West Stockbridge, MA Homes

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  /58

  $1,395,000

  • 6 Beds
  • 3.5 Baths
  • 3,905 Sq Ft

  21 Stockbridge Rd, West Stockbridge, MA 01266

  Tucked away on a private 2.35-acre knoll, this beautifully updated residence offers a rare blend of antique charm and modern ease in one of the Berkshires' most sought-after villages. With six generously sized bedrooms, a chef's kitchen designed for entertaining, and multiple inviting living spaces with fireplaces, the home is ideal for gatherings or quiet retreats alike. A stunning contemporary

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 675-5317

  21 Stockbridge Rd, West Stockbridge, MA 01266
• 

  

  

  /60

  $2,480,000 Sold Oct 16, 2025

  • 4,468 Sq Ft
  • $555/SF
  • 374 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1986

  180 W Center Rd, West Stockbridge, MA 01266

  Experience serene living at the end of a picturesque tree-lined driveway in a secluded family estate in the heart of West Stockbridge. Crafted as a berm home artfully built into the rolling hillside, this turnkey residence glows with natural light in its park-like setting. Ideal for both grand entertaining and quiet retreats, the multi-level home features over five bedrooms or flexible sleeping

  Stephen Schoenfeld WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  180 W Center Rd, West Stockbridge, MA 01266
• 

  

  

  /27

  Est $557,870 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,255 Sq Ft

  7 Stockbridge Rd, West Stockbridge, MA 01266

  7 Stockbridge Rd, West Stockbridge, MA 01266
• 

  

  

  /34

  $810,000 Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,294 Sq Ft

  15 Mahkeenac Heights Rd, West Stockbridge, MA 01266

  Chic and modern Berkshires retreat. Completed in 2022, this fully renovated property is one of only a handful of homes within Mahkeenac Heights to have a rare double lot -- offering space, privacy, and direct connection to nature just moments from Stockbridge Bowl and minutes to Tanglewood.The design is simple, modern, and sophisticated: a wall of glass frames the surrounding woods, with light

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 779-8896

  15 Mahkeenac Heights Rd, West Stockbridge, MA 01266
• 

  

  

  /23

  $440,000 Sold Oct 15, 2025

  • 900 Sq Ft
  • $489/SF
  • 18 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1957

  23 High St, West Stockbridge, MA 01236

  Recently renovated home offering clean lines and a modern European feel; move-in ready with nothing to do. Furnishings are available, making it easy to settle in with style and comfort. Inside, enjoy one-level living with 2 spacious bedrooms at opposite ends of the house, a sleek kitchen, an elegant bathroom, a convenient mudroom and a washer/dryer in the partially finished basement. Step onto

  Kate Lascar COMPASS MASSACHUSETTS , LLC GB

  23 High St, West Stockbridge, MA 01236
• 

  

  /21

  Est $317,851 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft

  123 State Line Rd, West Stockbridge, MA 01266

  123 State Line Rd, West Stockbridge, MA 01266
• 

  

  /47

  $1,790,000 Pending

  • 6 Beds
  • 6.5 Baths
  • 5,115 Sq Ft

  76 Lenox Rd, West Stockbridge, MA 01266

  New World charm meets timeless elegance in this thoughtfully designed French Country-style home, perfectly sited to take in stunning westerly mountain and sunset views. Privately nestled on 3.76 manageable acres, it's just minutes to Tanglewood, downtown Lenox, and West Stockbridge.Designed with both comfort and hospitality in mind, the home offers a flexible layout with six bedrooms and seven

  Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

  76 Lenox Rd, West Stockbridge, MA 01266
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  /5

  $129,900 Sold Oct 08, 2025

  • 1,000 Sq Ft
  • $130/SF
  • 54 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  11 Jennifer Ln, West Stockbridge, MA 01266

  Spacious 1998 Titan double-wide with 3 bedrooms, 2 baths, cathedral ceilings, and an open living area. Features a cozy fireplace and efficient pellet stove. The primary suite includes a private bath and ample closet space. Bright kitchen and dining area with plenty of storage. Great layout for comfortable living in a peaceful setting.

