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40 Photos
BERKSHIRE BUSINESS PROPERTIES
$1,990,000
11 BD | 5 BA
Residential - Single Family

HISTORIC BERKSHIRE FARM Gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns and maintenance building. 161 acres with stunning views, mountain paths, and Jim Kelly's stunning giant stonewalls throughout. Gorgeous New England marble stone farmhouse built in 1780, with modern addition featuring vaulted ceiling and massive windows which flood the dining and kitchen area with light. Enormous custom built hearth and fireplace, mahogany full bar, artisan-made bookcases, wrap-around deck. Close to Williams College and Jiminy Peak. The property offers swimming in two private ponds, 6 bay carriage barn with second floor for offices, studios., or storage.


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THE KINDERHOOK GROUP - PITTSFIELD
$1,995,000
5 BD | 2 BA
Residential - Single Family

Welcome to Camp Mohawk, a pristine lakefront property in the heart of the Berkshires. Located on Cheshire Reservoir, a virtually uninhabited lake, located just off the main north-south artery of Berkshire County. Once a summer camp, the existing main house and barns are listed on the National Register of Historic Places, and date to the late 1700's. Would make a lovely family compound, or could be developed as a spa/resort, corporate/wellness retreat, condominium/single family and retirement housing,


64 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$1,995,000
4 BD | 6 BA
Residential - Single Family

Tucked in the Berkshires of Western Massachusetts, this Williamstown contemporary boasts over 7,000 sq. ft. of undeniable form and function mixed with the highest degree of finishes. It's been said that homes can be duplicated anywhere, but a setting with unique and rare attributes cannot. Gently Sited amidst a spectacular 34-acre backdrop bordering 8,000 +/- acres of protected land is incredibly rare. Architecturally designed to contour with the natural topography of the site greatly reduced disturbance when built. This multi-tiered footprint affords picturesque sunset views of the village below and Berkshire hills beyond. Watch a soccer game at Cole field from your Gunite pool, walk to the village for dinner or go hiking on Chestnut/Pine Cobble Trails right off your property...


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$2,200,000
4 BD | 3 BA
Residential - Single Family

This quintessential country property is what everyone wants. Located in the Southern Berkshires close to the towns of Great Barrington, New Marlborough and Southfield and Norfolk, CT. This sleek historic and beautifully restored home is conveniently located for skiing, hiking, arts and culture, restaurants and all other Berkshire offerings. This home is beautifully restored and includes a stunning 'party ' barn, and separate garage/storage shed. The house glows, filled with light and sun. A large living room with fireplace and several seating areas has views to fields and flowers. A cook's kitchen with a counter-height fireplace looks out onto a stone patio with fire pit. The library, tv/ media room and powder room complete the 1st floor.Four.bedrooms, 2.5 baths. Restored barn.


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Compass Massachusetts, LLC
$2,215,000
4 BD | 4 BA
Residential - Single Family

Built in 1904 this historic home sits on a beautiful 1.4-acre lot, which offers privacy while being in the most coveted and accessible neighborhood of Great Barrington. High ceilings and adorned with oak and mahogany woodwork throughout, this home has been tastefully renovated while retaining its period charm. The spacious layout, with 4 bedrooms, 31/2 bathrooms and an expansive porch provide comfort and grace. A fully updated kitchen, new windows, central air and natural gas enhance the living experience with modern ease. The surrounding landscape is adorned with perennial beds, and mature specimen trees. Walkable to town's restaurants, shops and farmers market, this property offers laid-back charm along with convenience and style.


39 Photos
BERKSHIRE PROPERTY AGENTS, LLC
$2,495,000
2 BD | 3 BA
Residential - Single Family

Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side captures the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere you look you stop to take in the view, large bath with walk-in closet and laundry. The inner courtyard has a heated pool, sunken jacuzzi, outdoor shower, screened porch with fireplace and beautiful perennial gardens. Hidden off the drive is a guest cottage with open living area, bedroom and full bath.


