142 properties for sale in Great Barrington

Welcome to 12 Mountain St, a quintessential colonial masterpiece that blends classic elegance with modern functionality. Spanning over three expansive, light-filled floors, this stunning home offers five spacious bedrooms and 3.5 bathrooms, providing the ideal layout for those who love to entertain. The chef's kitchen is designed to inspire with high-end finishes, including a vast center island, a professional-grade Six-burner gas stove w/pot filler, chic quartz countertops. With an abundance of cabinetry and a dedicated, organized pantry featuring custom built-ins, this kitchen is as practical as it is beautiful. Gleaming hardwood floors flow throughout the main level, creating a seamless, inviting atmosphere. Ascend to the second floor, where you will find a tranquil primary en suite wit spa shower alongside two additional bedrooms connected by a well-appointed Jack-and-Jill bath. The third floor offers incredible flexibility with two more large, sun-drenched bedrooms and a dedicated

This exquisite single-family home spans an impressive 4,300 square feet, offering an unmatched blend of elegance and modern comfort. With 5 spacious bedrooms and 4.5 beautifully renovated bathrooms, every detail has been meticulously crafted to perfection. Walking distance to downtown Great Barrington's shops and restaurants, the house is in one of the quietest areas of 'The Hill'. 12 rooms including a formal dining room, a sophisticated library/den, and a versatile media/recreation room. The chef's kitchen, featuring premium counters, a WOLF range, a Sub Zero refrigerator, a wine cooler, and a butler's pantry for seamless entertaining. The home is filled with natural light. Comfort is ensured year-round with air conditioning and central heating on every floor

Your own sports compound and sanctuary tucked away on a quiet Great Barrington road: this private four-acre retreat centers around an in-ground heated swimming pool and a dedicated tennis/pickleball court framed by natural landscape. Inside, clean mid-century architectural lines deliver remarkable flow, highlighted by two fireplaces, four bedrooms, three baths, space to work from home, and a sunroom overlooking the grounds. Substantial energy upgrades include a high-output ground-mount solar array and an updated heating system that keep operational costs remarkably low, offering a turnkey private playground just minutes from downtown dining, skiing, and cultural landmarks

Charming In-Town Cape on a Spacious Lot with Inground Pool. Located in a delightful neighborhood close to town. This inviting home built in 1951 offers 5 bedrooms and 2 full baths. Inside, the residence seamlessly balances ample room to spread out with warm, light-filled spaces tailored for everyday living and entertaining. Timeless architectural details throughout bring character and charm, including a wood-burning fireplace, graceful arched doorways and custom built-in cabinetry. Outdoors, a private in-ground pool is set within a large, sunny yard, creating a wonderful oasis. Turn-key peace of mind is provided by recent upgrades, including a newer including a newer furnace, water heater and pool filter. Town water, town sewer and natural gas from the street. Close to everything - A must see!

Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure. Inside, the home is thoughtfully designed to host both family and guests in complete comfort, offering five well-appointed bedrooms, six full bathrooms, and a half bath, providing privacy and ease for all. The first-floor primary suite serves as a true sanctuary, complete with two separate full bathrooms for an elevated sense of luxury. MORE The main level of the home includes a generous living room, a formal dining room featuring a custom four-wall mural by noted (formerly local) artist Laurel Tewes, a cozy library or den, a well-appointed kitchen with three refrigeration units including a side-by-si

Moments from Lake Mansfield and Main Street, this turnkey contemporary offers clean lines, natural light, and effortless Berkshire living. The main level features an open-concept floor plan anchored by a show-stopping Duvemala tiled stove, serving as a striking centerpiece for gatherings and cozy evenings by the fire. Enjoy the convenience of a first-floor bedroom alongside one of the home's three well-appointed full baths. Upstairs, an expansive primary suite impresses with vast cathedral ceilings. The finished lower level adds a versatile bonus room, providing extra square footage for a home gym or game room. Outside, relax and entertain on the sun-soaked deck overlooking the oversized grounds of this rare double-sized parcel

Perched above the historic Great Barrington railroad station, this bright turn-of-the-century Victorian offers an appealing combination of character, privacy, and in-town convenience. Lovingly maintained and renovated over 25 years of ownership, the home has benefited from numerous improvements including a new roof and boiler. With an elevated setting overlooking downtown, the property enjoys a surprising sense of seclusion while remaining just two blocks from the heart of town. Inside, three bedrooms, two full baths and an eat-in kitchen provide comfortable everyday living. Additional bonus spaces in the attic and basement offer flexibility. Filled with the character and warmth of an earlier era, enjoy the pleasure of living within easy walking distance of the town's shops and resturants

