Stockbridge

Berkshire County, Massachusetts

VIEW 35 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.

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

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
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
1 Devon Rd
Stockbridge, MA $25,000/mo

1 Devon Rd

Stockbridge, MA

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

5 Glendale Rd

Stockbridge , MA

$14,000/mo
  • 3 Beds
  • 2.00 Baths
  • 3,000 Sqft
4 Old Colonial Rd
Stockbridge , MA $13,000/mo

4 Old Colonial Rd

Stockbridge , MA

$13,000/mo
  • 2 Beds
  • 2 Baths
33 East St
Stockbridge , MA $8,000/mo

33 East St

Stockbridge , MA

$8,000/mo
  • 4 Beds
  • 2/1 Baths
  • 2,732 Sqft
5 Glendale Rd  #Cottage
Stockbridge , MA $3,000/mo

5 Glendale Rd #Cottage

Stockbridge , MA

$3,000/mo
  • 1 Beds
  • 1 Baths
  • 1,000 Sqft

Stockbridge

Area Map

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

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Featured Communities Within

The Berkshires

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Stockbridge

Market Snapshot

Median Sales Price

February 2025 - Single Family Homes

$210K
image description -69.9% vs

Percentage of Asking Price

February 2025 Single Family Homes

107%
image description +7.6% vs
107%
image description +7.6% vs