West Stockbridge, MA Homes

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  /61

  $500,000 Sold Jul 25, 2025

  5 Stockbridge Rd, West Stockbridge, MA 01266

  • 4 Beds
  • 2 Baths
  • 2,356 Sq Ft
  • Built 1900

  Last Sold Summary

  • 22% Below List Price
  • $212/SF
  • 100 Days On Market

  Current Estimated Value $558,521

  Last Listing Agent Lori Rose STONE HOUSE PROPERTIES, LLC

  5 Stockbridge Rd, West Stockbridge, MA 01266
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  /13

  Est $405,925 Not Listed For Sale

  19 Lenox Rd, West Stockbridge, MA 01266

  • 3 Beds
  • 1 Bath
  • 1,218 Sq Ft
  • Built 1900

  19 Lenox Rd, West Stockbridge, MA 01266

  Last Sold Summary

  • 10% Above List Price
  • $302/SF
  • 6 Days On Market

  Last Sold Price $368,000

  Last Listing Agent Lauren Dones Executive Real Estate, Inc.
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  /42

  $559,000

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft

  16 Swamp Rd, West Stockbridge, MA 01266

  The George Tyler Homestead appears on West Stockbridge maps as early as 1855. This charming 3-bedroom cottage exudes warmth and character with plenty of original detail. The wood-paneled living room features a handsome brick hearth with beehive oven and beautifully aged pine floors. The L-shaped kitchen offers ample storage and opens to a formal dining room, where a large window overlooks the

  Vashti Poor WILLIAM RAVEIS - BERKSHIRE

  16 Swamp Rd, West Stockbridge, MA 01266
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  /2

  $172,000 Sold Aug 15, 2025

  0 Great Barrington Rd, West Stockbridge, MA 01266

  • Land
  • 4.38 Acres
  • $39,314 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 2 Days On Market

  Last Listing Agent Lauren Rosen WILLIAM RAVEIS - BERKSHIRE

  0 Great Barrington Rd, West Stockbridge, MA 01266
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  /60

  Not Listed For Sale

  5 Water St, Housatonic, MA 01236

  • 6 Beds
  • 5 Baths
  • 3,136 Sq Ft
  • Built 1850

  5 Water St, Housatonic, MA 01236

  Last Sold Summary

  • $430/SF
  • 5 Days On Market

  Last Sold Price $1,350,000

  Last Listing Agent Sarah Dixon WILLIAM RAVEIS - BERKSHIRE
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  /47

  $425,000

  • 2 Beds
  • 1 Bath
  • 1,164 Sq Ft

  3 van Schaack Rd, West Stockbridge, MA 01266

  Charming home in a private setting, close to all area attractions. The oversized front porch leads you inside to a light filled first floor, with newly finished hardwood floors and high ceilings. The living and dining rooms offer flexible space for relaxing or entertaining. The kitchen has lovely southern light, as well as access to the back deck for summer dining. Upstairs are two generously

  Katie Williams STONE HOUSE PROPERTIES, LLC

  3 van Schaack Rd, West Stockbridge, MA 01266
• 

  

  /14

  $180,000 Sold Dec 19, 2025

  7 Silver Mine Ln, West Stockbridge, MA 01266

  • Land
  • 3.62 Acres
  • $49,724 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 21 Days On Market

  Last Listing Agent Laurie Nikituk RED HORSE REAL ESTATE, LLC

  7 Silver Mine Ln, West Stockbridge, MA 01266
• 

  

  /27

  Est $680,299 Not Listed For Sale

  6 W Alford Rd, West Stockbridge, MA 01266

  • 2 Beds
  • 2 Baths
  • 1,084 Sq Ft
  • Built 1900

  6 W Alford Rd, West Stockbridge, MA 01266

  Last Sold Summary

  • 10% Above List Price
  • $572/SF
  • 4 Days On Market

  Last Sold Price $620,000

  Last Listing Agent Claire Pollart WILLIAM RAVEIS - BERKSHIRE
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  /83

