West Stockbridge, MA Homes

• 

  

  

  /20

  $435,000 Sold Aug 04, 2025

  • 1,772 Sq Ft
  • $245/SF
  • 134 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1920

  26 High St, Housatonic, MA 01236

  This charming colonial home is located within walking distance of the quaint center of Housatonic Village. Situated just over the border in West Stockbridge where property taxes are more favorable. Originally constructed as one of the manager's homes for the local mills, this residence has wood floors & high ceilings creating a spacious atmosphere. The first floor features generous living room &

  Molly Thomas COMPASS MASSACHUSETTS , LLC GB

  26 High St, Housatonic, MA 01236
• 

  

  

  /73

  Est $3,605,111 Not Listed For Sale

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

  19 W Alford Rd, West Stockbridge, MA 01266

  19 W Alford Rd, West Stockbridge, MA 01266
• 

  

  

  /22

  $849,000

  • Land
  • 29 Acres
  • $29,276 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
• 

  

  

  /43

  $316,500 Sold Jul 28, 2025

  • 2,775 Sq Ft
  • $114/SF
  • 74 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1958

  268 East Rd, West Stockbridge, MA 01266

  Truly a unique opportunity! A rare two family home in the town of Alford. Situated in a private setting this home has just over two and half acres of land, a two-car garage, and two spacious decks to enjoy the mountain views. The left unit features a one bedroom and one bathroom unit with an updated kitchen. Potential to expand this unit if more space is desired. Included in the right unit are

  Cory Evangelisto NOCHER REALTY

  268 East Rd, West Stockbridge, MA 01266
• 

  

  

  /94

  Not Listed For Sale

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

  14 Easland Rd, West Stockbridge, MA 01266

  14 Easland Rd, West Stockbridge, MA 01266
• 

  

  /49

  $780,000

  • 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
• 

  

  /61

  $500,000 Sold Jul 25, 2025

  • 2,356 Sq Ft
  • $212/SF
  • 100 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1900

  5 Stockbridge Rd, West Stockbridge, MA 01266

  The best of village living. A gracious in-town colonial with spacious rooms, high ceilings, wood floors and an abundance of natural light. Delightful first and second floor back porches overlooking the lovely backyard with walking bridge over a gentle brook and the winter views of Lenox Mt. Restaurants, shops, recreational and cultural venues are just a short walk down the street. Only 4

  Lori Rose STONE HOUSE PROPERTIES, LLC

  5 Stockbridge Rd, West Stockbridge, MA 01266
• 

  

  /9

  Est $4,072,316 Not Listed For Sale

  • 5 Beds

  Unlisted Address

  Unlisted Address
• 

  

  /109

  $3,395,000

  • 6 Beds
  • 9 Baths
  • 9,564 Sq Ft

  55 & 0 Maple Hill Rd, West Stockbridge, MA 01266

  MAPLE HILL MANOR.....Your Private Berkshire Escape! Step into Maple Hill Manor, a newly renovated, one-of-a-kind Berkshire estate delivering over 9,500 sq ft of professionally curated country-style living across a breathtaking 68.6 acres of rolling meadows, mature woodlands and expansive mountain panoramas-all enveloped by over 500 acres of protected natural beauty. Equestrian essentials &

  Brandon White COHEN & WHITE ASSOCIATES

  55 & 0 Maple Hill Rd, West Stockbridge, MA 01266
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  /52

  $1,180,000 Sold Jul 11, 2025

  • 3,642 Sq Ft
  • $324/SF
  • 12 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1984

  46 W Center Rd, West Stockbridge, MA 01266

  LOCATION, LOCATION!
Discover your Berkshire County sanctuary on one of the most picturesque roads in the region. This spacious 8-room, 4-bd home offers the perfect blend of privacy and comfort. A Chef's kitchen with a large living room centered around a cozy fireplace, flows into a sunny porch--to a four season lap pool/grand hot tub room for cooling off in the summer or soaking in warmth

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  46 W Center Rd, West Stockbridge, MA 01266
• 

  

  /42

  Est $826,441 Not Listed For Sale

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

  4 Austerlitz Rd, West Stockbridge, MA 01266

  4 Austerlitz Rd, West Stockbridge, MA 01266
• 

  

  /15

  $649,000

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  17 Beachwood Dr, Stockbridge, MA 01262

  OPEN HOUSE: Saturday, Oct 18, 11-12:30. Discover a truly exceptional opportunity to own a spacious 3-bedroom seasonal cottage on 1.3 acres of uniquely private land in one of the Berkshires' most desirable lakeside enclaves.Nestled in the serene and exclusive Beachwood community on Stockbridge Bowl, this property offers the perfect balance of natural beauty, privacy, and cultural access. Residents

  Franz Forster FRANZ J. FORSTER R. E.

