Cheshire, MA Real Estate & Homes for Sale

18 Listings Found:
  • Communities Cheshire
  • Price
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132 Outlook Ave

Cheshire, MA

132 Outlook Ave Under Contract
$549,900
  • 3 bed
  • 2/1 bath
  • 2,134 sqft
  • 4.32 acres

Listing Courtesy of William Pitt Sotheby's - Lenox.

12 South St

Cheshire, MA

12 South St
$599,000
  • 1.7 acres

Listing Courtesy of Steepleview Realty - N. Adams.

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.

80 Church St

Cheshire, MA

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

Listing Courtesy of Nocher Realty.

104 Church St

Cheshire, MA

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

Listing Courtesy of Steepleview Realty - Adams Branch.

106 Church St

Cheshire, MA

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

Listing Courtesy of Steepleview Realty - Adams Branch.

12 South St

Cheshire, MA

12 South St
$599,000
  • 1.7 acres

Listing Courtesy of Steepleview Realty - N. Adams.

867 Notch Rd

Cheshire, MA

867 Notch Rd
$539,900
  • 5 bed
  • 3/1 bath
  • 3,307 sqft
  • 7.25 acres

Listing Courtesy of Lamacchia Realty, Inc.

750-760 S State Rd

Cheshire, MA

750-760 S State Rd
$699,000
  • 8,452 sqft
  • 4.47 acres

Listing Courtesy of Bishop West Real Estate.

268 Devonshire Dr

Cheshire, MA

268 Devonshire Dr
$539,000
  • 4 bed
  • 2/1 bath
  • 2,892 sqft
  • 0.37 acres

Listing Courtesy of Nocher Realty.

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115 Main St

Cheshire, MA

115 Main St
$152,000
  • 3 bed
  • 1 bath
  • 1,335 sqft
  • 0.53 acres

16 Jenks Road Lot 16

Cheshire, MA

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

20 Pleasant View Dr

Cheshire, MA

20 Pleasant View Dr Under Contract
$849,000
  • 4 bed
  • 2/1 bath
  • 2,438 sqft
  • 15.38 acres

Listing Courtesy of Moresi Real Estate Partners.

230 Curran Rd

Cheshire, MA

230 Curran Rd Under Contract
$549,000
  • 3 bed
  • 2 bath
  • 2,184 sqft
  • 4.05 acres

Listing Courtesy of Lamacchia Realty, Inc.

Cheshire Real Estate Market

Single Family Homes
January 2026
January 2025
Cheshire, MA Average Days on Market
January 2026 31
January 2025 90 -65.4%
Median Sales Price homes in Cheshire
January 2026 $175K
January 2025 $367K -52.3%
Cheshire, MA Average Price per Square Foot
January 2026 $175
January 2025 $238 -26.7%
Total Single Family Homes Sold in Cheshire, MA
January 2026 1
January 2025 3 -66.7%

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 © 2026 Berkshire County Board of Realtors.