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  • For Sale

    24 & 30 Berkshire Heights Rd

    Great Barrington, MA 01230

    $4,900,000

    A rare estate offering in the Berkshires. Breathtaking southern and western views from this historically important Great Barrington estate. Designed by Charles Platt for Charles Freer of the renowned...

    • Bed4
    • Bath3
    • Sqft6,240
    • MLS232672
  • Reduced

    6 Seekonk Cross Rd

    Alford, MA 01230

    $4,500,000

    When the Interior Design Hall of Famers were commissioned to build a family compound in the beautiful Berkshires, they first started by getting acquainted with the land. Calvin Tsao...

    • Bed4
    • Bath4
    • Sqft7,000
    • MLS233896
  • For Sale

    20 Jug End Rd

    Egremont, MA 01258

    $4,400,000

    Gracious and stately New England colonial farmhouse on 230 acres.Antique barns and outbuildings, pool with amazing views. A babbling brook runs near the house and into a small pond...

    • Bed5
    • Bath4
    • Sqft3,240
    • MLS234456
  • For Sale

    535 Sheffield Egremont Rd

    Sheffield, MA 01257

    $3,995,000

    SUNSET MOUNTAIN VIEWS, PRIVACY & WONDERFUL AMENITIES IN YOUR OWN PRIVATE HOME RESORT…….Architect designed 5 br, 6 bath Contemporary with spacious open common living, stunning main level primary bedroom...

    • Bed5
    • Bath6
    • Sqft6,746
    • MLS235743
  • For Sale

    27 Hemlock Hill Rd

    Great Barrington, MA 01230

    $3,450,000

    NY architect Kenneth Nadler designed this custom built home on 43 acres ( 5.07 acres/38.46 acre lot). 4 bedrooms, 4.5 baths. Main level living room with fireplace (gas insert)...

    • Bed4
    • Bath4
    • Sqft5,497
    • MLS233686
  • For Sale

    263 East Hill Rd

    New Marlborough, MA 01230

    $3,100,000

    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,...

    • Bed5
    • Bath5
    • Sqft5,953
    • MLS228551
  • For Sale

    112 Brush Hill Rd

    Great Barrington, MA 01230

    $2,995,000

    Custom-built five-bedroom Timbercraft home on 8+ acres. Private tennis/basketball court, in-ground Gunite heated pool. Pennsylvania Stone and cedar shake exterior, three-sided fireplace and Timberframe truss ceiling in great room....

    • Bed5
    • Bath4
    • Sqft5,764
    • MLS232761
  • For Sale

    78 Mountain Rd

    Mt Washington, MA 01258

    $2,990,000

    Welcome to Mount Washington, Hilltop Town of one hundred and sixty five full time residents spread out over fourteen thousand acres. The majority of which is protected land. This...

    • Bed4
    • Bath3
    • Sqft4,600
    • MLS235087
  • For Sale

    18 West Rd

    Alford, MA 01230

    $2,875,000

    Industrial Modern Chic in Alford on 11+ wooded acres, just 5 minutes to downtown Great Barrington. Designed by award-winning architects, this single level home has 5 bedrooms, 4.5 baths...

    • Bed5
    • Bath4
    • Sqft4,200
    • MLS235136
  • For Sale

    4 & 8 Boice Rd

    Egremont, MA 01230

    $2,749,000

    Unique Berkshire Riverfront Retreat offering privacy & tranquility bounded on one side by the pristine Green River (782′ frontage). Playground for all ages! Sited on 9+ rolling acres. High-end...

    • Bed6
    • Bath6
    • Sqft6,350
    • MLS233961
  • For Sale

    21 Kalliste Hill

    Great Barrington, MA 01230

    $2,600,000

    Privacy, expansiveness & spectacular views into CT! This contemporary cedar home is an idyllic, private sanctuary in a dream location featuring a hilltop swimming pool w/ stone patio, horse...

    • Bed3
    • Bath2
    • Sqft2,900
    • MLS234767
  • For Sale

    281 Main St

    Great Barrington, MA 01230

    $2,295,000

    This gorgeous and successful bed and breakfast offers a unique opportunity to live and work in the heart of Great Barrington. Each of the six exquisite suites features a...

    • Bed8
    • Sqft6,800
    • MLS233982
  • Pending

    21 Kalliste Hill

    Great Barrington, MA 01230

    $2,100,000

    Privacy, expansiveness & spectacular views into CT! This contemporary cedar home is an idyllic, private sanctuary in a dream location featuring a hilltop swimming pool w/ stone patio, horse...

    • Bed3
    • Bath2
    • Sqft2,900
    • MLS235495
  • For Sale

    Ox Bow Rd

    Egremont, MA 01230

    $2,000,000

    A magnificent property with 360 degree views. Perfect for one estate parcel or divisible in up to four parcels. Views of Catamount and the Catskills to the west and...

    • Acres2310000.00
    • MLS234939
  • Reduced

    83 Hurlburt Rd

    Great Barrington, MA 01230

    $1,985,000

    This meticulously renovated home on one of Great Barrington’s most desirable roads is perfect for both a full-time home or weekends in the country. Traditional exterior but thoroughly moderized...