  17 Beachwood Dr, Stockbridge, MA 01262
• 

  

  /32

  $465,000 Sold Jul 11, 2025

  • 1,600 Sq Ft
  • $291/SF
  • 15 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1840

  17 Stockbridge Rd, West Stockbridge, MA 01266

  Welcome to this lovely village home in the desirable town of West Stockbridge. Super location; walkable to Six Depot for coffee, The Foundry for theater, and Ella Mae's for ice cream-just a few of the benefits of living in town. In addition, just a quick drive to Tanglewood and Norman Rockwell Museum. Meticulously maintained with newer windows throughout and offering a perfect blend of charm and

  Lori Rose STONE HOUSE PROPERTIES, LLC

  17 Stockbridge Rd, West Stockbridge, MA 01266
• 

  

  /25

  Est $401,461 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,744 Sq Ft

  126 State Line Rd, West Stockbridge, MA 01266

  126 State Line Rd, West Stockbridge, MA 01266
• 

  

  /33

  $569,000

  • 3 Beds
  • 2.5 Baths
  • 1,424 Sq Ft

  19 Washington Square, West Stockbridge, MA 01266

  Charm. You'll find it in this 3BR, 2.5BA West Stockbridge home. The charm of a farmhouse fence, lush with white hydrangeas, roses, and day lilies, set along a peaceful street where neighbors jog, push strollers, or walk their dogs. The charm of luminous freshly painted interiors and windows framing views of greenery on all sides--mists atop Lenox Mountain, vivid sunsets, and star-spangled night

  Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  19 Washington Square, West Stockbridge, MA 01266
• 

  

  /74

  $1,350,000 Sold Jul 03, 2025

  • 2,249 Sq Ft
  • $600/SF
  • 3 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1850

  279 Great Barrington Rd, Housatonic, MA 01236

  Nestled in the picturesque village of Williamsville, West Stockbridge, this 1850s antique colonial offers an exceptional blend of history, craftsmanship, and modern comfort. Set on over 400 feet of pristine Williams River frontage, with a 12 acre private island, the main house features 3 bedrooms, 2.5 baths, wide plank wood floors, and two wood-burning fireplaces. A recently renovated farmhouse

  Lauren Rosen LANCE VERMEULEN RE, INC

  279 Great Barrington Rd, Housatonic, MA 01236
• 

  

  /30

  Est $449,445 Not Listed For Sale

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

  64 Lenox Rd, West Stockbridge, MA 01266

  64 Lenox Rd, West Stockbridge, MA 01266
• 

  

  /3

  $325,000

  • Land
  • 14.74 Acres
  • $22,049 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
• 

  

  /25

  $213,000 Sold Jul 01, 2025

  • 1,117 Sq Ft
  • $191/SF
  • 5 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1875

  17 Swamp Rd, West Stockbridge, MA 01266

  Nestled on serene Shaker Mill Pond, this unique property offers a rare opportunity to own a slice of peaceful paradise with boundless possibilities. The main home, though in need of significant renovation, boasts an unbeatable location with direct water access and panoramic views--perfect for those with a vision to restore or rebuild.Set on over .65 acre, the property includes a charming old barn

  Mary Jane Dunlop BISHOP WEST REAL ESTATE

  17 Swamp Rd, West Stockbridge, MA 01266
• 

  

  /23

  Est $442,573 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,434 Sq Ft

  7 Main St, West Stockbridge, MA 01266

  7 Main St, West Stockbridge, MA 01266
• 

  

  /49

  $949,000

  • 1 Bed
  • 1.5 Baths
  • 3,810 Sq Ft

  30 Great Barrington Rd, West Stockbridge, MA 01266

  The renovation of this 1930's Cape Cod by a master craftsman and his designer wife into the stunning modern day Contemporary it is today, while preserving some of the original highlights,is nothing short of a design miracle. The immense Great Room with the 60 foot wall of glass overlooking the terraced stone wall that leads to a stream and pine forest is the focal point of this special home. The

  Cortney Dupont COHEN & WHITE ASSOCIATES

  30 Great Barrington Rd, West Stockbridge, MA 01266
• 

  

  /34

  $885,000 Sold Jun 30, 2025

  • 2,189 Sq Ft
  • $404/SF
  • 17 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1996

