Berkshire, MA Homes

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  /27

  $499,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,634 Sq Ft

  1068 Main St, Housatonic, MA 01236

  Very unique duplex in the heart of Housatonic! This very cool house combines antique charm, contemporary style, and a convenient village location to suit many uses and lifestyles. Currently configured as two leased 2 br/1ba apartments, it could easily be converted back to a single-family residence or provide income to an owner-occupant. Each unit offers a bright & cheery eat-in kitchen, living

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 728-1160

  1068 Main St, Housatonic, MA 01236
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  /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
• 

  

  

  /44

  Est $506,566 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,372 Sq Ft

  296 N Plain Rd, Housatonic, MA 01236

  296 N Plain Rd, Housatonic, MA 01236
• 

  

  

  /27

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,618 Sq Ft

  212 Highland St, Housatonic, MA 01236

  Nestled on a corner lot in the desirable town of Housatonic, this New England Farmhouse offers an abundance of space, a rocking chair front porch, a private rear courtyard, and a one-car garage. On the first floor is a comfortable living room with wood floors, a primary bedroom, a full bathroom, a dining room, a kitchen, and a gathering room with a wood stove. The second floor has 2 bedrooms and

  Lori Rose STONE HOUSE PROPERTIES, LLC

  212 Highland St, Housatonic, MA 01236
• 

  

  

  /17

  $375,000 Sold Aug 01, 2025

  • 1,691 Sq Ft
  • $222/SF
  • 22 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1958

  75 van Deusenville Rd, Great Barrington, MA 01230

  This sweet ranch has been in the same family for over 40 years and awaits the updates and personal touches of its next owners. Situated on a spacious & level 2.43 acre lot (ideal for gardening) this home is conveniently located on the outskirts of the village of Housatonic, just up the road from the Guthrie Center and few minutes drive to downtown Great Barrington. The home offers over 1,600 sq

  Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

  75 van Deusenville Rd, Great Barrington, MA 01230
• 

  

  /42

  Est $821,830 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 3,372 Sq Ft

  4 Kirk St, Housatonic, MA 01236

  4 Kirk St, Housatonic, MA 01236
• 

  

  /27

  $439,000

  • 3 Beds
  • 1 Bath
  • 1,192 Sq Ft

  370 Park St, Great Barrington, MA 01230

  Charming New England farmhouse featuring some modern updates and newer mechanical systems. Enjoy the perfect blend of rustic character and warmth of country living with modern conveniences in this delightful home. New full house insulation, Heat/ AC splits, updated electrical system. Large open backyard offers endless possibilities of outdoor activities and enjoyment. With a Berkshire Mountain

  Stephen Schoenfeld WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  370 Park St, Great Barrington, MA 01230
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  /33

  $486,000 Sold Jul 15, 2025

  • 2,330 Sq Ft
  • $209/SF
  • 27 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1900

  230 Prospect St, Great Barrington, MA 01236

  Tucked at the end of a dead-end street, this sun-drenched 4 bedroom is set on a corner lot w/ direct access to scenic trails - a rare find just minutes from local amenities. Step inside through a practical mudroom w/ a tiled floor, oversized closet, & powder room. The main level features an open-concept layout, seamlessly connecting the living, dining & kitchen w/ granite countertops and

  Kate Lascar COMPASS MASSACHUSETTS , LLC GB

  230 Prospect St, Great Barrington, MA 01236
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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
• 

  

  /59

  $899,000

  • 4 Beds
  • 3.5 Baths
  • 4,072 Sq Ft

  311 N Plain Rd, Housatonic, MA 01236

  This historic 4-bedroom 3.5-bath home sits on a beautifully landscaped 1-acre lot surrounded by ornamental trees, vibrant flower gardens and mature plantings. Originally built around 1800, this comfortable well-maintained house features high ceilings, warm wood flooring, and plenty of period charm. The main level welcomes you with a spacious living room accented with Greek Revival moldings, an

