Great Barrington Classified Ad Listings

286 Lee Rd. A once-in-a-lifetime opportunity to build your dream home on a large waterfront parcel in Lenox. This spectacular 14-acre property offers privacy, tranquility, and direct frontage on beautiful Laurel Lake while remaining just minutes from downtown Lenox, Tanglewood, shopping, dining, and all the Berkshires has to offer. Enter through the stone and metal electric gate, cross the ston...

153 Hurlburt Rd. Nestled on a highly desirable road in Great Barrington, this unique acre-plus property offers a rare opportunity to create your Berkshire retreat. The land features two existing structures with endless possibilities. A detached two-car garage includes a rear room, ideal for a workshop, studio, or flex space, plus a second level for additional storage. The property's historic fo...

73 Plymouth St. Recently off market for needed maintenance on the exterior siding and landscaping, this home is now a must-see! Colonial style home is bright and airy featuring windows that invite abundant natural sunlight into every room. The main level offers a easy flow between the inviting living spaces and a convenient half-bath, while the second floor hosts three generous bedrooms and a f...

18 Osceola Dr. Unique Opportunity! Lakefront on Center Pond. Original lake cabin built circa 1950 set on.79 acres with 100 feet of lake frontage. Located within 25 feet of the lake the structure will require extensive renovations. The cabin does have electricity and will need well and septic. Great spot and well worth the effort!. 1 Bedroom. 1 Bathroom. 720 ft

399 Under Mountain Rd. Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, wal...

103 Long View Dr. This striking modern retreat was designed by internationally recognized architect Alfredo Brillembourg to feel completely at home in its Berkshire setting. Clean contemporary lines, warm natural materials, and expansive walls of glass create a seamless connection between the house and the surrounding landscape. Seasonal views and changing natural light bring a different feel t...

80 River Birch Ln Unit 20. One of 59 detached homes homes at Silver Maple Farm in Dalton. Just 18 minutes to Tanglewood, close to shopping, The Berkshire Medical Center and all of the cultural and outdoor activities The Berkshires have to offer. SMF is arguably the best and most sought after condo community in the area. The amenities at SMF feature a clubhouse/library/kitchen and a sports compl...

11 Allessio St. Surpisingly spacious cape style home with beautiful hardwood floors, offering comfortable living for everyone. First floor blends traditional floorplan with certain wheelchair conveniences that make for easy one-level living. First floor kitchen sink access, two full baths, primary bedroom suite, inside and outside deck access with ramps. Upstairs enjoy three private bedrooms--g...

14 Woodland Hill Rd. Tucked away in a peaceful, private setting, this charming mid-century ranch offers easy one -level living , warm and inviting. Featuring 3 bedrooms and 2 full baths, the home combines classic character with fresh updates. New oak floors throughout, fresh interior and exterior paint create a clean, move-in ready feel. Relax by the fire or enjoy time on the screened porch or ...

38-40 Grove St. Two-family flat ideally located and offering an excellent opportunity for investors. Each apartment features 3 bedrooms and separate utilities. The property is serviced by public water and sewer and includes two electric meters, two boilers, and two hot water heaters, with natural gas heating and hot water. The first-floor unit features a newer kitchen. The second-floor unit off...

186 Burbank St. Welcome to 186 Burbank Street! This charming colonial-style home offers two bedrooms, one full bathroom, and 1,158 square feet of living space. Situated on a level corner lot in an residential neighborhood, the home features a functional layout with plenty of potential. The main level includes a spacious kitchen with ample cabinet and counter space, a formal dining room, comfort...

Swamp Rd. Offered for the first time in generations, this exceptional 10-acre parcel presents a rare opportunity to create a home in one of the Berkshires' most picturesque settings. Nestled among open farmland and rolling countryside, the property offers a beautiful blend of gently rolling meadows, a private pond, mature trees, and seasonal wildflowers, creating a landscape that feels both pea...

15 Cobble Rd. A RARE RIVERFRONT COUNTRY ESTATE - 38.9 ACRES OF BEAUTY, PRIVACY and HISTORY. Set along the Hollenbeck River, this extraordinary 1820 Colonial offers a rare opportunity to own nearly 39 acres in one of Litchfield County's most beautiful settings, surrounded by open meadows, mature woodland, and picturesque river frontage. Thoughtfully updated while preserving the warmth and charac...

1100 North St. Great opportunity to own a two family flat with 2 bedroom and 1 bath in each apartment. Both units offer warm and inviting wood floors while the first floor unit includes a finished room in the basement. Enjoy peace of mind with a newer heating and hot water system. Outside you will find a deck overlooking a large yard with shed and ample parking all conveniently located on a bus...

Johnson Rd Lot 9. Nearly five acre waterfront building lot on lightly travelled Johnson Road with frontage on a pond. Successfully perced in 2004. No HOA fees or regulations. Low carrying costs, real estate taxes $257.00 per year. Over a thousand acres of protected state land across the street. New construction underway on nearby waterfront lot.

26 Pine St. 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...

365 Churchill St. MOTIVATED SELLER! Discover the ideal setting for your new home, private retreat, or future investment on this beautiful 15-acre parcel in desirable West Pittsfield. Much of the groundwork has already been completed, including installed electricity, a newly constructed driveway, and a prepared building pad.The property offers a wonderful combination of open and wooded land, wit...

Eastbrook Ln Lot 144. Nestled on a quiet street among upscale homes, this 1.08-acre lot offers a prime setting to build your custom residence. Underground utilities are available at the road for a seamless start. Enjoy the privacy and natural beauty of the Berkshires with easy access to downtown Pittsfield, Tanglewood, hiking trails, and more. Protective covenants preserve the integrity and las...

500 Creamery Rd. Impeccably maintained contemporary home set on four manicured acres bordering Massachusetts Fish and Game conservation lands and surrounded by approximately 4,500 acres of protected land in Hinsdale. Enjoy a private, serene setting just 1.6 miles from 287-acre Ashmere Lake. Inside, open entertaining spaces blend seamlessly with quiet retreats. The main level features a designer...

162 Alford Rd. BEAUTIFUL, PRIVATE LOT! Gently sloped and lightly wooded parcel awaits your thoughtful build. Bring your design to life at this private and convenient location. Electric has been brought to the site, perc test available. Seasonal views. Wonderful location with easy access to Great Barrington town center, shops, restaurants, hiking and skiing!