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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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Great Barrington MA 01230

Great Barrington, MA

Price$3,200,000

Est. Mortgage: $/month

MLS Number 226629

  • Single Family
  • Year Built 2006
  • Parking Spaces 2
  • Bedrooms 4
  • Bathroom 5

Wind up the gated drive through the expansive lawn to this private and classic/contemporary residence. From the car park, enter a gracious and welcoming paneled foyer to striking views through the double-height living room overlooking the stone terrace, pool and grounds to Monument Mountain and the hills beyond. Unmatched attention to the creation of this estate by a noted architect and discerning owners is apparent throughout the home with its views, flow of public and private areas, proportion of design, attention to detail, custom finishes and elegant kitchen. Its attention to both comfort and style appeals to discerning buyers of all age groups with easy access to all rooms, as well as elevator to second story and attached garage. Offer includes two adjacent building parcels.

Listed by BERKSHIRE PROPERTY AGENTS, LLC

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$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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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263 East Hill Rd New Marlborough MA 01230

New Marlborough, MA263 East Hill Rd

Price$3,100,000

Est. Mortgage: $/month

MLS Number 228551

  • Single Family
  • Address 263 East Hill Rd
  • Village Berkshire - South
  • Year Built 1992
  • Parking Spaces 3

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, drive up the long romantic winding drive to this sensitively sited and quality built home with huge windows and glass doors that draws one outside from almost every room to the truly stunning views. Large airy rooms with high ceilings, tall doorways, hardwood floors, multiple fireplaces, along with separate master and guest bedroom wings, all with ensuite baths, flow easily throughout the main house. The heated three-car garage has a Tesla charger and a guest or caretaker apartment above, with a fireplace and deck. Total seclusion, trails to a stream gorge, and magnificent serenity.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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

Lenox, MA1 Pinecroft Dr

Price$2,950,000

Est. Mortgage: $/month

MLS Number 229619

  • Single Family
  • Address 1 Pinecroft Dr
  • Village Berkshire - South
  • Year Built 2004
  • Parking Spaces 3

Exquisite in every detail, this home graces more than an acre of prime Berkshire property! In a league of it's own as part of the Pinecroft subdivsion of Canyon Ranch, this luxurious haven offers the option of membership to the world class health and wellness facility. A gourmet kitchen, fireplaced living room with wet bar and gracious dining room welcome you home!Numerous exceptional amenities abound including an eight seat hi-def movie theater, climate controlled wine cellar, sauna and soda fountain. Other features include a heated three car garage, heated gunite pool with spa and a fully equipped outdoor kitchen in the pool house!

Listed by LENOX CANYON REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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 229747

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

A unique mountain top estate with 180 degree views of Vermont, Williamstown and Mount Greylock. This meticulously curated sanctuary intimates simple luxury by combining the best materials with an inspired concept. The design and stunning architecture marry to create energy and flow for this 5 bedroom estate. The home itself benefits from a commitment towards precision engineering. Noted Jackson Hole architect shipped hand hewn beams from Montana to create this vision. Only minutes to Williams College you can gather with family and friends with formal and informal spaces. 72 Unspoiled acres afford privacy, Soaring ceilings, large fireplaces, in-ground pool, gourmet kitchen, open plan and views from almost every room. This home is awaiting its next chapter, let it be part of yours.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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

Williamstown, MA260 Northwest Hill Rd

Price$2,650,000

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: 3.49% last updated on Feb 20, 2020
* 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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25 Cliffwood St Lenox MA 01240

Lenox, MA25 Cliffwood St

Price$2,600,000

Est. Mortgage: $/month

MLS Number 228145

  • Single Family
  • Address 25 Cliffwood St
  • Village Berkshire - South
  • Year Built 1889
  • Bedrooms 10

Proudly presenting this newly refurbished 10 Bedroom, 9 and half bath, privately owned, walk to town, historic Lenox ''Cottage''. Lovingly named Osceola after the dramatic view of Osceola Mountain on the Yokun Ridge experienced upon entering the columned and balustraded front porch. Osceola Mansion was designed by world renowned architects Rotch and Tilden in 1889 and commissioned by Sarah Pollock Livingston. Today, this comfortable and beautifully appointed home features an entry foyer with a fireplace to warm your hands and toes after a winter's sleigh ride. Enter the Grand Hall which invites you into the Living Room to your right or draws your attention to the unique Oval Dining Room to your left. Straight ahead is the picturesque outdoor covered 80 feet in length Veranda

Listed by BERKSHIRE HOMES AND CONDOS

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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

Richmond, MA2650 Swamp Rd

Price$2,550,000

Est. Mortgage: $/month

MLS Number 221750

  • Single Family
  • Address 2650 Swamp Rd
  • Village Berkshire - Central
  • Year Built 1850
  • Bedrooms 5

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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

Williamstown, MA148 Stone Hill Rd

Price$2,500,000

Est. Mortgage: $/month

MLS Number 226918

  • Single Family
  • Address 148 Stone Hill Rd
  • Village Berkshire - North
  • Year Built 2005
  • Parking Spaces 2

Perfectly sited at the crest of its thirteen acre property, this stunning architectural masterpiece evokes thoughts of a serene refuge from the harried pace of everyday life. A truly breathtaking panorama unfolds before you as you approach, and you are immersed in 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 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: 3.49% last updated on Feb 20, 2020
* 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

Egremont, MA46 Bow Wow Rd

Price$2,500,000

Est. Mortgage: $/month

MLS Number 221749

  • Single Family
  • Address 46 Bow Wow Rd
  • Village Berkshire - South
  • Year Built 1915
  • Bedrooms 5

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: 3.49% last updated on Feb 20, 2020
* 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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99 Shaker Museum Rd Old Chatham NY 12136

Old Chatham, NY99 Shaker Museum Rd

Price$2,500,000

Est. Mortgage: $/month

MLS Number 229391

  • Single Family
  • Address 99 Shaker Museum Rd
  • Year Built 1790
  • Bedrooms 12
  • Bathroom 10

This large historic property available with component pricing:*House with 30+/- acres, all or some accessory buildings/greenhouse @ $2,500,000* 43,000' barn complex on 170+/- acres @$1,950,000* entire 207 acres all buildings and barns @ $3,95,000The Old Chatham Sheepherders Estate dates back to 1790 and is a landmark property in Upper Hudson Valley, only 30 min from Albany Int'l Airport and Hudson's Amtrak. IDEAL AS A FAMILY COMPOUND, AGRICULTURAL ENTERPRISE OR LIVESTOCK/HORSE FARM, The estate includes a grand 12 room Federal home with 5 bedrooms and 5 1/2 baths, large living room w/ FP, den w/ FP, library, hand muraled dining room and bi-level porches. Formerly a Relais&Chateau ( no longer allowed as an inn) all of the systems have been engineered to the highest commercial

Listed by LANDVEST, INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* 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