The Berkshires

Massachusetts

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This ideal getaway offers sophisticated rural living at its best, combining all of the amenities of a big city with the pastoral beauty of the country

The Berkshires is a beautiful year-round resort destination in Western Massachusetts, known for its scenic hills and mountains, lovely rivers and lakes, and numerous recreational activities and cultural attractions. Popular events include summer performances by the Boston Symphony Orchestra at Tanglewood Music Center, theatre at Shakespeare & Company, and the country’s longest running dance festival, Jacob’s Pillow. Ski enthusiasts can explore the various resorts in the Berkshires including Ski Butternut, and those who enjoy nature often visit the area for its stunning park and forest land as well as its many hiking trails, including parts of the Appalachian Trail.

The region is also host to several exceptional restaurants, boutique shopping, art museums and studios, and historic mansions and gardens. Rich in history, the rural towns throughout the Berkshires feature fine properties and grand estates that can serve as full-time residences or weekend retreats, close to all of the amenities the area has to offer.

The Berkshires is a beautiful year-round resort destination in Western Massachusetts, known for its scenic hills and mountains, lovely rivers and lakes, and numerous recreational activities and cultural attractions. Popular events include summer performances by the Boston Symphony Orchestra at Tanglewood Music Center, theatre at Shakespeare & Company, and the country’s longest running dance festival, Jacob’s Pillow. Ski enthusiasts can explore the various resorts in the Berkshires including Ski Butternut, and those who enjoy nature often visit the area for its stunning park and forest land as well as its many hiking trails, including parts of the Appalachian Trail.

The region is also host to several exceptional restaurants, boutique shopping, art museums and studios, and historic mansions and gardens. Rich in history, the rural towns throughout the Berkshires feature fine properties and grand estates that can serve as full-time residences or weekend retreats, close to all of the amenities the area has to offer.

The Berkshires is a beautiful year-round resort destination in Western Massachusetts, known for its scenic hills and mountains, lovely rivers and lakes, and numerous recreational activities and cultural attractions. Popular events include summer performances by the Boston Symphony Orchestra at Tanglewood Music Center, theatre at Shakespeare & Company, and the country’s longest running dance festival, Jacob’s Pillow. Ski enthusiasts can explore the various resorts in the Berkshires including Ski Butternut, and those who enjoy nature often visit the area for its stunning park and forest land as well as its many hiking trails, including parts of the Appalachian Trail.

The region is also host to several exceptional restaurants, boutique shopping, art museums and studios, and historic mansions and gardens. Rich in history, the rural towns throughout the Berkshires feature fine properties and grand estates that can serve as full-time residences or weekend retreats, close to all of the amenities the area has to offer.

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The Berkshires

Area Map

The Berkshires is in Massachusetts and borders Litchfield Hills.

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The Berkshires Communities

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The Berkshires

Market Snapshot

Median Sales Price

November 2025 - Single Family Homes

$590K
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Percentage of Asking Price

November 2025 Single Family Homes

96%
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96%
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96%
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96%
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96%
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96%
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Featured Listings

30 East Rd
Alford, MA $13,500,000

30 East Rd

Alford, MA

$13,500,000
  • 7 Beds
  • 7/2 Baths
  • 10,429 Sqft
77 Seekonk Cross Rd
Great Barrington, MA $6,850,000

77 Seekonk Cross Rd

Great Barrington, MA

$6,850,000
  • 5 Beds
  • 3/1 Baths
  • 3,474 Sqft
319 Under Mountain Rd
Lenox, MA $4,995,000

319 Under Mountain Rd

Lenox, MA

$4,995,000
  • 7 Beds
  • 6/2 Baths
  • 13,261 Sqft
764 East Hill Rd
New Marlborough, MA $4,995,000

764 East Hill Rd

New Marlborough, MA

$4,995,000
  • 5 Beds
  • 5/1 Baths
  • 5,002 Sqft
764 East Hill Road
New Marlboro, MA $4,995,000

764 East Hill Road

New Marlboro, MA

$4,995,000
  • 5 Beds
  • 5/1 Baths
  • 5,002 Sqft
1 Pinecroft Dr
Lenox, MA $4,950,000

1 Pinecroft Dr

Lenox, MA

$4,950,000
  • 7 Beds
  • 8/1 Baths
  • 7,073 Sqft
6 & 8 Webster Rd
Tyringham, MA $4,600,000

6 & 8 Webster Rd

Tyringham, MA

$4,600,000
  • 5/3 Baths
  • 5,885 Sqft
8 Webster Rd
Tyringham, MA $4,600,000

8 Webster Rd

Tyringham, MA

$4,600,000
  • 7 Beds
  • 5/3 Baths
  • 5,885 Sqft