Great Barrington Classified Ad Listings

117 Lucia Dr. Move-in ready and filled with upgrades, this southeast Pittsfield colonial home offers five bedrooms and flexible living space. The first floor includes a bedroom and full bath, while the second floor features a primary ensuite plus three additional spacious bedrooms. Enjoy a beautifully landscaped, very private backyard with an above-ground pool and convenient access from the kit...

551 Otis Rd. Experience year-round magic at this classic 1925 lakefront cottage, set on a private point of Shaw Pond with 60' of direct shoreline. Panoramic water and mountain views unfold from the screened porch, while a stone fire pit sets the scene for sunset gatherings. Inside, renovated, light-filled spaces include an open living room with stone fireplace, fully equipped kitchen, updated f...

41 Pearl St Unit 1-2. Welcome to 41 Pearl Street- a 1900s two-family residence nestled on a quiet street just moments from downtown Great Barrington. This spacious 4-bedroom, 2-bathroom (both sides are 2 BR/1 BA) home offers 1,964 square feet of living space on a generous 0.25-acre lot, containing that classic period charm. Step inside to discover a welcoming floor plan with ample natural light...

189 New Marlboro Southfield Rd. Loads of room for family and friends in this semi-private country home near The Old Inn on the Green and The Southfield Store Cafe. The first floor features spacious living areas, including a living room with a wood-burning fireplace, a large eat-in kitchen and dining area, and a paneled den, along with an attached two-car garage. Two of the six bedrooms are on t...

2650 Swamp Rd. April Hill, an exquisite 1850 Greek Revival masterpiece. This architectural gem has been carefully restored and enhanced to exceptional standards, preserving its storied heritage while seamlessly integrating contemporary conveniences. The exceptional property features an elegant Main House, inviting Guest Cottage, Potting Shed/Studio and Barn. Framed by breathtaking panoramic vis...

54 Holmes Rd. This charming and move-in ready home invites you to settle into an easy Berkshire lifestyle. The first floor offers the comfort of one-level living, with a bedroom, full bath, laundry, and welcoming living spaces, while the second floor provides additional bedrooms and room for guests. Recent updates include an updated electrical service, refreshed interiors, and a beautiful enclo...

37 Elm St. Prime downtown opportunity! Almost 4 acres ready for your development ideas. One of Pittsfield's last remaining sites large enough for drive thru permit. Ther front of the property is BG, the back is CWS. Very versatile site on one of Pittsfield's finest streets.

132 Cascade St. Build your Berkshire dream on this 5.68-acre parcel ideally located on a paved road just moments from Pittsfield State Forest. Offering a beautiful blend of privacy and accessibility, this property provides the perfect setting for a year-round home or weekend retreat. Enjoy easy access to miles of trails, hiking, biking, and outdoor recreation, all while being just a short drive...

48 Brookside Dr. Meticulously maintained and lovingly cared for, this spacious four-bedroom, two-and-a-half-bath home offers the perfect combination of comfort, quality, and location. Featuring generously sized rooms throughout, this home provides ample space for both everyday living and entertaining. Pristine wood floors lie beneath the carpeting, offering the opportunity to uncover their time...

1 Cornwall Dr. 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 bac...

80 Taconic Ave Apt 2. Lovely single level condo on The Hill. Just a short walk to town , The Oakwood provides a quiet community with a lovely pool, garaged parking , and mature landscaping. 2 bedrooms, 2 baths, a cozy living room with fireplace and sliders to a sunny patio. Freshly painted and ready to move into.. 2 Bedrooms. 2 Bathroom. 1308 ft

30 Walden Ln. Meticulously cared for by its original owner, this bright and welcoming 2 bedroom, 2.5 bathroom home offers the ease and comfort of true one level living in the highly desirable Walden Village community. The thoughtfully designed main floor features everything you need on one level, including a dedicated main floor laundry area with no need to carry baskets up and down stairs. Ste...

421 Elm St. A rare opportunity to acquire two neighboring properties, offered together on separate lots, in a desirable Pittsfield neighborhood. The former Pilgrim Holiness Church presents a distinctive space filled with character and exciting possibilities for adaptive reuse, creative pursuits, community-oriented activities, or future redevelopment. Next door, the former rectory is a well-main...

80 Taconic Ave. Lovely single level condo on the Hill. Just a short walk to town, The Oakwood provides a quiet community with a lovely pool, garaged parking, and mature landscaping. 2 bedrooms, 2 baths, a cozy living room with a wood burning fireplace and sliders to a sunny deck. Freshly painted, neat as a pin, and ready to move into.. 2 Bedrooms. 2 Bathroom. 1308 ft

4 Caratina Dr. Space, comfort, and flexibility awaits in this beautifully renovated home, built in 1988 and designed with room for everyone. The main level features a tastefully renovated kitchen, a large living room with French doors opening to a wonderful deck overlooking the mountains, plus a convenient half bath and laundry. Upstairs, you'll find 4 spacious bedrooms with generous closets, i...

316 Lake Shore Dr. Prime Location + Privacy + Fiber Internet at the Street A rare opportunity to build your Berkshire dream home on one of the largest lots ever offered in Otis Wood Lands - 3.029 acres of peaceful, gently rolling terrain in a premier location close to all community amenities. This property offers excellent privacy while keeping you just minutes from the lake, clubhouse, pool, t...

20 E Dugway Rd. Just 3 miles from Tanglewood and moments from the heart of Lenox, this 36+ acre estate offers rare scale, privacy, and flexibility in one of the Berkshires' most sought-after settings. A long, tree-lined driveway creates a strong sense of arrival, unfolding into two separate residences surrounded by woods, open land, and long-range possibility. The acreage offers both seclusion ...

80 Preston Ave. A Charming Southeast Pittsfield Cape with classic character and an inviting sense of ease. This three bedroom and one bathroom home offers a spacious living room, dedicated dining room and an inviting country kitchen. A first floor bedroom and bathroom provides flexibility while two additional bedrooms are upstairs. Outside, a sweet backyard with a stone wall creates a lovely se...

229 Hamilton Rd. Tucked well back from the road on 3.5 private acres, this modern, lightly used home offers an effortless blend of low-maintenance living, single-story convenience, and quintessential Berkshires charm. Designed with an open, light-filled layout, the main level features gleaming hardwood floors and an seamless flow throughout the common living areas. At the heart of the main floo...

Ma-41 Lot 2. Discover your Berkshire retreat on this 2.516-acre wooded estate lot in Richmond, Massachusetts, near Lenox and Stockbridge. Offered at $109,900, this level, easy-to-build property features beautiful legacy hardwood trees and multiple areas to choose from to build your custom home or weekend escape. No time frame to build--purchase now and build when you're ready. Enjoy the charm o...