617 houses for sale in Great Barrington town

Get ready to relax in the Berkshires in your new condo with the big windows and the high ceilings! Owner retiring and moving down south, giving up his beloved in town Great Barrington location. You'll love being close to stores and provisions for your various adventures, while being close to all the attractions that the Berkshires have to offer. And, at an approximately two and 1/2 hours from Boston or NYC, your location can't be beat. Come experience worry free living while the condo cuts your grass in the summer, or plows your driveway while you're up here to ski. 9 Stanley is simply country living at it's best! Come see it today!

Compare for value in the Lenox market! Sweet, petite, move-in ready ranch. Living room and bedrooms with hardwood floors; two nicely updated bathrooms; eat-in kitchen opens to spacious, private rear deck. Bonus features include the oversized two car garage, Buderus boiler for natural gas heat, and over a 1/2 acre of open sunny lawn. Easy access to shopping, dining and all of the Berkshires' cultural attractions

Located on a quiet street in Housatonic, this charming cottage offers easy single-level living in a peaceful neighborhood setting. Set on a sunny double lot, the property provides extra outdoor space and flexibility with room to garden, entertain, play, or simply enjoy the surroundings. Inside, the home features an efficient layout filled with natural light, creating a bright and comfortable feeling. An oversized garage adds valuable storage and space for hobbies, tools, or workshop use. One of the highlights of this location is being within walking distance to Old Maids Park, where you can enjoy fishing, swimming, and a picnic area along the river. This sweet cottage offers a wonderful opportunity for those seeking a manageable home with everyday simplicity and nearby recreation. Minutes to downtown GB, and local amenities!

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 clapboard. Inside, original period charm takes center stage with wide-plank wood floors and glowing fireplaces, perfectly paired with a rare, substantial footprint featuring 7 generous bedrooms and 6.5 bathrooms. Designed for effortless hosting, this expansive retreat offers an incredible canvas for a lucrative rental investment, a boutique bed-and-breakfast, or a magnificent private country compound

CONTEMPORARY FARMHOUSE! Sited on a knoll dotted with old apples trees overlooking scenic views all framed by a meandering fence. All you could ask for is in this well-built home, offering a first floor primary ensuite, library with fieldstone fireplace, A well appointed kitchen opens to both the dining and a living room with fireplace. A screen porch, 1/2 bath, laundry room/mudroom leading to a 2 car garage completes the first floor. The second floor offers 3 addition bedrooms, full bath, built-in bookcase with window seat. Kick back and relax on the front porch! A fabulous Berkshire house close to all Berkshire cultural venues, skiing, shopping, restaurants and, just plain fun!

Nestled within the absolute privacy of the 1,700-acre Doolittle Lake Company woods, this beautifully maintained 100-acre estate across two parcels features a magnificent 5,670-square-foot 1780 Center Hall Colonial blending colonial and Art Deco charm. Painstakingly relocated in the 1930s by architect Robert Carrere, the home boasts grand reception rooms with soaring ceilings, wide red pine floors, two wet bars, and nine wood-burning fireplaces. Authentic 1930s nostalgia is preserved through functioning rotary dial phones and butler bells, while the gourmet kitchen is updated with a fireplace, custom cabinetry with antique glass, and a unique trout-cleaning fish sink on the back porch. The main floor opens to stone-walled perennial gardens and a custom, heated oval gunite pool, complete with a dramatic arched pool house featuring kitchenette, half bath, dressing rooms, and an outdoor shower. Upstairs, the primary suite offers a private sitting area, fireplace, and steam shower alongside

Views, privacy, and frontage on Mill Pond. This custom built classic Gilligan house is the perfect home for hosting family and friends with plenty of space both inside, and out. There are 4 plus bedrooms and 5 baths, including a generous primary suite on the first floor, a large den, and a bonus room above the 2 car garage. The property includes a fenced, in- ground pool, extensive flat lawn, perfect for soccer or croquet, and a private dock for paddle boats, fishing and watching out for the resident Bald Eagle! The house sits on 4.49 acres and also includes 4 additional lots for a total of almost 13 acres

The mid-century retreat you've been waiting for. This classic home sits on over 4 private acres, delivering the ultimate Berkshire lifestyle with a bright, open floor plan and two cozy fireplaces. With 4 bedrooms, 3 baths, a large office, and a sun room looking overlooking your oasis, the layout offers perfect flexibility for guests or remote work. Outside, your private resort features a heated swimming pool and a dedicated tennis or pickle ball court tucked at the end of a quiet road for unmatched seclusion. Modern upgrades including a large solar array and a new heating system drastically reduce utility costs. Experience total privacy while staying minutes from everything that makes Great Barrington a premier Berkshire destination