  John Ciepiela BISHOP WEST REAL ESTATE

  11 Jennifer Ln, West Stockbridge, MA 01266
• 

  

  /27

  Est $534,925 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,132 Sq Ft

  14 Interlaken Rd, Stockbridge, MA 01262

  14 Interlaken Rd, Stockbridge, MA 01262
• 

  

  /68

  $1,195,000

  • 3 Beds
  • 3 Baths
  • 2,002 Sq Ft

  276 Great Barrington Rd, West Stockbridge, MA 01236

  A unique farming opportunity on a self-sufficient 51-acre parcel, highlighted by an 1802 antique Colonial exuding historical charm. A thoughtfully conserved agrarian sanctuary with organic soil, a fruit orchard, maple sugar house, trails, gated pastures, and a running brook. The large barn and mature gardens are framed by stone walls and outbuildings. Bright rooms with wood floors, antique beams,

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  276 Great Barrington Rd, West Stockbridge, MA 01236
• 

  

  /23

  $525,000 Sold Oct 03, 2025

  • 2,620 Sq Ft
  • $200/SF
  • 105 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  9 Iron Mine Rd, West Stockbridge, MA 01266

  Located in the town of West Stockbridge just 1 1/2 miles from the village center home to an eclectic array of shops, restaurants, a very cool bookstore, No. Six Depot Roastery & Cafe and the annual West Stockbridge Zucchini Festival is this contemporary style home. With smart planting the home on 2+ acres feels totally private. Enjoy the great outdoors from the spacious deck or lawn. Inside

  Deborah Mielke CORASHIRE REALTY

  9 Iron Mine Rd, West Stockbridge, MA 01266
• 

  

  /43

  Est $1,055,632 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,966 Sq Ft

  388 West Rd, West Stockbridge, MA 01266

  388 West Rd, West Stockbridge, MA 01266
• 

  

  /37

  $1,498,000

  • 4 Beds
  • 3.5 Baths
  • 3,724 Sq Ft

  5 Silver Mine Ln, West Stockbridge, MA 01266

  This must see outstanding, Move-in Ready, Beautifully Upgraded, Open Floor Plan, Country Contemporary is on a cul-de-sac located just minutes from Tanglewood! The main level features an En Suite Primary Bedroom and Bath, with large 2 walk-in closets! The bright spacious Great Room boasts a vaulted ceiling and a propane fireplace. Like to cook? The gourmet kitchen sports stainless appliances

  George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  5 Silver Mine Ln, West Stockbridge, MA 01266
• 

  

  /53

  $586,500 Sold Sep 26, 2025

  • 1,500 Sq Ft
  • $391/SF
  • 143 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1875

  6 Bryan Rd, West Stockbridge, MA 01266

  Nature Lover's Paradise on 17+ Acres - Private Forests, Manicured Lawns, and Protected Wetlands!Centrally located to all Berkshire attractions. Easy access to NY and Boston higway exits, yet quiet and peaceful.Entirely private, 6 Bryan Road features spectacular wetland vistas, green meadows, and serene untouched woods.Stunning west-facing views from your deck overlook 8+ acres of protected

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  6 Bryan Rd, West Stockbridge, MA 01266
• 

  

  /23

  Est $524,828 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,409 Sq Ft

  7 State Line Rd, West Stockbridge, MA 01266

  7 State Line Rd, West Stockbridge, MA 01266
• 

  

  /34

  $1,795,000

  • 4 Beds
  • 4 Baths
  • 3,524 Sq Ft

  1 Old Tree Farm Rd, Stockbridge, MA 01262

  Impeccably Renovated Stockbridge Country Retreat. Minutes from Stockbridge, Lenox and Tanglewood, in the heart of the Berkshires cultural corridor, a rare opportunity in a perfect setting on 4.16 level, landscaped acres. Surrounded by mature trees and curated gardens, this home blends classic design with modern updates, offering refined style throughout. White oak floors, three full baths, a gas

