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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1 Pinecroft, Lenox, MA 01240

Price$3,795,000

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

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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: 3.94% last updated on Dec 21, 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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450 Monterey, Great Barrington, MA 01230

Price$3,400,000

Est. Mortgage: $/month

MLS Number 221283

  • Listings Residential
  • Address 450 Monterey Rd
  • Square Feet 40175
  • Acreage 37.72

MOTIVATED SELLER (s) 12 parcels 33 acres in Gt.Barrington, MA on North & South sides of (Rt#23 E) Monterey Rd w/ a combined frontage of 2604 ft. See MLS #221357 for additional parcel. Formerly a campus including housing, classrooms, athletic fields, buildable land & existing fiber connectivity it is zoned residential (R-2) which by right include single family dwellings, government owned or non-profit educational facilities, municipal parks, agricultural uses & swimming pools. Uses allowed by special permit include two-family dwellings, lodging houses, private schools, summer camps, country clubs, and professional buildings. Easily accessible in the heart of Southern Berkshire County three miles from downtown Gt. Barrington this property being sold "as is''.

Listed by Christian G Deckert and Deborah Levinson of BERKSHIRE PROPERTY AGENTS

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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: 3.94% last updated on Dec 21, 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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222 Ide, Williamstown, MA 01267

Price$2,950,000

Est. Mortgage: $/month

MLS Number 217915

  • Listings Residential
  • Address 222 Ide Rd
  • Bedrooms 8
  • Bathroom 8
  • Square Feet 7215

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 seven to eight bedrooms, seven and one-half baths, and 7,215 square feet of living space.Superb design and the finest quality of materials and workmanship are the defining characteristic of this splendid estate. Bluestone walls, terraces and walkways wind through beautiful gardens in the lovely backyard with its heated pool, rustic outdoor shower, and an array of spaces for dining, including a snack bar which opens from the guest house.The impressive grounds include a circular perennial garden surrounding a flagpole, a small orchard of flowering fruit trees, gorgeous mountain view.See floor plans in documents.

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

{$agent->Name}

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: 3.94% last updated on Dec 21, 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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53 White's Hill, Egremont, MA 01230

Price$2,650,000

Est. Mortgage: $/month

MLS Number 219625

  • Listings Residential
  • Address 53 White'S Hill Rd
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 4723

A stunning home proposed to be built by famed architect, steven haas! Very likely the best view in berkshire county in the low tax town of egremont. An exceptional chance to collaborate with a world class architect to design the home of your dreams! See supplement for more information.See mls #213035 for lot alone. A house that truly brings the outdoors in. Loads of glass, incredible long distance views, infinity pool connected to the house via pergola and an expansive viewing terrace.A separate gazebo overlooks the pool and view beyond. An open plan offers a huge kitchen, living room with fireplace and a glassed in dining area with expansive views. There is a generous first floor master suite with an office cum fourth bedroom, and a screened porch to die for! Lower level offers two generous bedrooms with en suite baths and a family room. Views abound!

Listed by Jonathan Hankin of BERKSHIRE PROPERTY AGENTS

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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: 3.94% last updated on Dec 21, 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 221750

  • 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

{$agent->Name}

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: 3.94% last updated on Dec 21, 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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34 Ox Bow, Egremont, MA 01230

Price$2,275,000

Est. Mortgage: $/month

MLS Number 221052

  • Listings Residential
  • Address 34 Ox Bow Rd
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 6800

Bright & Open Contemporary Home on 16+ acres. Open floor plan with easy flow from room to room. This 6,800 SF home owes it charm to the architectural details of homes in the Hamptons. Wooded setting with scenic mountain and field views. 5 Bedrooms all with en suite baths, including first and second floor master suites. Great room with chef's kitchen, dining area and living room. Library, formal dining room & computer room/office on first floor. Pantry and Bar area. Fitness/Playroom. Professional Home Theatre on lower level. Craftsman finishes throughout. Large open yard, mahogany front porch, stone patios, established perennial gardens and room for a pool. Custom stone fire pit. Oversized 2 car plus garage. Convenient to the Taconic Parkway and downtown Great Barrington. Agent owned.

Listed by Karen Climo of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

{$agent->Name}

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: 3.94% last updated on Dec 21, 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 222499

  • 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

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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: 3.94% last updated on Dec 21, 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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8 Stone Hill, Stockbridge, MA 01262

Price$2,240,000

Est. Mortgage: $/month

MLS Number 220955

  • Listings Residential
  • Address 8 Stone Hill Rd
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 4476

Living is easy in this impressive Stockbridge contemporary located on a fantastic plot of land with western view, blazing sunsets and heated pool all minutes from Tanglewood. Three levels of thoughtful living spaces with soaring two level Great Room open to informal dining and gourmet kitchen make the perfect gathering space around the fireplace on cool fall days while taking in the view from the walls of glass. Wander out to the extensive decking on those warm fall days that overlook the heated pool and look forward to making memories of Berkshire summers. The master bedroom, with "His & Her" baths, are on the main level; guests have their own floor. Lower level family room with fireplace and galley kitchen with bar make this wonderful family space most convenient for exercising,

