Great Barrington Classified Ad Listings

12 Birch Hill Road. Lots and Land for sale in Craryville, NY for $250,000. The lot size is 5.45.. Build your dream home at Stonegate, an exclusive, tranquil subdivision with 425 acre Copake Lake access, an HOA private community dock and available boat slip. This 5+ acre prime vacant lot (Lot 12) is BOHA approved and offers serene natural surroundings with utilities available. Perfect for nature...

2044 State Rd. With 22+ acres of residential/agricultural zoned land, open fields, wooded borders, and a lovely little pond, the simplistic, quiet, natural beauty of this Richmond property evokes feelings of peace and tranquility. The property features a 1950's ranch style home with 3 bedrooms, 1-1/2 baths, recently refinished hardwood floors, attached 2-car garage, full basement, additional ov...

309 Tamarack Trl. Rustic Contemporary in Otis Wood Lands that abuts the State Forest! This cozy home has an open concept kitchen/living/dining area with vaulted ceilings. Access the screened-in porch and deck from the sunken living room. Primary bedroom with skylight and deck access. Detached two-car garage with space above for artist's studio. An easy-to-maintain property. Association amenitie...

20 Alfred Dr. Welcome to this inviting 4-bedroom, 1.5-bath Colonial offering classic charm and comfortable living. The home features a welcoming atmosphere, highlighted by wood floors, and a wood-burning fireplace that creates the perfect setting for cozy evenings. A breezeway connects the home to the oversized attached 2-car garage, providing convenient access and a practical transition betwee...

5 Birch Hill Road. Lots and Land for sale in Craryville, NY for $295. The lot size is 6.8.. Build your dream home at Stonegate, an exclusive, tranquil subdivision with 425 acre Copake Lake access, an HOA private community dock and available boat slip. This 6+ acre prime vacant lot (Lot 5) is BOHA approved and offers serene natural surroundings with utilities available. Lot 5 is at the end of a ...

226 Grove St. Duplex in the hills of Housatonic. Three bedroom, one bathroom on each side. Enclosed front porches and open back porches, large garage, all on a corner lot. Located on the Grove St turn overlooking the village of Housatonic and only a few short steps from the Flag Rock conservation area, this is both in town and in a lovely mountain setting. Both units have large walk-up attic an...

191 Fort Hill Ave. A rare opportunity to own 5.2 acres in Pittsfield for under $400,000! Set in the scenic countryside of West Pittsfield, this spacious 1820s farmhouse offers nearly 2,000 sq. ft. of living space, historic character, and room to make it your own. Inside, you'll find hardwood floors, a fireplace, beautiful central staircase, oversized bedrooms, enclosed porch, and walk-up attic....

3 Lake Buel Rd. Tucked into the rolling hills of Great Barrington just minutes from downtown and the slopes of Ski Butternut, The Turning Point is a storied 3,600-square-foot Berkshire landmark operating as an active short-term rental. Steeped in history dating back to its 1800s stagecoach tavern roots, the property showcases an enduring dual-facade of classic New England brick and weathered cl...

2 Kemble St. The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental. The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests an...

16 S Atlantic Ave. Step inside this turnkey 4-bedroom, 1.5-bath New England farmhouse and immediately feel at home. Additional room/office space on the first floor. Fully renovated in 2022 and freshly painted from top to bottom (2026), this vacant beauty is completely ready for its next chapter. The traditional farmhouse aesthetic offers timeless appeal, while the 2022 updated bring modern comf...

35 Meadow Ridge Dr. Set in a peaceful West Pittsfield neighborhood, 35 Meadow Ridge is a sophisticated contemporary home with spacious thoughtfully designed living. Soaring 12 foot ceilings and cherry hardwood floors welcome you inside. The main level features a family room with built-ins, living room with gas fireplace, dining room, eat-in kitchen and access to the outdoor deck. The second flo...

1169 NY-295. Single Family Home for sale in Canaan, NY for $339,800 with 3 bedrooms and 1 full bath, 1 half bath. This 1,372 square foot home was built in 1930 on a lot size of 0.5.. 1st Open House Sunday October 18 1-3PM!! East Chatham (Canaan) Starter Home with all the I wants! Sop Close to the Berkshires Ski Resorts, Takonic PKWY Lee Ma, Remodeled 3 Bedrooms 1.5 Baths w/ Open Bright Spacious...

23 Westover St. Move-in ready and completely renovated! This home was remodeled down to the studs in 2023 with new wiring, plumbing, insulation, windows, and walls. Features beautifully refinished hardwood floors, new interior and exterior lighting, and a brand-new on-demand heating system. The first floor offers a large living room, dining room, kitchen, office, and half bath, while the second...

33 Reuter Ave. Lovely southeast Colonial on a dead-end street. This spacious home has a beautiful new kitchen, living room, sunroom/office, hardwood floors throughout and plenty of living space. The 1st floor bedroom could be used as a in-law or primary suite, featuring family room, fireplace with wood stove insert, half bath and sliding doors for privacy from the rest of the house. This home a...

18 Butternut Dr. Tucked away on an peaceful cul-de-sac off Lake Buel Road, this spacious, well-built, multi-level 3 bedroom, 2 full-bath home is priced approximately $200,000 below its current assessment, which supplies more than enough room for the interior renovation it needs and deserves. Originally built in 1997 and surrounded by 2.65 acres of wooded privacy, it was thoughtfully designed wi...

46 Pomeroy Ave. Discover urban living at its finest in the heart of Pittsfield with this striking, one-of-a-kind Mansard-style brownstone. Spanning three levels, this 5-bedroom, 2.5-bathroom townhouse seamlessly blends historic architectural character with modern convenience. Soaring 11-foot ceilings, striking exposed brick accent walls, vintage hardwood floors running throughout, and a classic...

108 Route 344. Multi-Family Home for sale in Copake, NY for $495,000. This 5,512 square foot home was built in 1856 on a lot size of 1.2.. Welcome to the Taconic Wayside Inn, a roadside tavern and boarding house dating to 1856, set on 1.2 acres in the hamlet of Copake Falls at the edge of Taconic State Park and just a few miles from Bash Bish Falls. The 5,512-square-foot main building holds a c...

112 Union St. The building has the potential to be a great income producing property. There are 4 units with plenty of off street parking. It has vinyl siding, replacement windows and is close to the downtown area. 3 Units are lead safe. Check the documents section referencing a letter from the City Commissioner. The owner is in the process of having plans drawn by a local architect firm to add...

295 Smith Hill Rd. Introducing Turkey Hill You only have to stand at the edge of the property, framed by stone walls and century-old trees, to know this is a special place. Beyond the stone pillars, down a crushed-stone driveway, you're led into a true country farm estate. The main house, substantial barn, multi-car garage, pool, and tennis court give you a multitude of reasons not to stray far...

203 Bartlett Ave. Gracious colonial style home in the heart of the southeast historic neighborhood minutes to upstreet cultural art and theatre district with museums, galleries, theatres, eclectic dining, and more. This home awaits your finishing touches is search of a new homeowner with a sense of style and interior design to make this beauty the show piece it deserves to be. Abundance of livi...