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51 Photos
COUNTRY LIFE REAL ESTATE LLC
$2,750,000
6 BD | 5 BA
Residential - Single Family

A rare opportunity to own a masterfully reimagined circa-1861 post-and-beam barn, transformedinto a one-of-a-kind luxury estate set on 89 pristine acres in the heart of Columbia County.Surrounded by sweeping pastoral views, open fields, and tranquil natural beauty, thisexceptional property offers privacy, scale, and timeless craftsmanship.The residence spans approximately 6,000 square feet across two levels, seamlessly blendinghistoric character with modern sophistication. Soaring ceilings, exposed beams, and wide-plankwood floors milled from trees harvested directly from the property*create an authenticconnection to the land and the home's heritage.At the heart of the home is a dramatic great room, ideal for entertaining or quiet evenings


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NOCHER REALTY
$325,000
3 BD | 2 BA
Residential - Single Family

OPEN HOUSE: SATURDAY, MAY 16th 10:00-11:30 AMWelcome to this charming three-bedroom, two-bath home located in the beautiful town of Dalton. Offering the perfect blend of comfort, space and convenience, the finished basement adds additional living space that can be used as a family room, game room or home gym- tailored to fit your lifestyle needs this home is ideal for anyone looking to enjoy small- town charm with easy access to nearby amenities.


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ROBERTS & ASSOC. REALTY, INC
$664,500
3 BD | 3 BA
Residential - Single Family

Must see offering in Indian Lake Estates! This contemporary truly has it all! Enter into the great room with vaulted ceiling, woodstove for chilly evenings, wood floors, and featuring natural woodwork and built-ins in the dining area. Open kitchen, guest bedroom/full bath on the main level along with den/office that leads to the primary suite. Stairway leads to an open loft and private third bedroom/full bath. Nature surrounds you here! Year-round sunroom w wall of windows; then entertain in style on the screened porch that opens to rear deck. Stay-cation on one of the three beaches at Indian Lake, non-motorized with canoe/kayak storage. Tennis courts and play area. Location on a paved road for easy access to Jacob's Pillow, and other nearby Berkshire attractions.


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LAMACCHIA REALTY, INC
$275,000
3 BD | 1 BA
Residential - Single Family

Enjoy this charming three-bedroom Cape-style home located in desirable Southeast Pittsfield. Gleaming hardwood floors run throughout most of the home. The first floor features a comfortable living room filled with natural light and a fireplace, a dining room, and a kitchen, along with a first-floor bedroom and full bathroom. Upstairs, you'll find two additional bedrooms, along with extra space for storage.Additional highlights include a spacious basement offering ample storage, a workshop area, and a laundry room with an additional sink. The home also features a one-car attached garage, public water and sewer, and low-maintenance brick siding. The kitchen includes a newer refrigerator, stove, and dishwasher.


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BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD
$825,000
5 BD | 3 BA
Residential - Single Family

Located in one of Lenox most sought after neighborhoods. Surrounded by woods, it gives you a rural feel, yet you're only minutes to the center of town. This Home features 5 bedrooms 3 Full Bathrooms and a Den with a connecting door to the 1st floor bath which gives you the options of a 6th Bedroom / Suite, Large finished sunroom, Family room with fireplace, a beautiful Kitchen, Combined Formal Dining room and Living room area great holiday and entertaining, nice details like Pocket doors and Walk-in closets and large private yard. Whether you're planning to move here or already call it home, you know why we live in the beautiful Berkshires! A picture is worth a thousand words, please enjoy them.


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KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$618,000
4 BD | 3 BA
Residential - Single Family

Stunning home in one of Dalton's most desirable neighborhoods. Set on approximately half an acre, this exceptional property offers 2,833 square feet of thoughtfully designed living space, combining comfort, style, and functionality throughout. This spacious 9-room home features 4 bedrooms and 2.5 baths with an inviting open-concept floor plan ideal for both everyday living and entertaining. Well appointed kitchen showcases granite countertops, stainless steel appliances, abundant cabinetry, and seamless flow into the expansive living room, where a striking stone fireplace serves as the focal point of the space. Natural light pours into the heated sunroom, creating the perfect year-round retreat overlooking the backyard.The finished basement adds valuable additional living space,


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COMPASS MASSACHUSETTS , LLC GB
$735,000
4 BD | 3 BA
Residential - Single Family

Spacious 4-bedroom, 2.5-bath Southeast Pittsfield Colonial on over half an acre blends classic charm with thoughtful updates and is truly move-in ready. The kitchen opens to a screened-in porch and flows into a generous dining room with built-in shelving. The light-filled living room centers around a wood-burning fireplace creating a warm gathering space. The second floor offers four bedrooms, two full bathrooms, and ample storage throughout. The large fenced backyard with professional landscaping offers exceptional outdoor living. Major updates include a new roof, central air, furnace, replaced sewer line, newer appliances, and freshly painted exterior. A two-car garage and partially finished basement round out the package.


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COMPASS MASSACHUSETTS , LLC GB
$575,000
4 BD | 3 BA
Residential - Single Family

Tucked away on a private cul-de-sac, this stunning 4-bedroom, 2.5-bath residence combines elegant upgrades with an effortlessly open and sun-drenched floor plan.The main-level primary suite is a true retreat, offering a walk-in closet and a beautifully appointed en suite with radiant heat tile, a soaking tub, and marble finishes. A convenient first-floor laundry room and a mudroom directly off the garage add everyday practicality without sacrificing style.Three additional bedrooms and a full bath complete the upper level. The walkout basement, already plumbed for a bath, presents exceptional finishing potential.Outside, an expansive deck with a pergola, an above ground saltwater pool, storage shed, and two-car garage round out this exceptional offering.