  Vashti Poor LANCE VERMEULEN RE, INC

  311 N Plain Rd, Housatonic, MA 01236
• 

  

  /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 $418,208 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,588 Sq Ft

  2 Walnut St, Great Barrington, MA 01230

  2 Walnut St, Great Barrington, MA 01230
• 

  

  /46

  $649,900

  • 9 Beds
  • 4 Baths
  • 4,152 Sq Ft

  1057 Main St, Great Barrington, MA 01236

  Great investment opportunity! A very rare property offered for the first time outside the family in over 90 years! This is a well maintained and loved four unit income property that can produce over seventy five thousand dollars per year in rents! Lifetime metal roof, freshly painted exterior and updated units are just a few of the benefits of this investment. In the bustling village of

  Ryan Lane GILCREST PROPERTIES

  1057 Main St, Great Barrington, MA 01236
• 

  

  /28

  $285,000 Sold Jun 12, 2025

  • 1,089 Sq Ft
  • $262/SF
  • 51 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  230 Grove St, Great Barrington, MA 01230

  Nestled just moments from the village center, this adorable three-bedroom cottage is full of character and opportunity. Featuring a bright and inviting living space, this home offers both charm and convenience.The semi-finished lower level provides a fantastic bonus area--perfect for a home office, playroom, or additional living space. Whether you're looking to move right in or add your personal

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  230 Grove St, Great Barrington, MA 01230
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  /32

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,593 Sq Ft

  32 Kirk St, Great Barrington, MA 01230

  32 Kirk St, Great Barrington, MA 01230
• 

  

  /36

  $729,000

  • 3 Beds
  • 3 Baths
  • 2,272 Sq Ft

  204 Cottage St, Great Barrington, MA 01236

  TWO HOMES FOR FAMILY LIVING OR INVESTMENT! So much to love about this property. The Main House exudes charm & warmth, and across the way a 2004 Cottage was added, creating the perfect income producer, family dwelling or Guest house. The Main house is tastefully updated preserving the cozy esthetic. 2 Bedroom, 2 Bath, Den, Great Room, and Country Kitchen. The Cottage, w/open plan living has

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  204 Cottage St, Great Barrington, MA 01236
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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
• 

  

  /36

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,560 Sq Ft

  6 Depot St, Great Barrington, MA 01236

  6 Depot St, Great Barrington, MA 01236
• 

  

  /53

  $849,000

  • 8 Beds
  • 4 Baths
  • 3,044 Sq Ft

  328 Park St, Great Barrington, MA 01230

  Two beautifully renovated duplexes within walking distance to the charming village of Housatonic. Enjoy scenic views of the Housatonic River from each unit. All utilities are separate, making this an ideal investment. All units are fully rented.

  Michael Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  328 Park St, Great Barrington, MA 01230
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  /14

  $350,000 Sold May 19, 2025

  • 1,000 Sq Ft
  • $350/SF
  • 189 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1948

  214 South St, Great Barrington, MA 01230

  Great starter home in town. Nice private back yard. Three bedrooms with one bath. Wood floors new carpets freshly painted. Empty and ready to go. Attic space could be finished for more space.

  Suzann Ward HOUSATONIC REAL ESTATE

  214 South St, Great Barrington, MA 01230
• 

  

  /33

  Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,285 Sq Ft

  216 Oak St, Great Barrington, MA 01230

  216 Oak St, Great Barrington, MA 01230
• 

  

  /30

  $699,000

  • 5 Beds
  • 3 Baths
  • 3,035 Sq Ft

  133 Front St, Great Barrington, MA 01236

  Unique Mixed-Use Property in Downtown HousatonicPrime opportunity for investors or owner-occupants! This charming property features a successful ground-floor retail space and two spacious, income-producing 2-bedroom apartments above. Each unit includes a large kitchen, full bath, washer/dryer hookups, and an enclosed porch with town views.The commercial space has its own kitchen and bath ideal

