The Berkshires, MA Real Estate & Homes for Sale

1,306 Listings Found:
  • Communities The Berkshires
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4 Madisons Way

Stockbridge, MA

4 Madisons Way
$25,000/mo
  • 4 bed
  • 3/1 bath
  • 2,536 sqft
  • 25.99 acres

355 South Undermountain

Sheffield , MA

355 South Undermountain
$6,000/mo
  • 3 bed
  • 2/1 bath
  • 1,712 sqft
  • 1 acres

185 Stockbridge Rd

Lee, MA

185 Stockbridge Rd
$9,500/mo
  • 4 bed
  • 2/1 bath

14 Glendale Rd

West Stockbridge, MA

14 Glendale Rd
Upon Request
  • 4 bed
  • 3/1 bath

3 White Birch Ln

Great Barrington, MA

3 White Birch Ln
$17,000/season
  • 5 bed
  • 4/1 bath
  • 3,100 sqft
  • 1.13 acres

271 Lee Rd

Lenox , MA

271 Lee Rd
$12,000/mo
  • 3 bed
  • 2/1 bath
  • 1,833 sqft
  • 1.2 acres
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58 Mt Hunger Rd

Monterey, MA

58 Mt Hunger Rd
$15,000/mo
  • 3 bed
  • 3 bath
  • 2,100 sqft
  • 10 acres

26 Mcgee Rd

Egremont, MA

26 Mcgee Rd
$25,000/mo
  • 4 bed
  • 3 bath
  • 2,282 sqft
  • 2.3 acres

74 East Rd

Sheffield , MA

74 East Rd
$1,975/mo
  • 1 bed
  • 1.00 bath
  • 700 sqft

5 Glendale Rd #Cottage

Stockbridge , MA

5 Glendale Rd #Cottage
$2,400/mo
  • 1 bed
  • 1 bath
  • 1,000 sqft

238 Hayes Hill Rd

New Marlborough , MA

238 Hayes Hill Rd
$18,000/mo
  • 3 bed
  • 3/1 bath
  • 2,400 sqft
  • 12.54 acres

0 Route 57

New Marlborough, MA

0 Route 57
$1,200,000
  • 86 acres

Listing Courtesy of William Pitt Sotheby's - Gt Barrington.

44 Main St

Stockbridge, MA

44 Main St
$9,500/mo
  • 3 bed
  • 2 bath
  • 1,500 sqft

Listing Courtesy of William Pitt Sotheby's - Gt Barrington.

21-25 First St

Pittsfield, MA

21-25 First St
$309,000
  • 3,000 sqft
  • 0.07 acres

Listing Courtesy of William Pitt Sotheby's - Lenox.

The Berkshires Real Estate Market

Single Family Homes
May 2026
May 2025
The Berkshires, MA Average Days on Market
May 2026 160
May 2025 142 +12.2%
Median Sales Price homes in The Berkshires
May 2026 $548K
May 2025 $530K +3.3%
The Berkshires, MA Average Price per Square Foot
May 2026 $357
May 2025 $331 +7.8%
Total Single Family Homes Sold in The Berkshires, MA
May 2026 33
May 2025 25 +32.0%

The Berkshires, Massachusetts

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