Berkshire, MA Homes

• 

  

  

  /28

  $495,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  36 Castle Ln, Great Barrington, MA 01230

  Charming Renovated Cottage on The Hill - Great Barrington, MADiscover this beautifully renovated Four Square-style cottage in the heart of Great Barrington's coveted ''The Hill'' neighborhood--a rare pied-a-terre offering classic charm with modern upgrades. This delightful 2-bedroom home is nestled in the Southern Berkshires, just moments from downtown, Lake Mansfield, and preserved natural

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 414-5590

  36 Castle Ln, Great Barrington, MA 01230
• 

  

  

  /4

  $2,000 - $3,500 per month

  Mahaiwe Building

  1 - 3 Beds

  4 Castle St, Great Barrington, MA 01230

  4 Castle St, Great Barrington, MA 01230
• 

  

  

  /38

  $905,000 Sold Aug 05, 2025

  • 2,472 Sq Ft
  • $366/SF
  • 92 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1760

  270 Hillsdale Rd, Great Barrington, MA 01230

  This beautifully renovated former Stage Coach stop blends modern comfort with historic charm. Inside, you'll find an updated, open kitchen and dining area, perfect for entertaining. There is a screened porch for dining al fresco. The living room features a stunning stone fireplace and sun-filled windows. A 1st floor guest suite offers a kitchenette, full bath and gas fireplace. Upstairs, the

  Kate Lascar COMPASS MASSACHUSETTS , LLC GB

  270 Hillsdale Rd, Great Barrington, MA 01230
• 

  

  

  /17

  Est $430,947 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 781 Sq Ft

  281 Main St Unit 4, Great Barrington, MA 01230

  281 Main St Unit 4, Great Barrington, MA 01230
• 

  

  

  /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
• 

  

  /36

  $17 per month

  • 2 Baths
  • 2,490 Sq Ft
  • Property for Rent

  789 Main St, Great Barrington, MA 01230

  An updated commercial condo in a prime location! This versatile space features flexible layout options, and abundant natural light--ideal for office, retail, or professional use. Situated in a high-traffic area with excellent visibility and easy access to major roads and public transit. Perfect for businesses seeking a polished, move-in-ready space in a thriving commercial hub.

  Michael Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  789 Main St, Great Barrington, MA 01230
• 

  

  /37

  $644,000 Sold Aug 01, 2025

  • 1,224 Sq Ft
  • $526/SF
  • 21 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  284 Brewer Branch Rd, Great Barrington, MA 01230

  MID CENTURY MODERN: Built in 1973 of a minimalist design. This very cool home is tucked on a country road. Three bedrooms, two baths with upper level open plan overlooking beautiful light forest. A Fire place anchors the lovely open concept with a wall of windows letting in the sunshine. Perfect as a short term rental when not in use offering guests a beautiful in-ground pool to cool off in the

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  284 Brewer Branch Rd, Great Barrington, MA 01230
• 

  

  /10

  Est $350,972 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 567 Sq Ft

  281 Main St Unit 3, Great Barrington, MA 01230

  281 Main St Unit 3, Great Barrington, MA 01230
• 

  

  /23

  $125,000

  • Land
  • 0.49 Acre
  • $255,107 per Acre

  28 Pearl St, Great Barrington, MA 01230

  Nestled on a quiet dead-end street, this .49-acre parcel offers a unique combination of privacy, scenic beauty, and walk-to-town convenience. The property has been thoughtfully divided to meet local zoning requirements within the defined build envelope as shown (see documents for survey & building envelope). A 200-foot riparian buffer protects the riverfront, ensuring that no structures can ever

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 408-5316

  28 Pearl St, Great Barrington, MA 01230
• 

  /2

  Call for Price

  Apartment for Rent

  1 Bed

  343 Main St, Great Barrington, MA 01230

  343 Main St, Great Barrington, MA 01230
• 

  

  /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
• 

  

  /44

  Est $480,568 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
• 

  

