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, Lenox, MA 01240

Price$3,450,000

Est. Mortgage: $/month

MLS Number 222383

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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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: 4.45% last updated on Jan 17, 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, 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: 4.45% last updated on Jan 17, 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, 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: 4.45% last updated on Jan 17, 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: 4.45% last updated on Jan 17, 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, 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 and Maggie Barry of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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, Lenox, MA 01240

Price$798,000

Est. Mortgage: $/month

MLS Number 221888

  • Listings Residential
  • Address 7 Fairway Dr
  • Bedrooms 3
  • Bathroom 3
  • 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 McLean Realtors

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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 Woods, Lenox, MA 01240

Price$655,000

Est. Mortgage: $/month

MLS Number 225569

  • Listings Residential
  • Address 8 Woods Ln
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3017

This prime, light-filled end unit at Cranwell/Miraval, Lenox, offers space, privacy, and a terrific floor plan, along with access, with membership, to wonderful array of resort amenities and golf, and proximity to restaurants and shops and cultural venues in Lenox and Stockbridge. You'll love its intelligent layout, featuring a master suite, great room and patio on the main level, plus two additional bedroom suites with private bath and sitting rooms upstairs. Owner upgrades include new bamboo and slate flooring, perennial garden, and updated kitchen.

Listed by Leslie G Chesloff and Maggie Barry of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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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229 Bailey, Lanesboro, MA 01237

Price$429,000

Est. Mortgage: $/month

MLS Number 224281

  • Listings Residential
  • Address 229 Bailey Rd
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2356

Privacy abounds this spacious 3/3 1/2 contemporary home nestles on over 6 acres of land just minutes away from one of The Berkshire's finest ski resorts. Upon entering this immaculately maintained home you are welcomed by soaring ceilings and wall to wall windows to enjoy the picturesque views from every angle within the open concept living space.

Listed by Derek Eisenberg of CONTINENTAL REAL ESTATE GROUP, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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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622 Main, Lanesboro, MA 01237

Price$399,000

Est. Mortgage: $/month

MLS Number 224803

  • Listings Residential
  • Address 622 North Main St
  • Bedrooms 4
  • Bathroom 1
  • Square Feet 2560

Own a piece of history stepping back into another era in this quaint farmhouse dated in the early 1800's offering lots of original details. Over-sized 2-car garage with workshop. Huge barn all nestled on 90 acres close to Route 7 and Mt. Greylock Reservation. Gorgeous land for house site or farming. 710' of road frontage allows for 3 building lots (frontage & min. land - NO PERCS) Located just minutes from Jiminy Peak Ski Resort with a central location between Pittsfield/Lenox/Gt. Barrnington to the south and Williamstown/North Adams to the North.

Listed by Colleen Zajac of MONARCH REALTY, INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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