  Suzann Ward Housatonic Real Estate

  1 Old Tree Farm Rd, Stockbridge, MA 01262
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  /38

  $895,000 Pending

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

  33 Interlaken Rd, Stockbridge, MA 01262

  Enjoy convenient one level living in this expanded contemporary ranch. Super location - Located less than 5 minutest to the main gates of Tanglewood, the Stockbridge Bowl for swimming, and Gould Meadows for a nature lovers hike. Sited at the end of a long winding driveway this 2+ acre parcel is level and sunny (ideal for a pool). 5+ bedrooms and 3 1/2 bathrooms including a suite with a

  Lori Rose STONE HOUSE PROPERTIES, LLC

  33 Interlaken Rd, Stockbridge, MA 01262
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  /25

  Est $682,656 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  17 Glendale Rd, West Stockbridge, MA 01266

  17 Glendale Rd, West Stockbridge, MA 01266
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  /68

  $2,200,000

  • 5 Beds
  • 4.5 Baths
  • 3,354 Sq Ft

  176 W Center Rd, West Stockbridge, MA 01266

  The lovely approach to this gorgeous estate property ensures serenity, privacy, and the beauty of living in the country and includes a 3 bed 2 1/2 bath main house and a gorgeous architect designed guest house. Offering 2 ensuite bedrooms with balconies, dramatic exposed beams, vaulted ceilings, and gas fireplace the guest house is an extraordinary place to host family and friends both

  Lori Rose STONE HOUSE PROPERTIES, LLC

  176 W Center Rd, West Stockbridge, MA 01266
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  /37

  $250,000 Sold Sep 23, 2025

  • 1,155 Sq Ft
  • $216/SF
  • 19 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1890

  19 Great Barrington Rd, West Stockbridge, MA 01266

  Two to three bedroom country colonial just minutes from West Stockbridge Village. Large 1.26 acre level lot is perfect for entertaining and relaxation day or night! Direct access to Card Pond; close proximity to Tanglewood, shopping, dining, galleries, theatre, hiking/biking, boating and all the cultural and recreational amenities of South Berkshire County and beyond. Bring your vision and

  Amy Wood STEEPLEVIEW REALTY - N. ADAMS

  19 Great Barrington Rd, West Stockbridge, MA 01266
• 

  

  /16

  Est $457,668 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,532 Sq Ft

  15 State Line Rd, West Stockbridge, MA 01266

  15 State Line Rd, West Stockbridge, MA 01266
• 

  

  /56

  $1,395,000

  • 4 Beds
  • 2 Baths
  • 2,058 Sq Ft

  45 Swamp, West Stockbridge, MA 01266

  1950s retro home, rich with family history, situated on 30+ acres of land & offering expansive westerly views & gentle sloping fields. Pathways lead to Shaker Mill Pond & Cone Brook which run the entire length of the property. Interior features include 2 BRs, office & full bath on the main level, 2 BRs & full bath on the second floor, a quaint kitchen, & living room. Additionally, a fully heated

  Paige Paluch LANCE VERMEULEN RE, INC

  45 Swamp, West Stockbridge, MA 01266
• 

  

  /28

  $685,000 Sold Sep 12, 2025

  • 1,488 Sq Ft
  • $460/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1985

  52 Lenox Rd, West Stockbridge, MA 01266

  Welcome to your Berkshires getaway, where rustic meets modern in all the right ways! Nestled among towering trees, just 3 miles from Tanglewood and the Kripalu Center for Yoga & Health, this renovated 3-bedroom, 2-bathroom log cabin offers the perfect blend of rustic charm and contemporary comfort.Step inside and be greeted by a vaulted ceiling that enhances the open, airy layout while

  Leslie Claus Van Hise BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  52 Lenox Rd, West Stockbridge, MA 01266
• 

  

  /38

  Est $1,242,221 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 1,638 Sq Ft

  258 East Rd, West Stockbridge, MA 01266

  258 East Rd, West Stockbridge, MA 01266
• 

  