  $3,325,000

  • 4 Beds
  • 7.5 Baths
  • 7,957 Sq Ft

  83 Maple Hill Rd, West Stockbridge, MA 01266

  Hawks Nest Ridge. Quiet privacy on 8.6 acres. Decks, patio, screened porch and pool all enjoy the view and the natural setting. Dramatic open floor plan with walls of windows to the views, soaring stone wood burning fireplace spanning three stories. Cook's kitchen with walk-in pantry. First floor primary suite with gas fireplace and dressing room all abutting library and office. 4 private bedroom

  Sheila Thunfors STONE HOUSE PROPERTIES, LLC

  83 Maple Hill Rd, West Stockbridge, MA 01266
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  /40

  $545,000 Sold May 30, 2025

  278 Great Barrington Rd, Housatonic, MA 01236

  • 3 Beds
  • 1 Bath
  • 1,672 Sq Ft
  • Built 1976

  Last Sold Summary

  • 7% Below List Price
  • $326/SF
  • 187 Days On Market

  Current Estimated Value $579,562

  Last Listing Agent Kristin Clayborne WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  278 Great Barrington Rd, Housatonic, MA 01236
• 

  

  /73

  Est $3,731,653 Not Listed For Sale

  19 W Alford Rd, West Stockbridge, MA 01266

  • 6 Beds
  • 6 Baths
  • 7,045 Sq Ft
  • Built 2002

  19 W Alford Rd, West Stockbridge, MA 01266

  Last Sold Summary

  • 13% Below List Price
  • $610/SF
  • 155 Days On Market

  Last Sold Price $4,300,000

  Last Listing Agent Mary Jane White COHEN & WHITE ASSOCIATES
• 

  

  /22

  $824,000

  • Land
  • 29 Acres
  • $28,414 per Acre

  416 West Rd, Alford, MA 01266

  Experience the Berkshires Like Never BeforeNestled on West Road in Alford, this exceptional 29-acre estate offers a rare blend of natural beauty, flexibility, and investment potential. A meandering brook, Alford Brook gently courses through the property, creating serene waterside vistas and the soothing soundtrack of flowing water day and night.From the open meadows and wooded glens, enjoy

  Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  416 West Rd, Alford, MA 01266
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  /7

  $98,900 Sold Sep 11, 2025

  27 Gwenn Ln, West Stockbridge, MA 01266

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft
  • Built 1970

  Last Sold Summary

  • 10% Below List Price
  • $147/SF
  • 61 Days On Market

  Last Listing Agent John Ciepiela BISHOP WEST REAL ESTATE

  27 Gwenn Ln, West Stockbridge, MA 01266
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  /94

  Not Listed For Sale

  14 Easland Rd, West Stockbridge, MA 01266

  • 8 Beds
  • 7.5 Baths
  • 6,255 Sq Ft
  • Built 1794

  14 Easland Rd, West Stockbridge, MA 01266

  Last Sold Summary

  • $528/SF
  • 191 Days On Market

  Last Sold Price $3,300,000

  Last Listing Agent Vashti Poor WILLIAM RAVEIS - BERKSHIRE
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  /28

  $329,000

  • 4 Beds
  • 3 Baths
  • 2,276 Sq Ft

  44 Main St, West Stockbridge, MA 01266

  Discover the charm of downtown living in this Colonial home located in the heart of West Stockbridge. This home features four bedrooms, two full baths, kitchen, living room, dining room and a deck overlooking the river. In addition to the main living area the property also includes an in-law or studio apartment with it's own kitchen and bathroom. With a nice flat yard for outdoor activities,

  Molly Thomas COMPASS MASSACHUSETTS , LLC GB

  44 Main St, West Stockbridge, MA 01266
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  /43

  $316,500 Sold Jul 28, 2025

  268 East Rd, West Stockbridge, MA 01266

  • 4 Beds
  • 3 Baths
  • 2,775 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Below List Price
  • $114/SF
  • 74 Days On Market

