Sheffield

Berkshire County, Massachusetts

VIEW 43 COMMUNITY LISTINGS

Incorporated in 1733 after being purchased from a group of Stockbridge Indians, Sheffield is Berkshire County’s oldest town.

This beautiful community, made up of the two villages of Sheffield and Ashley Falls, lies on the southern border of Massachusetts next to Litchfield County, Connecticut. The town is located in the Housatonic River Valley, surrounded by the Taconic Mountains and Berkshire Hills, with sloping terrain, state forestland, rivers and waterfalls, a portion of the Appalachian Trail and the Schenob Brook wetland complex all adding to its scenic appeal. Sheffield is regarded as one of the area’s most picturesque towns, with its mountain views, expansive river valley setting and fertile agricultural land.

This beautiful community, made up of the two villages of Sheffield and Ashley Falls, lies on the southern border of Massachusetts next to Litchfield County, Connecticut. The town is located in the Housatonic River Valley, surrounded by the Taconic Mountains and Berkshire Hills, with sloping terrain, state forestland, rivers and waterfalls, a portion of the Appalachian Trail and the Schenob Brook wetland complex all adding to its scenic appeal. Sheffield is regarded as one of the area’s most picturesque towns, with its mountain views, expansive river valley setting and fertile agricultural land.

This beautiful community, made up of the two villages of Sheffield and Ashley Falls, lies on the southern border of Massachusetts next to Litchfield County, Connecticut. The town is located in the Housatonic River Valley, surrounded by the Taconic Mountains and Berkshire Hills, with sloping terrain, state forestland, rivers and waterfalls, a portion of the Appalachian Trail and the Schenob Brook wetland complex all adding to its scenic appeal. Sheffield is regarded as one of the area’s most picturesque towns, with its mountain views, expansive river valley setting and fertile agricultural land.

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Featured Listings

232 Giberson Rd
Sheffield, MA $2,690,000

232 Giberson Rd

Sheffield, MA

$2,690,000
  • 4 Beds
  • 3/1 Baths
  • 3,459 Sqft
GET MORE DETAILS
1373 Boardman St
Sheffield, MA $2,500,000

1373 Boardman St

Sheffield, MA

$2,500,000
  • 4 Beds
  • 4/1 Baths
  • 3,100 Sqft
GET MORE DETAILS
905 West Rd
Sheffield, MA $1,250,000

905 West Rd

Sheffield, MA

$1,250,000
  • 3 Beds
  • 2/1 Baths
  • 2,204 Sqft
GET MORE DETAILS
1460 Ashley Falls Rd
Sheffield, MA $799,000

1460 Ashley Falls Rd

Sheffield, MA

$799,000
  • 3 Beds
  • 2/1 Baths
  • 1,866 Sqft
GET MORE DETAILS
700 S Main St
Sheffield, MA $695,000

700 S Main St

Sheffield, MA

$695,000
  • 0/1 Baths
  • 3,360 Sqft
GET MORE DETAILS
355 South Undermountain
Sheffield , MA $6,000/mo

355 South Undermountain

Sheffield , MA

$6,000/mo
  • 3 Beds
  • 2/1 Baths
  • 1,712 Sqft
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74 East Rd
Sheffield , MA $1,975/mo

74 East Rd

Sheffield , MA

$1,975/mo
  • 1 Beds
  • 1.00 Baths
  • 700 Sqft
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268 County Rd
New Marlborough, MA $1,650,000

268 County Rd

New Marlborough, MA

$1,650,000
  • 4 Beds
  • 4/1 Baths
  • 3,900 Sqft
GET MORE DETAILS
view all 43 Sheffield listings

Sheffield

Area Map

Sheffield is within The Berkshires, Massachusetts and borders New Marlborough and Great Barrington.

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Featured Communities Within

The Berkshires

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Sheffield

Market Snapshot

Avg. Price Sqft

Single Family Homes

$212 November 2025
image description -25.3% image description +52.5% since

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Median Sales Price

November 2025 - Single Family Homes

$336K
image description +1.9% image description -15.9% since

Percentage of Asking Price

November 2025 Single Family Homes

92%
image description -7.2% image description +3.4% since
92%
image description -7.2% image description +3.4% since
92%
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