Stockbridge

Berkshire County, Massachusetts

VIEW 37 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

7 Prospect Hill Rd
Stockbridge, MA $9,950,000

7 Prospect Hill Rd

Stockbridge, MA

$9,950,000
  • 5 Beds
  • 6/3 Baths
  • 9,339 Sqft
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14 Pine St
Stockbridge, MA $1,995,000

14 Pine St

Stockbridge, MA

$1,995,000
  • 6 Beds
  • 3/5 Baths
  • 10,507 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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1 Devon Rd
Stockbridge, MA $25,000/mo

1 Devon Rd

Stockbridge, MA

$25,000/mo
  • 5 Beds
  • 5/1 Baths
  • 4,952 Sqft
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5 Glendale Rd
Stockbridge , MA $14,000/mo

5 Glendale Rd

Stockbridge , MA

$14,000/mo
  • 3 Beds
  • 2.00 Baths
  • 3,000 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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33 East St
Stockbridge , MA $8,000/mo

33 East St

Stockbridge , MA

$8,000/mo
  • 4 Beds
  • 2/1 Baths
  • 2,732 Sqft
GET MORE DETAILS
view all 37 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

$620 March 2025
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Median Sales Price

March 2025 - Single Family Homes

$1.6M
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Percentage of Asking Price

March 2025 Single Family Homes

120%
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120%
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120%
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120%
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120%
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