Great Barrington Classified Ad Listings

233 Algerie Rd. Big, 2800 square foot log home privately set on a seven plus acres. The great room, framed with massive log timbers, opens onto the large deck leading to the hot tub and fire pit. Kitchen features include granite and butcher block counters and an eat in island. Two bedrooms - each with private half baths - plus a full bath in the hallway complete the main level. The upper level ...

852 Churchill St. Single Family Home for sale in Pittsfield, MA for $579,000 with 3 bedrooms and 3 full baths. This 2,214 square foot home was built in 1998 on a lot size of 2.22.. Private, peaceful, and surrounded by nature, discover your own secluded Berkshire escape! Nestled on over 2 acres, this inviting property welcomes you along a winding serpentine driveway to a private retreat where na...

198 Allengate Ave. Welcome to this charming four-bedroom, one-bath home in a desirable neighborhood, offering comfort, updates, and an exceptional location. Featuring a newer roof, vinyl siding, replacement windows, and a new sewer line, this home offers many of the major improvements already in place. Beautiful wood flooring adds warmth and character, while the fully finished basement provides...

820 Robinson Rd. On the Dalton/Hinsdale line atop Tully Mountain! A wonderful chalet style raised ranch on just over 5 acres offering the kind of privacy, space, and versatility that makes a home feel truly special! Built and maintained by its original owners, this is a solid, well-constructed home that has been exceptionally well cared for over the years. Generous rooms, abundant closet space,...

130 S Main St. A rare opportunity to become the next steward of a remarkable piece of Sheffield history. Dating to 1819 and prominently situated on South Main Street in Sheffield's Historic District, this extraordinary antique is filled with the character, warmth, and craftsmanship of another era. Currently configured as a four-family residence, the property includes three beautiful apartments ...

42 Wendell Ave. Built by Thomas Colt in 1865, 42 Wendell Avenue is a striking Italian Villa style property with a rich place in Pittsfield's history. Once owned by Simon England Sr., who deeded it in memory of his wife, the building later became the Women's Club of Pittsfield and most recently served as the Whitney Center for the Arts. The arched entrance opens to more than 7,700 square feet ac...

24 Southern Ave. Two-family flat offering strong potential for investors or owner-occupants seeking rental income. Located close to town, this property features a 3-bedroom, 1 bath first-floor unit with a de-lead certificate that will soon be vacant and a 2-bedroom 1-bath second-floor unit that has been de-leaded but has no certificate and is currently on a month-to-month lease. An enclosed fro...

232 First St. Located on the edge of Pittsfield's Downtown Creative District, this versatile colonial has served as professional office space for 20+ years and offers endless possibilities. Features include 6 private offices, a reception/waiting area, half bath, bonus room, handicap-accessible ramp, off-street parking, and a detached 4-bay garage with income potential. Ideal for medical, profes...

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...

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...

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...

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.

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...

151 Onota St. Great opportunity to own a three-family property in Pittsfield! 151 Onota Street offers three spacious units, each featuring 2 bedrooms, providing flexibility for both investors and owner-occupants. The first and third-floor units are currently occupied, while the second-floor unit is vacant and ready for a new tenant or an owner looking to move in and offset their mortgage with r...

92 Ridge Ave. Wake up each morning to breathtaking sunrises over beautiful Pontoosuc Lake from this exceptional waterfront retreat. Perfectly positioned to capture panoramic water views, this stunning 4 bedroom, 3 bath home offers the ideal blend of comfort and style. An inviting open-concept floor plan is designed to maximize the spectacular views, seamlessly connecting the spacious living, di...

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...

148 Hudson Avenue 1. Multi-Family Home for sale in Chatham, NY for $590,000 with 6 bedrooms and 4 full baths. This 3,200 square foot home was built in 1930 on a lot size of 0.53.. Attractive early 20th century home on the edge of Chatham Village. Gorgeous oak center-hall staircase in the main house which has 4 bedrooms and 2 baths. Two income producing units in small building to the rear of the...

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...

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...

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