Vacation Homes in the Berkshires

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

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902 West, Pittsfield, MA 01201

Price$1,995,000

Est. Mortgage: $/month

MLS Number 216962

  • Listings Residential
  • Address 902 West St
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 4496

Mother nature has been kind to the Berkshires with its rolling hills and the lakes, meadows and woodlands between.Long has its beauty and tranquility appealed to those vacationing from nearby New York or Boston.Among the many notable features of the Berkshire landscape is a clear blue gem, known as Lake Onota. A 617 acre glacially molded and spring fed lake offering a full menu of recreational activities and a lifestyle of leisure and beauty rarely combined. On the southern shore, nestled among other spacious residential Estate parcels rests "White Deer Way". With water on two sides and 6.5 acres abutting conservation land this home is private and attuned to nature's splendor. As one traverses the private drive, fields give way to old woodlands. As the beaten path fades from sight and mind, the trees open to an impressive 4,500sf home, 3+car garage, gardens and guest parking. The home visually blends with the environment, its contemporary architecture inviting the surrounding trees, water and sky inside as if part of the d'cor. This is truly an environment to savor. All 4 seasons are in full display from the magnificent sweeping views across the lake to the Berkshire hills and Mt. Greylock. The 6 bedroom 4 bath home is sited so the beach and dock are readily accessible yet not intrusive. The expansive water frontage offers superior access for swimming, boating and fishing. A recent extensive home renovation was completed to opulent standards, with top quality materials and craftsmanship. New technology and systems are employed to achieve comfort, efficiency, convenience and trouble free maintenance. A chef's kitchen, Master suite, splendidly crafted fireplaces, impressive gathering spaces, entertainment amenities and accommodations for family and guests amply address all creature comforts to discriminating standards. An old pine grove along the driveway, a large granite monolith in the foyer and curving open stairs connecting levels are only some of White Deer Way's many distinguishing features. Truly one of the best the Berkshires has to offer and well worth a closer look.

Listed by Jeff Rose of ROSE REAL ESTATE

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McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

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$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 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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286 Great Barrington, West Stockbridge, MA 01266
Pending

MLS Number 218644

  • Listings Commercial
  • Year Built 1797
  • Acreage 10

Turn this property into anything you want Here you can have it all... the perfect commercial and mixed use development - integrate residential, cultural, institutional or industrial uses. Backyard paradise with two 5 acres building lots (one for development), pool & clay tennis court. 12, 000 sqft living space. 700 sqft state of the art kitchen. Open to selling property turn-key and fully furnished Turn this property into anything you want What if every day felt like you're on vacation. Here you can have it all .....whether you're looking for a multi family or mixed-use integrate residential, cultural, commercial, institutional or industrial development, camp site or boarding school. Located in the heart of the 4-season-resort area of New England (Western Massachusetts), "The Berkshires," just a few minutes drive to Tanglewood and all major cultural and recreational activities, and just two hours from Boston and NYC. Zoned: Residential and commercial. 2017 Annual tax only $8,654 This 10 acres property can be subdivided into two five-acres building lots. (already approved) One of the 5 acres building lots can be used to expand, develop and/or farming. The other 5-acres properties was developed into a stunning estate with panoramic mountain views, beautiful garden grounds with large fire pit, pool, clay tennis court, organic farm and 18 bedrooms all with en-suite bathrooms (main house built in 1797, historic barn and two connecting cottages). Main house offers light filled lounge and sunroom, central A/C, beautifully restored 1797 hardwood floors, and historic details. Completely renovated in 2003. A stunning 700 sqft state-of-the-art commercial kitchen wing was also added in 2003 with radiant heat and sky lights, miles of stainless steel, top-of the line equipment including a Rational Combi Steamer, 6 gas burner, 2 French tops, 2 ovens, 1 salamander, 8 x 10' walk-in fridge, freezers, butcher block, garde manger station, pot filler faucet, pantry, plus separate bar and Hobart dish washing area. The bar area has separate red and white wine fridges, and ice maker. The main house also offers a beautiful 3-room, 1 full bath with soaking tub and half bath owner or caretaker quarter. The handicap accessible dining/meeting/ multi function room (2 handicapped restrooms & 2 regular restrooms) can seat 80 indoor and 20 outdoor. Exceptional event destination & fun...

