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Berkshire County Homes with a Pool

Browse current home with a pool for sale in Berkshire County and Southern Vermont. Find the perfect home from a variety of listings. Remember to register with us to save your favorites, & receive updates with similar properties are posted. Already have an account with us? Log in here!

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2 Glendale Middle, Stockbridge, MA 01262

Price$6,900,000

Est. Mortgage: $/month

MLS Number 215244

  • Listings Residential
  • Address 2 Glendale Middle Rd
  • Bedrooms 8
  • Bathroom 10
  • Square Feet 10971

SOUTHMAYD FARM Gilded Age at its finest in Stockbridge. This 1870 Berkshire estate has been fully restored & is privately sited on 33+ acres within walking distance of town. Adjacent to the Stockbridge Golf Club & the Norman Rockwell Museum, the view includes a mile of Housatonic River frontage. The 8500' main house w/ 8 bedrooms is complemented by a carriage house, greenhouse/studio, pool,

Listed by Cindy Welch and Keith Ross of LANDVEST, INC.

Alton & Westall Real Estate Agency
77 Water Street
Williamstown MA, 01267
Office: 413.458.8366

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.02% last updated on May 25, 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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720 West, Richmond, MA 01254

Price$4,250,000

Est. Mortgage: $/month

MLS Number 216720

  • Listings Residential
  • Address 720 West Rd
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4228

Set on 154 secluded acres, this Adirondack style home features the finest in craftsmanship & design. Open floor plan, high vaulted ceilings, balconies & large windows throughout bring the magical outdoor surroundings indoors. Large level backyard w/ gunite pool, many pvt trails & streams right outside your door - ideal for horse riding, hiking, xc skiing & snow shoeing. Truly a yr round paradise.

Listed by Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Alton & Westall Real Estate Agency
77 Water Street
Williamstown MA, 01267
Office: 413.458.8366

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.02% last updated on May 25, 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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151 Walker, Lenox, MA 01240

Price$4,250,000

Est. Mortgage: $/month

MLS Number 214688

  • Listings Residential
  • Address 151 Walker St
  • Bedrooms 10
  • Bathroom 10
  • Square Feet 6934

Thistlewood - A classic Berkshire Cottage that has been meticulously restored & updated for a modern lifestyle. Designed by noted Boston architects Rotch & Tilden, the main house offers classic proportions and elegant details throughout. The grounds wrap the house with stately gardens, pool & poolhouse.

Listed by Dan Alden and Nick Geranios of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Alton & Westall Real Estate Agency
77 Water Street
Williamstown MA, 01267
Office: 413.458.8366

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.02% last updated on May 25, 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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1 Pinecroft Drive, Lenox, MA 01240

Price$3,950,000

Est. Mortgage: $/month

MLS Number 218940

  • Listings Residential
  • Address 1 Pinecroft Drive Dr
  • Bedrooms 6
  • Bathroom 7
  • Square Feet 7816

This exquisite home is in the Canyon Ranch subdivision of Pinecroft, walking distance to the wonderful village of Lenox. Ownership offers the option of membership to the world class health and wellness resort. The home is being offered furnished. Features include a gated and heated driveway and courtyard, heated in ground pool and fabulous fully equipped pool house with outdoor kitchen. The home boasts custom interior design, steam shower, gourmet kitchen and a wet bar in the living room. The lower level offers a sauna, climate controlled wine cellar, hi-def movie theatre and a magically nostalgic soda fountain!

Listed by Mike Taxter of LENOX CANYON REALTY

Alton & Westall Real Estate Agency
77 Water Street
Williamstown MA, 01267
Office: 413.458.8366

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.02% last updated on May 25, 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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390&399 Under Mountain, Lenox, MA 01240

Price$3,650,000

Est. Mortgage: $/month

MLS Number 219053

  • Listings Residential
  • Bedrooms 7
  • Bathroom 9
  • Square Feet 10629
  • Year Built 1900

''High Wick Farm, '' a magnificent, superbly located 106-Acre estate--a once-in-a-lifetime opportunity. At its centerpiece is a baronial Tudor mansion with impressive yet comfortable light-filled rooms, exquisite architectural details, 7 bedrooms, 11 fireplaces, indoor & outdoor swimming pools. The mansion is set on 11 acres across from a 95-acre parcel, providing gorgeous open views of fields & mountains to the south. Abutting future Berkshire Natural Resources conservation land, this parcel contains an indoor riding ring, stables (50 stalls, a 2BR/1BA groom's quarters), several residences (5BR, 2BA) (3BR, 2BA), on a building envelope limited to 10 acres. Minutes to Tanglewood and Lenox village, Shakespeare & Co., restaurants, and shops. See also MLS 213169.

