Cheshire

Berkshire County, Massachusetts

VIEW 18 COMMUNITY LISTINGS

The Berkshire County valley town of Cheshire, boasting about 3,400 residents, derived its name from the county of Cheshire in England. Settled in 1766 by Baptists and officially incorporated in 1793, the town was said to have established the first factory in the western part of the state to manufacture cotton-making machinery. Lime kilns, a tannery, saw and grist mills, forges and glass manufacturing also flourished in the town’s early years. In recent times, rural Cheshire, encompassing 27.5 square miles, has evolved into a recreational/residential haven, particularly for skiers who flock to its slopes and traverse its trails. Situated in the valley of the Hoosic River, the town is bordered to the west by Mount Greylock State Reservation, and the Appalachian Trail crosses through its center. North Mountain looms to the community’s southeast, providing outstanding views. Those who enjoy the great outdoors often spend time on the Ashuwillticook Rail Trail, an 11-mile paved path popular with bikers, walkers, rollerbladers and joggers. Students in town are served by a regional school district formed with neighboring Adams. Municipal resources include the town’s public library which is connected to the town hall and is part of the regional library network, as well as local police, fire and public works. Regional transportation service is available in North Adams and Pittsfield, and Albany International Airport is the nearest option for air travelers.

The Berkshire County valley town of Cheshire, boasting about 3,400 residents, derived its name from the county of Cheshire in England. Settled in 1766 by Baptists and officially incorporated in 1793, the town was said to have established the first factory in the western part of the state to manufacture cotton-making machinery. Lime kilns, a tannery, saw and grist mills, forges and glass manufacturing also flourished in the town’s early years. In recent times, rural Cheshire, encompassing 27.5 square miles, has evolved into a recreational/residential haven, particularly for skiers who flock to its slopes and traverse its trails. Situated in the valley of the Hoosic River, the town is bordered to the west by Mount Greylock State Reservation, and the Appalachian Trail crosses through its center. North Mountain looms to the community’s southeast, providing outstanding views. Those who enjoy the great outdoors often spend time on the Ashuwillticook Rail Trail, an 11-mile paved path popular with bikers, walkers, rollerbladers and joggers. Students in town are served by a regional school district formed with neighboring Adams. Municipal resources include the town’s public library which is connected to the town hall and is part of the regional library network, as well as local police, fire and public works. Regional transportation service is available in North Adams and Pittsfield, and Albany International Airport is the nearest option for air travelers.

The Berkshire County valley town of Cheshire, boasting about 3,400 residents, derived its name from the county of Cheshire in England. Settled in 1766 by Baptists and officially incorporated in 1793, the town was said to have established the first factory in the western part of the state to manufacture cotton-making machinery. Lime kilns, a tannery, saw and grist mills, forges and glass manufacturing also flourished in the town’s early years. In recent times, rural Cheshire, encompassing 27.5 square miles, has evolved into a recreational/residential haven, particularly for skiers who flock to its slopes and traverse its trails. Situated in the valley of the Hoosic River, the town is bordered to the west by Mount Greylock State Reservation, and the Appalachian Trail crosses through its center. North Mountain looms to the community’s southeast, providing outstanding views. Those who enjoy the great outdoors often spend time on the Ashuwillticook Rail Trail, an 11-mile paved path popular with bikers, walkers, rollerbladers and joggers. Students in town are served by a regional school district formed with neighboring Adams. Municipal resources include the town’s public library which is connected to the town hall and is part of the regional library network, as well as local police, fire and public works. Regional transportation service is available in North Adams and Pittsfield, and Albany International Airport is the nearest option for air travelers.

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Featured Listings

132 Outlook Ave
Cheshire, MA $549,900

132 Outlook Ave

Cheshire, MA

$549,900
  • 3 Beds
  • 2/1 Baths
  • 2,134 Sqft
20 Pleasant View Dr
Cheshire, MA $849,000

20 Pleasant View Dr

Cheshire, MA

$849,000
  • 4 Beds
  • 2/1 Baths
  • 2,438 Sqft
750-760 S State Rd
Cheshire, MA $699,000

750-760 S State Rd

Cheshire, MA

$699,000
  • 8,452 Sqft
12 South St
Cheshire, MA $599,000

12 South St

Cheshire, MA

$599,000
  • 1.70 Acres
12 South St
Cheshire, MA $599,000

12 South St

Cheshire, MA

$599,000
  • 1.70 Acres
230 Curran Rd
Cheshire, MA $549,000

230 Curran Rd

Cheshire, MA

$549,000
  • 3 Beds
  • 2 Baths
  • 2,184 Sqft
573 Stafford Hill Rd
Cheshire, MA $539,900

573 Stafford Hill Rd

Cheshire, MA

$539,900
  • 4 Beds
  • 1/1 Baths
  • 1,865 Sqft
867 Notch Rd
Cheshire, MA $539,900

867 Notch Rd

Cheshire, MA

$539,900
  • 5 Beds
  • 3/1 Baths
  • 3,307 Sqft

Cheshire

Area Map

Cheshire is within The Berkshires, Massachusetts and borders .

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The Berkshires

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Cheshire

Market Snapshot

Median Sales Price

January 2026 - Single Family Homes

$175K
image description -52.3% image description -65.2% since

Percentage of Asking Price

January 2026 Single Family Homes

64%
image description -33.4% image description -36.9% since
64%
image description -33.4% image description -36.9% since