Listed by Jason Saphire of www.EntryOnly.com

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McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

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 Jul 13, 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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286 Great Barrington, West Stockbridge, MA 01266
Pending

MLS Number 218649

  • Listings MultiFamily
  • Bedrooms 18
  • Bathroom 24
  • Square Feet 12000
  • Year Built 1797

What if every day felt like you're on vacation Beautiful Berkshire estate set on 10 acres of backyard paradise with pool & clay tennis court, perfect for entertaining & multi family, even add your dream business. 10+ bedrooms all with en-suite baths, 12, 000 sqft. Cook for 2 or 200 in 700 sqft state of the art kitchen. Sale incl. 5 acres building lot. Open to selling property fully furnished. Beautiful retreat property with endless possibilities Here you can have it all.... become the new owner of this one-of-a-kind estate fabulous for entertaining family, friends and guests, and even add a home business and mixed use development. Zoned residential and commercial. Low taxes. Set in the heart of the Berkshires, just a few minutes' drive to Tanglewood and all major cultural and recreational attraction, 2 hours from Boston and NYC, enjoy the 10 acres backyard paradise with park-like garden grounds; beautiful swimming pool; fenced-in clay tennis court, panoramic mountain views, large fire pit, organic farm and gardens. Ample parking. You'll love the 12,000 sqft of light-filled living space in the main house, built in 1797 by Christopher French, in the converted 18th century barn and two connecting cottages; 10+ bedrooms all with en-suite bathrooms; central A/C; wood stoves; gas fireplaces; sound system; private in-law suite, nanny or caretaker's quarter, sunroom; two lounge areas, and beautifully restored original 1797 hardwood floors. Two large basement with laundry area and wine cellar. Completely renovated in 2003. Cook for 2 or 200 in the 700 sqft gourmet state of the art kitchen with miles of stainless steel; radiant heat; skylights and windows; butcher block; walk-in fridge; six burner stove plus two French tops,; 2 ovens; Rational Combi Steamer; and separate Hobart dish washing area. Fully functional bar with individual red and white wine fridges, and ice maker. Pick you own herbs, vegetables and fruits in the organic gardens right outside the kitchen. Enjoy fresh eggs every day from ducks and chickens roaming around in the fenced in orchard. You could also add more farm animals (Right to Farm) The back of the barn can be easily converted to anything you want - more rooms, an art studio or work shop. The Berkshires offers an excellent school system. The bus stops right outside the house. Go hiking; herb-, ramp- and mushroom picking right on t...

Listed by Jason Saphire of www.EntryOnly.com

{$agent->Name}

McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

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 Jul 13, 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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286 Great Barrington, West Stockbridge, MA 01266
Pending

MLS Number 218961

  • Listings Residential
  • Bedrooms 18
  • Bathroom 24
  • Square Feet 12000
  • Year Built 1797

What if every day felt like you're on vacation Beautiful Berkshire estate set on 10 acres of backyard paradise with pool & clay tennis court, perfect for entertaining & multi family, even add your dream business. 10+ bedrooms all with en-suite baths, 12, 000 sqft. Cook for 2 or 200 in 700 sqft state of the art kitchen. Sale incl. 5 acres building lot. Open to selling property fully furnished. What if every day felt like you're on vacation Stunning Berkshire estate set on a 10-acres retreat property with backyard paradise fabulous for entertaining family, friends and guests, and even add a business and mixed use development. 5 acres building lot included. Zoned residential and commercial. Low taxes. Set in the heart of the Berkshires, just a few minutes' drive to Tanglewood and all major cultural and recreational attraction, 2 hours from Boston and NYC, enjoy the 10 acres backyard paradise with park-like garden grounds; beautiful swimming pool; fenced-in clay tennis court, panoramic mountain views, large fire pit, organic farm and gardens. Ample parking. You'll love the 12,000 sqft of light-filled living space in the main house, built in 1797 by Christopher French, in the converted 18th century barn and two connecting cottages; 10+ bedrooms all with en-suite bathrooms; central A/C; wood stoves; gas fireplaces; sound system; private in-law suite, nanny or caretaker's quarter, sunroom; two lounge areas, and beautifully restored original 1797 hardwood floors. Two large basement with laundry area and wine cellar. Completely renovated in 2003. Cook for 2 or 200 in the 700 sqft gourmet state of the art kitchen with miles of stainless steel; radiant heat; skylights and windows; butcher block; walk-in fridge; six burner stove plus two French tops,; 2 ovens; Rational Combi Steamer; and separate Hobart dish washing area. Fully functional bar with individual red and white wine fridges, and ice maker. Pick you own herbs, vegetables and fruits in the organic gardens right outside the kitchen. Enjoy fresh eggs every day from ducks and chickens roaming around in the fenced in orchard. You could also add more farm animals (Right to Farm) The back of the barn can be easily converted to anything you want - more rooms, an art studio or work shop. The Berkshires offers an excellent school system. The bus stops right outside the house. Go hiking; herb-, ramp- and mus...

