Great Barrington, MA Homes for Sale

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  /28

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft

  418 Monterey Rd, Great Barrington, MA 01230

  THE ULTIMATE FOUR SEASON BERKSHIRE RETREAT- Tucked away on 3.6 serene acres, this bright & airy single-level home is the perfect year-round escape. This completely renovated home offers an open concept main living area including the dining room, efficient eat-in kitchen with stainless steel appliances & family room with wood stove, perfect for relaxation & entertaining. Two additional guest rooms

  Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  418 Monterey Rd, Great Barrington, MA 01230
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  /5

  $119,000

  • Land
  • 4.85 Acres
  • $24,536 per Acre

  0 Division St, New Marlborou, MA 01230

  A beautiful land offering with a combination of natural features and convenience. This property borders the Housatonic River providing a peaceful setting, some distant southern mountain views create a scenic backdrop. Fairly level, well suited for a variety of potential uses.

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  0 Division St, New Marlborou, MA 01230
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  /49

  $749,000

  $50K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,008 Sq Ft

  1 Cornwall Dr, Great Barrington, MA 01230

  Fantastic opportunity to own a home in a peaceful cul-de-sac within the desirable Cornwall Estates. This lovely home sits on a level lot w/ almost 2.5 bucolic acres. Spanning just over 2,000 square feet, the home features a convenient first-floor primary bedroom and bathroom, vaulted ceiling in the living room and a screened in porch that leads to a large, partially fenced in backyard. Many

  Stephen Schoenfeld WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  1 Cornwall Dr, Great Barrington, MA 01230
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  /27

  $349,000

  • 3 Beds
  • 1 Bath
  • 875 Sq Ft

  11 Wyantenuck St, Housatonic, MA 01236

  Located on a quiet street in Housatonic, this charming cottage offers easy single-level living in a peaceful neighborhood setting. Set on a sunny double lot, the property provides extra outdoor space and flexibility with room to garden, entertain, play, or simply enjoy the surroundings. Inside, the home features an efficient layout filled with natural light, creating a bright and comfortable

  Paige Backhaus WILLIAM RAVEIS - BERKSHIRE

  11 Wyantenuck St, Housatonic, MA 01236
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  /34

  $679,000

  • 2 Beds
  • 2 Baths
  • 1,308 Sq Ft

  80 Taconic Ave Unit 8, Great Barrington, MA 01230

  Enjoy the best of Great Barrington from this beautifully updated ground-level condominium in On the Hill. Offering easy one-level living, this inviting home features an updated kitchen with abundant storage, new appliances, and bar seating, plus a spacious dining area perfect for gathering with family and friends. The sunken living room boasts a wood-burning fireplace and opens to a private patio

  Michael Linden WILLIAM RAVEIS - BERKSHIRE

  80 Taconic Ave Unit 8, Great Barrington, MA 01230
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  /32

  $734,900

  $44K PRICE DROP

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

  165 Maple Ave Unit D, Great Barrington, MA 01230

  Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless

  Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

  165 Maple Ave Unit D, Great Barrington, MA 01230
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  /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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  /71

  $875,000

  $275K PRICE DROP

  • 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
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  /15

  $550,000

  • 4 Beds
  • 2 Baths
  • 2,346 Sq Ft

  88 Main St, Great Barrington, MA 01230

  Building has been used as an antique business for the last 50 years. Seller had previously lived in the upstairs apartment. Located across the street from Mend and Calgary's and .5 miles from downtown Great Barrington. Selling as is, business and inventory for sale separately - negotiable with owner. Near all the cultural events specific to the Berkshires!

  Freddy Friedman Birch Properties

  88 Main St, Great Barrington, MA 01230
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  /37

  $7,250,000

  New Construction

  • 6 Beds
  • 7 Baths
  • 13,175 Sq Ft

  209 Blue Hill Rd, Great Barrington, MA 01230

  A rare French Manor estate on one of the most scenic and sought-after country roads, this extraordinary 45+/- acre sanctuary offers unmatched privacy, panoramic mountain views, and a setting of timeless beauty. Bordering protected state forest, the property unfolds across rolling meadows, tranquil ponds, and a gently flowing brook-creating a secluded retreat that feels worlds away, yet remains

