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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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2 Glendale Middle Rd, Stockbridge, MA 01262

Price$6,875,000

Est. Mortgage: $/month

Pending

MLS Number 215244

  • Single Family
  • Selling Office Name LANDVEST, INC.
  • Selling Agent LANDVEST, INC.
  • Year Built 1870
  • Bedrooms 8

SOUTHMAYD FARM Gilded Age at its finest in Stockbridge. This 1870 Berkshire estate has been fully restored & is privately sited on 33+ acres within walking distance of town. Adjacent to the Stockbridge Golf Club & the Norman Rockwell Museum, the view includes a mile of Housatonic River frontage. The 8500' main house w/ 8 bedrooms is complemented by a carriage house, greenhouse/studio, pool, , 3 bedroom guest house, barn complex and paddocks, a magnificent maze, and additional formal gardens. See documents file for detail of each building, room and floor plan.

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

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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 01258

Price$6,150,000

Est. Mortgage: $/month

MLS Number 220002

  • Single Family
  • Year Built 2008
  • Parking Spaces 6
  • Bedrooms 6
  • Bathroom 6

Listed by Thomas McGowan and Elyse Morris of Elyse Harney Real Estate

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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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14 Weber Rd, Sharon, CT 06069

Price$5,945,000

Est. Mortgage: $/month

MLS Number 210878

  • Single Family
  • Year Built 1988
  • Parking Spaces 2
  • Bedrooms 5
  • Bathroom 7

Macedonia State Forest and the crest of 284.4 acres of rolling mountains provide the superb setting for a newly renovated 5 Bedroom, 5.5 Bath home for sale in Sharon, CT. The grandeur of the setting is reflected by the luxury and spaciousness of the architecture that takes full advantage of the 360 degree protected views spanning the Litchfield Hills and Hudson Valley.

Listed by Elyse Morris and Elyse Harney of Elyse Harney Real Estate

{$agent->Name}

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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 & 114 Cliffwood St, Lenox, MA 01240

Price$4,750,000

Est. Mortgage: $/month

MLS Number 217523

  • Single Family
  • Year Built 1883
  • Parking Spaces 3
  • Bedrooms 8
  • Bathroom 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 Mary Jane White and Nancy Kalodner of COHEN & WHITE ASSOCIATES

{$agent->Name}

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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

185 Beartown Mountain Rd, Monterey, MA 01245

Price$4,500,000

Est. Mortgage: $/month

MLS Number 220508

  • Single Family
  • Year Built 2004
  • Bedrooms 4
  • Bathroom 4
  • Total Full Baths 3

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 Timothy Lovett of BERKSHIRE PROPERTY AGENTS

{$agent->Name}

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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

90 Bowne Rd, Sharon, CT 06069

Price$4,450,000

Est. Mortgage: $/month

MLS Number 214809

  • Single Family
  • Year Built 1998
  • Bedrooms 3
  • Bathroom 5
  • Total Full Baths 3

European Country EleganceA meandering driveway approaches this artistically designed stone & wood Country Home with hand hewn beams throughout. Impeccably built, combining the warmth of the Kitchen/Great Room's Rumford Fireplace with the sophistication of the Living Room's soaring ceilings and pillared entry. The Mead Hall's whimsical accents bely the formality of the Living Room, exemplifying

Listed by Elyse Morris and Elyse Harney of Elyse Harney Real Estate

{$agent->Name}

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

89 Cliffwood St, Lenox, MA 01240

Price$3,950,000

Est. Mortgage: $/month

MLS Number 217574

  • Single Family
  • Year Built 1888
  • Bedrooms 6
  • Bathroom 8
  • Total Full Baths 5

SUPREMELY WELCOMING...One of Lenox's19th century Berkshire''cottages'' that has been meticulously restored and updated.

Listed by Deborah Levinson of BERKSHIRE PROPERTY AGENTS

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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

27 Hemlock Hill Rd, Great Barrington, MA 01230

Price$3,600,000

Est. Mortgage: $/month

MLS Number 219342

  • Single Family
  • Year Built 2006
  • Bedrooms 4
  • Bathroom 5
  • Total Full Baths 4

GREAT BARRINGTON MASTERPIECE. Designed by the world renowned and award winning architect, Kenneth Nadler. Reminiscent of an Arts and Crafts mansion. This superb stone and cedar Contemporary home sits majestically on 10 acres of privacy within walking distance to downtown. The features are a mixture of old world with every modern day convenience including soaring ceilings, intricate moldings, a kitchen that will satisfy the most discerning of chefs, a sumptuous master suite that is serene and beautiful and an elevator just to name of few. Delightful from beginning to end this home offers quality, charm, and grandeur. Nothing was spared in this unique and truly special home. Nadler designed a home for Beyonce and Jay Z.

Listed by Maureen Kirkby of BARNBROOK REALTY, INC.

{$agent->Name}

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

65 Shun Toll Rd, Egremont, MA 01230

Price$3,500,000

Est. Mortgage: $/month

MLS Number 219302

  • Single Family
  • Year Built 2006
  • Parking Spaces 3
  • Bedrooms 4
  • Bathroom 7

Many dream of converting a historic barn into a country house. A barn tells a story, has a past, and the old beams, posts and boards have a patina and a magic which new construction can never recreate. This 26 acre estate is masterfully designed and crafted from two 18th & 19th century barns on one of the Berkshire's finest country lanes in North Egremont. 65 Shun Toll Road embodies a rustic elegance that will simply captivate you as you gaze across the soaring, yet brilliantly intimate spaces and through the expanses of glass to the inspiring and extraordinary distant views of farmland below and mountains beyond. Offering nearly every luxury imaginable in its 6, 600 square feet, yet in an ultimately comfortable and authentic manner - the perfect Berkshire country home.

Listed by L. Chapin Fish of BROCKMAN REAL ESTATE, LLC

{$agent->Name}

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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

50 Mount Hunger Estates --, Monterey, MA 01245

Price$2,995,000

Est. Mortgage: $/month

MLS Number 219713

  • Single Family
  • Year Built 2005
  • Parking Spaces 4
  • Bedrooms 7
  • Bathroom 5

THREE STATE SOUTH WESTERLY VIEW over Lake Garfield to the Catskill range all the way on the other side of the Hudson River. Built on a mountaintop in 2005 down a long gated drive, this seven-bedroom, five-bath, 5700sf Contemporary home in Monterey, MA enjoys ultimate privacy on over 16 acres. Enter a two-story great room and be immediately knocked out by the view, possibly the best from any home in the southern Berkshires. The generous first floor master suite has an office library, and there are two more bedrooms on the main floor. Guests have their own floor with four bedrooms, two baths, and a second kitchen and family room, all with the same panoramic vistas. Four fireplaces, two-car attached garage, and separate two car garage for county and lake toys. The ultimate mountainside lodge.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS

{$agent->Name}

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 2017
* 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