Cheshire

Berkshire County, Massachusetts

VIEW 18 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

131 Wilshire Dr
Cheshire, MA $585,000

131 Wilshire Dr

Cheshire, MA

$585,000
  • 4 Beds
  • 4 Baths
  • 3,814 Sqft
68 Mallard Cove
Cheshire, MA $499,000

68 Mallard Cove

Cheshire, MA

$499,000
  • 2 Beds
  • 1 Baths
  • 1,698 Sqft
459 Stafford Hill Rd
Cheshire, MA $444,900

459 Stafford Hill Rd

Cheshire, MA

$444,900
  • 4 Beds
  • 2/1 Baths
  • 2,992 Sqft
54 Pleasant View Dr
Cheshire, MA $358,200

54 Pleasant View Dr

Cheshire, MA

$358,200
  • 4 Beds
  • 2 Baths
  • 2,600 Sqft
116 Wells Rd
Cheshire, MA $299,900

116 Wells Rd

Cheshire, MA

$299,900
  • 3 Beds
  • 1/1 Baths
  • 2,004 Sqft
75-79 Depot St
Cheshire, MA $289,000

75-79 Depot St

Cheshire, MA

$289,000
  • 6 Beds
  • 3 Baths
  • 2,788 Sqft
65 Prospect St
Cheshire, MA $263,000

65 Prospect St

Cheshire, MA

$263,000
  • 4 Beds
  • 2 Baths
  • 1,612 Sqft
119 Yorkshire Dr
Cheshire, MA $249,000

119 Yorkshire Dr

Cheshire, MA

$249,000
  • 3 Beds
  • 1 Baths
  • 1,371 Sqft

Cheshire

Area Map

Cheshire is within The Berkshires, Massachusetts and borders .

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Featured Communities Within

The Berkshires

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Cheshire

Market Snapshot

Median Sales Price

October 2023 - Single Family Homes

$458K
image description +27.2% image description +12.3% vs

Percentage of Asking Price

October 2023 Single Family Homes

103%
image description +8.7% image description +9.3% vs
103%
image description +8.7% image description +9.3% vs