  Mauren White-Kirkby Barnbrook Realty

  209 Blue Hill Rd, Great Barrington, MA 01230
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  /2

  $2,400,000

  • Land
  • 38.2 Acres
  • $62,827 per Acre

  3 Jenssen Rd, Great Barrington, MA 01230

  3 lots available to develop in EgremontParcels, 008.0-0000-0123.0, 008.0-0000-0283.0, 008.0-0000-0048.0

  Jeremy Casey SR Commercial Realty

  3 Jenssen Rd, Great Barrington, MA 01230
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  /39

  $600,000

  • 6 Beds
  • 5 Baths
  • 3,502 Sq Ft

  53 Mahaiwe St, Great Barrington, MA 01230

  Prime investment opportunity! This five-unit property features a desirable mix of four, one-bedroom apartments & one, two-bedroom. All units have their own separate heating & electrical systems! Convenient location ensures high demand due to proximity to stores and the hospital. On-site parking. Detached garage/workshop could be rented separately for additional income or used as storage for

  Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

  53 Mahaiwe St, Great Barrington, MA 01230
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  /26

  $399,900

  • 4 Beds
  • 1 Bath
  • 1,337 Sq Ft

  153 State Rd, Great Barrington, MA 01230

  Neat as a pin cape walking distance to downtown Great Barrington and amenities, this home has been thoughtfully renovated top to bottom. This sweet property, also zoned commercially, has 4 bedrooms, a full bath, and even a partially finished basement. The kitchen, complete with a large pantry, retains the charming mid century details, while appealing to the modern aesthetic. Outside, there is a

  Lauren Rosen WILLIAM RAVEIS - BERKSHIRE

  153 State Rd, Great Barrington, MA 01230
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  /59

  $2,265,000

  $130K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,600 Sq Ft

  10 Berkshire Heights Rd, Great Barrington, MA 01230

  Luxurious, fully-modernized 1850s Victorian in the heart of Great Barrington. Elegant, four-story 3600 sq. ft. newly renovated clapboard and shingle house with covered porch. Meticulous renovation features chef's kitchen, four+ bedrooms, 4.5 bath, second floor and basement laundry, walk-out finished basement with private entrance and bathroom, perfect for guest suite or professional office.

  Suzann Ward HOUSATONIC REAL ESTATE

  10 Berkshire Heights Rd, Great Barrington, MA 01230
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  /48

  $769,000

  • 3 Beds
  • 3 Baths
  • 1,747 Sq Ft

  9 Abbey Hill Dr, Great Barrington, MA 01230

  Minutes to the vibrant town of Gt. Barrington, you'll find this immaculate move-in ready contemporary home on a quiet country road. House is set nicely back from the street; over an acre of landscaped rolling lawn and very private setting. Bluestone walk-way leads to the front entry. Step inside and find the main level featuring a delightful open plan -great room has gleaming hardwood flooring,

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  9 Abbey Hill Dr, Great Barrington, MA 01230
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  /64

  $3,500,000

  • 5 Beds
  • 6.5 Baths
  • 6,088 Sq Ft

  110 Alford Rd, Great Barrington, MA 01230

  Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire

  Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  110 Alford Rd, Great Barrington, MA 01230
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  /50

  $935,000

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

  20 Cooper Rd, Great Barrington, MA 01230

  The mid-century retreat you've been waiting for. This classic home sits on over 4 private acres, delivering the ultimate Berkshire lifestyle with a bright, open floor plan and two cozy fireplaces. With 4 bedrooms, 3 baths, a large office, and a sun room looking overlooking your oasis, the layout offers perfect flexibility for guests or remote work. Outside, your private resort features a heated

  Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

  20 Cooper Rd, Great Barrington, MA 01230
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  /17

  $629,000

  • 2 Beds
  • 2 Baths
  • 1,308 Sq Ft

  80 Taconic Ave, Great Barrington, MA 01230

  Lovely single level condo on the Hill. Just a short walk to town, The Oakwood provides a quiet community with a lovely pool, garaged parking, and mature landscaping. 2 bedrooms, 2 baths, a cozy living room with a wood burning fireplace and sliders to a sunny deck. Freshly painted, neat as a pin, and ready to move into.

