Resort Properties in the Berkshires

Search through current resort properties for sale in the Berkshire County area. Find a variety of listings in towns like Lenox, Dalton, Lee, & many more! The real estate professionals at McLean realtors can help you find the right home for you!

Be sure to create an account with us so you can keep track of your favorite listings. You will also receive updates when new properties that match your criteria come on the market. If you already have an account with us, sign in here. Feel free to contact us for more information and to schedule a tour for any listing below.

1 Pinecroft Dr Lenox MA 01240

Price$3,250,000

Est. Mortgage: $/month

MLS Number 222383

  • Listings Residential
  • Address 1 Pinecroft Dr
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 7816

Enjoy the ultimate Berkshire luxury lifestyle in this turn-key residence, with a preferred membership to Canyon Ranch resort, which is just steps away. This extraordinary home features a beamed great room with stone fireplace, formal dining room, gourmet eat-in kitchen, main-level master with fireplace & two walk-in closets, main level guest suite, four additional bedrooms, a lower level with vintage soda fountain, screening room, wine room & sauna, a deck & patio, heated swimming pool, & pool house containing a guest suite & full kitchen for outdoor entertaining. Impeccable details throughout, including a heated courtyard parking area; offered fully furnished. Ideally located near Lenox village & the cultural, culinary & recreational amenities for which the Berkshires are renowned.

Listed by Gladys Montgomery of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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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165 Kemble St. #17 -- Lenox MA 01240

Price$2,300,000

Est. Mortgage: $/month

MLS Number 220577

  • Listings Residential
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1950
  • Year Built 2017

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 19 units, it features a spacious great room, master suite, kitchen, two fireplaces, private patio. Mandatory annual resort membership affords access to its unparalleled facilities, close to the cultural, culinary, and outdoor amenities in the Berkshires.

Listed by Leslie G Chesloff and Gladys Montgomery of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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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165 Kemble St Lenox MA 01240

Price$1,850,000

Est. Mortgage: $/month

MLS Number 220572

  • Listings Residential
  • Address 165 Kemble St
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1683

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 19 units, it features a spacious great room, master suite, kitchen, two fireplaces, private patio. Mandatory annual resort membership affords access to its unparalleled facilities, close to the cultural, culinary, and outdoor amenities in the Berkshires.

Listed by Leslie G Chesloff and Gladys Montgomery of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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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11 Londonderry Dr Great Barrington MA 01230

Price$1,650,000

Est. Mortgage: $/month

MLS Number 226719

  • Listings Residential
  • Address 11 Londonderry Dr
  • Bedrooms 8
  • Bathroom 10
  • Square Feet 8000

Totally secluded with views to Ski Catamount, yet just minutes from Great Barrington center. From the moment you enter, attention to detail is apparent, along with the dramatic wall of glass to the westerly view from the two-story great room. The same view is found from the sumptuous first floor master suite which leads out to a large sun-soaked deck. A virtual resort for country house guests - the kitchen has two of everything, the gorgeous pool area has a pool house and basketball court, the finished walk-out lower level offers exercise, play and workspace for everyone, and there's separate guest wings for fun-filled weekends. The words ''spotless'' and ''well-cared for'' do not do this property justice, as it's triple mint. Attached three-car garage for collectors. Call us for a tour.

Listed by Timothy Lovett and Fintan T Hanley of BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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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165 Kemble St. #2 -- Lenox MA 01240

Price$1,350,000

Est. Mortgage: $/month

MLS Number 220568

  • Listings Residential
  • Address 165 Kemble St. #2 --
  • Bedrooms 1
  • Bathroom 2
  • Square Feet 1109

Unit #2. 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 19 units, it features a spacious great room, master suite, kitchen, two fireplaces, private patio. Mandatory annual resort membership affords access to its unparalleled facilities, close to the cultural, culinary, and outdoor amenities in the Berkshires.