Listed by Jason Saphire of www.EntryOnly.com

{$agent->Name}

McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

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 Jul 13, 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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74 Yokun, Lenox, MA 01240

Price$1,595,000

Est. Mortgage: $/month

MLS Number 220862

  • Listings Residential
  • Address 74 Yokun Ave
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4744

CONTEMPORARY ELEGANCE in harmony with nature. Ideal as a year round or vacation living in a park like setting with an interior that features the best in quality, taste, detail and design. Located on one of the most prestigious streets in Lenox and just a short walk to the center of town, Tanglewood and Kennedy Park and a short drive to many of the cultural and outdoor activities The Berkshires have to offer, including proximity to many of the local ski mountains. The master bedroom suite is located on the first floor. The home has three AC and heating units and a generator that fully powers the entire home. It features a gourmet kitchen that a world class chef would be proud of. ONE OF A KIND!!

Listed by Buddy Lewis of BARNBROOK REALTY, INC.

{$agent->Name}

McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

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 Jul 13, 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 Highcrest, Lenox, MA 01240

Price$699,000

Est. Mortgage: $/month

MLS Number 218574

  • Listings Condominium
  • Address 14 Highcrest Rd # 14
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2691

Just gorgeous and truly priced to sell. This home affords bright and cheerful spaces with custom built-ins, lovely mountain views and privacy. This is the ideal vacation home setting with private pool, tennis and clubhouse. Plenty of space for family and guests with en-suite bedrooms. Act now and don't miss this beauty! Hardwoods throughout.

Listed by Paula McLean of McLean Realtors

{$agent->Name}

McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

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 Jul 13, 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 Woods, Lenox, MA 01240

Price$629,000

Est. Mortgage: $/month

MLS Number 204611

  • Listings Condominium
  • Address 14 Woods Ln # 14
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 3017

Totally turn key townhouse at FairWynds II at Cranwell Resort. Beautifully and professionally decorated and furnished interior with inviting first floor master suite and private guest suites with sitting rooms. Private patio, rights to Cranwell pools, fitness and skiing. This makes vacationing in the Berkshires as simple as can be on a world class resort with golf, heavenly spa and restaurants.

Listed by Paula McLean of McLean Realtors

{$agent->Name}

McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

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 Jul 13, 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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182 Division, Great Barrington, MA 01230

Price$575,000

Est. Mortgage: $/month

MLS Number 219784

  • Listings Residential
  • Address 182 Division St
  • Bedrooms 7
  • Bathroom 4
  • Square Feet 4965

Dormered two story home with wonderful views and privacy. Oversized windows bring in generous sunlight. Decks, patios and porch take in the view and great outdoor spaces overlook well tended gardens.Plenty of space, (7 bedrooms), for family and friends. Lower level ideal for self sufficient guest quarters or in-law suite. Minutes to town center, health club, skiing & schools. This home has a lucrative history as a premier vacation rental, close to 2 Ski Areas and notable Berkshire attractions.

Listed by Helen Mullany of HELEN MULLANY REAL ESTATE, LLC

{$agent->Name}

McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

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 Jul 13, 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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77 Alpine, Pittsfield, MA 01201

Price$549,000

Est. Mortgage: $/month

MLS Number 220447

  • Listings Residential
  • Address 77 Alpine Trail
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4178

Live in the lap of luxury in the HEART of the BERKSHIRES!This exquisite 4 BR/4 1/2 BA home is an ideal year round family home or a perfect vacation home with room to spare. After a day of skiing come home to a warm fire and cozy up in your very own movie theater!! Spend a summer day swimming in the pool then enjoy a peaceful evening relaxing on your screened in porch.Close to shopping, skiing, theaters, hiking, Tanglewood...stop your search right now. You have FOUND your DREAM home!!!!!

Listed by Shana Powell of SIGNATURE ASSOCIATES

{$agent->Name}

McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

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 Jul 13, 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

77 Alpine, Pittsfield, MA 01201

Price$549,000

Est. Mortgage: $/month

MLS Number 220448

  • Listings Condominium
  • Address 77 Alpine Trail # 77
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4178

Live in the lap of luxury in the HEART of the BERKSHIRES!This exquisite 4 BR/4 1/2 BA home is an ideal year round family home or a perfect vacation home with room to spare. After a day of skiing come home to a warm fire and cozy up in your very own movie theater!! Spend a summer day swimming in the pool then enjoy a peaceful evening relaxing on your screened in porch.Close to shopping, skiing, theaters, hiking, Tanglewood...stop your search right now. You have FOUND your DREAM home!!!!!

Listed by Shana Powell of SIGNATURE ASSOCIATES

{$agent->Name}

McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

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 Jul 13, 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