Baths: 3 Half Baths: 1

Room Information

Rooms Total: 9 Has Basement: Yes Basement: Concrete, Full
Flooring Information

Carpet, Ceramic Tile, Laminate, Wood
Interior Features

Appliances: Dryer, Range, Refrigerator, Washer Window Features: Skylight(s)
Heating & Cooling

Has Heating: Yes Heating: Oil, Hot Water

Building Information

Year Built: 1987 Building Area Total: 3744 Patio And Porch Features: Deck Private Pool: No View: Mountain(s)

Lot Information

Lot Dimensions: 228x697 Main Square Feet: 3.24 Acres Lot Size Acres: 3.24 Lot Size Square Feet: 141134 Lot Description: Landscaped

Listing Price Information

Listing Price: $749900

Tax Information

Parcel Number: M 14 L 115 Tax Year: 2025 Annual Tax: $5263

Parking Information

Off Street, Attached

Garage Information

Has Garage: Yes Has Attached Garage: Yes Garage Space: 2

School Information

Elementary School: Berkshire Trail

Junior High School: Nessacus Regional

Senior High School: Wahconah Regional
Location Information

WaterSource: Private, Well

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Nearby Home Value

Address	Estimate	Bed	Bath	Sq. Ft	Lot Size
43 Access Road 4 Rd, Windsor, MA, 01270	$114,999	3	1	600	600 SqFt
2241 Berkshire Rt 9 Trail, Windsor, MA, 01270	$450,000	3	3	2,720	2,720 SqFt

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Information from the Berkshire County Board of REALTORS®, Inc. or its Multiple Listing Service, Information herein believed to be accurate, but not warranted. All right, title and interest in the exclusively listed property information represented on this website was created, maintained and copyrighted by the Berkshire County Board of REALTORS®, and in copyrights therein, shall at all times remain vested in the Berkshire County Board of REALTORS®. As a Participant of the Berkshire County Multiple Listing Service, this company was granted a lease to use this information in accordance with all rules and regulations of the Service. This information is being provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Copyright ©2026 Berkshire County Multiple Listing Service. All rights reserved.

ByOwner last updated this listing 07/23/2026 @ 20:44

MLS: 250133 LISTED BY: Jesse Dimitropolis, RE/MAX COMPASS 413-394-4543 SOURCE: Berkshire County Board of REALTORS