Berkshire, MA Homes in ZIP Code 01266

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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
• 

  

  

  /17

  $12,500 per month

  • 3 Beds
  • 2 Baths
  • 1,861 Sq Ft
  • House for Rent

  5 Beachwood Dr, Stockbridge, MA 01262

  Delightful, classic Berkshires summer cottage in the Beachwood enclave. Shares in gorgeous community beach at south end of the Stockbridge Bowl (Lake Mahkeenac.) Enjoy swimming, kayaking, etc. Minutes to Tanglewood and all the cultural delights of the Berkshires. 3BR including primary suite with bath. 1 Queen BR, 1 Br with double bunk beds. Fantastic large screened porch with dining. LR with

  

  Selina Lamb

  Birch Properties

  (413) 610-3637

  5 Beachwood Dr, Stockbridge, MA 01262
• 

  

  

  /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
• 

  

  

  /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

  $975,000 Sold Jul 25, 2025

  • 2,010 Sq Ft
  • $485/SF
  • 10 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1948

  66 Interlaken Rd, Stockbridge, MA 01262

  Handsome redesign and total renovation in 2017. Living space all on one convenient level. Light bright interior. Well-designed kitchen opens to the great room with cathedral ceiling, fireplace and access to the three-season porch. Primary suite privately set at one end of the house and additional 3 bedrooms and 2 baths (1 ensuite) at the other end of the house. Den. Beautiful wood floors.

  Sheila Thunfors STONE HOUSE PROPERTIES, LLC

  66 Interlaken Rd, Stockbridge, MA 01262
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /6

  $650,000

  • Land
  • 19 Acres
  • $34,211 per Acre

  0 Mohawk Lake Rd, Stockbridge, MA 01262

  Discover a rare opportunity to own a piece of history in Stockbridge, available for the first time in over 120 years. This stunning land offers a private setting perfect for building your dream home, while being just moments away from the renowned Norman Rockwell Museum, Chesterwood, the enchanting Berkshire Botanical Gardens, and the charming downtown Stockbridge, all within a 3-mile radius.

  

  Gary Fuls Jr

  RE/MAX TRANSITIONS

  (413) 884-5511

  0 Mohawk Lake Rd, Stockbridge, MA 01262
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /29

  $1,100,000

  • 4 Beds
  • 3.5 Baths
  • 2,895 Sq Ft

  10 Alford Center Rd, Great Barrington, MA 01230

  1815 Antique Alford Colonial Beauty on 13.5 Acres! It has been over 25 years since this one of a kind property has been listed for sale. Not only does this home sport 4 bedrooms and 3 1/2 bathrooms, but it also has a fabulous two-story barn-like structure ready to be made into a terrific entertainment area for events large and small. Did you know that Alford was one of the first Berkshire

  George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  10 Alford Center Rd, Great Barrington, MA 01230
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /77

  $3,700,000 Sold May 30, 2025

  • 2,882 Sq Ft
  • $1284/SF
  • 4 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2011

  25 Mahkeenac Terrace, Stockbridge, MA 01262

  Nestled on the shores of the legendary Stockbridge Bowl, this immaculate contemporary lakefront home offers a perfect blend of casual luxury & tranquility. Ideally located moments from Tanglewood & the quintessential Berkshire towns of Lenox & Stockbridge. Cathedral height windows frame breathtaking, unobstructed views of the lake & the majestic Berkshire Hills creating a seamless harmony of

  Gary Lazarus COMPASS MASSACHUSETTS , LLC GB

  25 Mahkeenac Terrace, Stockbridge, MA 01262
• 

  

  /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
• 

  

  /76

  $1,075,000

  • 3 Beds
  • 4 Baths
  • 2,900 Sq Ft

  29 Old Village Rd, Great Barrington, MA 01230

  First-time for this treasured dwelling to be available for purchase. This magical setting surrounded by lush gardens and plantings is just the beginning of the enchantment. Distant mountain views to the east brings your viewscape to Butternut Ski & beyond. Inside the dwelling is a large open living space & kitchen on the first floor. Separately, there is a first-floor Ensuite. Abutting the first

  Thomas Doyle, Sr. BISHOP WEST REAL ESTATE

  29 Old Village Rd, Great Barrington, MA 01230
• 

  

  /11

  $375,000 Sold May 28, 2025

  • Land
  • 1.50 Acres
  • $250,000 per Acre

  • 16 Days On Market

  14 Partridge Way, Stockbridge, MA 01262

  A rare opportunity to own a 1.5-acre parcel on a quiet road in the highly sought-after Beachwood community, available only once in many decades. This property is ideally located in a peaceful, nature-filled setting with deeded rights to the Stockbridge Bowl, and is just minutes from the private Beachwood beach and swimming area and is connected to town sewer. It's also conveniently close to

  Gary Lazarus COMPASS MASSACHUSETTS , LLC GB

  14 Partridge Way, Stockbridge, MA 01262
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /43

  $1,890,000

  • 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
• 

  

  /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
• 

  

  /35

  Est $860,445 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
• 

  

  /44

  $1,325,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,300 Sq Ft

  26 N Egremont Rd, Great Barrington, MA 01230

  This lovely single-level Alford home has been extensively updated over the past two years with a new roof, HVAC systems, a paved driveway, and fresh interior and exterior paint among other improvements. The primary bath is brand new, and the other two baths have been recently renovated. The sellers are relocating to the West Coast and offer the home in move-in-ready condition. The open layout

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  26 N Egremont Rd, Great Barrington, MA 01230
• 

  

  /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
• 

  

  /63

  Est $1,773,761 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,024 Sq Ft

  15 West Rd, Alford, MA 01266

  15 West Rd, Alford, MA 01266

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