  /43

  $1,790,000

  • 5 Beds
  • 4.5 Baths
  • 6,000 Sq Ft

  248 East Rd, West Stockbridge, MA 01266

  A luxurious home on one of the most scenic roads in The Berkshires, surrounded by 15 pastoral acres, with picturesque mountain views. Enter a sun-drenched living room with a soaring cathedral ceiling and an elegant fireplace centerpiece. Enjoy an expansive 3-season porch, with panoramic windows and classic mahogany floors. A recently updated eat-in kitchen features Sub Zero appliances and a

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  248 East Rd, West Stockbridge, MA 01266
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  /47

  $1,550,000 Sold Aug 25, 2025

  • 3,826 Sq Ft
  • $405/SF
  • 15 Days On Market

  • 1 Bed
  • 2 Baths
  • Built 1981

  293 East Rd, West Stockbridge, MA 01266

  A Hidden Berkshire Gem - With a Cottage, a Dream, and over 30 Acres of PossibilityWelcome to BarKing Cow Farm ! Your future compound that is tucked away on almost 30 private acres of peace and possibility, this rare offering is a true diamond awaiting its final polish. Located in one of the Berkshires' most sought-after townsa"boasting the lowest tax rate in South Countya"this property invites

  William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  293 East Rd, West Stockbridge, MA 01266
• 

  

  /30

  Est $474,572 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,020 Sq Ft

  34 W Center Rd, West Stockbridge, MA 01266

  34 W Center Rd, West Stockbridge, MA 01266
• 

  

  /50

  $1,825,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 3,225 Sq Ft

  5 Easland Rd, West Stockbridge, MA 01266

  A Home Designed for Living and RetreatNestled at the base of Harvey Mountain on over 10 private acres, 5 Easland Road is a custom-designed contemporary sanctuary where nature, luxury, and thoughtful craftsmanship come together in perfect harmony.This 5-bedroom, 5.5-bath home features soaring vaulted ceilings, dramatic walls of glass, and gleaming hardwood floors throughout. Each of the three

  Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  5 Easland Rd, West Stockbridge, MA 01266
• 

  

  /51

  $662,500 Sold Aug 12, 2025

  • 3,095 Sq Ft
  • $214/SF
  • 10 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1988

  256 Great Barrington Rd, Housatonic, MA 01236

  Perched on four-plus acres, this contemporary home offers a private woodland setting while maintaining easy access to both Great Barrington and West Stockbridge. Inviting airy floor plan offering a dramatic cathedral ceilinged living/dining room with skylight, direct access to a screened porch, and a bonus room with french doors, used as a music room but also perfect for a home office. Large

  Lori Rose STONE HOUSE PROPERTIES, LLC

  256 Great Barrington Rd, Housatonic, MA 01236
• 

  

  /42

  Est $625,153 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  2 Carlotto Rd, Housatonic, MA 01236

  2 Carlotto Rd, Housatonic, MA 01236
• 

  

  /98

  $13,500,000

  • 7 Beds
  • 9 Baths
  • 10,429 Sq Ft

  30 East Rd, West Stockbridge, MA 01266

  Majestic 71 acre Tudor Estate atop Tom Ball Mountain in the quaint hamlet of Alford, MA. Enjoy total privacy and breathtaking views from nearly every room. The main house features 5 en-suite bedrooms, a gourmet kitchen, formal living and dining rooms, den, family room, gym, billiard room and massage room. A separate 2-bedroom guest house offers beamed ceilings and full amenities. Manicured

  Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  30 East Rd, West Stockbridge, MA 01266
• 

  

  /36

  $472,000 Sold Aug 08, 2025

  • 2,232 Sq Ft
  • $211/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1880

  45 State Line Rd, West Stockbridge, MA 01266

  Meticulously maintained colonial within walking distance to town. The main level features a family room, an open-concept kitchen and dining area, a convenient half bath, and a versatile bonus room perfect for a home office. Upstairs, the primary suite includes a jetted tub and walk-in closet, accompanied by two additional bedrooms and another full bath. A heated sunroom leads to the large

