Berkshire, MA Homes

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  /58

  $1,595,000

  • 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
• 

  

  

  /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
• 

  

  

  /27

  Est $586,000 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
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  /61

  $1,280,000

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

  276 Great Barrington Rd, West Stockbridge, MA 01236

  Price Improvement! Motivated Seller!This 52-acre homestead blends early American heritage with modern sustainability and self-sufficiency. Originally built in 1802, this stunning property offers privacy, fertile farmland, and breathtaking mountain views-including Monument Mountain/Flag Rock. Mature fruit orchard with over 15 trees, 30-tree sugar bush with a sugarhouse for maple syrup

  

  Keytoria Jenkins

  THE KINDERHOOK GROUP - PITTSFIELD

  (413) 675-5502

  276 Great Barrington Rd, West Stockbridge, MA 01236
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  /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
• 

  

  /21

  Est $321,239 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
• 

  

  /7

  $109,900

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  27 Gwenn Ln, West Stockbridge, MA 01266

  

  John Ciepiela

  BISHOP WEST REAL ESTATE

  (413) 323-3952

  27 Gwenn Ln, West Stockbridge, MA 01266
• 

  

  /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
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  /28

  Est $418,032 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,092 Sq Ft

  18 Albany Rd, West Stockbridge, MA 01266

  18 Albany Rd, West Stockbridge, MA 01266
• 

  

  /5

  $129,900

  • 3 Beds
  • 2 Baths
  • 1,000 Sq Ft

  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

  (413) 414-5197

  11 Jennifer Ln, West Stockbridge, MA 01266
• 

  

  /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
• 

  

  /27

  Est $558,038 Not Listed For Sale

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

  14 Interlaken Rd, Stockbridge, MA 01262

  14 Interlaken Rd, Stockbridge, MA 01262
• 

  

  /61

  $1,790,000

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

  76 Lenox Rd, West Stockbridge, MA 01266

  New World meets Old in this impeccably designed and elegant French Country inspired estate nestled perfectly on the hillside, affording gorgeous westerly mountain and sunset views. Situated on 3.76 acres, the home offers ample privacy, yet it is just a stone's throw from Tanglewood and downtown Lenox and West Stockbridge. Designed for hosting extended family and friends, it offers generously

  Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

  76 Lenox Rd, West Stockbridge, MA 01266
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  /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
• 

  

  /43

  Est $3,640,110 Not Listed For Sale

  • 6 Beds
  • 6.5 Baths
  • 7,253 Sq Ft

  62 W Center Rd, West Stockbridge, MA 01266

  62 W Center Rd, West Stockbridge, MA 01266
• 

  

  /40

  $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 4.25 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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  /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
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  /23

  Est $530,145 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
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  /71

  $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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  /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
• 

  

  /25

  Est $716,142 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
• 

  

  /49

  $1,875,000

  • 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 Tom Ball 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
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  /26

  $730,000 Sold Jun 30, 2025

  • Land
  • 68 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
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  /16

  Est $443,789 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
• 

  

  /3

  $600,000 Sold Jun 25, 2025

  • Land
  • 35 Acres
  • $17,109 per Acre

  • 76 Days On Market

  0 Interlaken Cross Rd, Stockbridge, MA 01262

  Large parcel of land centrally located on a quiet road in Stockbridge. Minutes to the town centers of Stockbridge, Lenox, and West Stockbridge, as well as Tanglewood, Kripalu, the Norman Rockwell Museum, and the Berkshire Botanical Gardens. It is also walking-distance to the Stockbridge Bowl outlet and the Berkshire Art Center.The land is mostly wooded, level, and dry with some open areas. Town

  Carole Murko BOULDERWOOD GROUP

  0 Interlaken Cross Rd, Stockbridge, MA 01262
• 

  

  /38

  Est $1,190,651 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
• 

  

  /55

  $1,075,000 Pending

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

  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
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  /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
• 

  

  /30

  Est $470,473 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
• 

  

  /3

  $325,000

  • Land
  • 15 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
• 

  

  /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
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  /51

  Est $2,743,594 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 5,800 Sq Ft

  123 W Center Rd, West Stockbridge, MA 01266

  123 W Center Rd, West Stockbridge, MA 01266
• 

  

  /25

  $160,000

  • 3 Beds
  • 1 Bath
  • 792 Sq Ft

  59 High St, West Stockbridge, MA 01236

  This lovely spot is in South County, close to Stockbridge, Lenox, and Great Barrington. You can kayak or canoe as you're not far from the Housatonic River. 1.16 acres of mostly open land with a mobile home. The town of West Stockbridge clears the roads, and Housatonic Water Company supplies water. The boiler was installed in 2018, the roof was redone in 2014, and the windows were replaced in

  Mark Harris SIGNATURE ASSOCIATES

  59 High St, West Stockbridge, MA 01236
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  /17

  $225,000 Sold Mar 24, 2025

  • Land
  • 10 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
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  /42

  Est $625,754 Not Listed For Sale

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

  2 Carlotto Rd, Housatonic, MA 01236

  2 Carlotto Rd, Housatonic, MA 01236
• 

  

  /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
• 

  

  /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
• 

  

  /46

  Est $1,472,238 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,546 Sq Ft

  47 East Rd, West Stockbridge, MA 01266

  47 East Rd, West Stockbridge, MA 01266
• 

  

  /58

  $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. This uniquely designed 3-bedroom, 3-bath home includes a versatile accessory apartment, making it ideal for those seeking a combination of residential comfort and business flexibility. Enjoy water views from two

  Conor Meehan STONE HOUSE PROPERTIES, LLC

  4 Main St, West Stockbridge, MA 01266

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