Great Barrington Classified Ad Listings

37 Broadview Ter. Fall in love with this beautifully renovated Ranch offering easy, one-level living in a lovely neighborhood. The gleaming hardwood floors throughout, a spacious and sleek new kitchen with quartz counters, a stylishly renovated bath, three comfortable bedrooms, and a bright welcoming layout. The unfinished walkout basement offers excellent potential for additional living space,...

40 Reed St. 14 Unit investment opportunity! Located just outside of downtown Pittsfield and within walking distance to shops, restaurants, and the Colonial Theater. Classic brick exterior and excellent off street parking. All units feature one bedroom and separate utilities. Coin-op laundry located on site for additional income.. 14 Bedrooms. 14 Bathroom. 9928 ft

310-314 Wahconah St. Fantastic investment opportunity on Wahconah St! This four-family property offers immediate income potential with two front, two bedroom units ready to rent while you complete the two rear, one bedroom units and build additional value. The front units feature attractive hardwood floors, tile in the kitchens and bathrooms, and a distinctive interior layout that adds charm an...

60 Woodland Rd. Opportunity to own approximately 1 acre of land in the Berkshires with October Mountain State Forest close by. Previously used as a cow pasture, this open parcel offers a pastoral setting with convenient access to downtown Lee, and Lenox, area attractions and Massachusetts Turnpike. An additional 3-acre parcel at 75 Woodland Road is also available, see MLS # for 75 Woodland Rd.,...

39 South St. SET ON A GENEROUS IN -TOWN PARCEL THIS 1850 VICTORIAN IS POISED FOR A MODERN TRANSFORMATION. THE RESIDENCE BEAUTIFULLY RETAINS ITS ORIGINAL STAIRCASE AND PERIOD DETAILS THROUGHOUT. HIGH CEILINGS AND EXPANSIVE WINDOWS ILLUMINATE THE MAIN ENTRY, LIVING AND DINING ROOMS, WHILE THREE FIREPLACES AND MULTIPLE PORCHES ADD TO THE TIMELESS CHARM. UPSTAIRS, THE SECOND FLOOR FEATURES FIVE BED...

320 Lake Shore Dr. WINTER RENTAL FROM 10/1/2026 TO 3/15/2027. Wow! Rent for two weeks, four weeks, or longer. You must see to fully appreciate how special this home truly is. The construction quality is not only exceptional, but it is also new this year. The open floor plan log home features impactful vaulted ceilings, a spacious eat-in kitchen and pantry, a bright dining area, and an eye-catch...

80 Taconic Ave Apt 8. Enjoy the best of Great Barrington from this beautifully updated ground-level condominium in On the Hill. Offering easy one-level living, this inviting home features an updated kitchen with abundant storage, new appliances, and bar seating, plus a spacious dining area perfect for gathering with family and friends. The sunken living room boasts a wood-burning fireplace and ...

18 Highcrest Rd. Condo at Twelve Oaks Village. End of Cul-de-sac with Mountain views. This unit offers lots of Privacy being an end unit. Come enjoy Tennis Swimming pool and Fitness center all on property. 3 Full floors of living space with Primary Suite/Walk in Closet on 1st floor. Spacious open floor plan to enjoy entertaining with plenty of outdoor space with screened in porch and private de...

4 Gilmore Ave. Set on two-thirds of an acre in a residential area, walkable to all Great Barrington has to offer, this versatile home offers 4+ bedrooms and 3 bathrooms. The main floor boasts two bedrooms, a dedicated office or guest space, one and a half baths, laundry, as well as the main living, dining, and kitchen areas. Upstairs you will find 2 additional bedrooms and another half bath. Wo...

39 Castle St. THE BEST OF GREAT BARRINGTON RIGHT OUTSIDE YOUR DOOR! Set high up on a knoll, this home boasts good, solid construction, wood floors, brick fireplace, a year round sunroom and a detached garage. The mature trees and perennials give the lot wonderful privacy. Easy manageable living, a block from the NYC bus this classic Berkshire house with the luxury of leaving your car behind.. 2...

5 Crimson Ln. Set in a lovely neighborhood just outside downtown Great Barrington, this center-hall Colonial with contemporary flair offers a wonderful combination of space, light, and easy Berkshire living. The sunny, south-facing open floor plan brings together the kitchen, breakfast area, and family room, with granite counters, a center island, uand a see-through fireplace connecting to the ...

The original fat custom icon, now with bright chrome finishes. The original fat custom icon, now with bright chrome finishes. Hot rod riders who like satin chrome and a steamroller stance. Commanding the road with the fattest tires available in the lineup. Milwaukee-Eight 114 V-Twin engine and Lakester disc wheels. You ll feel the difference the instant you crack the throttle. Authentic heritag...

23 Easton Ave. Nestled on Easton Avenue in a quaint, tight-knit, and highly walkable neighborhood, this beautiful Gambrel-style home blends classic character with key modern updates. Step inside this Spacious 3 bedroom, 1 full bath home to find warm hardwood floors running throughout the home and a cozy living room complete with a pellet stove--perfect for keeping warm on chilly Berkshire night...

153-155 Pomeroy Ave. Welcome to this immaculately maintained two-family home --a turnkey property that meets today's timeless standards! This choice 2-family home beautifully balances sophisticated living with incredible versatility, making it an ideal match for owner-occupants, multigenerational families, or savvy investors alike. Including features you are sure to love: Modern Living: Bright,...

9 Fairwynds Dr. Move-in ready and beautifully upgraded, freestanding home offers the ease of one-level living paired with over 4,600 sf over three finished levels. Four br, 4.5 bat and a walkout lower level. Live at the desirable Miraval golf/resort campus. Hardwood floors flow throughout the main living area, anchored by a striking double-sided fireplace wi stone hearth connecting the living a...

8 Birch Hill Road. Lots and Land for sale in Craryville, NY for $195,000. The lot size is 2.39.. Prime vacant land at Stonegate, a tranquil exclusive subdivision at Copake lake to build your dream home. Lot 8 is BOHA approved and offers serene natural surroundings with utilities available.Perfect for Lake enthusiasts and all that nature has to offer.Enjoy convenient access to amenities and near...

55-57 Brinton Hill Rd. Renegade Farm is a breathtaking 85+ acre luxury countryside estate where the romance of farm-to-table living meets the indulgence of a private resort. The sprawling grounds feature a beautifully appointed 4-bedroom main house(4,504 sq ft) and a completely separate, spacious 4-bedroom guest house(4,074 sq.ft) making it an unmatched haven for multi-generational gatherings a...

275 Division St. Located in a ''hidden'' neighborhood behind a stonewall entrance, this newly built home offers tranquil living just 5 minutes from the heart of Great Barrington. The spacious farmhouse front porch is the perfect spot to enjoy quiet mornings or gather in evenings with family and friends. Light-filled and open, the main level features an elegant living and dining area framed by F...

405 Pittsfield Rd Lot F2. Totally renovated and move-in ready mobile home in Lenox! This 2-bedroom home is located on a quiet dead-end street in the Berkshire Mobile Park and offers a nice deck along with an ample side yard to enjoy. Shed in the back needs some repairs to the roof.

14 Roosterville Rd. At the end of a quiet dead-end road in Sandisfield, this c.1892 four-bedroom farmhouse sits less than twenty feet from the Wild and Scenic West Branch of the Farmington River, a federally protected, free-flowing trout river. Four bedrooms. Two full baths plus a half. 2,516 sq ft. 4.61 acres. Beautifully transformed interior: a granite-island kitchen rebuilt from the ground u...