Great Barrington, MA Homes for Sale

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  /28

  $599,000

  Open Sun 10AM - 1PM

  • 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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• 

  

  

  /54

  $2,595,000

  • 5 Beds
  • 5 Baths
  • 4,305 Sq Ft

  95 Lewis Ave, Great Barrington, MA 01230

  This exquisite single-family home spans an impressive 4,300 square feet, offering an unmatched blend of elegance and modern comfort. With 5 spacious bedrooms and 4.5 beautifully renovated bathrooms, every detail has been meticulously crafted to perfection. Walking distance to downtown Great Barrington's shops and restaurants, the house is in one of the quietest areas of ''The Hill''.12 rooms

  Martin Albert COMPASS MASSACHUSETTS , LLC GB

  95 Lewis Ave, Great Barrington, MA 01230
• 

  

  

  /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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  /22

  $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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  /45

  $575,000

  • 4 Beds
  • 2 Baths
  • 2,103 Sq Ft

  60 Cottage St, Great Barrington, MA 01230

  Positioned within walking distance to the vibrant downtown of Great Barrington, this property offers a unique opportunity for Homeowners, investors, non-profits, or developers seeking flexibility and future upside. Previously utilized as professional offices for mental health services, with vision, this could be converted into a 1 or 2 family home. Significant capital improvements have already

  Tim Gallagher STONE HOUSE PROPERTIES, LLC

  60 Cottage St, 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
• 

  

  /31

  $649,000

  • 4 Beds
  • 2 Baths
  • 3,000 Sq Ft

  783 Main St, Great Barrington, MA 01230

  Renovated, well-maintained, multi-use building perfect for a live-work situation in prime location! All 4 floors offer opportunity for offices, a studio, storage, retail showroom and more! Highlights include: a large parking lot, handicap accessible ramp, 2 half baths & finished 3rd floor attic. Finished basement w/ vault & video security system. The current retail space is bright & sunny with a

  Claudia Laslie WILLIAM RAVEIS - BERKSHIRE

  783 Main St, Great Barrington, MA 01230
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  /76

  $950,000

  $200K 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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  /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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  /58

  $2,265,000

  $130K PRICE DROP

  • 4 Beds
  • 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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  /42

  $1,495,000

  • 3 Beds
  • 3.5 Baths
  • 3,999 Sq Ft

  37 Kalliste Hill, Great Barrington, MA 01230

  Amazing custom-built countryside retreat in The Berkshires. Meticulously maintained since it was built in 1999, this unbeatable 3 BR 3.5 Bath contemporary is located in one of the most sought after neighborhoods in Great Barrington. Perfect for those seeking a serene tranquil setting or a weekend/summer getaway, this home offers a unique inviting layout & is the definition of quality! From the

  James Wood Coldwell Banker Realty - Boston

  37 Kalliste Hill, Great Barrington, MA 01230
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  /64

  $3,500,000

  • 5 Beds
  • 7 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
  • 3 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
• 

  

  /19

  $280,000

  $31K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 1,792 Sq Ft

  54 Division St, Great Barrington, MA 01230

  For the buyer looking to infuse their personal style into a home that has already undergone significant, high value upgrades. The interior offers a bright, refreshed layout awaiting your final aesthetic finishes. Beyond the main residence, this property boasts a substantial 2 story barn. the 70x20 footprint is an incredible asset. Perfectly primed for transformation into an ADU, art studio, or

  Melissa Zoe Hirsch ZOE MELISSA HIRSCH REAL ESTATE

  54 Division St, Great Barrington, MA 01230
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  /54

  $1,375,000

  $120K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 4,200 Sq Ft

  6 Thrushwood Ln, Great Barrington, MA 01230

  MOTIVATED SELLER. Indulge in refined Berkshire living on an exclusive cul-de-sac, where effortless HOA services complement this exquisite new construction. Offering 4,200 sq ft of thoughtfully designed, environmentally conscious living less than a mile from downtown Great Barrington, this home is the perfect modern retreat. Enter through a covered portico into a soaring cathedral-ceiling great

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  6 Thrushwood Ln, 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

  $1,290,000

  $100K PRICE DROP

  • 5 Beds
  • 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
  • 4 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 4,200 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
• 

  

  /37

  $475,000

  • 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
• 

  

  /38

  $1,195,000

  $100K PRICE DROP

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

  260 Maple Ave, Great Barrington, MA 01230

  Timeless Craftsmanship Meets Modern Living-Built in 2004, this exquisitely crafted historic reproduction home 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

  Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  260 Maple Ave, Great Barrington, MA 01230
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  /27

  $365,000

  • 3 Beds
  • 1 Bath
  • 872 Sq Ft

  26 Pine St, Great Barrington, MA 01230

  LAKE BUEL, NEW MARLBOROUGH COTTAGE!For the past 60 years this cottage has been a source of joy for the same family, now it is your turn. Affordable, simple, rustic three season cottage with deeded access to the lake. Well loved and nicely maintained, with updated kitchen, and a beautiful stone fireplace for those chilly evenings. Nice open plan Living/Dining area. Relax on the Deck or gather

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  26 Pine St, 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
  • 4 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

  $2,495,000

  • 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 adjoins

  Suzann Ward HOUSATONIC REAL ESTATE

  17 Cronk Rd, Great Barrington, MA 01230
• 

  

  /25

  $599,900

  • 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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  /53

  $675,000

  • 3 Beds
  • 2 Baths
  • 2,059 Sq Ft

  6 Beacon Hill, Great Barrington, MA 01230

  Welcome to 6 Beacon Hill Rd. where Old world charm meets New world convenience. Antique touches add that history of the Victorian era. If you're lookingfor a quiet neighborhood, walking distance to town and filled with sunlight and style, come and take a look! Enter through the lovely glass enclosed front porch or around back through the muddroom. Get lost in the recent renovated kithen with

  Lawrence Reilly THE KINDERHOOK GROUP

  6 Beacon Hill, Great Barrington, MA 01230
• 

  

  /18

  $525,000

  $100K PRICE DROP

  • 3 Beds
  • 2 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
• 

  /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
• 

  

  /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
• 

  

  /55

  $1,480,000

  • 4 Beds
  • 3 Baths
  • 2,828 Sq Ft

  233 Monument Valley Rd, Great Barrington, MA 01230

  CONTEMPORARY FARMHOUSE! Sited on a knoll dotted with old apples trees overlooking scenic views all framed by a meandering fence. All you could ask for is in this well-built home, offering a first floor primary ensuite, library with fieldstone fireplace, A well appointed kitchen opens to both the dining and a living room with fireplace. A screen porch, 1/2 bath, laundry room/mudroom leading to a 2

  Mandy Victor-pieczarka STONE HOUSE PROPERTIES, LLC

  233 Monument Valley Rd, Great Barrington, MA 01230
• 

  

  /23

  $599,000

  • 2 Beds
  • 1 Bath
  • 1,296 Sq Ft

  39 Castle St, Great Barrington, MA 01230

  Set high up on a knoll, this home boasts good, solid construction, wood floors throughout and an easy, manageable floor plan. Within walking distance to Main Street, this adorable home has been lovingly cared for. Immaculate condition, a cozy fireplace and a detached garage. A sweet place to call home in a convenient location. So much potential but move-in ready. The yard has perennials & mature

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  39 Castle St, Great Barrington, MA 01230

Showing Results 41 - 80, Page 2 of 3