  Current Estimated Value $514,974

  Last Listing Agent Cory Evangelisto NOCHER REALTY

  268 East Rd, West Stockbridge, MA 01266
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  /42

  Est $865,156 Not Listed For Sale

  4 Austerlitz Rd, West Stockbridge, MA 01266

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft
  • Built 1936

  4 Austerlitz Rd, West Stockbridge, MA 01266

  Last Sold Summary

  • 1% Below List Price
  • $502/SF
  • 23 Days On Market

  Last Sold Price $875,000

  Last Listing Agent Tom Lynch COMPASS MASSACHUSETTS , LLC GB
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  /46

  $680,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft

  7 Stockbridge Rd, West Stockbridge, MA 01266

  The Amasa Spencer House, circa 1791, is a beautifully preserved gem for antique-home lovers. Tucked into a bucolic yet convenient setting in West Stockbridge, it offers the rare ability to stroll to shops, restaurants, hardware store, market, arts & entertainment, coffee shop and a bookstore in the charming village center. Thoughtfully detailed from top to bottom in vibrant Farrow & Ball colors,

  Lauren Molk ELYSE HARNEY REAL ESTATE

  7 Stockbridge Rd, West Stockbridge, MA 01266
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  /17

  $210,000 Sold Oct 30, 2025

  0 Pixley Hill Rd, West Stockbridge, MA 01266

  • Land
  • 4.63 Acres
  • $45,356 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 531 Days On Market

  Last Listing Agent Lori Rose STONE HOUSE PROPERTIES, LLC

  0 Pixley Hill Rd, West Stockbridge, MA 01266
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  /30

  Est $477,708 Not Listed For Sale

  64 Lenox Rd, West Stockbridge, MA 01266

  • 2 Beds
  • 2 Baths
  • 1,022 Sq Ft
  • Built 1974

  64 Lenox Rd, West Stockbridge, MA 01266

  Last Sold Summary

  • 29% Above List Price
  • $362/SF
  • 5 Days On Market

  Last Sold Price $370,000

  Last Listing Agent Samantha Homeyer BIRCH PROPERTIES
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  /49

  $765,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,046 Sq Ft

  17 Iron Mine Rd, West Stockbridge, MA 01266

  Designed for country living and entertaining, the heart of the home centers around a sun-filled great room with vaulted ceilings, wood beams, and French doors leading to a private deck. The chic kitchen has marble counters, subway tile, stainless steel appliances, gas stove and a peninsula for prep and dining. The 1st-floor primary suite offers a walk-in closet, updated full bath and deck access.

  Tracy Crawford COMPASS MASSACHUSETTS , LLC GB

  17 Iron Mine Rd, West Stockbridge, MA 01266
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  /38

  $895,000 Sold Sep 25, 2025

  33 Interlaken Rd, Stockbridge, MA 01262

  • 5 Beds
  • 3.5 Baths
  • 3,194 Sq Ft
  • Built 1979

  Last Sold Summary

  • 19% Below List Price
  • $280/SF
  • 43 Days On Market

  Current Estimated Value $959,296

  Last Listing Agent Lori Rose STONE HOUSE PROPERTIES, LLC

  33 Interlaken Rd, Stockbridge, MA 01262
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  /42

  Est $516,065 Not Listed For Sale

  4 Lenox Rd, West Stockbridge, MA 01266

  • 3 Beds
  • 2 Baths
  • 1,533 Sq Ft
  • Built 1900

  4 Lenox Rd, West Stockbridge, MA 01266

  Last Sold Summary

  • 27% Above List Price
  • $264/SF
  • 30 Days On Market

  Last Sold Price $405,000

  Last Listing Agent Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
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  /5

  $315,000

  • Land
  • 14.74 Acres
  • $21,370 per Acre

  0 E Alford Rd, West Stockbridge, MA 01266

  Beautiful and pristine 14.7 acre lot, family owned since 1963. 3-4 acres are an open field; a former Christmas tree farm. Rear portion of property is largely wooded with a stream. This area of East Alford Road has many million dollar plus homes. Perfect lot to build your tranquil dream home. Lot was perc tested in 2007. 10 Minutes to the center of West Stockbridge, 15 minutes to Great