Listed by Gladys Montgomery and Leslie G Chesloff of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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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165 Kemble St Lenox MA 01240

Price$1,350,000

Est. Mortgage: $/month

MLS Number 220566

  • Listings Residential
  • Address 165 Kemble St
  • Bedrooms 1
  • Bathroom 2
  • Square Feet 1109

Unit #1. 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 19 units, it features a spacious great room, master suite, kitchen, two fireplaces, private patio. Mandatory annual resort membership affords access to its unparalleled facilities, close to the cultural, culinary, and outdoor amenities in the Berkshires.

Listed by Leslie G Chesloff and Gladys Montgomery of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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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8 Fairway Dr Lenox MA 01240

Price$1,100,000

Est. Mortgage: $/month

MLS Number 227962

  • Listings Residential
  • Address 8 Fairway Dr
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4191

Imagine having a Relais & Chateaux, Forbes Five-Star Resort and an award winning golf course as your neighbors. If you live on Fairway Drive, you not only have the privacy of single family living, you also have amenities such as snow removal, weekly landscaping and private trash pickup. With over 4,000 square feet all on one floor, this home has been meticulously cared for by the current owners of the last 25 years. From the front door, you can see all the way through past the great room and out to the large back patio. This home has a way of really bringing the outside in with large windows throughout overlooking botanical gardens. There is so much usable space you could have the whole extended family staying under one roof.

Listed by Reciprocal Listing: See Realtor Remarks of NON-MEMBER

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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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4 East Mountain Rd Great Barrington MA 01230

MLS Number 223259

  • Listings Residential
  • Address 4 East Mountain Rd
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 3180

Spacious, light-filled Arts & Crafts Contemporary in a private setting, minutes from Butternut Ski Resort, Great Barrington restaurants & shops, cultural venues, and outdoor recreation. Custom Arts & Crafts details enhance interiors throughout this supremely comfortable home. The main level comprises a spacious master suite, living room with stone fireplace & cathedral ceiling, cook's kitchen with granite countertops, dining area, and deck. Upstairs, is a comfortable arrangement of three bedrooms, including a second master, and laundry. The walk-out lower level features a family room with home entertainment area, space for billiard/ping pong table, and compact home gym or office space. Tucked into a pretty woods threaded with mountain laurel, and discrete mountain views.

Listed by Gladys Montgomery of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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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6 Deer Hill Rd West Stockbridge MA 01266

Price$795,000

Est. Mortgage: $/month

MLS Number 227546

  • Listings Residential
  • Address 6 Deer Hill Rd
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 6291

Potential to renovate into a $Million plus property! Perfectly situated on its own private promontory w/ expansive sunset views from almost all rooms, this home is actually 2 houses in one; a 2 bed/2.5 bath house plus a 2 bed/2 bath guest wing. Well separated yet easily accessed, the wing is reminiscent of a resort chalet, with dramatic indoor pool w/ sliding glass walls, Swedish sauna, kitchenette, multiple bonus rooms, & the 3rd story Tower Room, sporting the most stunning view of all! Grandchildren have grown up happily splashing in the distinctive, octopus decorated year-round pool & snowboarding down the sloping front yard, now it's your turn! All this is within a short drive to Tanglewood, Kripalu, multiple ski areas, and the charming village of West Stockbridge.

Listed by Brian Farrell of STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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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7 Fairway Dr Lenox MA 01240

Price$749,000

Est. Mortgage: $/month

MLS Number 221888

  • Listings Residential
  • Address 7 Fairway Dr
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 3210

Privately tucked away at Coldbrooke East, this free standing home features bucolic, unobstructed views of Cranwell Resorts manicured 13th fairway and the hills beyond. Private gardens and shade trees enhance this picture perfect setting. The bright and natural light filled single level contemporary interior welcomes luxurious living with soaring ceilings, a see thru fireplace and sky-lit rooms. A perfect design for indoor and outdoor entertaining with built-in wet bar, an eat-in cook's kitchen, formal dining space, an inviting deck and brick patio as well as a spectacular sun-room that completely opens to the views beyond. Three/four bedrooms and four full baths are perfectly placed to provide privacy for both owner and guests when it's time to retire. A two car garage, lots

Listed by Paula McLean of PAULA MCLEAN REALTORS INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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