  /47

  $1,750,000

  • 5 Beds
  • 3 Baths
  • 2,808 Sq Ft

  353 State Rd, Great Barrington, MA 01230

  The Woodlands, A RARE OPPORTUNITY TO OWN YOUR OWN 74-ACRE PRIVATE SANCTUARY IN THE HEART OF GREAT BARRINGTON.This property abuts the Thomas & Palmer Brook preserve on three sides, is a two-minute drive to Ski Butternut and five minutes to dining and shopping in downtown Great Barrington. A picturesque pond flows into a babbling brook right outside of the large cathedral-ceiling primary suite's

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  353 State Rd, Great Barrington, MA 01230
• 

  

  /16

  $3,900 per month

  • 0.5 Baths
  • 1,100 Sq Ft
  • Property for Rent

  38 Railroad St, Great Barrington, MA 01230

  Seize the opportunity to establish your business in the vibrant heart of Great Barrington. Located on bustling Railroad Street, this retail space has been the home of a successful art supply store for many years, making it a proven location for success. Offering approximately 1,100 square feet of versatile retail space, with additional storage on the lower level, this storefront is perfectly

  Tony Segalla LANCE VERMEULEN RE, INC

  38 Railroad St, Great Barrington, MA 01230
• 

  

  /41

  $695,000 Sold Jul 31, 2025

  • 18,157 Sq Ft
  • $38/SF
  • 89 Days On Market

  • 8 Baths
  • Built 1959

  445 Monterey Rd, Great Barrington, MA 01230

  Unique property with potential for a wide range of educational, recreational, residential or other potential re-development uses. Formerly part of an residential school facility, the property consists of over 11 acres with extensive road frontage on both sides of Route 23. The buildings include: 1) 10,560 sq. ft. gymnasium w/ levels of office/conference rooms, 750 lb elevator, 4 bathrooms, and

  Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

  445 Monterey Rd, Great Barrington, MA 01230
• 

  

  /28

  Est $680,528 Not Listed For Sale

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

  5 Christian Hill Rd, Great Barrington, MA 01230

  5 Christian Hill Rd, Great Barrington, MA 01230
• 

  

  /69

  $5,900,000

  • 11 Beds
  • 10 Baths
  • 9,748 Sq Ft

  25 W Sheffield Rd, Great Barrington, MA 01230

  Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of future for generations

  Lauren Molk ELYSE HARNEY REAL ESTATE

  25 W Sheffield Rd, Great Barrington, MA 01230
• 

  

  /33

  $9,000 per month

  • 3 Baths
  • 2,200 Sq Ft
  • Property for Rent

  42/44 Railroad St, Great Barrington, MA 01230

  An incredible opportunity awaits in the heart of downtown Great Barrington. This 2,200 square foot space in a historic building features high ceilings, wood floors, a large commercial kitchen, and basement storage. An overhead garage-style door opens from the bar area onto the street, creating an ideal setup for vibrant, street-side dining. Indoor and outdoor seating areas maximize the potential

  Tony Segalla LANCE VERMEULEN RE, INC

  42/44 Railroad St, Great Barrington, MA 01230
• 

  

  /33

  $435,000 Sold Jul 25, 2025

  • 1,698 Sq Ft
  • $256/SF
  • 241 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1981

  12 W Plain Rd, Great Barrington, MA 01230

  Whether the perfect place to downsize to or as a weekend get-away, this comfortable home delivers! The sensible floor plan flows nicely. The main living area opens to a Great Room with tall ceilings, skylight and custom wood work. Relax, Dine & Entertain on the expansive deck, while enjoying the peaceful surroundings. Carefree and manageable one story living. With 7.5 Acres, there is plenty

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  12 W Plain Rd, Great Barrington, MA 01230
• 

  

  /38

  Est $1,180,206 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,047 Sq Ft

  3 Cornwall Dr, Great Barrington, MA 01230

  3 Cornwall Dr, Great Barrington, MA 01230
• 

  

  /52

  $935,000

  • 4 Beds
  • 2.5 Baths
  • 2,631 Sq Ft

  20 Cooper Rd, Great Barrington, MA 01230

  This is the one you've been waiting for. A classic mid-century home on over 4 private acres, offering the ultimate Berkshire lifestyle. The bright, open-mid century floor plan provides a seamless flow, while two fireplaces add classic comfort. The home features 4 bedrooms, 3 baths, large office and a media room, offering flexibility for family and guests. Outside, your private resort awaits. A

  Tony Segalla LANCE VERMEULEN RE, INC

  20 Cooper Rd, Great Barrington, MA 01230
• 

  

  /15

  $1,950 per month

  • 0.5 Baths
  • 2,000 Sq Ft
  • Property for Rent

  490 Main St, Great Barrington, MA 01230

  Second floor office space in a high-traffic location. Currently configured with three offices, a conference room, reception area, and half bath. This space also has air conditioning, forced air heat, and its own electric meter. Ample off-street parking available.

