Sheffield

Berkshire County, Massachusetts

VIEW 30 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

905 West Rd
Sheffield, MA $1,250,000

905 West Rd

Sheffield, MA

$1,250,000
  • 3 Beds
  • 2/1 Baths
  • 2,204 Sqft
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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
GET MORE DETAILS
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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60 Parsley Ln
Sheffield, MA $995,000

60 Parsley Ln

Sheffield, MA

$995,000
  • 5 Beds
  • 4/1 Baths
  • 2,841 Sqft
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1955 N Main St
Sheffield, MA $895,000

1955 N Main St

Sheffield, MA

$895,000
  • 5,540 Sqft
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65 Silver St
Sheffield, MA $795,000

65 Silver St

Sheffield, MA

$795,000
  • 8,500 Sqft
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1786 South Undermountain Road
Sheffield, MA $795,000

1786 South Undermountain Road

Sheffield, MA

$795,000
  • 3 Beds
  • 2/1 Baths
  • 2,408 Sqft
GET MORE DETAILS
view all 30 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

$468 January 2026
image description +57.6% image description +93.5% since

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Median Sales Price

January 2026 - Single Family Homes

$1.3M
image description +123.6% image description +203.1% since

Percentage of Asking Price

January 2026 Single Family Homes

97%
image description -1.7% image description -1.8% since
97%
image description -1.7% image description -1.8% since
 
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