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ENGEL & VOLKERS WELLESLEY
$625,000
3 BD | 4 BA
Residential - Single Family

Spectacular country contemporary tucked amidst the forest with breathtaking views across the valley. This three bedroom, 3.5 bath 3 level home enjoys a 14 acre backdrop for complete privacy. Your long driveway meanders throught the woods gently rising in elevation until the tree canopy opens to your view of Berkshire East Mountain Resort across the valley. Open floor plan with large wrap around deck and even a greenhouse for your early vegetable growing or flowers and fruit trees. Maybe outdoor fire to watch the stars. Equidistant to the cultural explosion of the Berkshires to the west or the Greenfield area shopping conveniences makes this a great location. Outdoor activities are moments away with the Deerfield River for fishing or white water fun and Berkshire East Mountain Resort.


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BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
$1,625,000
5 BD | 5 BA
Residential - Single Family

IMMACULATE, LIKE-NEW DESIGNER CONTEMPORARY HOME tucked away on a quiet country cul-de-sac just minutes from downtown Great Barrington. Thoughtfully planned for effortless luxury living, this exceptional residence is part of an HOA community that allows you to simply arrive, enjoy, and leave with peace of mind knowing your home will remain impeccably maintained.The open-concept floor plan is highlighted by soaring 12-foot tray ceilings, stunning wood floors, a dramatic linear fireplace, and beautifully designed living spaces filled with natural light. An oversized screened porch overlooks the lush green lawn, mature plantings, and serene backyard setting, creating the perfect extension of the home for relaxing or entertaining. A spectacular chef's kitchen: see supplement:


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HOUSATONIC REAL ESTATE
$435,000
2 BD | 2 BA
Residential - Single Family

OPEN HOUSE SAT May 16th 12-2pm Nestled on a quiet setback lot in the desirable Housatonic Village of Great Barrington, this beautifully renovated home (2021) offers a perfect blend of charm, comfort, and flexibility. The property features 2 bedrooms, a bonus room, and 1.5 baths.Recent upgrades include a new roof, new windows, Buderus boiler, beautiful large wood plank floors throughout the first and second levels. The thoughtfully updated kitchen boasts modern appliances, while the renovated full bath upstairs and newly added first-floor half bath provide everyday convenience.A finished third-floor space adds valuable extra living area and may serve as a third bedroom, home office, or studio. Enjoy scenic Berkshire views, a fenced front and side yard, and a welcoming front porch.


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HOUSATONIC REAL ESTATE
$479,000
3 BD | 3 BA
Residential - Single Family

The Hatfield House -- a rare 1793 Sheffield antique offering a unique renovated live/work opportunity, move-in ready; the main residence blends historic character with modern systems; including a new sealed basement. A separate one-bedroom apartment with its own entrance provides income or guest flexibility.Set on 1.5 acres with protected wetland views, commercial/residential zoning allows for gallery, studio, office, or home business use inside the adjacent 1,200 sq ft three-bay barn with electricity. Unusual space and privacy adds versatility for a Main Street location. Formerly a famous antiques destination, this property combines history, functionality, and long-term value just a quick drive from downtown Great Barrington.


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STONE HOUSE PROPERTIES, LLC
$1,895,000
6 BD | 5 BA
Residential - Single Family

A lovely, winding approach to this gorgeous 21-acre estate ensuring serenity, privacy, and the beauty of living in the country. The main house includes 3-4 bed, 2 1/2 bath. An impressive architect-designed guest house has 2 ensuite bedrooms with balconies, dramatic exposed beams and vaulted ceilings. The guest house is an extraordinary place to host family and friends both winter and summer. With views of Tom Ball mountain, this property is a combination of gardens, fields, forest, and offers several outdoor living spaces, including a stone patio off the kitchen. A short jaunt to No. Six Depot, The Foundry performing arts, and Tanglewood. Central to Gt. Barrington, Lenox and Stockbridge for theatres, boutiques, skiing, golfing, museums and so much more at your fingertips!


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$2,650,000
5 BD | 5 BA
Residential - Single Family

A UNIQUE NEW HOME UNDER CONSTRUCTION IN THE HEART OF STOCKBRIDGE, MASSACHUSETTSHistoric Living: In an era of increasingly homogenized architecture, this extraordinary timber frame Dutch house replica offers something rare: a true sense of place. Rooted in the early traditions of the surrounding Housatonic Valley, the home is a thoughtful homage to the region's European heritage--crafted with authenticity, integrity, and many locally sourced materials designed to age gracefully.Inspired by early 18th-century Dutch design, the residence features massive anchor beam construction, a steeply pitched roof, thick plank floors and richly textured materials that develop warmth and patina over time. Traditional casement windows with deep sills, exposed timber framing, and masonry fireplaces


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COHEN & WHITE ASSOCIATES
$779,000
3 BD | 3 BA
Residential - Single Family

MOVE IN READY! CLOSE TO GOOSE POND! IN GROUND POOL! PRIVACY! CONVENIENT LOCATION! Beautifully maintained timber framed cape with central A/C and generator set in a convenient location near Goose Pond. The main level boasts afully renovated kitchen with hickory cabinets that's open to the dining room, half bath, gracious living room with Hearthstone wood stove and Pella glass door to the deck and screen porch that overlooks the in ground pool and private wooded lot. The second level includes a primary en suite, second bedroom and full bath. Both bedrooms have vaulted ceilings, wood floors and great natural light. The third bedroom, flex room has ample space located above the attached garage allowing for privacy. Large walk out basement with convenient direct access to the po