Listed by Mary Jane White and Brandon White of COHEN & WHITE ASSOCIATES

{$agent->Name}

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: 3.94% last updated on Dec 21, 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$1,999,000

Est. Mortgage: $/month

MLS Number 222322

  • Listings Residential
  • Address 11 Londonderry Dr
  • Bedrooms 8
  • Bathroom 10
  • Square Feet 5074

Extraordinary home, minutes from Great Barrington and all Berkshire activities. Expansive Living Room with Bar and Fireplace. Built for entertaining. Large Dining Room w/gourmet Kosher Kitchen that boasts 2 refrigerators, 2 dishwashers, 2 ovens and a large granite prep area. Master bedroom suite on the main floor with tremendous Master Bath and plenty of storage. Two guest wings offer 6 additional Bedrooms and 5 full Baths. 2 Laundry rooms, one the main floor and one on the second floor. The lower level sports a Home Gym, Billiard Room, office and play area with an additional Bedroom and 2 full Baths. The yard features an in-ground Pool with Pool House and Basketball Court. All have been carefully woven into the natural surroundings with mountain views. 3 bay Garage with custom storage.

Listed by Maggie C Merelle and Steven J. Weisz of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

{$agent->Name}

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: 3.94% last updated on Dec 21, 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$1,895,000

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! A winding driveway through dappled sunlight and mature trees leads to the picturesque setting for this exceptional home. The house is surrounded by expansive landscaped gardens, with seasonally blooming perennials, rock garden plants, rare species, and extensive stonework. Enter the gracious spacious two-story foyer. Step down into the sun filled living room with fireplace. The exceptional library is lined with bookshelves. Dining room has its own fireplace as does the adjacent dining porch. The large eat-in country kitchen has a wall of windows looking out to the gardens. The butler's pantry and the large back mudroom provide terrific work spaces for household activities and entertaining. Complete with wine cellar in the basement. The flow of spaces is excellent and there are multiple accesses to the outdoors. On the second floor is the master suite with a sunny southern exposure, his and her walk-in closets with custom cabinetry, and a grand European styled bath. Two other bedrooms, one with a fireplace, open onto an open balcony porch overlooking the gardens. The rooms are beautifully sized and have a dedicated bath. Two more bedrooms with a sitting area are easily available just steps away in the charming guesthouse reached by a covered stone colonnade. This building also contains a large open office space that could be used as a family game space or studio. On the lower of the three levels is a garden studio/workshop. Through the gardens and stone paths is the in-ground swimming pool for summer enjoyment. Take walks on the country back roads, stroll to Chesterwood. Terrific location near the Norman Rockwell Museum and the Berkshire Botanical Garden. 7 miles to Great Barrington and 6 miles to Tanglewood.

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

{$agent->Name}

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: 3.94% last updated on Dec 21, 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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27 Townhouse Hill, Egremont, MA 01230

Price$1,725,000

Est. Mortgage: $/month

MLS Number 222718

  • Listings Residential
  • Address 27 Townhouse Hill Rd
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4050

Your Berkshires paradise awaits! Set on approximately 8.5 splendid acres w/ beautifully manicured gardens, orchards, mature plantings, heated gunite pool w/ bluestone patio & huge deck. This turn-key home features a large, eat-in chef's kitchen; super cozy year-round sunroom; luxurious library & stunning master bedroom suite w/ huge his & hers walk-in closets. Perfect for entertaining family & friends or relaxing amidst the natural splendor or in front of 1 of the 4 wood burning fireplaces. Ideal location - minutes to vibrant downtown Great Barrington, very close to Ski Butternut and Catamount Ski Area and close to so many of the Berkshires' premier cultural attractions. Don't miss this gem!

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

{$agent->Name}

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: 3.94% last updated on Dec 21, 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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280 DIVISION, Great Barrington, MA 01230

Price$1,700,000

Est. Mortgage: $/month

MLS Number 218213

  • Listings Residential
  • Address 280 Division St
  • Bedrooms 7
  • Bathroom 6
  • Square Feet 6080

Affording the perfect combination of privacy and luxury, this fabulous Contemporary is an outstanding choice for the Berkshires. It's stunning interior with 7 bedrooms, 5 baths and powder room, includes a guest wing with separate entrance, uniquely suitable for a professional in-home office. The luxurious master bedroom features his and her bathrooms en suite. Situated on beautiful, professionally landscaped five plus acres, spacious decking and a dramatic gunite pool, this home is just a few short miles from town and is a convenient location for all the Berkshires offers.

Listed by Steve Erenburg of COHEN & WHITE ASSOCIATES

{$agent->Name}

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: 3.94% last updated on Dec 21, 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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