  Judi Panzano HOUSATONIC REAL ESTATE

  133 Front St, Great Barrington, MA 01236
• 

  

  /39

  $425,000 Sold Apr 01, 2025

  • 1,381 Sq Ft
  • $308/SF
  • 198 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1900

  17 Cone Ave, Great Barrington, MA 01230

  This lovingly cared for classic New England Farmhouse boasts a wrap-around porch and picket fence that will return you to times gone by, but with all the modern conveniences. Situated at the end of a quiet street in the bucolic town of Housatonic sits this gem where you can walk out your back door to hike up Monument Mountain or walk down the street to the bakery or restaurants. Light and bright

  Michael Linden WILLIAM RAVEIS REAL ESTATE

  17 Cone Ave, Great Barrington, MA 01230
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  /60

  Est $429,612 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,530 Sq Ft

  207 North St, Great Barrington, MA 01230

  207 North St, Great Barrington, MA 01230
• 

  

  /13

  $325,000

  • Land
  • 10 Acres
  • $33,854 per Acre

  297 N Plain Rd, Housatonic, MA 01236

  Perfect for a very private family compound. GB zoning allows three dwelling units to be built by right. Cleared one acre level house site with driveway and underground utilities brought in. Over $44,000 in site improvements plus survey and perc testing. 700' of frontage on the lovely clear, Williams River including three islands. Bathe, swim, fish, tube, cold plunge, let your imagination run

  Claudia Crane COMPASS MASSACHUSETTS , LLC GB

  297 N Plain Rd, Housatonic, MA 01236
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  /26

  $235,000 Sold Feb 26, 2025

  • 1,464 Sq Ft
  • $161/SF
  • 70 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1954

  11 Fairview Rd, Great Barrington, MA 01230

  One level living on corner lot with Mountain Views. This is a major renovation/update. Great private spot. Good size back yard for gardening. Well worth the investment. Attached one car garage that could be easily be turned into more living space. No basement. just a concreate slab.

  Suzann Ward HOUSATONIC REAL ESTATE

  11 Fairview Rd, Great Barrington, MA 01230
• 

  

  /7

  Est $1,556,205 Not Listed For Sale

  • 5 Beds

  Unlisted Address

  Unlisted Address
• 

  

  /32

  $795,000

  • 4 Beds
  • 2.5 Baths
  • 2,422 Sq Ft

  367 N Plain Rd, Housatonic, MA 01236

  1880 4 Bedroom Colonial in a beautiful Pastoral setting. Open Living and Kitchen plan.Permitted wood burning stove in living room. Second floor has 3 bedrooms, one is a generously sized en-suite. Garage was converted partially for a perfect home office or 4th bedroom. Laundry facilities and half bath located on 1st floor. Outdoor space includes a deck, a partially fenced portion of yard for a dog

  Mark Rosengren LANCE VERMEULEN RE, INC

  367 N Plain Rd, Housatonic, MA 01236
• 

  

  /25

  $340,000 Sold Jan 21, 2025

  • 1,680 Sq Ft
  • $202/SF
  • 71 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1898

  1 Forest St, Great Barrington, MA 01236

  Welcome to your next home project - a delightful in-town charmer with views of Flag Rock. This property, new to the market, offers a unique blend of character, potential.Step inside to discover a retro kitchen that exudes nostalgic charm. Complete with a pantry, this kitchen offers ample storage and space to create culinary masterpieces. The large rooms throughout the house boast high ceilings,

  Suzann Ward HOUSATONIC REAL ESTATE

  1 Forest St, Great Barrington, MA 01236
• 

  

  /31

  Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,382 Sq Ft

  224 Highland St, Great Barrington, MA 01230

  224 Highland St, Great Barrington, MA 01230
• 

  

