Berkshire Country, Massachusetts
Real Estate & Rentals
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Page 1 of 20Results 1 - 50 (984 total)
List Price: $8,750,000
Single Family Home
  • 250 Long Pond Rd, Great Barrington, MA
  • 9 Bedroom
  • Contemporary
  • 120.00 Acre(s)
Contemporary masterpiece beautifully situated on 120 acres offers privacy and breathtaking views in every season. Main House and Guest House were ...more »
List Price: $6,950,000
Single Family Home
  • 119 Center Rd, West Stockbridge, MA
  • 6 Bedroom
  • Other
  • 68.00 Acre(s)
When New England Hall of Fame Interior Designer Dalia Tamari decided to devote 3 years to designing and building this 6,700+/- sq.ft. European ...more »
List Price: $5,950,000
Single Family Home
  • 278 Hillsdale Rd, Egremont, MA
  • 6 Bedroom
  • Contemporary
  • 61.31 Acre(s)
From the 1300' elevation amidst the 60+/- acres of open fields, the views from this contemporary are 360 degrees: to Catamount, to the Taconic Crest ...more »
List Price: $5,300,000
Single Family Home
  • 115 Purple Mountain Pass Rd, Williamstown, MA
  • 5 Bedroom
  • Cabin, Log
  • 72.00 Acre(s)
''Jackson Hole in the Berkshires'' has a commanding mountain presence on 72+/- lush acres with views to Vermont, Williamstown proper and Mt. Greylock...more »
List Price: $4,500,000
Single Family Home
  • 185 Beartown Mountain Rd, Monterey, MA
  • 4 Bedroom
  • Contemporary, Shingle Style
  • 35.11 Acre(s)
Casually elegant and beautiful shingled eco-luxury mountaintop home with rare and extraordinary protected southerly long-range views, abutting 12000 ...more »
413-743-9000 or Contact Us Online
William Pitt Sotheby's International Realty
List Price: $4,475,000
Single Family Home
  • 104 Interlaken Rd, Stockbridge, MA
  • 5 Bedroom
  • Contemporary
  • 4.92 Acre(s)
Your lakefront paradise awaits! Live out your dreams in this stunning 5 bedroom Stockbridge Bowl home designed by an award winning architect! Set on ...more »
List Price: $3,900,000
Single Family Home
  • 106 Cliffwood St, Lenox, MA
  • 8 Bedroom
  • Historic
  • 3.60 Acre(s)
Unsurpassed 19th Century Queen Anne Style Berkshire Lenox ''Cottage'' restored and reinvented for today's most discriminating family wishing for an ...more »
List Price: $3,850,000
Single Family Home
  • 20 Berkshire Heights Rd, Great Barrington, MA
  • 6 Bedroom
  • Contemporary, Federal
  • 3.17 Acre(s)
Complete 2012 rebuild and seamless expansion of a gracious home on The Hill in Great Barrington, into a stunning timeless and modern Federal estate, ...more »
List Price: $3,500,000
Single Family Home
  • 82 Interlaken Rd, Stockbridge, MA
  • 3 Bedroom
  • A-Frame, Cabin
  • 11.11 Acre(s)
RARE WATERFRONT OPPORTUNITY ON THE STOCKBRIDGE BOWL: A PARADISE FOR YOUR FAMILY. Photo is a rendering. 11 Acres on the beautiful Bowl. Over 400 feet ...more »
List Price: $3,450,000
Single Family Home
  • 1 Pinecroft Dr, Lenox, MA
  • 6 Bedroom
  • Contemporary
  • 1.14 Acre(s)
Enjoy the ultimate luxury of a turn-key residence, steps from the Canyon Ranch resort and all of its wellness lifestyle amenities. Offered fully ...more »
List Price: $3,300,000
Single Family Home
  • 192 Burnt Hill Rd, Charlemont, MA
  • 7 Bedroom
  • A-Frame, Contemporary, Other
  • 21.71 Acre(s)
Exquisite craftsmanship and thoughtful design of this exceptional property, creates an environment of casual elegance and sophisticated style for the ...more »
List Price: $2,999,000
Single Family Home
  • Egremont, MA
  • 6 Bedroom
  • Contemporary, Cottage, NE Farmhouse
  • 65.00 Acre(s)
An exceptional Berkshire estate, The Paddocks is peacefully private on 65+/- acres of pastoral countryside. Harmonizing with the natural setting - ...more »
List Price: $2,900,000
Single Family Home
  • 108 Raup Rd, Chatham, NY
  • 3 Bedroom