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WILLIAM PITT SOTHEBY'S - LENOX
$2,600,000
5 BD | 4 BA
Residential - Single Family

A setting surrounded by classic Columbia County views of rolling hills and bucolic farmland, smack in the middle of Old Chatham hunt country is the ideal location for this grand, turn of the century five bedroom farmhouse with a in-law suite, guest cottage, in-ground stone pool, pedigree three story barn, a studio outbuilding, and three car garage. A traditional layout prevails throughout with a gracious entrance complete with dutch door, stone flooring and a wood burning fireplace. The large, light filled country kitchen is the heart of the home with expansive views and doors leading to a deck and sublime stone patio, making it ideal for entertaining. The first floor is complete with three more fireplaces and many more rooms for dining, gathering, studying, reading and creating.


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LANCE VERMEULEN RE, INC
$2,975,000
5 BD | 4 BA
Residential - Single Family

Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it offers plenty of room to entertain and relax. The large cook's kitchen is perfect for preparing meals for large gatherings, while the heated sun room provides a cozy spot to enjoy your morning coffee and take in the stunning views of the surrounding fields. This home also features 5 spacious bedrooms (primary with en-suite, four jack-and-jill), each with their own unique charm and character.


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PIRETTI REAL ESTATE
$2,995,000
7 BD | 9 BA
Residential - Single Family

Stunning renovations just completed on this beautiful Lenox Contemporary! First floor primary with gorgeous new bath and walk in closet plus 5 additional bedrooms and 4 full baths on the 2nd floor and an additional bedroom and full bath on the lower level. Plenty of room for family or guests and wonderful entertaining spaces, including a fabulous back yard, in ground gunite pool, recently completed pool house with kitchen, bath and living area...and if that's not enough in the way of fun, there's a full outdoor kitchen in the Pavilion overlooking the pool. In addition there's a hot tub, 2 fire pits and a finished lower level with family room, game room and full bar and wine room! This home is truly a ''Staycation'' with 4 fireplaces, vaulted ceilings, privacy on almost 5A and


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$3,100,000
7 BD | 6 BA
Residential - Single Family

Custom built salt box home situated on 32 subdividable acres at the end of dirt town maintained road.. Beartown State forest abuts this property. Amenities include: PRIVACY, heated inground Gunite pool, stunning views of Monument Mnt., established gardens include apple orchard, Lilies and Peonies. Main House inc. living room, kitchen, dining room and library all with fireplaces. 4 bedrooms, 2 full baths, expansive ensuite primary with views. 3rd floor with two bedrooms and full bath. Finished lower level with gym, screening room, pool table space. New oil fired boiler and HWH Free standing 3 bedroom caretakers house with additional 2 bedroom apartment. A LITTEL PIECE OF HEAVEN! Minutes to Great Barrington and Stockbridge. If you seek privacy .....we have it here!


48 Photos
LANCE VERMEULEN RE, INC
$3,750,000
4 BD | 5 BA
Residential - Single Family

Custom Built Craftsman Contemporary Home nestled in a beautifully landscaped property with an orchard, gardens and path to a seasonal brook. Inside this well appointed home you will find large rooms, radiant floor heat throughout & forced air, Vaulted ceilings, whimsical lighting, Fireplaces, Indoor pool, hot tub and sauna. Two primary suites on main floor and 2/3 more bedrooms in the lower walkout portion of the home. Large Timber Frame screen porch and deck overlooking rear of the property. Media room and recreation room with more space for added entertainment. A 4+ car plus heated garage with an ample unfinished area above for storage or a creative mind. Bonus Option (not included in listed price)to this property is a brand new 2 bedroom contemporary guest house for an expanded fami


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Compass Massachusetts, LLC
$3,785,000
7 BD | 3 BA
Residential - Single Family