  Robin Ban COMPASS MASSACHUSETTS , LLC GB

  80 Taconic Ave, Great Barrington, MA 01230
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  /28

  $995,000

  $205K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,328 Sq Ft

  3 Pleasant View Dr, Great Barrington, MA 01230

  Rare offering of over six acres ''On the Hill'', sprawling residence with first floor primary, large eat-in kitchen with cozy fireplace.. porch-privacy-garage..open acreage bordered by woods.. walking distance to Main Street, Skiing and Lake Mansfield nearby...Five bedrooms, three baths. Formal living room.Plenty of room for expansion.

  Martha Piper THE KINDERHOOK GROUP

  3 Pleasant View Dr, Great Barrington, MA 01230
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  /27

  $379,000

  $51K PRICE DROP

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

  9 Stanley Dr, Great Barrington, MA 01230

  Get ready to relax in the Berkshires in your new condo with big windows, high ceilings, plus brand new boiler & A/C! Owner retiring and moving down south, giving up his beloved in town Great Barrington location. You'll love being close to stores and provisions for your various adventures, while being close to all the attractions that the Berkshires have to offer. And, at an approximately two and

  Richard Needelman BISHOP WEST REAL ESTATE

  9 Stanley Dr, Great Barrington, MA 01230
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  /24

  $615,000

  $80K PRICE DROP

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

  14 Prospect St, Great Barrington, MA 01230

  'ON THE HILL' Cozy 4 bedroom 1925 Cape,OPEN HOUSE JULY 25, Saturday 2:00-3;30WALK TO CENTER OF GREAT BARRINGTON AND LAKE MANSFIELD. Living room with mini split, custom built in cabinets in dining room, Large primary bedroom with mini split, large family room, OPEN FRONT PORCH WITH VIEWS.BACK YARD PATIO FOR COOK OUTS.Attached 1 car garage,TOWN WATER AND SEWER.So much charm,

  Rosemary Baumann HOUSATONIC REAL ESTATE

  14 Prospect St, Great Barrington, MA 01230
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  /29

  $307,000

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  9 Forest Row, Great Barrington, MA 01230

  Why rent when you can own in a delightful neighborhood. Immaculate ground level unit in the private country community of Forest Row., located just a few minutes from downtown Great Barrington. Forest Row is a Community Land Trust Neighborhood. Easy care one level living with an open floor plan, private screened porch and a patio bordered by gardens and woods, surrounded by 21 acres of protected

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  9 Forest Row, Great Barrington, MA 01230
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  /71

  $2,250,000

  • 4 Beds
  • 6 Baths
  • 4,846 Sq Ft

  302 Egremont Plain Rd, Great Barrington, MA 01230

  A completely transformed barn renovated into a chic home with every modern convenience. Located in the desirable town of Egremont and just minutes from Great Barrington, this delightful property offers long-range pasture views with direct Green River waterfront.Thoughtful living spaces for every walk of life featuring a roomy primary suite on the first floor, an additional primary suite that

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  302 Egremont Plain Rd, Great Barrington, MA 01230
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  /43

  $1,250,000

  $140K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 2,900 Sq Ft

  228 East St, Great Barrington, MA 01230

  Great Barrington A masterful rebuild with reverence for Great Barrington's past and a bold reimagining for modern living. This 5-bedroom, 4-1/2 bath colonial sits in-town and blends historic charm with contemporary luxury for effortless, years-long comfort. Property Highlights 5 Bedrooms | 4 Full Baths + 1 Half Bath**Complex rebuild from the ground up** - preserved nod to the town's heritage

  Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  228 East St, Great Barrington, MA 01230
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  /15

  $447,300

  $10K PRICE INCREASE

  • 1 Bed
  • 1 Bath
  • 568 Sq Ft

  148 Maple Ave Unit 12, Great Barrington, MA 01230

  Nestled amidst the picturesque embrace of Great Barrington, where the harmonious blend of nature and small-town charm unfolds, The Laurel beckons you into a realm of opulence and refinement. As you step inside, a grand two-story glass atrium lobby welcomes you with a breathtaking display of contemporary design and lavish furnishings. Lush plants and waterfalls adorn the walls, seamlessly

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  148 Maple Ave Unit 12, Great Barrington, MA 01230
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  /31