  • Colonial
  • 120.00 Acre(s)
Day-O Farm is the complete Hudson Valley estate, located in perfect privacy just minutes outside the village of Chatham. Available for the first time ...more »
List Price: $2,850,000
Single Family Home
  • 52 Upper Bryant Rd, Cummington, MA
  • 4 Bedroom
  • Colonial, Historic
  • 409.00 Acre(s)
400+ Acre, fourth generation working family farm with Impeccable views of the Westfield River Valley and beyond. Located in rural Western ...more »
List Price: $2,850,000
Single Family Home
  • 260 Northwest Hill Rd, Williamstown, MA
  • 4 Bedroom
  • Contemporary
  • 28.00 Acre(s)
We all know it: we have one life to live; one home of our heart; one family retreat in which all may thrive...YOURS may be available now for you in ...more »
List Price: $2,700,000
Single Family Home
  • 12 Red Rock Rd, West Stockbridge, MA
  • 5 Bedroom
  • Contemporary
  • 22.70 Acre(s)
Apple Tree Farm -A custom designed contemporary home in West Stockbridge, Massachusetts recalls the halcyon days of the mid-1980s. A magical private ...more »
List Price: $2,650,000
Single Family Home
  • 59 White's Hill Rd, Egremont, MA
  • 3 Bedroom
  • Contemporary
  • 17.97 Acre(s)
A STUNNING HOME PROPOSED TO BE BUILT BY FAMED ARCHITECT, STEVEN HAAS! VERY LIKELY THE BEST VIEW IN BERKSHIRE COUNTY IN THE LOW TAX TOWN OF EGREMONT. ...more »
List Price: $2,595,000
Single Family Home
  • 299 Ashpohtag Rd, Norfolk, CT
  • 11 Bedroom
  • Barn, Contemporary, NE Farmhouse, Salt Box
  • 21.12 Acre(s)
Exceptional Estate - price lowered and ready to sell. Two homes on the property include original saltbox farmhouse built in late 1700s + new estate ...more »
List Price: $2,550,000
Single Family Home
  • 2650 Swamp Rd, Richmond, MA
  • 5 Bedroom
  • Greek Revival, Historic
  • 5.65 Acre(s)
April Hill, a meticulously restored Greek Revival with privacy, guest house, swimming pool and spectacular views. See the supplement for details. more »
List Price: $2,500,000
Single Family Home
  • 189 Schnackenberg Rd, Ghent, NY
  • 4 Bedroom
  • Cape, Contemporary
  • 53.14 Acre(s)
Offered to the market for the first time, a meticulous contemporary cape with it all! Sitting on over 50 acres, only 10 miles to Hudson, and with ...more »
List Price: $2,500,000
Single Family Home
  • 46 Bow Wow Rd, Egremont, MA
  • 5 Bedroom
  • Other
  • 115.82 Acre(s)
Applegate Farm...Country residence with both formal and informal common spaces to accommodate a few or many with five fireplaces, two master suites ...more »
List Price: $2,500,000
Single Family Home
  • 148 Stone Hill Rd, Williamstown, MA
  • 4 Bedroom
  • Contemporary
  • 13.28 Acre(s)
Perfectly sited at the crest of its thirteen acre property, this stunning architectural masterpiece evokes thoughts of a serene refuge from the ...more »
List Price: $2,495,000
Single Family Home
  • 38 Miller Farm Rd, Claverack, NY
  • 4 Bedroom
  • Gambrel/Dutch
  • 53.68 Acre(s)
The Dutch House. Impeccably designed, constructed to the highest standard, and overlooking an extraordinary expanse of Catskill Mountain views.Three ...more »
List Price: $2,490,000
Single Family Home
  • 575 South St, Pittsfield, MA
  • 6 Bedroom
  • Historic, Tudor
  • 11.20 Acre(s)
Description: This gilded age mansion on the gateway to Pittsfield, the Berkshires' major commercial center, has been restored to Museum quality. With...more »
List Price: $2,489,000
Single Family Home
  • 123 West Center Rd, West Stockbridge, MA
  • 5 Bedroom
  • Contemporary
  • 18.43 Acre(s)
Prominently sited on 18 acres to offer views, privacy, and dramatic sunsets.A gentle sprawling lawn and private wooded background surround this custom...more »
List Price: $2,450,000
Single Family Home
  • 720 West Rd, Richmond, MA
  • 4 Bedroom
  • Contemporary
  • 150.00 Acre(s)
