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50 Photos
BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY
$2,395,000
5 BD | 5 BA
Residential - Single Family

Take in the unparalleled beauty and majestic views of this 24-acre riverfront property. This 5-bedroom well-appointed home and private guest house create the perfect luxury retreat. With airy open-plan living, the Craftsman-style main house offers 4,500+ sq. ft., 3 fireplaces, panoramic views and a private 1st floor master wing. Entertain family and friends throughout the 1st floor or unwind in the spacious informal living room on the 2nd floor. Explore the property on well- maintained walking trails or cool off in the tranquil Williams River, the perfect spot to fish, kayak or swim. Outdoor living spaces abound, including a large screened porch with fireplace and adjacent stone patio, ideal for watching a beautiful Berkshire sunset. Minutes to Great Barrington and Tanglewood.


35 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$2,450,000
5 BD | 7 BA
Residential - Single Family

SPACIOUS CONTEMPORARY WITH OPEN LIVING PLAN, POOL, TERRACES & GIANT VIEWS: Set on 13 plus acres, this 5800 SF home features 5 en suite bedrooms, including 1st floor master suite with sitting room. Gourmet kitchen, formal dining, great room & fitness/playroom with built in bunks. 4 fireplaces, central a/c & oversized 2 car garage. Gunite pool with hot tub. Extensive flagstone terraces and pergola with sweeping mountain and pastoral views. Covered flagstone from porch for entertaining. Near NY Border, one of the first homes in Massachusetts. Close to Catamount Ski Basin, Great Barrington and all Berkshire attractions.


41 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$2,499,000
6 BD | 4 BA
Residential - Single Family

An exceptional Berkshire estate, The Paddocks is peacefully private on 65+/- acres of pastoral countryside. Harmonizing with the natural setting - nestled among towering pines - the sun filled contemporary farmhouse overlooks the picturesque brook-fed wildlife pond, paddocks, and woodlands. Large windows bring the outdoors into this airy 5-bedroom, passive-solar-heated residence featuring a vaulted living room with fireplace. At the heart of the equestrian complex, the expandable 11-stall stable with tack room adjoins a large indoor riding arena, seen from the lounge/viewing room with wet bar. Across the stable yard is a garage/workshop with caretaker's apartment. The fenced paddocks are accompanied by an outdoor arena with fibar footing. Two antique cottages and an antique barn.


32 Photos
BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

REAL ESTATE ONLY. This property is a great opportunity for any investor. Currently being run as a twenty-four lane bowling alley with a bar, an arcade, a food stand, a Uhaul center and a mini golf course. You could easily add eight more bowling lanes to this property. Centrally located in Great Barrington so it is easy to get to CT, NY, the Turnpike, and all of Berkshire County. There is so much upside to this property. There is parking for over 100 cars and a very high traffic count daily.


3 Photos
WHEELER & TAYLOR REALTY CO., INC.

This scenic 56 acre lake and nature sanctuary can be all yours! 250+ acres of pristine water and woods. Round Pond is a private lake only 5 miles from downtown Great Barrington! The park-like setting includes a pure, spring-fed lake, hardwood forest, lovely plantings, nature trails, and sandy beach. Spectacular lake and mountain views! It just doesn't get any better than this.


46 Photos
BERKSHIRE PROPERTY AGENTS, LLC
$2,995,000
6 BD | 7 BA
Residential - Single Family

Complete 2012 rebuild and seamless expansion of a gracious home on The Hill in Great Barrington, into a stunning timeless and modern Federal estate, perched on a notable parcel with a barn and private spa pool. No detail was overlooked inside or out from custom everything to geothermal heating and cooling. Too many amenities to list, including central A/C, full house generator, Pella true divided light windows throughout, Rocky Mountain hardware, Lutron lighting, spray foam insulation, double insulated floors, and most all of the house has radiant heated floors and of course state-of-the-art mechanicals. The three acres are beautifully landscaped and include a spa pool with a waterfall and auto cover, bocci court, invisible dog fence, a seasonal stream, and a barn. Walk to town.


51 Photos
BERKSHIRE PROPERTY AGENTS, LLC
$3,100,000
5 BD | 6 BA
Residential - Single Family

Cookledge, is a sprawling contemporary compound spread over mountain top glacial outcroppings, with awe-inspiring views south over Connecticut and west to the Taconic Range. Nearby the Southfield Store Cafe, drive up the long romantic winding drive to this sensitively sited and quality built home with huge windows and glass doors that draws one outside from almost every room to the truly stunning views. Large airy rooms with high ceilings, tall doorways, hardwood floors, multiple fireplaces, along with separate master and guest bedroom wings, all with ensuite baths, flow easily throughout the main house. The heated three-car garage has a Tesla charger and a guest or caretaker apartment above, with a fireplace and deck. Total seclusion, trails to a stream gorge, and magnificent serenity.


52 Photos
BERKSHIRE PROPERTY AGENTS, LLC
$3,200,000
4 BD | 5 BA
Residential - Single Family

Wind up the gated drive through the expansive lawn to this private and classic/contemporary residence. From the car park, enter a gracious and welcoming paneled foyer to striking views through the double-height living room overlooking the stone terrace, pool and grounds to Monument Mountain and the hills beyond. Unmatched attention to the creation of this estate by a noted architect and discerning owners is apparent throughout the home with its views, flow of public and private areas, proportion of design, attention to detail, custom finishes and elegant kitchen. Its attention to both comfort and style appeals to discerning buyers of all age groups with easy access to all rooms, as well as elevator to second story and attached garage. Offer includes two adjacent building parcels.


49 Photos
STONE HOUSE PROPERTIES, LLC
$4,999,000
4 BD | 6 BA
Residential - Single Family

Breathtaking Tri-State views from this light filled, 12,000 sq. ft masterpiece featuring gourmet kitchen, huge library, wine cellar, indoor pool with sauna and steam room, as well as an elevator connecting all the levels. This stunning property has been designed by NY architect Michael Schmitt and completely renovated by Peter Whitehead.Private guest wing with three bedrooms and two bathrooms. Fiber Connect for Internet. Close to 90 acres of privacy on one of the most sought after roads in Southern Berkshires.


44 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$12,900,000
6 BD | 8 BA
Residential - Single Family

Set apart by its extraordinary scope, beauty, and privacy, this property stretches across 350A+/- acres of idyllic land in the Berkshire Hills, presiding over a mountaintop realm in the midst of vast rolling woodlands and open meadows which provide the setting for its various residences and comprehensive equestrian facilities. This one-of-a-kind estate creates a gathering place for family and friends to enjoy the relaxation and sporting life of this worlds-away natural paradise, glorious in every New England season, also offering an excellent opportunity for potential subdivision or expansion on numerous sites of the acreage. Winding its way through the sylvan landscape, highlighted by a tranquil pond, a mile-long drive arrives at the mountaintop main residence, designed

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