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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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Egremont, MA 01230

Price$2,999,000

Est. Mortgage: $/month

MLS Number 224418

  • Single Family
  • Year Built 1982
  • Bedrooms 6
  • Bathroom 4
  • Total Full Baths 3

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.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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108 Raup Rd, Chatham, NY 12037

Price$2,900,000

Est. Mortgage: $/month

MLS Number 224895

  • Single Family
  • Year Built 1792
  • Parking Spaces 6
  • Bedrooms 3
  • Bathroom 4

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 in nearly 30 years, Harry Belafonte's former Columbia County retreat is magical at every turn. Grandly sited, the 1792 main house is a purist's dream, and also offers a main floor master wing with fireplace. The adjacent original carriage house offers a guest suite and beamed ceiling game room, in addition to three car bays. Through the gardens, on the hillside overlooking the main house, is the spacious two bedroom guest house with sauna. The terrace overlooks the oversized gunite pool and pond, with path to the tennis court. Follow the trails through the woods to a one bedroom loft-style hunting cabin. Many tax savings options available.

Listed by Non-member

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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260 Northwest Hill Rd, Williamstown, MA 01267

Price$2,850,000

Est. Mortgage: $/month

MLS Number 225364

  • Single Family
  • Village Berkshire - North
  • Year Built 1995
  • Bedrooms 4
  • Bathroom 5

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 Williamstown! A Home of comfort, harmony and created with an unprecedented level of thoughtful attention to every detail from the perfectly aligned and matched Brazilian cherry flooring to the unsurpassed stone mason's craftsmanship of fireplace design; the Lazure hand painted walls; and perfection-achieved quality evident in every niche and corner of every room. Set perfectly on 27 private acres of lawns, patios and pool; woodlands, and extensive all season gardens opening onto magical views of hills and sky beyond. This is a home where life is inspired. This is a home for a most-fortunate family....perhaps it's yours! See Supplement....

Listed by COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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12 Red Rock Rd, West Stockbridge, MA 01266

Price$2,700,000

Est. Mortgage: $/month

MLS Number 225154

  • Single Family
  • Village Berkshire - South
  • Year Built 1986
  • Parking Spaces 2
  • Bedrooms 5

Apple Tree Farm -A custom designed contemporary home in West Stockbridge, Massachusetts recalls the halcyon days of the mid-1980s. A magical private setting with views, clay bottom swimming pond, over sized hot tub, incredible gardens and grounds....The stone walls , walk ways, expansive decks, pergola, Koi pond, screen porch and Birch tree forest are some of the amenities. Main house includes a spacious floor plan with large living room with stone fireplace, dining room with fireplace, open kitchen, library, two main floor bedrooms and baths. The second floor is comprised of the master suite, with window walls and roof deck to enjoy the mountain views. The free standing 2 bedroom guest house is just steps away. Use as a a studio, his and her offices, gardening room or cozy guest quarter

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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59 White's Hill Rd, Egremont, MA 01230

Price$2,650,000

Est. Mortgage: $/month

MLS Number 219625

  • Single Family
  • Village Berkshire - South
  • Year Built 2018
  • Parking Spaces 2
  • Bedrooms 3

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. An exceptional chance to collaborate with a world class architect to design the home of your dreams! See supplement for more information.See mls #213036 for lot alone. A house that truly brings the outdoors in. Loads of glass, incredible long distance views, infinity pool connected to the house via pergola and an expansive viewing terrace.A separate gazebo overlooks the pool and view beyond. An open plan offers a huge

Listed by BERKSHIRE PROPERTY AGENTS

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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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2650 Swamp Rd, Richmond, MA 01254

Price$2,550,000

Est. Mortgage: $/month

MLS Number 221750

  • Single Family
  • Village Berkshire - Central
  • Year Built 1850
  • Bedrooms 5
  • Bathroom 7

April Hill, a meticulously restored Greek Revival with privacy, guest house, swimming pool and spectacular views. See the supplement for details.

Listed by STONE HOUSE PROPERTIES, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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46 Bow Wow Rd, Egremont, MA 01258

Price$2,500,000

Est. Mortgage: $/month

MLS Number 221749

  • Single Family
  • Village Berkshire - South
  • Year Built 1915
  • Bedrooms 5
  • Bathroom 6

Applegate Farm...Country residence with both formal and informal common spaces to accommodate a few or many with five fireplaces, two master suites and guest wing with tennis court all overlooking your own lake with a western mountain view for backdrop. 100 + acres of very special land located on the border of Egremont and Sheffield on a back country road.

Listed by COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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148 Stone Hill Rd, Williamstown, MA 01267

Price$2,500,000

Est. Mortgage: $/month

MLS Number 225481

  • Single Family
  • Village Berkshire - North
  • Year Built 2005
  • Parking Spaces 2
  • Bedrooms 4

Perfectly sited at the crest of its thirteen acre property, this stunning architectural masterpiece evokes thoughts of a serene refuge from the hurried pace of everyday life. A truly breathtaking panorama unfolds before you as you approach, and you are immersed peaceful quietude and utter privacy. Reminiscent of both old world grace and an agrarian past, and in homage to the New England add-on tradition, with its granite wing off its cupola-topped host, the residence invites you to slow down, relax and indulge in the view. Light-filled and airy, the great room provides a soothing, restful ambiance, and yet, as open to the kitchen, the opportunity for gatherings both intimate and grand. The serious cook's kitchen with center island and large butler's pantry is ideally suited for entertaining.

Listed by ALTON & WESTALL REAL ESTATE AGENCY, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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79 Hawthorne St, Stockbridge, MA 01262

Price$2,500,000

Est. Mortgage: $/month

MLS Number 225611

  • Single Family
  • Village Berkshire - South
  • Year Built 1988
  • Parking Spaces 3
  • Bedrooms 4

An exquisite traditional Georgian-style brick manor house is the centerpiece of this rare 36-acre Stockbridge estate, which offers both privacy and proximity to Lenox village, Wheatleigh, Tanglewood, and myriad Berkshire amenities. In a jewel-like setting with mature landscaping and views of lawns and hills, the residence combines 21st-century conveniences with impeccable architectural details, including elements from historic Georgian and Federal homes. Conveying quality and luxury, these details--a welcoming arms staircase, graceful columns and mantels, Palladian windows--epitomize the finest in traditional American design and create an ideal place for entertaining. The photos, virtual tour and floor plans are helpful, but, for the discerning buyer, this property is a must see.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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189 Schnackenberg Rd, Ghent, NY 12075

Price$2,500,000

Est. Mortgage: $/month

MLS Number 225555

  • Single Family
  • Year Built 2008
  • Bedrooms 4
  • Bathroom 4
  • Total Full Baths 3

Offered to the market for the first time, a meticulous modernized farmhouse with it all! Sitting on over 50 acres, only 10 miles to Hudson, and with expansive Catskill Mountain views. Sleek and open chef kitchen with top of the line appliances, honed granite countertops, and window lined breakfast nook. Living room with rustic beams, gorgeous wood burning stone fireplace, and chestnut floors. First floor master suite. Wraparound porch. Crystal clear swim pond with a cozy cabin. Separate barn with workshop/studio space. A must see to truly appreciate.

Listed by STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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