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132 Outlook Ave

CHESHIRE, MA

132 Outlook Ave Under Contract
$549,900
45 Photos
  • 3 Beds
  • 2/1 Baths
  • 2,134 Sqft
  • 4.32 Acres

132 Outlook Ave

CHESHIRE, MA | Berkshire County

$549,900
  • 3 Beds
  • 2/1 Baths
  • 2,134 Sqft
  • 4.32 Acres
  • Elementary School: Hoosac Valley Elementary
  • MLS #248459

Listing Courtesy of William Pitt Sotheby's - Lenox.

12 South St

CHESHIRE, MA

12 South St
$599,000
11 Photos
  • 1.7 Acres

12 South St

CHESHIRE, MA

$599,000
Reduced from $799,000
  • 1.7 Acres
  • MLS #244420

Listing Courtesy of Steepleview Realty - N. Adams.

Lot 9E Stewart White Rd

CHESHIRE, MA

Lot 9E Stewart White Rd
$114,900
5 Photos
  • 1.38 Acres

Lot 9E Stewart White Rd

CHESHIRE, MA

$114,900
  • 1.38 Acres
  • Elementary School: Hoosac Valley Elementary
  • MLS #247369

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

80 Church St

CHESHIRE, MA

80 Church St
$400/mo
7 Photos
  • 0/2 Baths
  • 320 Sqft

80 Church St

CHESHIRE, MA | Berkshire County

$400/mo
  • 0/2 Baths
  • 320 Sqft
  • MLS #247632

Listing Courtesy of Nocher Realty.

104 Church St

CHESHIRE, MA

104 Church St
$1,800/mo
3 Photos
  • 3 Beds
  • 1 Baths

104 Church St

CHESHIRE, MA | Berkshire County

$1,800/mo
  • 3 Beds
  • 1 Baths
  • MLS #248132

Listing Courtesy of Steepleview Realty - Adams Branch.

106 Church St

CHESHIRE, MA

106 Church St
$1,500/yr
1 Photo
  • 0/1 Baths
  • 3,500 Sqft

106 Church St

CHESHIRE, MA | Berkshire County

$1,500/yr
  • 0/1 Baths
  • 3,500 Sqft
  • MLS #248272

Listing Courtesy of Steepleview Realty - Adams Branch.

12 South St

CHESHIRE, MA

12 South St
$599,000
1 Photo
  • 1.7 Acres

12 South St

CHESHIRE, MA

$599,000
  • 1.7 Acres
  • Elementary School: Hoosac Valley Elementary
  • MLS #248400

Listing Courtesy of Steepleview Realty - N. Adams.

867 Notch Rd

CHESHIRE, MA

867 Notch Rd
$539,900
37 Photos
  • 5 Beds
  • 3/1 Baths
  • 3,307 Sqft
  • 7.25 Acres

867 Notch Rd

CHESHIRE, MA | Berkshire County

$539,900
  • 5 Beds
  • 3/1 Baths
  • 3,307 Sqft
  • 7.25 Acres
  • Elementary School: Hoosac Valley Elementary
  • MLS #248491

Listing Courtesy of Lamacchia Realty, Inc.

750-760 S State Rd

CHESHIRE, MA

750-760 S State Rd
$699,000
25 Photos
  • 8,452 Sqft
  • 4.47 Acres

750-760 S State Rd

CHESHIRE, MA | Berkshire County

$699,000
  • 8,452 Sqft
  • 4.47 Acres
  • MLS #248504

Listing Courtesy of Bishop West Real Estate.

268 Devonshire Dr

CHESHIRE, MA

268 Devonshire Dr
$539,000
51 Photos
  • 4 Beds
  • 2/1 Baths
  • 2,892 Sqft
  • 0.37 Acres

268 Devonshire Dr

CHESHIRE, MA

$539,000
  • 4 Beds
  • 2/1 Baths
  • 2,892 Sqft
  • 0.37 Acres
  • Elementary School: Hoosac Valley Elementary
  • MLS #248586

Listing Courtesy of Nocher Realty.

115 Main St

CHESHIRE, MA

115 Main St
$152,000
13 Photos
  • 3 Beds
  • 1 Baths
  • 1,335 Sqft
  • 0.53 Acres

115 Main St

CHESHIRE, MA | Berkshire County

$152,000
  • 3 Beds
  • 1 Baths
  • 1,335 Sqft
  • 0.53 Acres
  • Elementary School: Pboe
  • MLS #73471328

16 Jenks Road Lot 16

CHESHIRE, MA

16 Jenks Road Lot 16 Under Contract
$99,000
10 Photos
  • 10.01 Acres

16 Jenks Road Lot 16

CHESHIRE, MA | Berkshire County

$99,000
Reduced from $110,000
  • 10.01 Acres
  • Elementary School: Hoosac Valley
  • MLS #73371521

20 Pleasant View Dr

CHESHIRE, MA

20 Pleasant View Dr Under Contract
$849,000
58 Photos
  • 4 Beds
  • 2/1 Baths
  • 2,438 Sqft
  • 15.38 Acres

20 Pleasant View Dr

CHESHIRE, MA | Berkshire County

$849,000
Reduced from $879,000
  • 4 Beds
  • 2/1 Baths
  • 2,438 Sqft
  • 15.38 Acres
  • Elementary School: Hoosac Valley Elementary
  • MLS #247079

Listing Courtesy of Moresi Real Estate Partners.

230 Curran Rd

CHESHIRE, MA

230 Curran Rd Under Contract
$549,000
39 Photos
  • 3 Beds
  • 2 Baths
  • 2,184 Sqft
  • 4.05 Acres

230 Curran Rd

CHESHIRE, MA | Berkshire County

$549,000
  • 3 Beds
  • 2 Baths
  • 2,184 Sqft
  • 4.05 Acres
  • Elementary School: Hoosac Valley Elementary
  • MLS #247299

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%

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.