Cheshire, MA Real Estate & Homes for Sale

18 Listings Found:
  • Communities Cheshire
  • Price
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12 South St

Cheshire, MA

12 South St
$599,000
  • 1.7 acres

Listing Courtesy of Steepleview Realty - N. Adams.

12 South St

Cheshire, MA

12 South St
$599,000
  • 1.7 acres

136-140 Church St

Cheshire, MA

136-140 Church St
$149,900
  • 5 bed
  • 3 bath
  • 2,250 sqft
  • 0.28 acres

83 Devonshire Dr

Cheshire, MA

83 Devonshire Dr
$319,900
  • 3 bed
  • 2 bath
  • 1,584 sqft
  • 0.31 acres

Listing Courtesy of Lamacchia Realty, Inc.

80 Church St

Cheshire, MA

80 Church St
$400/mo
  • 0/2 bath
  • 320 sqft

Listing Courtesy of Nocher Realty.

Lot 9E Stewart White Rd

Cheshire, MA

Lot 9E Stewart White Rd
$114,900
  • 1.38 acres

Listing Courtesy of Alton & Westall Real Estate Agency, Llc.

53 Depot St

Cheshire, MA

53 Depot St
$399,900
  • 3 bed
  • 2 bath
  • 1,756 sqft
  • 0.5 acres

Listing Courtesy of Alton & Westall Real Estate Agency, Llc.

104 Church St

Cheshire, MA

104 Church St
$1,800/mo
  • 3 bed
  • 1 bath

Listing Courtesy of Steepleview Realty - Adams Branch.

108 Church St #2

Cheshire, MA

108 Church St #2
$159,000
  • 4 bed
  • 2 bath
  • 1,850 sqft
  • 0.1 acres

Listing Courtesy of Key Realty.

18 Mountain Rd

Cheshire, MA

18 Mountain Rd
$389,900
  • 3 bed
  • 1/1 bath
  • 2,747 sqft
  • 1.08 acres

Listing Courtesy of Christopher A Warner Realty.

106 Church St

Cheshire, MA

106 Church St
$1,500/yr
  • 0/1 bath
  • 3,500 sqft

Listing Courtesy of Steepleview Realty - Adams Branch.

40 Curran Rd

Cheshire, MA

40 Curran Rd
$489,999
  • 3 bed
  • 2 bath
  • 2,670 sqft
  • 1.24 acres

Listing Courtesy of Paula Mclean Realtors Inc.

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573 Stafford Hill Rd

Cheshire, MA

573 Stafford Hill Rd
$539,900
  • 4 bed
  • 1/1 bath
  • 1,865 sqft
  • 1.42 acres

Listing Courtesy of Nocher Realty.

16 Jenks Road Lot 16

Cheshire, MA

16 Jenks Road Lot 16 Under Contract
$99,000
  • 10.01 acres

Cheshire Real Estate Market

Single Family Homes
November 2025
November 2024
Cheshire, MA Average Days on Market
November 2025 55
November 2024 77 -28.9%
Median Sales Price homes in Cheshire
November 2025 $430K
November 2024 $365K +17.8%
Cheshire, MA Average Price per Square Foot
November 2025 $239
November 2024 $204 +16.7%
Total Single Family Homes Sold in Cheshire, MA
November 2025 1
November 2024 6 -83.3%

Cheshire is within The Berkshires, Massachusetts

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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.