Berkshire, MA Homes

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  /61

  $846,000 Sold May 16, 2025

  • 3,020 Sq Ft
  • $280/SF
  • 6 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1987

  4 Pleasant View Dr, Great Barrington, MA 01230

  Nestled ''On The Hill'' in one of Great Barrington's most sought-after neighborhoods, this well-built expanded Cape sits on 1.69 acres, offering the perfect blend of privacy, charm, and space. From the moment you arrive, the home's warmth and character welcome you in, promising both comfort and versatility for its next steward.

  Nick Geranios WILLIAM PITT SOTHEBY'S - LENOX

  4 Pleasant View Dr, Great Barrington, MA 01230
• 

  

  

  /7

  Est $214,722 Not Listed For Sale

  • 2 Beds

  Unlisted Address

  Unlisted Address
• 

  

  

  /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
• 

  

  

  /40

  $276,000 Sold May 06, 2025

  • 1,800 Sq Ft
  • $153/SF
  • 62 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1900

  357 State Rd, Great Barrington, MA 01230

  This fixer-upper near Butternut Ski Area offers a unique opportunity for those looking to create their dream home. The property boasts abundant natural light, a wraparound lower level, and 4 spacious yet quaint bedrooms. Many original features are found in this 1900s home, which will add character to any remodeling. The enclosed front porch offers a peaceful place to enjoy the views of the

  Paige Paluch LANCE VERMEULEN RE, INC

  357 State Rd, Great Barrington, MA 01230
• 

  

  

  /39

  Est $878,666 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,110 Sq Ft

  213 Egremont Plain Rd, Great Barrington, MA 01230

  213 Egremont Plain Rd, Great Barrington, MA 01230
• 

  

  /45

  $1,495,000

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

  21 Kalliste Hill, Great Barrington, MA 01230

  SWEEPING MOUNTAIN VIEWS less than 5 minutes to Main Street. Sited on 5+ acres, this stylish contemporary is located in the most desirable section of Great Barrington. The home has an open living/dining/kitchen floor plan with a gas fireplace and huge windows taking in the view. A screened porch is conveniently located off the kitchen. The first floor also has a primary bedroom suite with full

  Tom Lynch COMPASS MASSACHUSETTS , LLC GB

  21 Kalliste Hill, Great Barrington, MA 01230
• 

  

  /63

  $740,000 Sold Apr 25, 2025

  • 3,284 Sq Ft
  • $225/SF
  • 183 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1780

  37 Egremont Plain Rd, Great Barrington, MA 01230

  This 1700s Dutch farmhouse is filled with history and was originally utilized for farming and wagon manufacturing. The residence boasts spacious, well-lit rooms with stunning wide plank wood flooring, offering a grand setting for gatherings and entertainment. The sizable kitchen and dining area, along with four bedrooms and two fully renovated bathrooms, provide ample living space. A highlight of

  Paige Paluch LANCE VERMEULEN RE, INC

  37 Egremont Plain Rd, Great Barrington, MA 01230
• 

  

  /27

  Est $677,459 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,929 Sq Ft

  77 Castle St, Great Barrington, MA 01230

  77 Castle 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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  /9

  $825,000 Sold Apr 14, 2025

  • 1,566 Sq Ft
  • $527/SF
  • 3 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2024

  281 Main St Unit 13, Great Barrington, MA 01230

  New York style living in the Berkshires! Poised above Main Street Great Barrington, this Southworth Penthouse Condo offers 1,566 sq ft comprised of 2 bedrooms, 2 1/2 baths, kitchen, laundry, storage, dining and living rooms with high ceilings and, views to the West. Walk to the heart of town, shopping, Coop market, restaurants, movie theater and, The Mahaiwe Performing Arts Center and more!

  Mandy Victor-pieczarka STONE HOUSE PROPERTIES, LLC

  281 Main St Unit 13, Great Barrington, MA 01230
• 

  

  /33

  Est $1,332,070 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,642 Sq Ft

  97 Corser Hill Rd, Great Barrington, MA 01230

  97 Corser Hill Rd, Great Barrington, MA 01230
• 

  

  /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
• 

  

  /22

  $830,000 Sold Apr 11, 2025

  • 2,500 Sq Ft
  • $332/SF
  • 49 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1963

  4 Highland Dr, Great Barrington, MA 01230

  Situated ''on the hill'' in Great Barrington, this sprawling ranch home offers the perfect combination of peace, privacy, and proximity to nature. Abutting McAllister Wildlife Refuge, you'll enjoy access to 94 acres of stunning conservation land and Green River access.The 5-bedroom, 2.5-bath single-level layout is filled with potential, whether you're looking to modernize or customize the space.

