Great Barrington Classified Ad Listings

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 ...

102 Tor Ct. Sought-after location! This inviting ranch offers the perfect blend of original charm, comfortable living spaces, and thoughtful modern updates. The fireplaced living room flows seamlessly into the dining area and kitchen, creating an open, welcoming space ideal for everyday living and entertaining, while overlooking the lovely semi-private yard. The home features three bedrooms and...

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...

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...

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...

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...

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...

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.

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...

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...

96 Boylston St Ext. Back on the market, and someone else's loss is about to be your gain. Some homes just feel right the moment you arrive. Sitting at the end of a dead-end street, 96 Boylston offers the kind of quiet and privacy that's hard to find this close to downtown Pittsfield. No through traffic, no neighbors driving past, just a peaceful street that's yours to enjoy. Step inside and you...

William Holmes Rd. Build your dream home on a 2.15-acre corner lot located in the peaceful Deerhaven neighborhood of East Becket, sitting right at the junction of William Holmes Road and Wade Inn Road. This vacant land offers enormous road frontage and scenic views, making it an absolute dream layout for builders and buyers alike. Town assessor's formal cyclical inspection in 2024, property was...

365 Deer Run. Welcome to 365 Deer Run, a beautifully refreshed four bedroom, 3.5-bathroom home tucked into the sought-after Otis Woodlands community. Inside, 2,297 square feet of cedar-wrapped warmth unfolds beneath cathedral ceilings and skylights, with east-facing windows that bring beautiful morning light into the home throughout the year. A window-lined three-season porch extends the living...

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!

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...

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...

Town Hill Rd Lot 3. Serene Sandisfield Setting! This 8+acre parcel enjoys a lovely combination of level areas, gentle slopes, historic stone walls and seasonal streams. Beautiful mature trees yet not overpopulated. Perfect to build your Berkshire country dream home. Power is at the street located conveniently at each corner of the lot.

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...

87 Canaan Rd Apt 2G. Here it is! Just what you have been waiting for. An updated unit in desirable Lions Head Condominium. Elegantly refreshed throughout from top to bottom. Recently redone hardwood floors, fresh interior paint and stylish new wallpaper create a clean, modern aesthetic. The gourmet eat-in kitchen with granite countertops, ample cabinet space, and stainless steel appliances beck...

3664 Jacobs Ladder Rd. Enjoy life on Greenwater Pond in the Berkshires! The views, boating, fishing or just relax and at the end of the day watch the beautiful sunsets all from your little piece of lakefront heaven. I'll let the pictures speak for themselves. This property features a cottage with 3 Bedrooms,eat-in Kitchen and 1 full bath, a large barn and storage shed. Just about a 4 mile trip ...