  Matt DeLucia William Pitt Sotheby's International Realty

  0 E Alford Rd, West Stockbridge, MA 01266
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  /17

  $475,000 Sold Mar 13, 2026

  18 Hill Rd, Stockbridge, MA 01262

  • 2 Beds
  • 1 Bath
  • 1,015 Sq Ft
  • Built 1973

  Last Sold Summary

  • 5% Below List Price
  • $468/SF
  • 8 Days On Market

  Current Estimated Value $502,082

  Last Listing Agent Marie Bourassa SIGNATURE ASSOCIATES

  18 Hill Rd, Stockbridge, MA 01262
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  /35

  Est $531,450 Not Listed For Sale

  4 Swamp, West Stockbridge, MA 01266

  • 2 Beds
  • 2 Baths
  • 1,368 Sq Ft
  • Built 1950

  4 Swamp, West Stockbridge, MA 01266

  Last Sold Summary

  • 1% Above List Price
  • $384/SF
  • 14 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Pamela Roberts ROBERTS & ASSOC. REALTY, INC
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  /2

  $289,000

  • Land
  • 3.69 Acres
  • $78,320 per Acre

  0 Interlaken Cross Rd, Stockbridge, MA 01262

  A pristine building lot in the heart of the Berkshires! Parcel B at Echo Valley is a 3.69-acre wooded, buildable lot offering a beautiful blank canvas for your dream home. Located off Interlaken Cross Road in Stockbridge, MA, this level parcel is easy to work with and provides excellent flexibility for siting your house, garage, and outdoor living spaces. Just minutes from Tanglewood, Stockbridge

  Lisa Berry Simply Sell Realty

  0 Interlaken Cross Rd, Stockbridge, MA 01262
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  /55

  $975,000 Sold Aug 06, 2025

  12 Harrison Calkins Rd, Alford, MA 01266

  • 4 Beds
  • 2.5 Baths
  • 1,986 Sq Ft
  • Built 1987

  Last Sold Summary

  • 9% Below List Price
  • $491/SF
  • 132 Days On Market

  Last Listing Agent Brandon White COHEN & WHITE ASSOCIATES

  12 Harrison Calkins Rd, Alford, MA 01266
• 

  

  /42

  Est $955,109 Not Listed For Sale

  4 Stockbridge Rd, West Stockbridge, MA 01266

  • 5 Beds
  • 5.5 Baths
  • 3,128 Sq Ft
  • Built 1825

  4 Stockbridge Rd, West Stockbridge, MA 01266

  Last Sold Summary

  • 16% Above List Price
  • $263/SF
  • 8 Days On Market

  Last Sold Price $822,000

  Last Listing Agent Cortney Dupont COHEN & WHITE ASSOCIATES
• 

  

  /14

  $399,000

  • 2 Beds
  • 1 Bath
  • 1,298 Sq Ft

  17 High St, West Stockbridge, MA 01236

  AFFORDABLE OPPORTUNITY TO BUILD EQUITY!This cozy fixer-upper is the perfect chance for a first time buyer to create a home of their own. With solid bones, a welcoming front porch, and a detached garage ideal for work shop or extra storage. Located in a convenient setting, it's ready for your vision. A little work could mean a big reward.Housatonic Village a few steps away. Being sold ''as-is''.

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  17 High St, West Stockbridge, MA 01236
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  /25

  $213,000 Sold Jul 01, 2025

  17 Swamp Rd, West Stockbridge, MA 01266

  • 2 Beds
  • 1 Bath
  • 1,117 Sq Ft
  • Built 1875

  Last Sold Summary

  • 8% Above List Price
  • $191/SF
  • 5 Days On Market

  Current Estimated Value $296,737

  Last Listing Agent Mary Jane Dunlop BISHOP WEST REAL ESTATE

  17 Swamp Rd, West Stockbridge, MA 01266
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  /45

  Est $483,384 Not Listed For Sale

  28 Oak St, West Stockbridge, MA 01266

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft
  • Built 1953

  28 Oak St, West Stockbridge, MA 01266

  Last Sold Summary

  • 15% Above List Price
  • $237/SF
  • 144 Days On Market

  Last Sold Price $420,000

  Last Listing Agent Donna DiGrigoli DIGRIGOLI REAL ESTATE
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  /36

