Cheshire

Berkshire County, Massachusetts

VIEW 5 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

329-339 State Rd
Cheshire, MA $375,000

329-339 State Rd

Cheshire, MA

$375,000
  • 3 Beds
  • 1 Baths
  • 943 Sqft
287 South State Rd
Cheshire, MA $480,000

287 South State Rd

Cheshire, MA

$480,000
  • 0/3 Baths
  • 3,954 Sqft
287 South State Rd
Cheshire, MA $450,000

287 South State Rd

Cheshire, MA

$450,000
  • 0/3 Baths
  • 3,954 Sqft
778 Lanesboro Rd
Cheshire, MA $325,000

778 Lanesboro Rd

Cheshire, MA

$325,000
  • 4 Beds
  • 2 Baths
  • 2,204 Sqft
206 Shadowland Cove Rd
Cheshire, MA $209,900

206 Shadowland Cove Rd

Cheshire, MA

$209,900
  • 1 Beds
  • 1 Baths
  • 856 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 2021 - Single Family Homes

$270K

Percentage of Asking Price

January 2021 Single Family Homes

95%
95%