Listed by Gladys Montgomery and Maggie C Merelle of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Alton & Westall Real Estate Agency
77 Water Street
Williamstown MA, 01267
Office: 413.458.8366

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.02% last updated on May 25, 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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11 Londonderry, Great Barrington, MA 01230

Price$2,990,000

Est. Mortgage: $/month

MLS Number 218034

  • Listings Residential
  • Address 11 Londonderry Dr
  • Bedrooms 8
  • Bathroom 10
  • Square Feet 7500

Custom built Berkshire home on 13 plus acres with magnificent views of Catamount Mtn., 5 minutes to downtown Great Barrington. Superior attention to detail. Over 7500 sq. ft, 7 plus bedrooms, 8 and 1/2 baths, First floor Master Suite, separate guest wing, Ultra Modern kitchen. Lower level game room, Home Gym, and Billiard room. Custom pool with gradual entrance. Central AC and Central vacuum.

Listed by Stephen R. Schoenfeld and Joanna Szwyd of STONE HOUSE PROPERTIES, LLC

Alton & Westall Real Estate Agency
77 Water Street
Williamstown MA, 01267
Office: 413.458.8366

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.02% last updated on May 25, 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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, Williamstown, MA 01267

Price$2,950,000

Est. Mortgage: $/month

MLS Number 217915

  • Listings Residential
  • Bedrooms 8
  • Bathroom 8
  • Square Feet 7215
  • Year Built 1911

Elegant simplicity is the trademark of this American Craftsman-style residence. Sited on 2.775 acres, this magnificent country home is well-suited to large-scale entertaining with a total of eight bedrooms, seven and one-half baths, and 7, 215 square feet of living space. Mature trees, stone walls, beautiful gardens, an in-ground pool and picturesque mountain views complete this rare offering.

Listed by Maureen M. Dietze and Cheryl Westall of Alton & Westall Real Estate Agency

Alton & Westall Real Estate Agency
77 Water Street
Williamstown MA, 01267
Office: 413.458.8366

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.02% last updated on May 25, 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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2650 Swamp, Richmond, MA 01254

Price$2,550,000

Est. Mortgage: $/month

MLS Number 215858

  • Listings Residential
  • Address 2650 Swamp Rd
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 4182

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

Listed by Scott W. Sawyer of STONE HOUSE PROPERTIES, LLC

Alton & Westall Real Estate Agency
77 Water Street
Williamstown MA, 01267
Office: 413.458.8366

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.02% last updated on May 25, 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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44 & 46 Lake, Stockbridge, MA 01262

Price$2,495,000

Est. Mortgage: $/month

MLS Number 216723

  • Listings Residential
  • Address 44 & 46 Lake Dr
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 3325

Huge Price Reduction! Spectacular lake front compound w/ 600+ feet of lake frontage & complete privacy. 2 homes on 2 separate tax lots w/ gorgeous gunite pool, pool house, 2 docks, level land, beautiful landscaping & large koi pond. Both homes are only steps to the lake w/ amazing lake & mountain views. A true swimming & boating paradise. Don't miss this rare opportunity to own your dream Stockbridge Bowl compound!

Listed by Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Alton & Westall Real Estate Agency
77 Water Street
Williamstown MA, 01267
Office: 413.458.8366

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.02% last updated on May 25, 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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21 Prospect Hill, Stockbridge, MA 01262

Price$2,250,000

Est. Mortgage: $/month

MLS Number 217160

  • Listings Residential
  • Address 21 Prospect Hill Rd
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 4194

Exquisitely renovated late 1700 antique home w/ perfect proportions & amazing grounds. High ceilings, multiple fireplaces & historic details, flooded with light. Beautifully sited on over 9 acres on one of the most prestigious roads in the county. Barn, apple orchard, specimen trees, masterful stonework. Secluded and private heated Gunite pool w/ classic pool house & adventurous boardwalk.

Listed by Christian G Deckert of BERKSHIRE PROPERTY AGENTS

Alton & Westall Real Estate Agency
77 Water Street
Williamstown MA, 01267
Office: 413.458.8366

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.02% last updated on May 25, 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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1 LAHEY CROSSROAD, Stockbridge, MA 01262

Price$2,150,000

Est. Mortgage: $/month

MLS Number 215909

  • Listings Residential
  • Address 1 Lahey Crossroad --
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4847

Total privacy on 22 acres with back country roads for strolling. Within a couple of miles you will find fresh baked bread, a pub, the Norman Rockwell Museum, the Berkshire Botanical Garden and Chesterwood. And within 6 or 7 miles you will find the boat ramp at Stockbridge Bowl, Kripalu Yoga Center and Tanglewood. Wonderful setting with mature trees, landscaped gardens, extensive stonework and in-gorund pool. Beautifully designed home with dramatic two-story foyer, spacious living room, exceptional library, dining room and porch each with fireplace, country kitchen. Great wall space to display art. A covered colonnade joins the main house to the guest house with 2 bedrooms, bath and gathering room plus a large office/studio and a garden workshop. A FABULOUS place to live!

Listed by Martha Piper and Sheila Thunfors of STONE HOUSE PROPERTIES, LLC

Alton & Westall Real Estate Agency
77 Water Street
Williamstown MA, 01267
Office: 413.458.8366

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.02% last updated on May 25, 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

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

Listed by Jason Saphire of www.EntryOnly.com

Alton & Westall Real Estate Agency
77 Water Street
Williamstown MA, 01267
Office: 413.458.8366

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.02% last updated on May 25, 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