Great Barrington Classified Ad Listings

64-66 Stratford Ave. An exceptional side-by-side duplex in Pittsfield's desirable Southeast neighborhood, offering two spacious 3-bedroom, 1-bath residences and an ideal combination of comfortable living and income potential. Both units feature bright, inviting interiors, granite countertops, updated finishes, and well-designed living spaces that feel more like individual homes than traditional...

497 Holmes Rd. A Landmark Berkshire Estate of Extraordinary Provenance, the Oliver Wendell Holmes summer cottage. Set on 15 private acres in the heart of the Berkshires, a rare American legacy estate commissioned in 1847 as the summer residence of renowned physician, poet, and author Oliver Wendell Holmes Sr. Two centuries later, this extraordinary property remains a testament to architectural ...

81 Calumet St. Rare opportunity to own a converted raised ranch home with full upper unit and lower unit for additional living space. spacious yard, deck and detached garage.. 4 Bedrooms. 3 Bathroom. 3152 ft

Lot 2 MA-41. Lots and Land for sale in Richmond, MA for $109,900. The lot size is 2.51.. 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...

422 Barker Rd. Introducing 422 Barker Road, a charming ranch-style home in Pittsfield! This hidden gem is centrally located to the Pittsfield's Cultural District but tucked away on a rural lot that offers privacy with convenience to all the Berkshires has to offer. The solid and stylish interior layout ideal for starting out or slowing down, there are so many possibilities with this home's thou...

594 Shunpike Rd. Modern elegance meets turnkey peace of mind in this fully reimagined Sheffield retreat. Set on 2.3 level acres, this 3BR, 3.5BA sanctuary spans 2,748 square feet across three finished levels. The sun-drenched main floor features wide-plank white oak floors, a gas fireplace, a large half bath, a chef's kitchen with stainless appliances, white quartz counters, and seamless access...

0 Mercer Mountain Road. Lots and Land for sale in East Chatham, NY for $225,000. The lot size is 12.5.. Situated in the rolling Taconic Mountains between the cultural corridor of the Berkshires and the breathtaking views of the Catskill Mountains is the prestige neighborhood of million dollar plus homes called Mercer Mountain. In the ever so popular Columbia County of the Hudson Valley, this of...

47-49 Lake St. Whether you are looking to add to your investment portfolio or purchase a property with the potential to offset your mortgage with rental income, this two-family offers plenty of possibilities. Featuring two separate units with a total of 3 bedrooms and 2 full baths, the property provides approximately 1,923 square feet of living space. Separate electric meters add convenience fo...

1 Lakewood Cir. OPEN HOUSE: SATURDAY, SEPTEMBER 19th: 10:00 am-11:00 am Bring your clothes and move into this immaculate well maintained two bedroom/two bathroom mobilehome is located on a wonderful corner lot. Very comfortable living space and all furniture will convey with the sale. The spacious deck is great for entertaining or just relaxing on- also included is a shed/workshop that has elec...

25 Valentine Ln. IMMACULATE 3 BEDROOM APARTMENT WITH DECK and ONE BEDROOM APARTMENT in SOUTH LEE on a quiet cul de sac. Zoned 2 family, partially fenced back yard, attached garage, CENTRAL AIR CONDITIONING - BRAND NEW VINYL SIDING DECEMBER 2025.. 4 Bedrooms. 2.5 Bathroom. 1636 ft

787 Churchill St. First time ever to Market! Charming Cape-style home on outer Churchill, directly abutting the Pittsfield State Forest with Onota lake nearby. This 3 bed, 1 bath property offers 1,529 square feet of living space and has been in the same family for decades, most recently operating as a successful Airbnb. The main level features mix of hardwood floors and luxury vinyl plank, 2 be...

5 Putnam Ave. Southeast brick cape ready for summer fun! This 3 bed 2 bath cape is filled with warmth, character, and inviting spaces ready for memories all season long. Bright open kitchen, which flows to the dining area and family room with vaulted ceilings and doors to the deck. Around the corner a 2nd family room, game room or whatever you decide with wood burning fireplace. 1st floor also ...

44 Pine Rd. Enjoy exceptional privacy and peaceful country living in this spacious 4 bedroom, 2.5 bath contemporary Cape set atop a long winding driveway surrounded by natural beauty. The open floor plan on the main level offers comfortable living and entertaining spaces, including an updated eat in kitchen with stainless steel appliances, a dining room with a cozy wood burning fireplace, a gen...

Broadview Ter. To Be Built, energy-efficient, low-maintenance 1,375 sq ft gable entry ranch with 3 bedrooms and 2 full baths. This home offers true single-level living with an open-concept layout connecting the kitchen, dining, and living areas, ideal for everyday living and entertaining. The primary suite includes a private full bath, while two additional bedrooms offer flexibility for guests ...

106 E Housatonic St Apt 2. Enjoy easy, low-maintenance living in this conveniently located ground-floor one-bedroom condo. The open floor plan creates a comfortable, inviting space with great flow between the living and dining areas. Sliders open to a private patio, providing a pleasant spot to relax, enjoy the outdoors, or entertain. A great opportunity for a first-time buyer, downsizer, or an...

15 Cherry Hill Dr. Brand new construction at Berkshire Country Meadows! This 2000 sf single-family condo is now ready for immediate occupancy. With the ease of one-level living, you'll enter into a great room with hardwood flooring, gas fireplace and bathed in natural light. Fully applianced kitchen with large work island. This unit features 3 bedrooms, 2 baths, central a/c, natural gas heat. M...

Westbrook Ter Lot 140. Nestled on a quiet street among upscale homes, this 1.23-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 la...

245 Cheshire Rd Trlr 5. Welcome to low-maintenance living in Allendale Pines! This updated 2-bedroom, 1-full-bath mobile home offers comfort, convenience, and low monthly lot rent. Inside, you'll find a beautifully remodeled kitchen, complete with modern updates throughout the living area. The home features a functional layout with 720 sq. ft. of living space, an enclosed entryway that includes...

1303 North St. Charming, move-in ready, and full of possibilities, this 3-bedroom, 1-bath home offers 1,428 square feet of comfortable living space. Inside, you'll find a bright and inviting layout with beautiful hardwood floors, an updated kitchen with plenty of cabinet and counter space, and a spacious upstairs that offers flexibility for bedrooms, a home office, or additional living space. S...

729 Hewins St. Marcel Breuer partner Tician Papachristou designed this home as a private paradise for his three-generation family: a long driveway leads past a tennis court, guest house, swimming pool, gazebo, and gym shed to a three-level modern house evoking the New England barn. From the third-floor master loft suite with private terrace and kitchenette, a skylit central stair leads to the m...