  Samantha Homeyer BIRCH PROPERTIES

  4 Highland Dr, Great Barrington, MA 01230
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  /64

  Est $1,128,522 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,312 Sq Ft

  20 Taconic Ln, Great Barrington, MA 01230

  20 Taconic Ln, Great Barrington, MA 01230
• 

  

  /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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  /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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  /43

  Est $1,170,592 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,416 Sq Ft

  21 Brainard Ave, Great Barrington, MA 01230

  21 Brainard Ave, Great Barrington, MA 01230
• 

  

  /31

  $499,000

  • 4 Beds
  • 2 Baths
  • 2,112 Sq Ft

  115 Bridge St, Great Barrington, MA 01230

  BRIDGERTOWN Investment opportunity or live with income potential. This 2 unit in-town has a 3 bedroom 1 bath on the 1st floor apartment and a 1 bedroom 1 bath on the 2nd floor with room to expand to in the 3rd floor attic space. Walk to town of Great Barrington with all it has to offer, 1/2 block to Co-op and Main St. Utilities are included in rent as electric and heat is combined. 1 car garage

  Mark Rosengren LANCE VERMEULEN RE, INC

  115 Bridge St, Great Barrington, MA 01230
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  /27

  $580,000 Sold Mar 31, 2025

  • 3,276 Sq Ft
  • $177/SF
  • 7 Days On Market

  • 6 Beds
  • 2 Baths
  • Built 1900

  34 Pleasant St, Great Barrington, MA 01230

  PLEASANT OPPORTUNITY! Check out this in-town two-family property on a quiet street. With a little work this is a great home to either live and have additional income, or as a great investment property. Close to downtown and all Great Barrington has to offer. Two-story home has large, bright rooms, newer heating system, large covered front porch and walk-out basement area for storage and work

  Mark Rosengren LANCE VERMEULEN RE, INC

  34 Pleasant St, Great Barrington, MA 01230
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  /32

  Est $1,095,070 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,400 Sq Ft

  89 Taconic Ave, Great Barrington, MA 01230

  89 Taconic Ave, Great Barrington, MA 01230
• 

  

  /29

  $795,000

  • 3 Beds
  • 2 Baths
  • 1,771 Sq Ft

  165 Maple Ave Unit D, Great Barrington, MA 01230

  Beautiful condo with open plan concept, wide pine flooring and so much light. Upscale kitchen, first floor primary with bath and laundry. Three bedrooms, two full baths plus a bonus room waiting to be finished. There is also a lovely screened porch plus a rear deck for grilling. Live on one level. The walk out lower level could also be additional living space. It is beautifully landscaped within

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  165 Maple Ave Unit D, Great Barrington, MA 01230
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  /45

  $715,000 Sold Mar 31, 2025

  • 2,352 Sq Ft
  • $304/SF
  • 138 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2001

  48 Quarry St, Great Barrington, MA 01230

  Immaculate and sparkling home within walking distance to downtown. Easy care with 4 bedrooms, 2.5 baths, open plan, gleaming wood floors, high ceilings, loads of light, updated chef's kitchen with brand new appliances, fireplace in large living room, family room, first floor laundry, ensuite spacious primary. The walk out lower level has a work out room or office and a two car garage. Quiet

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  48 Quarry St, Great Barrington, MA 01230
• 

  

  /31

  Est $861,237 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,304 Sq Ft

  193 East St, Great Barrington, MA 01230

  193 East St, Great Barrington, MA 01230
• 

  

  /48

  $3,750,000

  • 4 Beds
  • 4.5 Baths
  • 5,300 Sq Ft

  116 Brush Hill Rd, Great Barrington, MA 01230

  Custom Built Craftsman Contemporary Home nestled in a beautifully landscaped property with an orchard, gardens and path to a seasonal brook. Inside this well appointed home you will find large rooms Vaulted ceilings, whimsical lighting, Fireplaces, Indoor pool, hot tub and sauna, radiant floor & forced air throughout. Two primary suites on main floor and 2/3 more bedrooms in the lower walkout

  Mark Rosengren LANCE VERMEULEN RE, INC

  116 Brush Hill Rd, Great Barrington, MA 01230
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  /32

  $1,375,960 Sold Mar 31, 2025

  • 2,754 Sq Ft
  • $500/SF
  • 199 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1997

  142 Main Rd, Great Barrington, MA 01230

  On the Water in Monterey! This one owner Colonial styled residence is now on the market for the first time in 27 years. As part of the Steven's Lake private association, you can enjoy swimming and kayaking without the constant noise and the disruption of power boats. The screened porch and open area deck are idyllic for your own relaxation or for entertaining guests. With updating here and

  George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  142 Main Rd, Great Barrington, MA 01230
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  /23

  Est $475,535 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,016 Sq Ft

  913 Main St, Great Barrington, MA 01230

  913 Main St, Great Barrington, MA 01230
• 

  

  /26

  $660,000

  • 3 Beds
  • 2.5 Baths
  • 1,790 Sq Ft

  3 Roger Rd, Great Barrington, MA 01230

  Stylish Contemporary Home in a Prime Great Barrington Location! This beautifully maintained 3-bedroom, 2.5-bath Contemporary offers a lot of space and light-filled layout with high ceilings. The open-concept living area features a cathedral ceiling & gas fireplace, creating a warm and inviting atmosphere.Enjoy the convenience of a first-floor primary suite, filled with natural light from

  Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  3 Roger Rd, Great Barrington, MA 01230
• 

  