  Carrie Swift Heck COMPASS MASSACHUSETTS , LLC GB

  45 State Line Rd, West Stockbridge, MA 01266
• 

  

  /35

  Est $946,968 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,578 Sq Ft

  5 Lenox Rd, West Stockbridge, MA 01266

  5 Lenox Rd, West Stockbridge, MA 01266
• 

  

  /17

  $499,000

  • 2 Beds
  • 1 Bath
  • 1,015 Sq Ft

  18 Hill Rd, Stockbridge, MA 01262

  Log Cabin in Stockbridge! Tucked away at the end of a country road, this charming log home offers warmth, privacy, and convenience - and it's close to Tanglewood. Beautifully maintained inside and out, it sits on two wooded acres with a welcoming front porch. Inside you will find a cozy retreat - a living room with cathedral ceilings, pine floors, and a working fireplace. The updated kitchen

  Marie Bourassa SIGNATURE ASSOCIATES

  18 Hill Rd, Stockbridge, MA 01262
• 

  

  /55

  $975,000 Sold Aug 06, 2025

  • 1,986 Sq Ft
  • $491/SF
  • 132 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1987

  12 Harrison Calkins Rd, Alford, MA 01266

  Enjoy the magic of living in Alford in this Contemporary Cape surrounded by 8+ acres of privacy and the enjoyment of the sound of Scribner Brook running through the front yard from the spacious screened porch. This 4 br, 2.5 bath turn key property is ready for you to walk in and begin your most perfect life in the country. Gather in the Great Room with vaulted ceiling to enjoy the surrounding

  Brandon White COHEN & WHITE ASSOCIATES

  12 Harrison Calkins Rd, Alford, MA 01266
• 

  

  /13

  Est $397,735 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,218 Sq Ft

  19 Lenox Rd, West Stockbridge, MA 01266

  19 Lenox Rd, West Stockbridge, MA 01266
• 

  

  /14

  $219,000

  • Land
  • 3.62 Acres
  • $60,497 per Acre

  7 Silver Mine Ln, West Stockbridge, MA 01266

  This parcel of land is located off the beaten path yet very near civilization. Set in an area of casually elegant homes. This parcel has 3.62 acres, its southern boundary is Cone Brook and has lovely views to the south. The building area is level, the utilities (electric and internet) are underground, this property is on Town water. There is a 2004 percolation report. Homeowner Association

  Laurie Nikituk RED HORSE REAL ESTATE, LLC

  7 Silver Mine Ln, West Stockbridge, MA 01266
• 

  

  /49

  $800,000 Sold Aug 05, 2025

  • 1,979 Sq Ft
  • $404/SF
  • 62 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1978

  18 Glendale Rd, West Stockbridge, MA 01266

  Architect designed Mid Century home with spectacular western views from every window. Multi level living has been updated with new roof, Pella windows, entry and sliding doors, interior doors, refinished wood floors, modern primary bathroom, heat pump and mini-splits controlled remotely, a whole house generator and recently painted interior and exterior. There is a lovely two sided fireplace

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  18 Glendale Rd, West Stockbridge, MA 01266
• 

  

  /60

  Not Listed For Sale

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

  5 Water St, Housatonic, MA 01236

  5 Water St, Housatonic, MA 01236
• 

  

  /10

  $225,000

  • Land
  • 3.26 Acres
  • $69,018 per Acre

  88 Great Barrington Rd, West Stockbridge, MA 01266

  Cleared 3+ acre lot ready to be built in a desirable West Stockbridge location. Wonderful south facing site, set off the road with distant uninterrupted views. Existing driveway presents easy access. Previous owner had percolation tests done which allows for a below grade septic system. Plans for the septic system are included. The site has already be approved by the DEP. Architectural plans for

  Jennifer Capala WILLIAM PITT SOTHEBY'S - LENOX

  88 Great Barrington Rd, West Stockbridge, MA 01266

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