Stockbridge

Berkshire County, Massachusetts

VIEW 32 COMMUNITY LISTINGS

The charming Berkshire village of Stockbridge boasts perhaps the most well-known Main Street in the country, captured in a famous painting by Norman Rockwell.

Originally settled in the early 18th century and serving as an Indian mission, the area grew into a resort destination for the affluent in the mid 1800s and today maintains its reputation as a quiet, graceful retreat. Surrounded by mountains with the Housatonic River winding through its center, Stockbridge is known for its pastoral beauty, with lakes, the famed Tanglewood estate, and Stockbridge Bowl with its beach and boating club all nearby. The village’s small-town atmosphere preserves a nostalgic way of life, close to all of the Berkshire region’s sought-after amenities.

Originally settled in the early 18th century and serving as an Indian mission, the area grew into a resort destination for the affluent in the mid 1800s and today maintains its reputation as a quiet, graceful retreat. Surrounded by mountains with the Housatonic River winding through its center, Stockbridge is known for its pastoral beauty, with lakes, the famed Tanglewood estate, and Stockbridge Bowl with its beach and boating club all nearby. The village’s small-town atmosphere preserves a nostalgic way of life, close to all of the Berkshire region’s sought-after amenities.

Originally settled in the early 18th century and serving as an Indian mission, the area grew into a resort destination for the affluent in the mid 1800s and today maintains its reputation as a quiet, graceful retreat. Surrounded by mountains with the Housatonic River winding through its center, Stockbridge is known for its pastoral beauty, with lakes, the famed Tanglewood estate, and Stockbridge Bowl with its beach and boating club all nearby. The village’s small-town atmosphere preserves a nostalgic way of life, close to all of the Berkshire region’s sought-after amenities.

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Featured Listings

17 Prospect Hill Rd
Stockbridge, MA $4,150,000

17 Prospect Hill Rd

Stockbridge, MA

$4,150,000
  • 4 Beds
  • 4/1 Baths
  • 6,000 Sqft
2 South Hill Rd
Stockbridge, MA $865,000

2 South Hill Rd

Stockbridge, MA

$865,000
  • 2 Beds
  • 2 Baths
  • 2,111 Sqft
0 Prospecthill + Rattlesnake Mtn Rd
Stockbridge, MA $515,000

0 Prospecthill + Rattlesnake Mtn Rd

Stockbridge, MA

$515,000
  • 22.29 Acres
6 Bean Hill Rd
Stockbridge, MA $395,000

6 Bean Hill Rd

Stockbridge, MA

$395,000
  • 22.00 Acres
11 Beachwood Dr
Stockbridge, MA $389,900

11 Beachwood Dr

Stockbridge, MA

$389,900
  • 3 Beds
  • 1 Baths
  • 704 Sqft
0 Rattlesnake Mountain Rd
Stockbridge, MA $300,000

0 Rattlesnake Mountain Rd

Stockbridge, MA

$300,000
  • 15.65 Acres
Prospect Hill Rd
Stockbridge, MA $300,000

Prospect Hill Rd

Stockbridge, MA

$300,000
  • 4.19 Acres
0 Prospect Hill Rd
Stockbridge, MA $250,000

0 Prospect Hill Rd

Stockbridge, MA

$250,000
  • 6.64 Acres

Stockbridge

Area Map

Stockbridge is within The Berkshires, Massachusetts and borders Great Barrington, Lenox and Richmond.

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The Berkshires

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Stockbridge

Market Snapshot

Median Sales Price

April 2022 - Single Family Homes

$605K
image description -5.8% vs

Percentage of Asking Price

April 2022 Single Family Homes

106%
image description +12.9% vs
106%
image description +12.9% vs