  /23

  $630,000 Sold Mar 27, 2025

  • 1,799 Sq Ft
  • $350/SF
  • 112 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1900

  49 Pine St, Great Barrington, MA 01230

  Welcome to your dream investment opportunity or multi-generational living paradise! Nestled on a tranquil side street, this newly renovated two-family home offers the perfect blend of modern amenities and charming character. Located just minutes away from vibrant town parks, scenic hiking trails, the serene river walk, a local co-op, and a bustling shopping area, this property provides an ideal

  Suzann Ward HOUSATONIC REAL ESTATE

  49 Pine St, Great Barrington, MA 01230
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  /27

  Est $494,019 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft

  103 East St, Great Barrington, MA 01230

  103 East 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
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  /16

  $460,000 Sold Mar 14, 2025

  • 1,638 Sq Ft
  • $281/SF
  • 159 Days On Market

  • 2 Beds
  • 3.5 Baths
  • Built 1950

  273 State Rd, Great Barrington, MA 01230

  Spacious, wood-sided ranch with two large bedrooms and three full baths, on a partially wooded, one acre lot located close to town and Butternut Ski area. Open plan living spaces with skylight above the dining and living area. Formal dining room or den adjacent to the living room area and a large screen room off kitchen connected via French doors. Large family room and a bonus room in basement.

  Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  273 State Rd, Great Barrington, MA 01230
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  /42

  Est $1,118,720 Not Listed For Sale

  • 6 Beds
  • 2.5 Baths
  • 4,138 Sq Ft

  32 Benton Ave, Great Barrington, MA 01230

  32 Benton Ave, Great Barrington, MA 01230
• 

  

  /40

  $1,295,000

  • 3 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  247 Peter Menaker Rd, Great Barrington, MA 01230

  Experience the epitome of luxury and leisure in this exceptional custom-built contemporary home, nestled within a prestigious lakefront community. Sited on over four acres, this property offers exclusive access to a private beach and tennis courts, ensuring a lifestyle of both privacy and recreation. Boasting a sun-filled open floor plan, this residence features three well-appointed bedrooms and

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  247 Peter Menaker Rd, Great Barrington, MA 01230
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  /57

  $2,050,000 Sold Mar 07, 2025

  • 3,478 Sq Ft
  • $589/SF
  • 197 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1904

  3 Berkshire Heights Rd, Great Barrington, MA 01230

  Built in 1904 this historic home sits on a beautiful 1.4-acre lot, which offers privacy while being in the most coveted and accessible neighborhood of Great Barrington. High ceilings and adorned with oak and mahogany woodwork throughout, this home has been tastefully renovated while retaining its period charm. The spacious layout, with 4 bedrooms, 31/2 bathrooms and an expansive porch provide

  Martin Albert COMPASS MASSACHUSETTS , LLC GB

  3 Berkshire Heights Rd, Great Barrington, MA 01230
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  /37

  Est $779,188 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,640 Sq Ft

  680 S Egremont Rd, Great Barrington, MA 01230

  680 S Egremont Rd, Great Barrington, MA 01230
• 

  

  /3

  $349,000

  • Land
  • 73 Acres
  • $4,782 per Acre

  0 Lake Buel Rd, Great Barrington, MA 01230

  Beautiful Building Site - 72.98 acres in Great Barrington. Gently sloping land abuts the Appalachian Trail and East Mountain State Forest. Shared driveway off Aberdeen Road in New Marlborough. Cleared spot with a partially built barn/workshop on site. Rough driveway in place. Tranquil spot for your dream home!

  Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  0 Lake Buel Rd, Great Barrington, MA 01230
• 

  

  /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
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  /25

  Est $487,926 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,152 Sq Ft

  176 East St, Great Barrington, MA 01230

  176 East St, Great Barrington, MA 01230
• 

  

  /35

  $520,000

  • 3 Beds
  • 2.5 Baths
  • 1,922 Sq Ft

  220 N Plain Rd, Great Barrington, MA 01230

  An 1825 colonial has much of its original charm and features in place - wide plank floors, beamed ceiling, original hardware and fully renovated kitchen. Many new appliances, new windows, and foam insulation in the basement. The well insulated attic and walls along with a high efficiency furnace gives you modern comfort. The house is a legal two family. The Studio apartment is attached and could

  Martin Albert COMPASS MASSACHUSETTS , LLC GB

  220 N Plain Rd, Great Barrington, MA 01230
• 

  

  /23

  $155,000 Sold Feb 18, 2025

  • 1,280 Sq Ft
  • $121/SF
  • 64 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1880

  10 Tyrell Rd, Great Barrington, MA 01230

  Nestled in the charming town of Egremont, in the heart of the picturesque Berkshires, this property presents an incredible opportunity for those with a vision. This classic NE farmhouse sits on 1.6 acres and offers 3 bedrooms and 1 bathroom brimming with potential! A short drive from Great Barrington, Tanglewood, and numerous outdoor recreational opportunities, this home offers the perfect

  Christina Acor LAMACCHIA REALTY, INC

  10 Tyrell Rd, Great Barrington, MA 01230

Showing Results 121 - 160, Page 4 of 18