Stockbridge

Berkshire County, Massachusetts

VIEW 34 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

55 Main St
Stockbridge, MA $2,500,000

55 Main St

Stockbridge, MA

$2,500,000
  • 5 Beds
  • 4/1 Baths
  • 5,233 Sqft
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19 Hawthorne Rd #3B Stables
Stockbridge, MA $600,000

19 Hawthorne Rd #3B Stables

Stockbridge, MA

$600,000
  • 2 Beds
  • 2/2 Baths
  • 1,870 Sqft
GET MORE DETAILS
15 W Stockbridge Rd
Stockbridge, MA $550,000

15 W Stockbridge Rd

Stockbridge, MA

$550,000
  • 4 Beds
  • 3 Baths
  • 2,600 Sqft
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13 Rattlesnake Mountain Rd
Stockbridge, MA $239,000

13 Rattlesnake Mountain Rd

Stockbridge, MA

$239,000
  • 7.83 Acres
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4 Madisons Way
Stockbridge, MA $25,000/mo

4 Madisons Way

Stockbridge, MA

$25,000/mo
  • 4 Beds
  • 3/1 Baths
  • 2,536 Sqft
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4 Old Colonial Rd
Stockbridge , MA $13,000/mo

4 Old Colonial Rd

Stockbridge , MA

$13,000/mo
  • 2 Beds
  • 2 Baths
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1 Devon Rd
Stockbridge, MA $8,000/mo

1 Devon Rd

Stockbridge, MA

$8,000/mo
  • 5 Beds
  • 5/1 Baths
  • 4,952 Sqft
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5 Glendale Rd #Cottage
Stockbridge , MA $2,400/mo

5 Glendale Rd #Cottage

Stockbridge , MA

$2,400/mo
  • 1 Beds
  • 1 Baths
  • 1,000 Sqft
GET MORE DETAILS
view all 34 Stockbridge listings

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

Avg. Price Sqft

Single Family Homes

$421 November 2025
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Median Sales Price

November 2025 - Single Family Homes

$516K
image description -66.8% image description -30.7% since

Percentage of Asking Price

November 2025 Single Family Homes

103%
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103%
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103%
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103%
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