Immaculate and well-maintained contemporary home in an exceptionally convenient location set on 5+ wooded acres. Designed for easy living and low maintenance, this home offers an open floor plan with high ceilings, wood floors, and a beautiful fieldstone fireplace anchoring the main living space. The kitchen opens to another living area creating a comfortable flow for everyday living and entertaining. Enjoy the lovely screened porch and outdoor deck overlooking the natural setting. Three bedrooms and 3.5 baths, including guest quarters or apartment space for added flexibility. Large two-car garage. It is in a very private setting, but is also a short distance (walking distance) to the elementary and secondary schools. Easy transition for a first floor primary bedroom

STILL HOUSE brings a new level of contemporary design to the Berkshires-quietly luxurious, exquisitely detailed, and made to be lived in. Minutes from the center of Great Barrington, this newly completed 5,148-square-foot home pairs the distinctive vision of acclaimed Brooklyn studio Me and General Design with exceptional craftsmanship and materials throughout. Four bedrooms, five-and-a-half baths, a heated saltwater pool, bespoke spa and fitness spaces, solar energy and exceptional privacy make this as much a retreat as a home.Preserved stone walls from the original structure bring history, texture and a distinctly Berkshire character to the new architecture. The main living level opens into a dramatic kitchen, dining and living space with cathedral ceilings, two stories of glass and views into the surrounding landscape. The custom Porcelanosa kitchen features richly veined stone, a substantial island, induction cooking, double ovens, integrated refrigeration, microwave drawer, dedica

THIS HOME HAS BEEN UNDER CONSTRICTION SINCE 2018. PRICE DOES NOT REFLECT CURRENT MARKET CONDITIONS. PRICES ARE NOT AT THIS PRICE POINT ANY LONGER. Open plan living with, first floor master, fireplace, screened porch, high ceilings, two car garage, community pool. HOA covers all lawn maintenance, plowing, shoveling up to the front door. Quality New Construction. This price cannot be matched. 10 months to move into your beautiful new home. Photos are from a similar home with the same floor plan in the community, with upgrades. Build your dream home on one of the other beautiful lots. Single level with 2100 square feet or as large as 3800 square feet. 3-5 bedrooms with prices beginning at $689,000

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, hardwood floors, and period details. The kitchen and living areas are perfect for entertaining or relaxing with family. Upstairs, the bedrooms offer privacy and comfort, with plenty of storage throughout. Warm and efficient forced hot water heating. The back apartment has potential to turn the attic into living space: think office, den, TV room, or mediation space. Your ideas await! Enjoy the peaceful backyard, ideal for gardening, BBQ, play, or quiet evenings under the stars. Whether you're looking to settle into the vibrant Great Barrington community or invest in a high-demand rental market, 41 Pearl Street is a r

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. Wood-burning fireplace, exposed beams, hardwood floors, and a spacious three-season porch overlooking the stone patio all make this property a must-see. The lot offers a large yard as well as the patio, a two car garage and an additional outbuilding

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 BEDROOMS AND A BATH, LEADING UP TO AN UNFINISHED THIRD FLOOR WHICH HAS GREAT POTENTIAL

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, 4+ 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

Immaculate 3-bedroom ranch with additional 750 square feet of finished living space in lower level. Move in condition, cathedral ceiling in living room and 2 full baths, Prmary with ensuite. Set way back off Park Street North on 0.62 level acres. 8+ acres owned by Land Conservation in your back yard adds peace and privacy

Nestled within a mixed use residential/commercial block this renovated space is ready for the next creative commercial endeavor. Rent the house and use the studio for art, office, store or Live and work all within walking distance to town center. Thoughtfully brought from a commercial office space to a 2 bedroom, 1.5 bath, bright open and airy living space with 5 parking spots and a nice size yard

'Located in Great Barrington's coveted residential neighborhood surrounded by million-dollar-plus estates, this home offers an unbeatable entry point into luxury Berkshire living. Designed with distinct living zones, the two-level layout provides the ultimate setup for weekend guests, remote working, family room or great potential for multi-generational living. The main living level features bright, flowing living space framed by natural views, perfect for effortless entertaining after a day in town or on the trails. Enjoy beautiful mature landscaping, outdoor living spaces and prime proximity to downtown Great Barrington at an accessible price point