  /16

  $315,000

  • 2,950 Sq Ft

  16 Depot St, Great Barrington, MA 01230

  Prime Commercial / Residential / Multi-Family Space in Downtown Housatonic! A chance to create a central hub for commerce and discover the endless possibilities with a versatile commercial space. Spanning 2,950 square feet, this property offers a unique opportunity to breathe new life into the area and create a thriving business hub. Ready to be transformed into a cozy coffee shop, a vibrant meat

  John Segalla HOUSATONIC REAL ESTATE

  16 Depot St, Great Barrington, MA 01230
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  /44

  $3,970,000 Sold Dec 20, 2024

  • 13,350 Sq Ft
  • $297/SF
  • 609 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1900

  410 Park St, Great Barrington, MA 01230

  NOW UNDER $3M! Calling all creative minds - artists, musicians, recording artists, producers, makers, and lovers of historic mill building restorations! STUNNING, ONE-OF-A-KIND, modern and historic mill building in the dynamic village of Housatonic, MA is THE PLACE for you to Make Art | Make Music | Live Life in the heart of the Berkshires. Seize the moment to make this extraordinary property

  Selina Lamb BIRCH PROPERTIES

  410 Park St, Great Barrington, MA 01230
• 

  

  /19

  Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,416 Sq Ft

  211 Pine St, Great Barrington, MA 01230

  211 Pine St, Great Barrington, MA 01230
• 

  

  /34

  $589,000

  • 4 Beds
  • 4 Baths
  • 5,044 Sq Ft

  163 Front St, Great Barrington, MA 01230

  Suzann Ward HOUSATONIC REAL ESTATE

  163 Front St, Great Barrington, MA 01230
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  /38

  $1,070,000 Sold Dec 19, 2024

  • 3,963 Sq Ft
  • $270/SF
  • 7 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1987

  258 Great Barrington Rd, Housatonic, MA 01236

  Sanctuary ! Modern contemporary home, bathed in natural light, nestled on 5 acres. This 3 bedroom, all with ensuite baths, and a 1st floor half bath residence is perfect for outdoor enthusiasts-whether you're a hiker, birder, or gardener. Conveniently located less than 10 minutes from Great Barrington, West Stockbridge, Stockbridge and Lenox, this property offers both seclusion and accessibility.

  William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  258 Great Barrington Rd, Housatonic, MA 01236
• 

  

  /28

  Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,512 Sq Ft

  207 South St, Great Barrington, MA 01230

  207 South St, Great Barrington, MA 01230
• 

  

  /51

  $689,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,095 Sq Ft

  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
• 

  

  /8

  $230,000 Sold Dec 06, 2024

  • 1,096 Sq Ft
  • $210/SF
  • 167 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  360 Park St Unit 1, Great Barrington, MA 01230

  Presenting a captivating new addition to the market - a 2-bedroom, 1-bath condo that epitomizes the ease of one-level living. This exceptional end unit boasts soaring 12' high ceilings, creating a sense of spaciousness that is further accentuated by the abundant natural light streaming in through the charming bow windows. Additionally, the condo features a large walk-in closet, which can easily

  Suzann Ward HOUSATONIC REAL ESTATE

  360 Park St Unit 1, Great Barrington, MA 01230
• 

  

  /15

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  206 Highland St, Great Barrington, MA 01230

  206 Highland St, Great Barrington, MA 01230
• 

  

  /35

  $796,000 Open Sat 2PM - 5PM

  • 2 Beds
  • 2 Baths
  • 1,622 Sq Ft

  324 Park St, Great Barrington, MA 01230

  Architectural gem with lots of glass perched like a treehouse on the backside of Monument Mountain. The open, mid-century modern home was built in 2012 for maximum light, efficiency, and provides glittering views through the trees of the Housatonic River! 2 bedroom, 2 full baths-both ensuite + central AC, and a Scandinavian soapstone wood stove, permit included! Minutes from hiking trails, Taft

  Claudia Laslie LANCE VERMEULEN RE, INC

  324 Park St, Great Barrington, MA 01230

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