Absolutely one of a kind, Do you remember when you were 10 and would escape to your tree house to enjoy no sound other than the relaxing rustling of ...more »
List Price: $2,445,500
Single Family Home
  • 305 Moreau Rd, Tolland, MA
  • 8 Bedroom
  • Contemporary, Post and Beam
  • 9.60 Acre(s)
Presenting the most grand Waterfront Estate on Otis Reservoir! As you approach the gated drive to the property you soon feel you are entering another...more »
List Price: $2,445,000
Single Family Home
  • 1990 County Route 83 Rd, Pine Plaines, NY
  • 5 Bedroom
  • Timber Frame
  • 20.95 Acre(s)
Stissing Rising, in the heart of Pine Plains' Shekomeko Valley, sits high above a panoramic vista of neighboring farms and undulating landscapes. ...more »
List Price: $2,435,000
Single Family Home
  • 60 Old Cheshire Rd, Lanesboro, MA
  • 4 Bedroom
  • Contemporary, NE Farmhouse
  • 140.00 Acre(s)
Windy Ridge Farm is an elegant country estate on 140 acres with views to Mt Greylock and the valley to the south. The location off a 1/4 mile long ...more »
413-743-9000 or Contact Us Online
Berkshire Hathaway Homeservice Barnbrook Realty
List Price: $2,400,000
Single Family Home
  • 82b Interlaken Rd, Stockbridge, MA
  • 4 Bedroom
  • A-Frame, Cabin
  • 4.86 Acre(s)
RARE WATERFRONT OPPORTUNITY: A SUMMER PARADISE FOR YOUR FAMILY. Build your dream home. Photo is a rendering of a possibility on this nearly 5 acres on...more »
413-743-9000 or Contact Us Online
William Pitt Sotheby's International Realty
List Price: $2,300,000
Single Family Home
  • 165 Kemble St. #17 --, Lenox, MA
  • 2 Bedroom
  • Other
  • 0.00 Acre(s)
Unit #17. Enjoy the ultimate luxury of the wellness lifestyle in this residence at Canyon Ranch, Lenox, one of the nation's premier spas. One of only ...more »
List Price: $2,250,000
Single Family Home
  • 508 Canaan Rd, Richmond, MA
  • 4 Bedroom
  • Barn
  • 182.00 Acre(s)
This extraordinary 182 acre property includes a 20 acre/2200 tree mixed variety apple orchard , 15 acres of meadow and balance of the acreage in ...more »
List Price: $2,250,000
Single Family Home
  • 21 Prospect Hill Rd, Stockbridge, MA
  • 5 Bedroom
  • Colonial
  • 9.40 Acre(s)
Exquisitely renovated late 1700 antique home w/ perfect proportions & amazing grounds. High ceilings, multiple fireplaces & historic details, flooded ...more »
List Price: $2,240,000
Single Family Home
  • 8 Stone Hill Rd, Stockbridge, MA
  • 5 Bedroom
  • Contemporary
  • 4.88 Acre(s)
Living is easy in this impressive Stockbridge contemporary located on a fantastic plot of land with western view, blazing sunsets and heated pool all ...more »
413-743-9000 or Contact Us Online
William Pitt Sotheby's International Realty
List Price: $2,220,000
Single Family Home
  • 2 Easland Rd, West Stockbridge, MA
  • 4 Bedroom
  • Other
  • 20.00 Acre(s)
MONET HALL.European elegance in the Country. Beautiful, custom built Stone and Brick home. Grand & intimate spaces. First floor Master Bedroom Suite ...more »
List Price: $2,195,000
Single Family Home
  • 182 Jug End Rd, Egremont, MA
  • 5 Bedroom
  • Other
  • 5.40 Acre(s)
Privately situated on a beautiful Egremont hillside, this gracious Berkshire residence is one-of-a-kind. From the grand rotunda entry to the living ...more »
List Price: $2,145,000
Single Family Home
  • 34 Oxbow Rd, Egremont, MA
  • 5 Bedroom
  • Contemporary, NE Farmhouse
  • 16.81 Acre(s)
Bright & Open Contemporary Home on 16+ acres. Open floor plan with easy flow from room to room. This 6,800 SF home owes it charm to the architectural ...more »
List Price: $2,100,000
Single Family Home
  • 135 Fiddlehead Trail, Sheffield, MA
  • 5 Bedroom
  • Contemporary, Post and Beam, Timber Frame
  • 2.30 Acre(s)
NEWLY CONSTRUCTED POST & BEAM WATERFRONT PARADISE ON 168-ACRE LAKE WITHIN A 1,000 ACRE PROTECTED WILDLIFE AREA. Striking views & fabulous amenities ...more »
