Great Barrington Classified Ad Listings

163 Dublin Rd. Set on a quiet road in Falls Village, Connecticut, this enchanting 1790s Irish-inspired farmhouse offers magnificent western views to Falls Mountain and beyond. Recently renovated by a nationally recognized decorating editor and landscaped by an acclaimed garden designer, this timeless Litchfield County property seamlessly blends historic character with sophisticated modern touch...

62 Route 126. Looking to build your dream home? This 4 Acre property is level, lightly wooded and located in an area with fine homes. A beautiful county setting!

Sir Edwards Way. Discover the possibilities of this large lot in a private community just 20 minutes from Lee. This secluded 1.95-acre lot in Sherwood Forest, offers the opportunity to build your dream home--or purchase the adjoining residence (MLS #250354), too, and welcome family and friends to your private estate of nearly 3 acres. Residents enjoy 8 beaches on 5 no-wake lakes and ponds, plus...

144 Castle Hill Ave. Discover the potential of 144 Castle Hill Ave, a charming 1950 Cape in Great Barrington's sought-after On the Hill neighborhood, where in-town convenience meets the beauty of the Berkshires. This 2-bedroom, 1-bath home offers 1,250 sqr ft of living space, hardwood floors, a comfortable living room, dining room and built-in garage. A newer well-maintained furnace, and 1 year...

1071 Sheffield-Egremont Rd. This well-loved antique home offers a rare combination of history, thoughtful updates, and natural beauty. Set on 14+ acres with sweeping westerly mountain views, Carefully maintained over the years, the property has benefited from significant improvements, including an updated foundation, electrical and plumbing systems, heating system, windows, and roof. The home o...

8 Clydesdale Dr. Looking for one level living? Must see ranch in the southeast. This Polo Acres updated home is just over the Lenox line and close to all the Berkshires have to offer. Enter from the covered porch into a spacious welcoming entry. The light-filled living room with fireplace and gleaming wood floors flows into the dining area and three-season sunroom with awning. The large kitchen...

14 Valley View Rd. Sweet 1925 Village house set on 0.43 acres in a quiet neighborhood close to the village. South facing wrap around glass front porch. Living and dining rooms with inlaid design hardwood floors and kitchen on the main floor. Four bedrooms and one bath upstairs. Full basement split equally between a workshop with concrete floor, radiator, toilet, and walk out door and a mechanic...

31 Sharon Rd Unit 2. Experience sophisticated country living in this exceptional, fully furnished residence overflowing with natural light and elegant finishes. Located on the ground floor of this historic building, this two-bedroom, two-and-a-half-bath dwelling is designed for immediate, effortless occupancy. The unit features a sweeping open-concept living and dining area with warm wood floor...

19 Hemlock Ln. Peaceful Country Living Near Twin Lakes - Discover tranquility in this beautifully renovated 3-bedroom, 2.5-bath home, ideally located on a quiet county road just minutes from Twin Lakes. Set on over 3 acres of remarkably private land, this property offers the perfect blend of seclusion and accessibility. Enjoy seamless indoor-outdoor living with a spacious two-level deck that co...

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...

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...

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

506 Gale Ave. Enjoy the perfect blend of space, privacy, and convenience in this 5-bedroom, 2-full-bath home offering 2,252 square feet of living space on 5.9 acres in Pittsfield. The first floor kitchen features granite countertops, fireplace in the living room, three bedrooms and full bath. The additional lower-level living space fireplace in 2nd living room, kitchen, mudroom, 2 bedrooms, and...

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...

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...

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...

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...

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...

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...