Cheshire

Berkshire County, Massachusetts

VIEW 12 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.

Read MoreRead Less

Featured Listings

411 Lanesboro Rd
Cheshire, MA $529,000

411 Lanesboro Rd

Cheshire, MA

$529,000
  • 5 Beds
  • 3 Baths
  • 2,240 Sqft
Lot #13 Jenks Rd
Cheshire, MA $432,190

Lot #13 Jenks Rd

Cheshire, MA

$432,190
  • 3 Beds
  • 2 Baths
  • 1,248 Sqft
37 Main St
Cheshire, MA $355,000

37 Main St

Cheshire, MA

$355,000
  • 3 Beds
  • 2/1 Baths
  • 2,191 Sqft
28 Furnace Hill
Cheshire, MA $349,000

28 Furnace Hill

Cheshire, MA

$349,000
  • 4 Beds
  • 2 Baths
  • 2,211 Sqft
53 Depot St
Cheshire, MA $324,900

53 Depot St

Cheshire, MA

$324,900
  • 3 Beds
  • 2 Baths
  • 1,756 Sqft
108 Depot St
Cheshire, MA $324,900

108 Depot St

Cheshire, MA

$324,900
  • 4 Beds
  • 2 Baths
  • 1,913 Sqft
221-227 North St
Cheshire, MA $324,900

221-227 North St

Cheshire, MA

$324,900
  • 6 Beds
  • 4 Baths
  • 4,264 Sqft
192 Willow Cove Rd
Cheshire, MA $299,900

192 Willow Cove Rd

Cheshire, MA

$299,900
  • 1 Beds
  • 1 Baths
  • 1,032 Sqft

Cheshire

Area Map

Cheshire is within The Berkshires, Massachusetts and borders .

Loading...

Featured Communities Within

The Berkshires

view all communities +-
+-

Cheshire

Market Snapshot

Median Sales Price

April 2022 - Single Family Homes

$236K
image description +47.5% image description +148.4% vs

Percentage of Asking Price

April 2022 Single Family Homes

105%
image description +8.5% image description +21.3% vs
105%
image description +8.5% image description +21.3% vs
105%
image description +8.5% image description +21.3% vs
105%
image description +8.5% image description +21.3% vs