Berkshire, MA Homes

• 

  

  

  /56

  $1,150,000

  • 4 Beds
  • 4.5 Baths
  • 2,753 Sq Ft

  213 Egremont Plain Rd, Great Barrington, MA 01230

  This 1700's-era former inn has been recently renovated from top to bottom, preserving its historic New England charm & seamlessly blending all the modern amenities for a comfortable country cottage lifestyle. The home offers 4 bedrooms and 4 baths over 3 generous levels of living areas. The ground level first floor features a cozy & inviting great room with decorative antique fireplace and new

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 475-9305

  213 Egremont Plain Rd, Great Barrington, MA 01230
• 

  

  

  /11

  $3,300 per month

  • 2 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • House for Rent

  1046 County Rd, Great Barrington, MA 01230

  Beautiful, Rustic Converted Barn. 2 bedrooms + small office, 2 BA, meadow, fruit trees, chicken coup, plenty of ground floor storage, W/D. Property is set well off the road next to a seasonal brook. This unique property would make an excellent weekend retreat or full time residence. Field mowing and lawn care are included.

  1046 County Rd, Great Barrington, MA 01230
• 

  

  

  /24

  $550,000 Sold Aug 29, 2025

  • 1,137 Sq Ft
  • $484/SF
  • 72 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2019

  34 Bridge St Unit 201, Great Barrington, MA 01230

  A unique offering, this 2BR, 2BA condo, built in 2019, offers modern convenience & elegant details throughout. Walk out the door into iconic downtown Great Barrington &have all that the town has to offer at your fingertips. Shopping, restaurants, & groceries are less than a minute away. Take in the mountains & the historic Mahaiwe marquee from the French Door balcony opening onto Bridge Street.

  Lauren Rosen LANCE VERMEULEN RE, INC

  34 Bridge St Unit 201, Great Barrington, MA 01230
• 

  

  

  /17

  Est $434,743 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
• 

  

  

  /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
• 

  

  /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
• 

  

  /60

  $772,500 Sold Aug 22, 2025

  • 3,328 Sq Ft
  • $232/SF
  • 22 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 1900

  81 Egremont Plain Rd, Great Barrington, MA 01230

  The ''Broadmeadow Shapiro Farm'' rich with family history, sits on 4.5 private acres and is listed for the first time in 53 years. This antique home is situated minutes from downtown Great Barrington with a peaceful and quiet setting offering multiple living spaces. Charming features include built-in bookshelves and original wood floors, and abundant natural light enhancing each room. The 3,328

  Paige Paluch LANCE VERMEULEN RE, INC

  81 Egremont Plain 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
• 

  

  /29

  $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
• 

  

  /9

  $3,000 per month

  The Garage

  1 Bed

  343 Main St, Great Barrington, MA 01230

  343 Main St, Great Barrington, MA 01230
• 

  

  /25

  $250,000 Sold Aug 20, 2025

  • 1,414 Sq Ft
  • $177/SF
  • 166 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1900

  39 Christian Hill Rd, Great Barrington, MA 01230

  GREAT OPPORTUNITY FOR A SWEET FIXER-UPPER! A feel good house, that with some cosmetics, could be your happy home. So much potential, with wood floors, tall ceilings, front porch and a back deck over looking a lovely, private back yard. A good, solid house, renovation worthy. Not a drive by, interior has much to offer. Trail to Lake Mansfield and the town center within walking distance.

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  39 Christian Hill Rd, Great Barrington, MA 01230
• 

  

  /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

  $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
• 

  

  /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
• 

  

  /30

  $655,000 Sold Aug 14, 2025

  • 1,703 Sq Ft
  • $385/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1957

  33 Creamery Rd, Great Barrington, MA 01230

  Mid-century Ranch nestled on a lush 2.3 acre lot in a desirable Egremont location. Three bedrooms, 2 Full Baths, and a roomy open concept living/dining area with a wood burning Fireplace & vaulted ceiling. The kitchen is compact & thoughtfully laid out, white cabinetry with granite countertops. A wood paneled casual den, a cozy office and a delightful screened porch complete the home. Finished

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  33 Creamery 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
• 

  

  /47

  $1,650,000

  • 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
• 

  

  /4

  $2,000 - $3,000 per month

  Mahaiwe Building

  1 - 3 Beds

  4 Castle St, Great Barrington, MA 01230

  4 Castle St, Great Barrington, MA 01230
• 

  

  /27

  $450,000 Sold Aug 11, 2025

  • 1,512 Sq Ft
  • $298/SF
  • 29 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  8 Stanley Dr Unit A-4, Great Barrington, MA 01230

  SIMPLY IDEAL! UPDATED TOWN-HOUSE, walking distance to restaurants, shops and just minutes from Skiing and downtown Great Barrington. Bright open floor plan, central A/C, 3 BR, 2.5 Baths. Private deck with a fringe of woods bordering. In-unit laundry and an attached garage. Quiet, peaceful and convenient. Move-in ready! Be here for Summer!!

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  8 Stanley Dr Unit A-4, Great Barrington, MA 01230
• 

  

  /38

  Est $1,287,306 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
• 

  

  /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
• 

  

  /44

  $1,440,000 Sold Aug 08, 2025

  • 2,300 Sq Ft
  • $626/SF
  • 5 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1998

  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
• 

  

  /17

  Est $491,942 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
• 

  

  /31

  $799,000

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  77 Grove St, Great Barrington, MA 01230

  LOCATION LOCATION LOCATION! Nestled on a quiet dead-end street near the Great Barrington Food Co-op and River Walk, this beautifully maintained Victorian blends charm and convenience. Inside, you'll find many original details, including hardwood floors, classic moldings, and a welcoming wrap-around front porch. The updated kitchen features a cozy breakfast nook, and very recent improvements

  Kate Lascar COMPASS MASSACHUSETTS , LLC GB

  77 Grove St, 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
• 

  

  /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
• 

  

  /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

  $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
• 

  

  /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
• 

  

  /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
• 

  

  /25

  Est $660,884 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,638 Sq Ft

  33 Grove St, Great Barrington, MA 01230

  33 Grove 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /21

  Est $425,390 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
• 

  

  /58

  $1,660,000

  • 4 Beds
  • 3.5 Baths
  • 3,400 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
• 

  

  /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

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