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0 North St
$99,900
  • 4 acres

Listing Courtesy of Roberts & Assoc. Realty, Inc.

E Windsor Rd
$33,200
  • 5.2 acres

Listing Courtesy of Realty Street, Llc.

1689 East Windsor Rd Under Contract
$399,000
  • 3 bed
  • 1/1 bath
  • 1,632 sqft
  • 2.28 acres

Listing Courtesy of The Kinderhook Group.

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Windsor Real Estate Market

Single Family Homes
October 2025
October 2024
Windsor, MA Average Days on Market
October 2025 72
October 2024 57  +25.4%
Median Sales Price homes in Windsor
October 2025 $499K
October 2024 $440K  +13.3%
Windsor, MA Average Price per Square Foot
October 2025 $215
October 2024 $259  -16.9%
Total Single Family Homes Sold in Windsor, MA
October 2025 4
October 2024 3  +33.3%

The IDX information is provided exclusively for consumers’ personal, noncommercial use, it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Listings content © 2025 Berkshire County Board of Realtors.