List Price: $2,100,000
Single Family Home
  • 406 Canaan Valley Rd, New Marlborough, MA
  • 5 Bedroom
  • Colonial
  • 85.00 Acre(s)
Whiting Ridge: built in 1860 and renovated in 2009 by renowned AD100 architect and interior designer Daniel Romualdez. Set above the Whiting River on ...more »
List Price: $1,999,000
Single Family Home
  • 11 Londonderry Dr, Great Barrington, MA
  • 8 Bedroom
  • Contemporary
  • 13.20 Acre(s)
Extraordinary home, minutes from Great Barrington and all Berkshire activities. Expansive Living Room with Bar and Fireplace. Large Dining Room w/...more »
413-743-9000 or Contact Us Online
William Pitt Sotheby's International Realty
List Price: $1,995,000
Single Family Home
  • 907 Norfolk Rd, New Marlborough, MA
  • 7 Bedroom
  • Historic, NE Farmhouse
  • 10.00 Acre(s)
A pastoral paradise abutting conservation land, this country estate includes original farmhouse, guesthouse, horse barn, pond, an additional building ...more »
List Price: $1,995,000
Single Family Home
  • 465 Stratton Rd, Williamstown, MA
  • 7 Bedroom
  • Contemporary
  • 11.70 Acre(s)
You just found your heaven on earth. High above the banks of the Green River you stand in awe. The mountain ranges before you go on for miles. ...more »
List Price: $1,995,000
Single Family Home
  • 604 Hartsville New Marlboro Rd, New Marlborough, MA
  • 12 Bedroom
  • Colonial, Federal, Historic
  • 18.00 Acre(s)
Cassilis Farm. This historic New Marlborough landmark consists of two stately homes - one 7,666 square feet, the other 4,776 square feet - connected ...more »
List Price: $1,900,000
Single Family Home
  • 236 Bulkley St, Williamstown, MA
  • 3 Bedroom
  • Mid-Century Modern, Ranch
  • 42.50 Acre(s)
Designed by legendary Bauhaus architect Marcel Breuer, this Mid-Century Modern masterpiece is a rare, iconic work of art. Here, Breuer's bi-nuclear ...more »
List Price: $1,895,000
Single Family Home
  • 50 Shun Toll Rd, Egremont, MA
  • 4 Bedroom
  • Cape
  • 57.08 Acre(s)
BeBeautifully sited on 57 acres in North Egremont MA, this completely renovated Cape style home was originally built in the early 1900's. Peaceful and...more »
List Price: $1,895,000
Single Family Home
  • 11 Wellman Rd, Monterey, MA
  • 4 Bedroom
  • Colonial, Historic
  • 15.49 Acre(s)
FIDDLETOP, MONTEREYAn elegant, iconic Berkshire estate located on a country lane in prime Monterey. The driveway takes you past open fields and ...more »
List Price: $1,895,000
Single Family Home
  • 1 Lahey Crossroad --, Stockbridge, MA
  • 5 Bedroom
  • Other
  • 22.63 Acre(s)
Total privacy on 22 acres with back country roads for strolling. Within a couple of miles you will find fresh baked bread, a pub, the Norman Rockwell ...more »
413-743-9000 or Contact Us Online
William Pitt Sotheby's International Realty, Lenox
List Price: $1,875,000
Single Family Home
  • 235 Mccagg Rd, Kinderhook, NY
  • 5 Bedroom
  • Contemporary
  • 95.60 Acre(s)
Just like a fine Swiss watch, this exceptional property is masterfully designed, precisely constructed, and meticulously cared for. Neatly nestled on ...more »
List Price: $1,850,000
Single Family Home
  • 101 Green River Rd, Alford, MA
  • 5 Bedroom
  • NE Farmhouse
  • 14.69 Acre(s)
A Scandinavian-styled renovated modern Farmhouse with luminous light and glowing spaces, inside and out. 5 bedrooms, 3 full baths and 3 floors- ...more »
413-743-9000 or Contact Us Online
William Pitt Sotheby's International Realty
List Price: $1,850,000
Single Family Home
  • 165 Kemble St, Lenox, MA
  • 2 Bedroom
  • Other
  • 0.00 Acre(s)
Unit #8. Enjoy the ultimate luxury of the wellness lifestyle in this residence at Canyon Ranch, Lenox, one of the nation's premier spas. One of only ...more »
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