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Berkshire Single Family Properties

Discover single family homes for sale in the Southern Berkshires of Massachusetts. Find homes in Great Barrington, Egremont, Lee, and beyond. Search through a variety of current listings, including lakeside homes, antique luxury homes, and many more! Whether you're looking for multimillion dollar estates or modest cabins and camps, Southern Berkshire homes are truly diverse and offer options for most any homebuyer. Enjoy the mountains, lakes, and the area's many natural wonders from your new home!

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250 Long Pond Rd, Great Barrington, MA 01230

Price$8,750,000

Est. Mortgage: $/month

MLS Number 225029

  • Single Family
  • Village Berkshire - South
  • Year Built 2007
  • Parking Spaces 3
  • Bedrooms 9

Contemporary masterpiece beautifully situated on 120 acres offers privacy and breathtaking views in every season. Main House and Guest House were designed by Steven Haas, recognized by Architectural Digest as one of the world's foremost architects. Sorpetaler sliding glass walls and expansive decks create a harmonious interplay with nature. Beautiful barn adds to allure of this unique property. Outdoor features include 25-meter heated saltwater lap pool, hot tub, outdoor showers, stone fire pit, exquisite rock outcroppings, sweeping lawn, hiking trails and access to Williams River trout stream. Quintessential Berkshires setting off private road just minutes from vibrant town center of Great Barrington, selected in 2012 by Smithsonian Magazine as #1 of The 20 best small towns in America.

Listed by Non-member

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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119 Center Rd, West Stockbridge, MA 01266

Price$6,950,000

Est. Mortgage: $/month

MLS Number 223235

  • Single Family
  • Village Berkshire - South
  • Year Built 2007
  • Bedrooms 6
  • Bathroom 8

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 influenced country home, her first step was to select the best of settings in the heart of the Berkshires, MA. The chosen 68+/- acres, accessed by a long and winding drive leads to a hilltop with commanding views and privacy. Exceptionally designed, the home is both grand and family friendly. The kitchen, by the famed designer herself, is a prime gathering area to cook together, set against an elevated field stone fireplace. This magnificent property offers a 1st floor master and 5 add't bedrooms upstairs, all with baths ensuite. The pool is adjacent to a pool house with full scale kitchen and laundry. All set on beautifully landscaped grounds.

Listed by LANDVEST, INC.

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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278 Hillsdale Rd, Egremont, MA 01230

Price$5,950,000

Est. Mortgage: $/month

MLS Number 224222

  • Single Family
  • Village Berkshire - South
  • Year Built 2008
  • Parking Spaces 6
  • Bedrooms 6

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 and to the Catskills extending as far as Hunter Mtn 43 miles away!The residence is as large and engaging as the views. The over 7,000 +/- sq.ft. main house has 11 rooms, 6 bedrooms and 6 full baths. The Barn/ 2 bedroom Apt and 33' long Art studio (or auto display) adds 3500'. The dining room can seat 20 and the entire glass wall opens to the patio with a stone grill. The coffered ceiling living room spans the width of the house and opens to the patio seating with outdoor fireplace.

Listed by LANDVEST, INC.

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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115 Purple Mountain Pass Rd, Williamstown, MA 01267

MLS Number 224798

  • Single Family
  • Village Berkshire - North
  • Year Built 2003
  • Parking Spaces 3
  • Bedrooms 5

''Jackson Hole in the Berkshires'' has a commanding mountain presence on 72+/- lush acres with views to Vermont, Williamstown proper and Mt. Greylock. To add to the ultimate privacy, the property is surrounded by the 2600+/- acre Hopkins Memorial Forest owned by Williams College. While offering the utmost in privacy and tranquility, the house is minutes down the hill to the burgeoning North County cultural and recreational amenities fueled by MassMOCA, Williams College, Williamstown Theatre Festival, the Clark Art Museum and Jinny Peak. Designed by a famed Jackson Hole architect and constructed with beams hand hewn in Montana and shipped to Williamstown, the 10,000+/- ft* residence has two levels, a first floor Master bedroom and 4 other bedrooms, all with baths ensuite.

Listed by Cindy Welch and Keith Ross of LANDVEST, INC.

