Cheshire, MA Real Estate & Homes for Sale

17 Listings Found:
  • Communities Cheshire
  • Price
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27 Church St

Cheshire, MA

27 Church St Open House
$305,000
  • 4 bed
  • 2 bath
  • 1,531 sqft
  • 0.72 acres

Open House: Saturday, Jan 11, 1:00pm - 2:30pm

Listing Courtesy of Monarch Realty, Inc.

34 South St

Cheshire, MA

34 South St
$1,600/mo
  • 4 bed
  • 1/1 bath

Listing Courtesy of Nocher Realty.

236 Devonshire Dr

Cheshire, MA

236 Devonshire Dr Under Contract
$324,900
  • 2 bed
  • 2 bath
  • 1,431 sqft
  • 0.34 acres

Listing Courtesy of Nocher Realty.

527 State Rd

Cheshire, MA

527 State Rd
$260,000
  • 3 bed
  • 1 bath
  • 1,513 sqft
  • 0.31 acres

Listing Courtesy of 360berkshire Realty Group.

287 S State Rd

Cheshire, MA

287 S State Rd
$650,000
  • 3,954 sqft
  • 1.9 acres

Listing Courtesy of Bishop West Real Estate.

867 Notch Rd

Cheshire, MA

867 Notch Rd
$599,000
  • 5 bed
  • 3/1 bath
  • 3,307 sqft
  • 7.25 acres

Listing Courtesy of The Kinderhook Group - Pittsfield.

41 Curran Rd

Cheshire, MA

41 Curran Rd
$474,500
  • 3 bed
  • 2/1 bath
  • 2,546 sqft
  • 4.47 acres

Listing Courtesy of Nocher Realty.

1008 North State Rd

Cheshire, MA

1008 North State Rd
$289,900
  • 3 bed
  • 1 bath
  • 1,297 sqft
  • 0.37 acres

Listing Courtesy of Lamacchia Realty, Inc.

153 Shadowland Cove Rd

Cheshire, MA

153 Shadowland Cove Rd Under Contract
$399,000
  • 2 bed
  • 1 bath
  • 988 sqft
  • 0.82 acres

Listing Courtesy of Burnham Gold Real Estate, Llc.

64 North St

Cheshire, MA

64 North St Under Contract
$474,999
  • 5 bed
  • 2/1 bath
  • 3,906 sqft
  • 3.8 acres

Listing Courtesy of Lamacchia Realty, Inc.

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44 Richmond St

Cheshire, MA

44 Richmond St
$315,000
  • 3 bed
  • 2 bath
  • 1,984 sqft
  • 0.17 acres

Listing Courtesy of Lamacchia Realty, Inc.

57 Church St

Cheshire, MA

57 Church St
$130,000
  • 3 bed
  • 1 bath
  • 1,281 sqft
  • 0.11 acres

12 South St

Cheshire, MA

12 South St
$1,100,000
  • 1.7 acres

Listing Courtesy of Steepleview Realty - N. Adams.

12 South St

Cheshire, MA

12 South St
$1,100,000
  • 1.7 acres

Listing Courtesy of Steepleview Realty - N. Adams.

Cheshire Real Estate Market

Single Family Homes
December 2024
December 2023
Cheshire, MA Average Days on Market
December 2024 63
December 2023 73 -13.9%
Median Sales Price homes in Cheshire
December 2024 $231K
December 2023 $228K +1.1%
Cheshire, MA Average Price per Square Foot
December 2024 $126
December 2023 $140 -9.7%
Total Single Family Homes Sold in Cheshire, MA
December 2024 3
December 2023 5 -40.0%

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.