  $1,625,000

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

  5 Thrushwood Ln, Great Barrington, MA 01230

  Enjoy the relaxing Berkshire lifestyle on a friendly cul-de-sac within walking distance of town and Lake Mansfield. As the first house built on the street, the property has matured beautifully -- seasonal flowering trees and pollinator-friendly gardens bring color and life to the yard from spring through fall. Cedar columns frame a distinctive front door that opens into 3,800 square feet of

  Kevin White HARSCH ASSOCIATES

  5 Thrushwood Ln, Great Barrington, MA 01230
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  /86

  $4,250,000

  • 5 Beds
  • 8 Baths
  • 6,378 Sq Ft

  58 Round Hill Rd, Great Barrington, MA 01230

  Come relax amid sweeping pastoral and mountain views in this exceptional retreat designed for both entertaining and everyday comfort. The impressive great room, anchored by a massive stone fireplace, offers a welcoming focal point and flows into a spacious well-designed kitchen/dining area. A screened porch with fireplace overlooks the pool and rolling landscape, creating a seamless

  Sheila Thunfors STONE HOUSE PROPERTIES, LLC

  58 Round Hill Rd, Great Barrington, MA 01230
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  /62

  $2,400,000

  • 2 Beds
  • 3 Baths
  • 2,616 Sq Ft

  39 Pine Crest Cross Rd, Egremont, MA 01230

  Set in one of Egremont's most coveted locations, this remarkable contemporary residence commands sweeping views across the surrounding landscape, with beautifully curated gardens that create a setting of exceptional beauty and privacy. Thoughtfully conceived and meticulously crafted, the home seamlessly integrates sophisticated contemporary architecture with carefully preserved elements of the

  Sheila Thunfors STONE HOUSE PROPERTIES, LLC

  39 Pine Crest Cross Rd, Egremont, MA 01230
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  /37

  $415,000

  $60K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft

  8 Stillwell St, Great Barrington, MA 01230

  Step into effortless Berkshire living in this design-forward mid-century ranch. Perfectly positioned on a quiet downtown dead-end road, this 3-bedroom, 1-bathroom home seamlessly blends crisp, modern style with classic architectural character. Inside, original hardwood floors guide you through a bright, fluid one-level layout. The living room serves as a comfortable anchor for cozy mountain

  Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  8 Stillwell St, Great Barrington, MA 01230
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  /20

  $950,000

  $50K PRICE DROP

  • 5 Baths
  • 5,180 Sq Ft

  406 Main St, Great Barrington, MA 01230

  FOR SALE: Prime Downtown Great Barrington Gem - Endless Possibilities! Welcome to 406 Main Street, a rare opportunity in the heart of downtown Great Barrington, MA. Just steps from bustling Main Street shops and restaurants, this versatile 5,180 sq ft building offers exceptional potential for residential, commercial, or creative mixed-use transformation. Zoned B2, the property allows for

  Jason Saphire www.HomeZu.com

  406 Main St, Great Barrington, MA 01230
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  /38

  $1,195,000

  $100K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,688 Sq Ft

  260 Maple Ave, Great Barrington, MA 01230

  Sun Filled Historic Reproduction HomeBuilt in 2004 seamlessly blends old-world charm with contemporary comfort. Set on 1.82 acres with sweeping mountain views, this 3-bedroom, 2.5-bathroom home features meticulous hand-crafted details throughout-honoring traditional design while offering the conveniences of modern construction. The welcoming gourmet eat-in kitchen is perfect for everyday

  Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  260 Maple Ave, Great Barrington, MA 01230
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  /30

  $6,475,000

  • 9 Beds
  • 11 Baths
  • 12,968 Sq Ft

  250 Long Pond Rd, Great Barrington, MA 01230

  Experience a rare Zen-inspired retreat in the heart of the Berkshires, brilliantly designed to exist in harmony with its natural surroundings. Set on nearly 120 acres of protected land with striking rock outcroppings, sweeping mountain views, and frontage along the Williams River, this architecturally significant contemporary offers a true sense of privacy, tranquility, and escape- all just