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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185 Beartown Mountain Rd, Monterey, MA 01245

Price$4,500,000

Est. Mortgage: $/month

MLS Number 220508

  • Single Family
  • Village Berkshire - South
  • Year Built 2004
  • Bedrooms 4
  • Bathroom 4

Casually elegant and beautiful shingled eco-luxury mountaintop home with rare and extraordinary protected southerly long-range views, abutting 12000 acre Beartown State Forest. Carefully and exquisitely crafted, the gracious rooms feature four fireplaces with a hefty stone central core, mahogany windows and doors, and radiant heated wood floors. The horse barn has three generous stalls, a tack room, and caretaker's quarters. Horses enjoy organic pastures and an outdoor arena that could easily be a tennis court. The private setting and views are unmatched in the southern Berkshires, and the quality of construction speaks for itself.

Listed by BERKSHIRE PROPERTY AGENTS

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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104 Interlaken Rd, Stockbridge, MA 01262

Price$4,475,000

Est. Mortgage: $/month

MLS Number 225202

  • Single Family
  • Village Berkshire - South
  • Year Built 1981
  • Bedrooms 5
  • Bathroom 4

Your lakefront paradise awaits! Live out your dreams in this stunning 5 bedroom Stockbridge Bowl home designed by an award winning architect! Set on just under 5 verdant acres with 315 feet of lake frontage & your own private dock. Enjoy swimming & boating & spectacular lake & mountain views from your waterfront lawn, porches and terraces. The property also features a scenic babbling brook with footbridge plus many mature plantings & hardwoods. The privacy here is unequaled, with no neighboring homes in view. In addition to all of this, you're just down the road from Tanglewood, downtown Lenox & Stockbridge & many of the Berkshires' world class cultural attractions. Don't miss this once in a lifetime opportunity!

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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106 Cliffwood St, Lenox, MA 01240

Price$3,900,000

Est. Mortgage: $/month

MLS Number 217523

  • Single Family
  • Village Berkshire - South
  • Year Built 1883
  • Parking Spaces 3
  • Bedrooms 8

Unsurpassed 19th Century Queen Anne Style Berkshire Lenox ''Cottage'' restored and reinvented for today's most discriminating family wishing for an understatedly elegant, 'cool' and comfortable Twenty-First Century lifestyle. See attached document for all details. Shown by advance appointment only.

Listed by COHEN & WHITE ASSOCIATES

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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20 Berkshire Heights Rd, Great Barrington, MA 01230

MLS Number 223462

  • Single Family
  • Village Berkshire - South
  • Year Built 1915
  • Bedrooms 6
  • Bathroom 7

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.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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82 Interlaken Rd, Stockbridge, MA 01262

Price$3,500,000

Est. Mortgage: $/month

MLS Number 222056

  • Single Family
  • Village Berkshire - South
  • Year Built 1959
  • Bedrooms 3
  • Bathroom 2

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 of pristine lake frontage looking across the ''belly'' of the Bowl. Two beautiful site specific modern style plans have been drawn with walls of windows from every room facing the lake. Amazing mountain and water views in every season. Build one private home or a family compound. Three home sites with existing structure for rare opportunity to have your dream home within 71 feet of the lake. Minutes to Tanglewood, Kripalu, and Canyon Ranch.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1 Pinecroft Dr, Lenox, MA 01240

Price$3,450,000

Est. Mortgage: $/month

MLS Number 222383

  • Single Family
  • Village Berkshire - South
  • Year Built 2004
  • Parking Spaces 3
  • Bedrooms 6

Enjoy the ultimate luxury of a turn-key residence, steps from the Canyon Ranch resort and all of its wellness lifestyle amenities. Offered fully furnished, this extraordinary home features a beamed great room with stone fireplace, formal dining room, gourmet eat-in kitchen, fabulous lower level space with vintage soda fountain, screening room, wine room and sauna, six bedrooms, five full baths, deck, patio, heated swimming pool, and poolhouse containing a guest suite and full kitchen for outdoor entertaining. You'll appreciate its exquisite detailing, from the heated courtyard to Venetian-plaster walls. Ideally located near Lenox shops and restaurants, Tanglewood, Shakespeare & Company, and all of the cultural, culinary, and recreational amenities for which the Berkshires are renowned.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details