  Lance Vermeulen LANCE VERMEULEN RE, INC

  490 Main St, Great Barrington, MA 01230
• 

  

  /69

  $2,100,000 Sold Jul 21, 2025

  • 7,008 Sq Ft
  • $300/SF
  • 120 Days On Market

  • 7 Beds
  • 6 Baths
  • Built 1987

  300 Alcott Rd, Great Barrington, MA 01230

  Great Barrington Compound! Custom built salt box home situated the end of a town dirt road on 32 acres. Bear Town State Forest abuts the property. Heated gunite pool and stunning view of Monument Mountain. Enjoy established gardens including an apple orchard, lilies, peonies, etc. Main house with living room, library, dining room, eat in kitchen, laundry, two powder rooms, attached two car

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  300 Alcott Rd, Great Barrington, MA 01230
• 

  

  /17

  Est $460,548 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,424 Sq Ft

  3 Hillside Ave, Great Barrington, MA 01230

  3 Hillside Ave, Great Barrington, MA 01230
• 

  

  /37

  $796,000

  • 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
• 

  

  /33

  $18 per month

  • 2 Baths
  • 4,103 Sq Ft
  • Property for Rent

  34 Bridge St, Great Barrington, MA 01230

  Huge price adjustment! One of the most successful locations in Downtown Barrington! Located just one block off the vibrant Main St. and positioned to take advantage the ample foot and vehicle traffic in arguably the most recognizable location in South County. Share the same building as the iconic Berkshire Food Co-op. Four office/retail/studio spaces available. Ample free off-street parking as

  Anthony Blair STONE HOUSE PROPERTIES, LLC

  34 Bridge St, Great Barrington, MA 01230
• 

  

  /35

  $590,600 Sold Jul 16, 2025

  • 1,635 Sq Ft
  • $361/SF
  • 23 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1956

  147 Hurlburt Rd, Great Barrington, MA 01230

  Well constructed home by the notable Gilligan Brothers Construction. Nicely maintained, this solid 1956 Cape style is ready for its new owner.Hardwood floors throughout, Living Room with Fireplace, Open Kitchen/Dining, 3-4 Bedrooms, with Main bedroom and full bath on first floor. 4-Season great room with gas fireplace. Detached Garage and Barn, perennials, meadow, all on 1.29 acres. Convenient

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  147 Hurlburt Rd, Great Barrington, MA 01230
• 

  

  /26

  Est $585,676 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,826 Sq Ft

  30 Silver St, Great Barrington, MA 01230

  30 Silver St, Great Barrington, MA 01230
• 

  

  /52

  $1,295,000

  • 4 Beds
  • 2 Baths
  • 2,742 Sq Ft

  22 Sheffield Rd, Great Barrington, MA 01230

  Discover this enchanting 1900s Town Colonial, where historic charm meets modern sophistication. Nestled in a tranquil neighborhood, this home offers four spacious bedrooms, two updated full baths, and a stunning chef's kitchen, blending comfort with style. From the moment you enter through the newly renovated mudroom, you'll appreciate the original wood floors and built-in shelving that preserve

  Suzann Ward HOUSATONIC REAL ESTATE

  22 Sheffield Rd, Great Barrington, MA 01230
• 

  

  /7

  $1,495 per month

  • 1 Bath
  • 365 Sq Ft
  • Property for Rent

  313 Main St, Great Barrington, MA 01230

  The Berkshire Block on Main Street in Great Barrington has been recently renovated and still has beautiful office spaces available for lease on the second and third floor. Office sizes range from 254 SF to 589 SF, choice of flooring, and can be furnished. Prices start at $975/month. The spaces offer elevator access, fiber internet, common reception area, conference room and restrooms. Private