  Elyse Morris Elyse Harney Real Estate

  250 Long Pond Rd, Great Barrington, MA 01230
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  /55

  $1,295,000

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

  3 Cornwall Dr, Great Barrington, MA 01230

  Tucked away at the end of a private cul-de-sac on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The

  Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  3 Cornwall Dr, Great Barrington, MA 01230
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  /79

  $2,295,000

  $200K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 3,615 Sq Ft

  17 Cronk Rd, Great Barrington, MA 01230

  Originally built in the 1700s, this historic post-and-beam barn has been thoughtfully renovated over time while maintaining its unique character and charm. A recently installed solar energy system allows for highly efficient living with the potential for an off-grid lifestyle.The home features an open floor plan filled with natural light from numerous oversized windows. A chef's kitchen

  Suzann Ward HOUSATONIC REAL ESTATE

  17 Cronk Rd, Great Barrington, MA 01230
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  /25

  $549,900

  Open Thu 4PM - 5:30PM $50K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,257 Sq Ft

  15 Cone Ave, Great Barrington, MA 01230

  Built in 2019 and tucked away on 1.73 private acres in Housatonic, this beautifully maintained 3-bedroom, 3-bath ranch offers nearly 2,915 sq. ft. finished. The main level features a spacious primary suite with walk-in closet and private bath, main-floor laundry, and red oak flooring milled from trees harvested on the property during construction. The finished walkout lower level includes a huge

  Jesse Dimitropolis RE/MAX COMPASS

  15 Cone Ave, Great Barrington, MA 01230
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  /18

  $499,000

  $126K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,438 Sq Ft

  402 Park St, Great Barrington, MA 01230

  This well-maintained mixed-use property offers excellent flexibility for both commercial and residential use. The building is currently configured as two separate units. The first floor features a bright commercial space with large front-facing windows that provide excellent visibility and natural light--ideal for office or retail use. The space includes a private bathroom, dedicated heating and

  Suzann Ward HOUSATONIC REAL ESTATE

  402 Park St, Great Barrington, MA 01230
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  /17

  $629,000

  • 2 Beds
  • 2 Baths
  • 1,308 Sq Ft

  80 Taconic Ave Unit 2, Great Barrington, MA 01230

  Lovely single level condo on The Hill. Just a short walk to town , The Oakwood provides a quiet community with a lovely pool, garaged parking , and mature landscaping . 2 bedrooms, 2 baths, a cozy living room with fireplace and sliders to a sunny patio. Freshly painted and ready to move into.

  Robin Ban COMPASS MASSACHUSETTS , LLC GB

  80 Taconic Ave Unit 2, Great Barrington, MA 01230
• 

  /2

  $185,000

  • Land
  • 1.51 Acres
  • $122,516 per Acre

  0 Christian Hill Rd, Great Barrington, MA 01230

  Great LOCATION/TOWN WATER/SEWER Nice level building lot 1.51 acres 150' frontage with privacy and advantages of being close to Lake Mansfield and downtown Great Barrington. Great opportunity to won one of the few remaining building lots in town

  Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  0 Christian Hill Rd, Great Barrington, MA 01230
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  /3

  $95,000

  • Land
  • 2.92 Acres
  • $32,534 per Acre

  0 Hemlock Hill Rd, Great Barrington, MA 01230

  PREMIERE LOCATION JUST FIVE MINUTES FROM MAIN STREET. Building site cleared. Rough driveway in. Electricity easily accessible. Septic design in place. An excellent investment in the ''boom town'' of the Berkshires.

  Tom Lynch COMPASS MASSACHUSETTS , LLC GB

  0 Hemlock Hill Rd, Great Barrington, MA 01230
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  /74

  $3,495,000

  • 4 Beds
  • 4.5 Baths
  • 4,792 Sq Ft

  32 Crooked Hill Rd, Great Barrington, MA 01230

  Tucked into more than 20 private acres in the beautiful hills of Alford, 32 Crooked Hill Road is the kind of country home that invites you to settle in and stay awhile. Open meadows, mature woodland, mountain views, and expansive lawn creates a setting that feels wonderfully removed from the everyday. The approximately 4,600-square-foot home is generous yet welcoming. At its heart is a dramatic

  Nikki Carchedi STONE HOUSE PROPERTIES, LLC

  32 Crooked Hill Rd, Great Barrington, MA 01230

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