  3 Willard Hill Rd, Stockbridge, MA 01262

  LIGHT-FILLED CONTEMPORARY CAPE on a premier road in the historic Interlaken section of Stockbridge. The open-concept first floor includes a living area with a wood-burning fireplace, dining area with a glass door leading to a large deck, and a recently remodeled kitchen. A half bath and a primary bedroom suite with a full bath complete the first floor. Upstairs, is a second primary suite with a

  Tom Lynch COMPASS MASSACHUSETTS , LLC GB

  3 Willard Hill Rd, Stockbridge, MA 01262
• 

  

  /42

  Est $496,670 Not Listed For Sale

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

  4 Lenox Rd, West Stockbridge, MA 01266

  4 Lenox Rd, West Stockbridge, MA 01266
• 

  

  /41

  $635,000

  • 3 Beds
  • 3 Baths
  • 2,476 Sq Ft

  4 Main St, West Stockbridge, MA 01266

  Don't miss this one-of-a-kind opportunity to own a commercially zoned, mixed-use property offering exceptional live/work potential in a prime in-town location along the Williams River. Whether you're a small business owner, creative entrepreneur, or an astute homebuyer creating a unique lifestyle setup - this is your opportunity to own a space that works as hard as you do. This efficiently

  Conor Meehan STONE HOUSE PROPERTIES, LLC

  4 Main St, West Stockbridge, MA 01266
• 

  

  /26

  $730,000 Sold Jun 30, 2025

  • Land
  • 68.4 Acres
  • $10,673 per Acre

  • 263 Days On Market

  0 Baker St, West Stockbridge, MA 01266

  Offered for the FIRST time welcome to the beautiful local family farm!! This stunning property offers a unique combination of natural beauty, historical significance , and abundant wildlife conservation.The farm spans across an impressive 68 acres providing ample space for various activities and possible future development. It encompasses 8 total pastures perfect for livestock or equestrian

  Kimber Bradley Robin Delaney Real Estate

  0 Baker St, West Stockbridge, MA 01266
• 

  

  /42

  Est $1,012,694 Not Listed For Sale

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

  4 Stockbridge Rd, West Stockbridge, MA 01266

  4 Stockbridge Rd, West Stockbridge, MA 01266
• 

  

  /19

  $775,000

  • 8 Beds
  • 4 Baths
  • 3,192 Sq Ft

  35 Main St, West Stockbridge, MA 01266

  Introducing a beautiful in-town 4-family investment opportunity on the picturesque Main St, offering separate utilities for each unit. With a new roof, fresh paint, and renovations completed in units, 1,2 &3 all in 2023.

  Matt Carlino MACCARO REAL ESTATE

  35 Main St, West Stockbridge, MA 01266
• 

  

  /40

  $545,000 Sold May 30, 2025

  • 1,672 Sq Ft
  • $326/SF
  • 187 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1976

  278 Great Barrington Rd, Housatonic, MA 01236

  Charming Dutch Colonial on the prettiest piece of land. On the first floor is a bedroom, dining room with wood fireplace, eat-in kitchen with large pantry, half bath. Upstairs are two large bedrooms with full bath. Partially finished basement with two usable rooms and laundry in the utility room. Breezeway/mudroom to attached 2-car garage. Outside is a pool, barn and children's play shed.

  Kristin Clayborne WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  278 Great Barrington Rd, Housatonic, MA 01236
• 

  

  /45

  Est $471,662 Not Listed For Sale

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

  28 Oak St, West Stockbridge, MA 01266

  28 Oak St, West Stockbridge, MA 01266
• 

  

  /56

  $5,475,000

  • 5 Beds
  • 8 Baths
  • 9,400 Sq Ft

  Unlisted Address

  Nestled in the heart of Alford, Massachusetts, this extraordinary 35.6-acre Berkshire County estate offers unparalleled privacy with sweeping western Catskill Mountain views and direct access to conservation land. The impressive 9,400 sq ft main residence, built in 2003 and comprehensively updated beginning in 2020, features 4 bedrooms, 5 full baths, and resort-caliber amenities throughout its

  Elyse Morris ELYSE HARNEY REAL ESTATE

  Unlisted Address
• 

  

  /51

  $1,050,000 Sold Apr 04, 2025

  • 1,968 Sq Ft
  • $534/SF
  • 112 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1815

  300 East Rd, West Stockbridge, MA 01266

  This classic eyebrow colonial, set on 18 acres, has been transformed into an efficient modern two bedroom home. The interior lines are elegant and clean, the transitions to the outdoors simple and harmonious. A well-balanced landscape features marble stone work, fruit trees, blueberry bushes, a seasonal stream and a fenced garden ready for the next season.Climb the moderate west facing slope to

