Stockbridge

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.

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.

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.

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

14 Pine St
Stockbridge, MA $1,995,000

14 Pine St

Stockbridge, MA

$1,995,000
  • 6 Beds
  • 3/5 Baths
  • 10,507 Sqft
44 Prospect Hill Rd
Stockbridge, MA $1,299,900

44 Prospect Hill Rd

Stockbridge, MA

$1,299,900
  • 5 Beds
  • 4 Baths
  • 2,976 Sqft
176 Old Stockbridge Rd  #WH Chadsey 3
Stockbridge, MA $995,000

176 Old Stockbridge Rd #WH Chadsey 3

Stockbridge, MA

$995,000
  • 3 Beds
  • 3/1 Baths
  • 2,469 Sqft
13 Rattlesnake Mountain Rd
Stockbridge, MA $239,000

13 Rattlesnake Mountain Rd

Stockbridge, MA

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

4 Madisons Way

Stockbridge, MA

$25,000/mo
  • 4 Beds
  • 3/1 Baths
  • 2,536 Sqft
33 East St
Stockbridge , MA $15,000/mo

33 East St

Stockbridge , MA

$15,000/mo
  • 4 Beds
  • 2/1 Baths
  • 2,732 Sqft
4 Old Colonial Rd
Stockbridge , MA $13,000/mo

4 Old Colonial Rd

Stockbridge , MA

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

1 Devon Rd

Stockbridge, MA

$8,000/mo
  • 5 Beds
  • 5/1 Baths
  • 4,952 Sqft

Stockbridge

Area Map

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Stockbridge

Market Snapshot

Median Sales Price

June 2025 - Single Family Homes

$885K
image description +56.6% image description -19.5% vs

Percentage of Asking Price

June 2025 Single Family Homes

100%
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100%
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100%
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100%
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100%
image description +2.6% image description -5.4% vs