  $472,000 Sold Aug 08, 2025

  45 State Line Rd, West Stockbridge, MA 01266

  • 3 Beds
  • 2.5 Baths
  • 2,232 Sq Ft
  • Built 1880

  Last Sold Summary

  • $211/SF
  • 5 Days On Market

  Current Estimated Value $493,554

  Last Listing Agent Carrie Swift Heck COMPASS MASSACHUSETTS , LLC GB

  45 State Line Rd, West Stockbridge, MA 01266
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  /49

  Est $561,867 Not Listed For Sale

  34 Swamp, West Stockbridge, MA 01266

  • 3 Beds
  • 2.5 Baths
  • 1,855 Sq Ft
  • Built 1978

  34 Swamp, West Stockbridge, MA 01266

  Last Sold Summary

  • 16% Above List Price
  • $261/SF
  • 12 Days On Market

  Last Sold Price $485,000

  Last Listing Agent Matt Carlino MACCARO REAL ESTATE
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  /51

  $1,050,000 Sold Apr 04, 2025

  300 East Rd, West Stockbridge, MA 01266

  • 2 Beds
  • 2 Baths
  • 1,968 Sq Ft
  • Built 1815

  Last Sold Summary

  • 12% Below List Price
  • $534/SF
  • 112 Days On Market

  Current Estimated Value $1,096,315

  Last Listing Agent Claudia Crane COMPASS MASSACHUSETTS , LLC GB

  300 East Rd, West Stockbridge, MA 01266
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  /45

  Est $449,638 Not Listed For Sale

  27 Swamp, West Stockbridge, MA 01266

  • 3 Beds
  • 1 Bath
  • 1,452 Sq Ft
  • Built 1958

  27 Swamp, West Stockbridge, MA 01266

  Last Sold Summary

  • 20% Above List Price
  • $258/SF
  • 63 Days On Market

  Last Sold Price $375,000

  Last Listing Agent Craig Kahn ALL SEASONS REALTY GROUP
• 

  

  /10

  $119,900 Sold Jan 23, 2026

  31 Gwenn Ln, West Stockbridge, MA 01266

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft
  • Built 1970

  Last Sold Summary

  • $133/SF
  • 3 Days On Market

  Last Listing Agent John Ciepiela BISHOP WEST REAL ESTATE

  31 Gwenn Ln, West Stockbridge, MA 01266
• 

  

  /42

  Est $865,658 Not Listed For Sale

  16 Interlaken Rd, Stockbridge, MA 01262

  • 3 Beds
  • 2 Baths
  • 2,014 Sq Ft
  • Built 1983

  16 Interlaken Rd, Stockbridge, MA 01262

  Last Sold Summary

  • 19% Above List Price
  • $362/SF
  • 4 Days On Market

  Last Sold Price $730,000

  Last Listing Agent Katie Williams STONE HOUSE PROPERTIES, LLC
• 

  

  /10

  $193,000 Sold Jan 30, 2026

  88 Great Barrington Rd, West Stockbridge, MA 01266

  • Land
  • 3.26 Acres
  • $59,202 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 45 Days On Market

  Current Estimated Value $240,422

  Last Listing Agent Jennifer Capala WILLIAM PITT SOTHEBY'S - LENOX

  88 Great Barrington Rd, West Stockbridge, MA 01266
• 

  

  /23

  Est $264,895 Not Listed For Sale

  40 Interlaken Rd, Stockbridge, MA 01262

  • 2 Beds
  • 1 Bath
  • 749 Sq Ft
  • Built 1800

  40 Interlaken Rd, Stockbridge, MA 01262

  Last Sold Summary

  • 51% Above List Price
  • $234/SF
  • 79 Days On Market

  Last Sold Price $175,000

  Last Listing Agent Shelley Cozzaglio LAMACCHIA REALTY, INC

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