    • Bed4
    • Bath4
    • Sqft3,206
    • MLS232860
  • For Sale

    55 Stratford Rd

    New Marlborough, MA 01230

    $1,975,000

    Tranquility with privacy, gracious amount of water frontage on beautiful Lake Windermere, walking trails and sprawling lawn surround this dramatic contemporary. Gracious open common spaces, very large screened porch...

    • Bed5
    • Bath3
    • Sqft3,915
    • MLS230291
  • For Sale

    306 310 Main St

    Great Barrington, MA 01230

    $1,975,000

    Beautifully maintained mixed use property in prime Great Barrington downtown Main Street location. Originally a Masonic Lodge, the property now houses a realtor’s office in a spacious double-front ground-floor...

    • Bed9
    • Sqft6,156
    • Acres2875.00
    • MLS235212
  • Pending

    Great Barrington, MA 01230

    $1,895,000

    The beautiful & historic Windflower Inn is a terrific business or lifestyle opportunity. Built in 1850 & meticulously maintained, this rambling colonial with 13 en-suite guest rooms, several with...

    • Bed18
    • Bath17
    • MLS233794
  • Reduced

    684 South Egremont Rd

    Great Barrington, MA 01230

    $1,895,000

    The beautiful & historic Windflower Inn, is a terrific business or lifestyle opportunity. Built in 1850 & meticulously maintained, this rambling colonial with 13 en-suite guest rooms, several with...

    • Bed19
    • Bath17
    • Sqft17,551
    • MLS233793
  • Reduced

    684 South Egremont Rd

    Great Barrington, MA 01230

    $1,895,000

    The beautiful & historic Windflower Inn is a terrific business or lifestyle opportunity. Built in 1850 & meticulously maintained, this rambling colonial with 13 en-suite guest rooms, several with...

    • Bed18
    • Sqft17,551
    • Acres454331.00
    • MLS233792
  • New Listing

    104 Downs Rd

    New Marlborough, MA 01230

    $1,750,000

    LAKE BUEL WATERFRONT!! This remodeled home has tranquil lake & mountain views. The quality and attention to detail on the 3 living levels has been tastefully done, and includes...

    • Bed3
    • Bath3
    • Sqft2,500
    • MLS236023
  • New Listing

    30 Pinecrest Hill Rd

    Egremont, MA 01258

    $1,695,000

    From the gorgeous grounds to the stunning views to the cloistered pool area with Zen pool house to the beautiful home that somehow manages to be charming, hip and...

    • Bed3
    • Bath2
    • Sqft2,791
    • MLS236058
  • For Sale

    453 Stockbridge Rd

    Great Barrington, MA 01230

    $1,595,000

    Thornewood Inn (13 guest rooms plus owners’ apartment) with a full restaurant is available for its next owner for the first time in nearly 40 years. Greatly expanded and...

    • Bed14
    • Bath14
    • Sqft10,302
    • Acres118919.00
    • MLS232572
  • Reduced

    350 Maple Ave

    Great Barrington, MA 01230

    $1,595,000

    LOCATED 5 MINUTES TO DOWNTOWN GREAT BARRINGTON. If you want space, comfort, privacy, and room for the whole family to come, then this house is for you! Open concept...

    • Bed6
    • Bath5
    • Sqft7,800
    • MLS231411
  • For Sale

    453 Stockbridge Rd

    Great Barrington, MA 01230

    $1,595,000

    Perfect for large family or other looking to utilize10,000 sf plus of space for dwelling or other mixed-use purposes. Current configuration has 13 guest suites plus the owners’ apartment....

    • Bed14
    • Bath14
    • Sqft10,302
    • MLS232573
  • For Sale

    602 606 Hartsville New Marlborough Rd

    New Marlborough, MA 01230

    $1,525,000

    The ultimate family and friends compound with 23 rooms, 11 bedrooms, and 8 baths in 2 houses connected by a 2nd floor porch. The main house was built in...

    • Bed11
    • Bath7
    • Sqft11,065
    • MLS233958
  • For Sale

    8 Knight Rd

    New Marlborough, MA 01230

    $1,499,000

    Opportunity Knocks.A local Winery. Here is a complete turnkey business in a great location with 5 acres and a complete vineyard. Located about 6 miles from town in a...

    • Sqft5,000
    • Acres217800.00
    • MLS224028
  • For Sale

    204 Hillsdale Rd

    Egremont, MA 01230

    $1,375,000

    If you’re searching for a peaceful sanctuary that you could move right into, then you’ve found your place. This lovely four-bedroom, four-bath contemporary home is tucked away in a...

    • Bed4
    • Bath3
    • Sqft3,542
    • MLS233854
  • Pending

    30 Lake Mansfield Rd

    Great Barrington, MA 01230

    $1,290,000

    Wonderful Lakeside retreat on Lake Mansfield. Great room with Fireplace, chefs Kitchen, Sunroom, Den, Primary Bedroom Suite and 2 additional Bedrooms on the main floor. Upstairs is a Bonus...

    • Bed3
    • Bath2
    • Sqft2,336
    • MLS235408
  • For Sale

    158 Alford Rd

    Great Barrington, MA 01230

    $1,180,000

    Charming Yankee barn post and beam home with 4 bedrooms, 3 full baths, charming updated kitchen. (6 burner Viking) Open family, dining kitchen, screen porch. Large living room, dining...

    • Bed4
    • Bath3
    • Sqft3,700
    • MLS235248

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