Cheshire

Berkshire County, Massachusetts

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The Berkshire County valley town of Cheshire, boasting about 3,300 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 3,300 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 3,300 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

611 North State Rd
Cheshire, MA $779,900

611 North State Rd

Cheshire, MA

$779,900
  • 3 Beds
  • 3/1 Baths
  • 4,500 Sqft
147 Brough Rd
Cheshire, MA $699,000

147 Brough Rd

Cheshire, MA

$699,000
  • 3 Beds
  • 2/1 Baths
  • 3,240 Sqft
12 South St
Cheshire, MA $679,000

12 South St

Cheshire, MA

$679,000
  • 1.70 Acres
12 South St
Cheshire, MA $679,000

12 South St

Cheshire, MA

$679,000
  • 1.70 Acres
131 Wilshire Dr
Cheshire, MA $550,000

131 Wilshire Dr

Cheshire, MA

$550,000
  • 4 Beds
  • 4 Baths
  • 3,814 Sqft
149 Wilshire Dr
Cheshire, MA $514,900

149 Wilshire Dr

Cheshire, MA

$514,900
  • 4 Beds
  • 3 Baths
  • 4,302 Sqft
329 Lanesboro Rd
Cheshire, MA $499,900

329 Lanesboro Rd

Cheshire, MA

$499,900
  • 3 Beds
  • 2/1 Baths
  • 2,269 Sqft
632 N State Rd
Cheshire, MA $419,900

632 N State Rd

Cheshire, MA

$419,900
  • 4 Beds
  • 2 Baths
  • 2,100 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

June 2025 - Single Family Homes

$225K
image description -43.8% image description +8.7% vs

Percentage of Asking Price

June 2025 Single Family Homes

93%
image description -7.4% image description -27.0% vs
93%
image description -7.4% image description -27.0% vs