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255 High St Hill Rd, 
Windsor, MA 01270

$724,900

5

Beds

4

Baths

3,744

Sq Ft

Single Family

Active

Listed by

Jesse Dimitropolis

RE/MAX Compass

413-394-4543

Last updated:

August 19, 2026, 08:54 PM

MLS#

250133

Source:

MA BCMLS

About This Home

255 High St Hill Rd

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.

Home Facts

Single Family

4 Baths

5 Bedrooms

Built in 1987

Price Summary

724,900

$193 per Sq. Ft.

MLS #:

250133

Last Updated:

August 19, 2026, 08:54 PM

Added:

1 month(s) ago

Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

3

Interior

Living Area:

3,744 Sq. Ft.

Structure

Structure

Architectural Style:

Contemporary, Salt Box

Building Area:

3,744 Sq. Ft.

Year Built:

1987

Lot

Lot Size (Sq. Ft):

141,134

Finances & Disclosures

Finances

Price:

$724,900

Price per Sq. Ft:

$193 per Sq. Ft.

Source:MA BCMLS
The data relating to real estate for sale on this web page comes in part from the Internet Data Exchange (IDX) of the Southern Missouri Regional MLS, LLC, Inc. Real estate listings held by Brokerage firms other than Coldwell Banker Choice Properties are marked with the IDX logo and detailed information about them includes the name of the listing Brokers. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information being provided is not guaranteed, and all information should be verified by the consumer. Any representation that a web site contains all listings shall only mean that the website contains all listing available to the public through the IDX data feed. There may be other properties offered through a REALTOR® that have not been displayed on this site. © 2026 Southern Missouri Regional MLS, LLC. All rights reserved. www.somomls.com
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255 High St Hill Rd
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Sat, Aug 22
01:00 PM - 02:30 PM

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.