Cheshire

Berkshire County, Massachusetts

VIEW 21 COMMUNITY LISTINGS

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

116 Wells Rd
Cheshire, MA $259,000

116 Wells Rd

Cheshire, MA

$259,000
  • 3 Beds
  • 1/1 Baths
  • 2,004 Sqft
12 South St
Cheshire, MA $1,100,000

12 South St

Cheshire, MA

$1,100,000
  • 1.70 Acres
12 South St
Cheshire, MA $1,100,000

12 South St

Cheshire, MA

$1,100,000
  • 1.70 Acres
147 Richmond St
Cheshire, MA $524,900

147 Richmond St

Cheshire, MA

$524,900
  • 3 Beds
  • 2 Baths
  • 2,201 Sqft
41 Curran Rd
Cheshire, MA $515,000

41 Curran Rd

Cheshire, MA

$515,000
  • 3 Beds
  • 2/1 Baths
  • 2,546 Sqft
612 Notch Rd
Cheshire, MA $439,900

612 Notch Rd

Cheshire, MA

$439,900
  • 3 Beds
  • 2 Baths
  • 2,352 Sqft
77 Willow Ln
Cheshire, MA $435,000

77 Willow Ln

Cheshire, MA

$435,000
  • 3 Beds
  • 2 Baths
  • 1,581 Sqft
175 Church St
Cheshire, MA $409,900

175 Church St

Cheshire, MA

$409,900
  • 3 Beds
  • 2 Baths
  • 2,369 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

August 2024 - Single Family Homes

$500K
image description +76.4% image description +78.6% vs

Percentage of Asking Price

August 2024 Single Family Homes

105%
image description +8.6% image description +5.7% vs
105%
image description +8.6% image description +5.7% vs
105%
image description +8.6% image description +5.7% vs