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

Built in 2021, this custom contemporary offers about 5,670 sq ft of finished living space on 2+ acres, just 5 minutes to Great Barrington center, with mountain views and sunsets to the west. The open first floor features vaulted ceilings, a propane fireplace and a chef's kitchen with a large island, coffee bar and generous storage, opening to the dining and living areas. A large screened porch extends the living space three seasons a year. A mudroom with laundry off the oversized 3-car garage, two offices and a powder room complete the main level. Upstairs, two guest rooms with en suite baths and a primary suite with fireplace and a large bath. The finished lower level adds about 1,900 sq ft: game room, gym, media room, guest bedroom and full bath. Central air, high-speed fiber available, and truly turnkey, with sunset views over the neighboring private airport

Beautifully sited to capture light and long-range views, this architect-designed residence offers timeless elegance within a serene natural setting. Bright, sophisticated interiors open seamlessly to a screened porch and stone terraces overlooking the pool and manicured grounds. Generous proportions and refined architectural details define the living spaces, complemented by a beautifully reimagined library/office, dining, living media/den and kitchen. First-floor primary suite serves as a private retreat, while additional en-suite bedrooms provide comfort and discretion for guests. An upper-level loft (w/ elevator)offers space for gym, studio, or media. A rare offering of privacy, design, and distinction in the Berkshires

FOR SALE: Prime Downtown Great Barrington Gem - Endless Possibilities! Welcome to 406 Main Street, a rare opportunity in the heart of downtown Great Barrington, MA. Just steps from bustling Main Street shops and restaurants, this versatile 5,180 sq ft building offers exceptional potential for residential, commercial, or creative mixed-use transformation. Zoned B2, the property allows for single-family, multi-unit, or live/work conversion-with no sprinkler system required for up to 3 residential units. Already equipped with 1 full bath and 4 powder rooms, and featuring two finished floors, the layout adapts effortlessly to your vision-be it modern apartments, stylish offices, retail space, or a dynamic studio. - Spacious and bright with 5,180 sq ft across two levels - Excellent bone

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

'ON THE HILL' Cozy 4 bedroom 1925 Cape, HOUSE BEING SOLD 'AS IS' WALK TO TOWN AND LAKE MANSFIELD. Living room with mini split, custom built cabinets in DR, Large primary bedroom with mini split, large family room, OPEN FRONT PORCH WITH VIEWS. BACK YARD PATIO FOR COOK OUTS. Attached 1 car garage, TOWN WATER AND SEWER. So much charm, house needs updating. DONT MISS THIS GEM !

Prime investment opportunity! This five-unit property features a desirable mix of four, one-bedroom apartments and one, two-bedroom. All units have their own separate heating and electrical systems! Convenient location ensures high demand due to proximity to stores and the hospital. On-site parking. Detached garage/workshop could be rented separately for additional income or used as storage for tenants

Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless interaction during meals and gatherings. The living area extends outward to two distinct private spaces: a screened-in porch for three-season relaxation and a separate private deck. Designed for convenience and longevity, the first floor features a primary bedroom suite complete with a spacious en-suite bathroom and laundry

TO BE BUILT: Gorgeous neighborhood setting with lush landscaping and Indulge in refined Berkshire living on an exclusive cul-de-sac, where effortless HOA services complement this exquisite new construction. Offering 3,808 sq ft of thoughtfully designed, environmentally conscious living less than a mile from downtown Great Barrington, this home is the perfect modern retreat. Enter through a covered portico into a soaring cathedral-ceiling great room filled with natural light and serene woodland views. A wonderful screened porch expands the living space for peaceful mornings or easy entertaining. The open layout seamlessly connects the living, dining, and chef's kitchen, featuring premium appliances, quartz countertops, and a spacious island. A sophisticated split-bedroom design. Modern conveniences include a first-floor laundry, advanced electric heat pump systems promoting energy efficiency, and an electric vehicle charging station in the garage

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.

Set on a sunny half-acre lot, this classic 1900 ranch is ready for its next chapter and top/bottom reinvention.The home is now strictly an 'as-is' handyman special or contractor's dream. Features a cozy compact ( yes small ) kitchen, vintage vibes (meaning every room needs a facelift ),and dirt basement. Roof is holding strong for now, but you'll want to budget for a replacement soon (real sooner) The real star here' The land and location, half-acre of fantastic, usable Berkshires property, you have ample room to expand, build new, or execute a total dream renovation. Title V not complete, seller will not repair fails, will be the responsibility of the Buyer. Showings must be scheduled; the home is occupied. Won't qualify for most lending products

Building has been used as an antique business for the last 50 years. Seller had previously lived in the upstairs apartment. Located across the street from Mend and Calgary's and. 5 miles from downtown Great Barrington. Selling as is, business and inventory for sale separately. Negotiable with owner. Near all the cultural events specific to the Berkshires!

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!