Cheshire

Berkshire County, Massachusetts

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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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Lifestyle Features

Lifestyle Feature

Antique Homes

Berkshire County has a great history that is often reflected in the area's homes. There are many homes built before 1900 that has been preserved and restored to their original luster.

Lifestyle Feature

Waterfront

The Berkshires is an ideal setting not only for its picturesque country landscapes and stunning mountainous terrain, but also its many beautiful lakes. For those who enjoy the lakefront lifestyle and all of the peaceful views, relaxation and outdoor recreation that comes with it, please begin your Berkshires lakefront search here.

Lifestyle Feature

Farm & Equestrian

Vast acreage, equestrian properties, pristine lakes and rivers, and great expanses of mountains and forests to hike, explore and take in the wildlife: It’s all here in the Berkshires. Start here to discover the current selection of magnificent trophy ranches and spectacular retreats with distant views now available for sale in the beautiful Berkshires.

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Featured Listings

725 North State Rd
Cheshire, MA $493,000

725 North State Rd

Cheshire, MA

$493,000
  • 8 Beds
  • 7/1 Baths
  • 6,145 Sqft
725 North State Rd
Cheshire, MA $493,000

725 North State Rd

Cheshire, MA

$493,000
  • 8 Beds
  • 7/1 Baths
  • 6,145 Sqft
601 Stafford Hill Rd
Cheshire, MA $485,000

601 Stafford Hill Rd

Cheshire, MA

$485,000
  • 3 Beds
  • 3/1 Baths
  • 3,011 Sqft
287 South State Rd
Cheshire, MA $480,000

287 South State Rd

Cheshire, MA

$480,000
  • 0/3 Baths
  • 3,954 Sqft
130 Stewart White Rd
Cheshire, MA $399,000

130 Stewart White Rd

Cheshire, MA

$399,000
  • 4 Beds
  • 3/1 Baths
  • 2,739 Sqft
329-339 South State Rd
Cheshire, MA $375,000

329-339 South State Rd

Cheshire, MA

$375,000
  • 0/2 Baths
  • 2,796 Sqft
329-339 South State Rd
Cheshire, MA $375,000

329-339 South State Rd

Cheshire, MA

$375,000
  • 3 Beds
  • 1 Baths
  • 943 Sqft
244 Shadowland Cove Rd
Cheshire, MA $339,000

244 Shadowland Cove Rd

Cheshire, MA

$339,000
  • 3 Beds
  • 1 Baths
  • 1,045 Sqft

Cheshire

Area Map

Cheshire is within The Berkshires, Massachusetts and borders .

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Cheshire

Market Snapshot

Median Sales Price

February 2020 - Single Family Homes

$17K
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Percentage of Asking Price

February 2020 Single Family Homes

86%
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86%
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