This historic farmhouse, originally built in the 1790s, underwent a complete renovation in 2012, including a new foundation, septic system, roof, updated plumbing and electrical, 5-zone heating, central air, and other modern systems. In 2022, a new well and a boiler for radiant heat were also added. Step inside to find timeless Colonial charm-exposed beams, three original fireplaces, and gorgeous antique floors-seamlessly paired with an expansion which added a large family room with a fourth fireplace, finished basement storage, mudroom, and partially screened wraparound porch. Sun-filled living spaces feature vaulted ceilings and exposed beams. The chef's kitchen boasts premium appliances and a walk-in pantry. A versatile ground floor offers guest quarters or a private suite with full bath and separate entry. Upstairs, retreat to a luxurious master suite with spa-like bath, cedar walk-in closet, and beamed ceilings, plus two additional bedrooms and a spacious landing perfect for a hom

Rare offering of over six acres 'On the Hill', sprawling residence with first floor primary, large eat-in kitchen with cozy fireplace. porch-privacy-garage. open acreage bordered by woods. walking distance to Main Street, Skiing and Lake Mansfield nearby. Five bedrooms, three baths. Formal living room. Plenty of room for expansion

Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra storage. Inside, enjoy abundant natural light in the glassed-in sunroom or relax on the multiple porches and decks. A key feature is the large, private in-law apartment, perfect for multi-generational living or rental income. Ideally located in the heart of Sheffield village, you'll enjoy the comforts of downtown just steps from your doorstep

Custom built home situated on a private lot just minutes to GUIDOS! Impeccable home with open floor plan. kitchen, eating area, living room with fireplace. wood floors, tiled baths, gas heat, central air, established gardens including your very own blueberry patch!. A stunning house on a very special piece of take a look.

Tucked into a peaceful wooded setting in Lenox, this architecturally distinctive contemporary home offers 2,189 square feet of living space on a private half acre lot. Designed with an asymmetrical exterior and a split level floor plan spanning three levels, this home offers unique character. Large windows fill the interior with natural light, while the open living areas create an inviting space. With its distinctive contemporary design and solid architecture, this property presents an exciting opportunity for thoughtful updates that can enhance both style and value. A rare chance to create something truly special in one of Lenox's most desirable settings. View in person and experience the warmth, character, and connection to nature that make this home so unique

Old Historic Village downtown location! The centrally located Post Office building constructed in 1860, presents a unique opportunity for both residential and commercial use. Its strategic location ensures consistent foot traffic, making it an invaluable cornerstone of village life. With no mail delivery service in Ashley Falls, the Post Office attracts local residents daily. This building is offered with 3 business rentals and 2 apartments creating a living and income opportunity

Beautifully nestled in a gorgeous yard with wrap around deck and patio to enjoy the peace and tranquility of this setting! Pristine in every way with an open kitchen/dining area, which flows into the Living Room with gas fireplace, gorgeous formal dining room with lovely architectural details throughout; fabulous great room with stone, wood burning fireplace and cathedral ceiling plus a private office over the garage; the best mudroom ever with lots of cubbies and closets, updated kitchen and baths, large primary suite plus 2 additional bedrooms and full bath on the 2nd floor. The lower level is an added bonus with three finished rooms and a walk out to the stone patio and fire pit in the side yard. Brand new septic system! Nothing to do but move in and enjoy! Plus Lenox schools!

Spacious 4 bedroom Cape with several useful storage buildings for anyone with a business and attached 2 car garage. Heated sunroom with sliding windows, Eat in kitchen with access to back patio, Livingroom with knotty pine paneling and fireplace with wood burning stove. First floor has 2 bedrooms and a full bathroom with walk in shower offering first floor living. Two additional bedrooms upstairs and a half bath complete this well-kept 1950's home. Large wood furnace for basement heat and separate oil furnace for entire house. Passing Title V. Backup generator. Don't miss this one !

'A Perfect Place Farm' - a Berkshires Masterpiece on 17+ Acres The one you've been waiting for. a preeminent build in a premier location. 37 Main Rd checks off the wish list: sweeping views, modern comforts, privacy, location, and colonial era character, but in an immaculately kept turnkey 2002 home. Located in Tyringham valley, one of the Berkshires' most majestic locations, 37 Main Rd is idyllically sited on the northern slope of Tyringham valley, and faces to the southwest. The expansive front porch, sunroom, and living and sleeping quarters all are positioned to track the sun's daily arc across this picturesque east-west valley

Rare, renovated Berkshire investment compound on 0.59 acres in walkable Housatonic. This turnkey property features two separate legal duplexes (4 units total) offering stellar cash flow. The front home (392 Park St) features a 5BR/2BA unit, a sleek 2BR flat, and a prominent street-front walk-out lower level with incredible commercial/addition potential. The rear Swiss-Gothic home (394 Park St) hosts two updated 2BR units. Enjoy a sprawling backyard with mountain views, a community garden, and fruit-bearing trees. Fully insulated and optimized for easy management with 4 separate heating/electric systems, town sewer/water, and off-street parking for 10+ cars. Walk to Berkshire Mountain Bakery; minutes to Great Barrington and Tanglewood. A rare, turnkey find!

