Sheffield

Berkshire County, Massachusetts

VIEW 37 COMMUNITY LISTINGS

Incorporated in 1733, 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

1373 Boardman St
Sheffield, MA $2,500,000

1373 Boardman St

Sheffield, MA

$2,500,000
  • 4 Beds
  • 4/1 Baths
  • 3,100 Sqft
1955 N Main St
Sheffield, MA $1,295,000

1955 N Main St

Sheffield, MA

$1,295,000
  • 0/2 Baths
  • 5,540 Sqft
856 Barnum St
Sheffield, MA $998,000

856 Barnum St

Sheffield, MA

$998,000
  • 2 Beds
  • 3 Baths
  • 1,800 Sqft
Bull Hill Rd
Sheffield, MA $795,000

Bull Hill Rd

Sheffield, MA

$795,000
  • 18.00 Acres
1105 Boardman St
Sheffield, MA $695,000

1105 Boardman St

Sheffield, MA

$695,000
  • 3 Beds
  • 3/1 Baths
  • 2,576 Sqft
107 South Main St
Sheffield, MA $325,000

107 South Main St

Sheffield, MA

$325,000
  • 3 Beds
  • 3 Baths
  • 1,765 Sqft
107 S Main St
Sheffield, MA $325,000

107 S Main St

Sheffield, MA

$325,000
  • 3 Beds
  • 3 Baths
  • 1,765 Sqft
355 South Undermountain
Sheffield , MA $6,000/mo

355 South Undermountain

Sheffield , MA

$6,000/mo
  • 3 Beds
  • 2/1 Baths
  • 1,712 Sqft

Sheffield

Area Map

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

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The Berkshires

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Sheffield

Market Snapshot

Median Sales Price

February 2025 - Single Family Homes

$402K
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Percentage of Asking Price

February 2025 Single Family Homes

95%
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95%
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