  Claudia Crane COMPASS MASSACHUSETTS , LLC GB

  300 East Rd, West Stockbridge, MA 01266
• 

  

  /42

  Est $824,064 Not Listed For Sale

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

  16 Interlaken Rd, Stockbridge, MA 01262

  16 Interlaken Rd, Stockbridge, MA 01262
• 

  

  /3

  $975,000

  • Land
  • 131.69 Acres
  • $7,404 per Acre

  0 Lenox Rd Unit 246122, West Stockbridge, MA 01266

  This is a generous hillside parcel with a perc and potential views to the west. It is just over the hill from Stockbridge Bowl and Tanglewood, in an area of fine homes.

  Jim Stark L. J. STARK AND CO.

  0 Lenox Rd Unit 246122, West Stockbridge, MA 01266
• 

  

  /17

  $225,000 Sold Mar 24, 2025

  • Land
  • 10.4 Acres
  • $21,635 per Acre

  • 661 Days On Market

  Unlisted Address

  Prime Stockbridge land, prime Stockbridge location, and low Stockbridge taxes. A couple of short miles to Tanglewood in Lenox and a few minute drive to the Red Lion Inn in Stockbridge. Under a mile to Stockbridge public sandy beach on the Bowl. Includes drilled well already installed, septic design and roughed-in driveway. Excellent investment location for full or part-time

  Gary Johnston STONE HOUSE PROPERTIES, LLC

  Unlisted Address
• 

  

  /26

  Est $634,846 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,912 Sq Ft

  38 Interlaken Rd, Stockbridge, MA 01262

  38 Interlaken Rd, Stockbridge, MA 01262
• 

  

  /12

  $212,900

  • Land
  • 4 Acres
  • $53,225 per Acre

  0 Cross Rd, West Stockbridge, MA 01266

  Spectacular 4+/- acre parcel in a peaceful setting. It is backed up to a state conservatory so your privacy will remain in tact! This beautiful parcel is ready for your new home with a recent survey and perc test. Nestled in a tranquil area, that’s close to Card Pond and downtown Lenox. Come develop your dream home on this private parcel, but yet still be near all of the local attractions and

  Kimber Bradley Robin Delaney Real Estate

  0 Cross Rd, West Stockbridge, MA 01266
• 

  

  /23

  $175,000 Sold Feb 28, 2025

  • 749 Sq Ft
  • $234/SF
  • 79 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1800

  40 Interlaken Rd, Stockbridge, MA 01262

  Welcome to this cozy bungalow, ideally located just minutes from Tanglewood. This property has endless potential to create a delightful Airbnb or the perfect starter home. Featuring 2 bedrooms, 1 bathroom, and a three- season sunporch to enjoy your morning coffee or a good book. Don't miss out on this great opportunity to put your finishing touches on this adorable home- schedule your viewing

  Shelley Cozzaglio LAMACCHIA REALTY, INC

  40 Interlaken Rd, Stockbridge, MA 01262
• 

  

  /16

  Est $541,304 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,162 Sq Ft

  72 Interlaken Rd Unit 1, West Stockbridge, MA 01266

  72 Interlaken Rd Unit 1, West Stockbridge, MA 01266
• 

  

  /52

  $1,675,000

  • 12 Beds
  • 7 Baths
  • 8,881 Sq Ft

  29 Main St, West Stockbridge, MA 01266

  Step into a piece of history with the once Iconic Card Lake Inn Tavern, now transformed into a stunning residential haven in the heart of downtown West Stockbridge. This property offers not only a prime location but also an exceptional living experience, combining modern amenities with charming historic character. The building houses six completely renovated high-end apartments, each thoughtfully

  Suzann Ward HOUSATONIC REAL ESTATE

  29 Main St, West Stockbridge, MA 01266
• 

  

  /25

  $720,000 Sold Jan 31, 2025

  • 2,400 Sq Ft
  • $300/SF
  • 2 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1988

  275 East Rd, West Stockbridge, MA 01266

  Small ranch home set on ten beautiful acres with subtle southwestern views and an eastern view to Tom Ball Mtn. The acreage which is private and relatively flat beyond the existing house lends itself to a new build, expansion or an additional structure. The house has been partially renovated. The main living space, two bedrooms and two baths are on the second floor. The first floor, which is

  Claudia Crane COMPASS MASSACHUSETTS , LLC GB

  275 East Rd, West Stockbridge, MA 01266

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