  Tony Segalla LANCE VERMEULEN RE, INC

  313 Main St, Great Barrington, MA 01230
• 

  

  /42

  $995,000 Sold Jul 15, 2025

  • 2,208 Sq Ft
  • $451/SF
  • 33 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  72 Boice Rd, Great Barrington, MA 01230

  Contemporary Egremont Stunner on 6+ Acres with Artist's Studio!A sleek, design-forward renovation meets total privacy in this contemporary home on 6.3 wooded acres in low-tax Egremont. Set well back from the road amid a green, sun-filled lawn, the property offers sufficient frontage and acreage for multiple lots--providing flexibility to enjoy as-is or explore future build potential.Meticulously

  Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  72 Boice Rd, Great Barrington, MA 01230
• 

  

  /37

  Est $722,119 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,200 Sq Ft

  150 Hurlburt Rd, Great Barrington, MA 01230

  150 Hurlburt Rd, Great Barrington, MA 01230
• 

  

  /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
• 

  

  /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
• 

  

  /21

  Est $389,537 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 960 Sq Ft

  121 Jug End Rd, Great Barrington, MA 01230

  121 Jug End Rd, Great Barrington, MA 01230
• 

  

  /56

  $1,250,000

  • 3 Beds
  • 2.5 Baths
  • 2,447 Sq Ft

  6 Muddy Brook Cir, Great Barrington, MA 01230

  Stunning Contemporary Home in Great Barrington - Perfect Blend of Privacy and ConvenienceDiscover this beautifully designed 2,500 sq. ft. contemporary residence nestled in the desirable Great Barrington area. Offering 3 spacious bedroom suites , this home combines elegant style with everyday functionality.Step outside to your private fantasy backyard -- an entertainer's dream featuring a charming

  Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  6 Muddy Brook Cir, Great Barrington, MA 01230
• 

  

  /29

  $445,000 Sold Jul 11, 2025

  • 1,512 Sq Ft
  • $294/SF
  • 11 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  2 Emily Ct, Great Barrington, MA 01230

  Spotless home with so much to offer. Open plan living with wood floors, lots of windows, three bedrooms, two and a half baths. Ensuite second floor primary. Mini splits for air conditioning, a large and lovely deck with grilling area, dining and sitting area. This home offers privacy with the convenience of being in-town close to shopping, dining and so much more. Move right in and begin

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  2 Emily Ct, Great Barrington, MA 01230
• 

  

  /9

  Est $361,964 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft

  148 Hillsdale Rd, Great Barrington, MA 01230

  148 Hillsdale Rd, Great Barrington, MA 01230
• 

  

  /58

  $1,660,000

  • 4 Beds
  • 3.5 Baths
  • 3,800 Sq Ft

  105 Christian Hill Rd, Great Barrington, MA 01230

  CLASSIC ARCHITECTURE WITH CONTEMPORARY ELEGANCE! A beautifully maintained home set back from the road. Exceptional landscaping embraces the property, offering a private sanctuary. A front porch welcomes you to the first floor. A light-filled,capacious living room, dining room with a fireplace opened to both main rooms, a primary suite with two walk-in closets, a 1/2 bath, and study open to a

  Mandy Victor-pieczarka STONE HOUSE PROPERTIES, LLC

  105 Christian Hill Rd, Great Barrington, MA 01230
• 

  

  /12

  $45,000 Sold Jul 11, 2025

  • Land
  • 1.27 Acres
  • $35,433 per Acre

  • 162 Days On Market

  0 N Plain Rd, Great Barrington, MA 01230

  This 1.27 acre sloped lot offers unparalleled eastern views that stretch as far as the eye can see. Imagine waking up to the serene beauty of the sunrise over the rolling hills every morning!With the lot already cleared and ready for your vision, the possibilities are endless. Whether you're dreaming of building your dream home, a cozy weekend retreat, or an investment property, this is the

  Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  0 N Plain Rd, Great Barrington, MA 01230

Showing Results 1 - 40, Page 1 of 18