Positioned within walking distance to the vibrant downtown of Great Barrington, this property offers a unique opportunity for Homeowners, investors, non-profits, or developers seeking flexibility and future upside. Previously utilized as professional offices for mental health services, with vision, this could be converted into a 1 or 2 family home. Significant capital improvements have already been completed, including a newer boiler, newer hot water heater, a fully monitored smoke and CO detection system, and all windows replaced, ensuring efficiency and peace of mind for future ownership. The property sits on over one acre of land and features a large on-site parking lot and adjacent to a beautiful river. clients, or residents. Zoned residential, this property presents compelling redevelopment potential. Whether you envision a conversion to a single-family residence, multi-family housing, or a mixed-use concept (subject to approvals), the location and infrastructure support a wide ra

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 French doors, a gas fireplace, and a chef's kitchen designed for effortless entertaining. Also on the 1st floor, a guest bedroom suite enjoys a private bath with shower and soaking tub. On the 2nd floor the generous primary suite offers dual walk-in closets as well as an luxuriously oversized shower and soaking tub. Also on this level is a guest bedroom with ensuite bath plus two additional bedrooms with a shared bath and laundry. The lower level features approximately 1100 sf of finished space, brightened by a bank of sliding doors. These two rooms would be perfect for a family room, home office, or fitness space.

SOUTH BERKSHIRE COUNTY, UPDATED VILLAGE CENTER HOME and OFFICE This graciously restored vintage house has all the benefits of an ideal Sheffield setting with walkability to restaurants, Bushnell-Sage Library, Dewey Hall, post office, bank, and churches. With residential/commercial zoning, the house features an above-garage private large office/studio, a 1,000 sq. ft. outbuilding with plumbing and electric service, 4 auto car-bay doors, and a separate parking area. There are several possible uses for the property, including a business and/or accessory dwelling unit for possible rental income. The home itself is spacious and bright, combining period detail with updates. High ceilings, wonderful light, crown molding, soapstone counters, farmer's sink, cherry cabinets, and built in hutch. French doors, a large 1st floor Laundry Room, radiant heat in both upstairs bathrooms, and walk-in closets add to the appeal. The oversized garage, new septic system, new water heater, water softener, att

Luxurious, fully-modernized 1850s Victorian in the heart of Great Barrington. Elegant, four-story 3600 sq. ft. newly renovated clapboard and shingle house with covered porch. Meticulous renovation features chef's kitchen, four+ bedrooms, 4.5 bath, second floor and basement laundry, walk-out finished basement with private entrance and bathroom, perfect for guest suite or professional office. High-end appliances, including 6-burner Wolf stove and Bosch French door refrigerator with two freezer drawers, Bosch dishwasher, wine cooler and microwave in the island. Full-size prep sink in the kitchen island, 36' farmhouse sink in the main counter. Cabinets are all-wood with soft-close drawers and doors; vented whole-house A/C and heat pump with propane back-up; primary bath with heated floor gas grill. EV charging station in driveway. Walking distance to Lake Mansfield and Main Street shops, restaurants and theaters. House can be sold furnished

Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the 2-car garage is a sunny space for all of your seasonal gear. Upstairs, the large primary bedroom includes a 2nd wood-burning fireplace and en suite bath, while two additional bedrooms share a full bath. Main floor office and a finished lower level currently serves as guest accommodations, media room, fitness, laundry, and a variety of additional uses. New landscaping! 4 bed Title V, completed 4/26

Get ready to relax in the Berkshires in your new condo with the big windows and the high ceilings! Owner retiring and moving down south, giving up his beloved in town Great Barrington location. You'll love being close to stores and provisions for your various adventures, while being close to all the attractions that the Berkshires have to offer. And, at an approximately two and 1/2 hours from Boston or NYC, your location can't be beat. Come experience worry free living while the condo cuts your grass in the summer, or plows your driveway while you're up here to ski. 9 Stanley is simply country living at it's best! Come see it today!

This historic farmhouse, originally built in the 1790s, underwent a complete renovation in 2012, including a new foundation, septic system, roof, updated plumbing and electrical, 5-zone heating, central air, and other modern systems. In 2022, a new well and a boiler for radiant heat were also added. Step inside to find timeless Colonial charm-exposed beams, three original fireplaces, and gorgeous antique floors-seamlessly paired with an expansion which added a large family room with a fourth fireplace, finished basement storage, mudroom, and partially screened wraparound porch. Sun-filled living spaces feature vaulted ceilings and exposed beams. The chef's kitchen boasts premium appliances and a walk-in pantry. A versatile ground floor offers guest quarters or a private suite with full bath and separate entry. Upstairs, retreat to a luxurious master suite with spa-like bath, cedar walk-in closet, and beamed ceilings, plus two additional bedrooms and a spacious landing perfect for a hom