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.

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

8 Shamrock St
Stockbridge, MA $2,650,000

8 Shamrock St

Stockbridge, MA

$2,650,000
  • 5 Beds
  • 4/1 Baths
  • 3,700 Sqft
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1 Devon Rd
Stockbridge, MA $1,695,000

1 Devon Rd

Stockbridge, MA

$1,695,000
  • 6 Beds
  • 5/1 Baths
  • 4,952 Sqft
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9 Interlaken Rd
Stockbridge, MA $752,000

9 Interlaken Rd

Stockbridge, MA

$752,000
  • 3 Beds
  • 1/1 Baths
  • 1,750 Sqft
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46 Glendale Rd
Stockbridge, MA $729,000

46 Glendale Rd

Stockbridge, MA

$729,000
  • 3 Beds
  • 2 Baths
  • 2,015 Sqft
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1 Pixley Hill Rd
Stockbridge, MA $595,000

1 Pixley Hill Rd

Stockbridge, MA

$595,000
  • 3 Beds
  • 2 Baths
  • 1,582 Sqft
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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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44 Main St
Stockbridge, MA $9,500/mo

44 Main St

Stockbridge, MA

$9,500/mo
  • 3 Beds
  • 2 Baths
  • 1,500 Sqft
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44 Main St #1
Stockbridge, MA $8,500/mo

44 Main St #1

Stockbridge, MA

$8,500/mo
  • 3 Beds
  • 2 Baths
GET MORE DETAILS
view all 35 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

$479 May 2026
image description -38.8% image description +7.9% since

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Median Sales Price

May 2026 - Single Family Homes

$853K
image description -58.2% image description -32.1% since

Percentage of Asking Price

May 2026 Single Family Homes

91%
image description -9.8% image description -6.2% since
91%
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91%
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91%
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91%
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