Blue Hill Farm: an 1820 Center Hall Colonial farm and farmhouse in excellent condition on 249 high acres with organic hay meadows and pastureland, an apple orchard, woodlands, gardens, tennis court, a 1970's caretaker/farmer's house and multiple barns. The main house has 6/7 bedrooms and three baths, along with a three-car attached garage. The property consists of seven parcels of contiguous land surrounded by the Umpachene River on three sides. There are long views to the west of the Taconic Range from inside and outside of the home, and a grouping of supportive barns to the south across a very rarely traveled, narrow dirt road. Offered for the first time since 1967, this is truly an unusual and rare offering with development possibilities featuring extraordinary views.


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COHEN & WHITE ASSOCIATES
$3,960,000
5 BD | 8 BA
Residential - Single Family

The Birches....welcome to your new oasis in the Berkshires where every season is memorable. This magical compound has been architecturally redesigned & renovated using the finest materials offering all the modern amenities a buyer wants to live, play, relax and work from, surrounded by 20+ acres of privacy & far reaching protected views in all directions. This stunning contemporary has big open common areas for gathering, first floor primary en suite, guest bedrooms en suite and a private two bedroom guest quarters w/kitchenette, custom crafted wine room, and an exercise room all offering plenty of space for a large crowd or intimacy for a few. Just arrive with your suitcase and enjoy all this impeccably maintained estate has to offer; a beautiful gunite heated pool w/waterfall &


91 Photos
LANCE VERMEULEN RE, INC
$4,200,000
5 BD | 7 BA
Residential - Single Family

Discover unparalleled luxury and serenity in this extraordinary 5-BR, 7-BA estate nestled in the heart of New Marlborough. Spanning over 6,000 square feet, this stunning residence is set on expansive grounds, 70+ acres, featuring a harmonious blend of wooded areas, open fields & distant mountain views. Designed by renowned architect Allan Shope, this architectural masterpiece is an uplifting retreat, seamlessly integrating modern design with nature's beauty. The home's thoughtful design takes full advantage of the sloping hillside, offering dramatic views from every angle. Inside, you'll find meticulous attention to detail, from the finest materials to timeless craftsmanship. The modern open floor plan flows effortlessly, with an indoor lap pool for year-round enjoyment.


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COMPASS MASSACHUSETTS, LLC.
$4,250,000
7 BD | 7 BA
Residential - Single Family

Significantly restored in 2024! Sellers have masterfully updated this legacy home w/ a cool & fresh aesthetic that preserves the integrity of its Mid-century Modern design. Updates to the 1st floor primary suite, kit, entertainment kit, bathrooms & freshly painted interiors are just a few of the improvements. The airy main living spaces w/ their expansive sliding glass doors offer sublime views of the resort-like grounds complete w/ manicured lawns, patios, in-ground pool, playground, newly resurfaced tennis/pickle ball court, gardens curated by a Master Gardener & distant mountain views. The 7 bedroom, 7 bathroom estate w/ 8200 sq ft of versatile living space prominently sited on 57+ acres is 3 hours to NYC and 2 Hours to Boston!


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$5,150,000
7 BD | 9 BA
Residential - Single Family

Elegant Berkshire Stone Estate with 125 acres of Canyon Ranch Serenity. Thoughtful design combined with masterful craftsmanship in this exquisite turnkey home, a rare offering in the Pinecroft compound of Canyon Ranch. The split floor plan boasts 300 year old reclaimed timber floors, crown moldings throughout. A sumptuous primary wing with stone fireplace and dual walk-in closets and bathrooms. The great room is anchored by a floor to ceiling stone fireplace with incredible iron work and an artisanal custom designed wet bar. Nano doors bring the outdoors in during the warmer months. The heart of the home is the eat-in chef's kitchen with Sub Zero/ Thermador appliances, oversized island with dual dishwashers with pocket doors to the formal dining room. Rounding out the main floor

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