255 High St Hill Rd Windsor, MA ^$ 724,900

255 High St Hill Rd

^$ 724,900

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255 High St Hill Rd

Windsor, MA, 01270

^$ 724,900

Bedrooms5 Baths3.1 Sq 3,744

Monthly Estimate*

^$ 4,577

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Single Family Home for sale in Windsor, MA

for $724,900 with 5 bedrooms and 3 full baths, 1 half bath. This 3,744 square foot home was built in 1987 on a lot size of 3.24.

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 Family Active

Price

^$ 724,900

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 5,263

Style

Contemporary,Saltbox

Lot Size

3.24

Year Built

1987

Town/City

Windsor

County/Region

Berkshire

MLS | Web ID

73564933

List By

Reciprocal Reciprocal

Listing Agent

Berkshire Reciprocal

Broker

Affordability Calculator

$5,016

Per Month

Monthly Principal & Interest: $4,577
Monthly Property Taxes: $439
Monthly Home Insurance: --

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Yearly Home Insurance

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends

Single family listings in Windsor, MA

Average List Price ^$524,950

Percent of Sale Price 28%

About Windsor, MA

935 Population

4% Since 2002

^$77,083 Median Income

51.98 Median Age

22% Households with Children

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Trends Information provided by ATTOM Data Solutions.

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Pricing History

Date	Price	Price Change	Description
8/27/2026	$724,900	-3.33%	Price Down
8/18/2026	$749,900		Listed Price

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255 High St Hill Rd, Windsor, MA, 01270 is a Single Family Home for sale at $724,900 with 3,744 sqft and a lot size of 3.24. 255 High St Hill Rd has 5 bedrooms, 3.1 baths, and was built in 1987. The property's zip code is 01270 which is in Windsor, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Data is updated as of 9/13/2026.

The real estate information and related content displayed on this site is 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.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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255 High St Hill Rd

Single Family Home for sale in Windsor, MA

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