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$6,875,000

Est. Mortgage: $/month

Pending

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, , 3 bedroom guest house, barn complex and paddocks, a magnificent maze, and additional formal gardens. See documents file for detail of each building, room and floor plan.

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

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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 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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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

{$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 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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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 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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42 Alford, West Stockbridge, MA 01266

Price$2,850,000

Est. Mortgage: $/month

Pending

MLS Number 219875

  • Listings Residential
  • Address 42 East Alford Rd
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 7400

A private retreat on 15+/- acres with expansive Berkshire Mountain vistas from every room. The contemporary design allows for an open flow, antique beamed ceilings, and glass window walls to capture the views. Amenities abound and include a gunite pool, waterfall, sauna, exercise area, media room, game room, bar area, 3 fireplaces, 6 bedrooms, 7 baths, and 7, 400+/- sq.ft. of living space finished with the highest quality materials and exceptional design.

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

{$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 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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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

{$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 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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2650 Swamp, Richmond, MA 01254

Price$2,550,000

Est. Mortgage: $/month

MLS Number 220874

  • 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 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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465 Stratton, Williamstown, MA 01267

Price$2,450,000

Est. Mortgage: $/month

MLS Number 215736

  • Listings Residential
  • Address 465 Stratton Rd
  • Bedrooms 7
  • Bathroom 10
  • Square Feet 10349

This exquisite estate property, meticulously crafted with undeniable quality and style, consists of two main houses, connected via a separately housed, stunning indoor pool, creating a one of a kind main residence plus a charming guest house and separate detached garage. The three primary living areas merge together beautifully to create an unrivaled Williamstown retreat on 11.7 glorious Berkshire acres where you can start every morning and end every evening enjoying the breathtaking views that are the very heart of this property. This exquisite estate property, meticulously crafted with undeniable quality and style, consists of two main houses, connected via a separately housed, stunning indoor pool, creating a one of a kind main residence plus a charming guest house and separate detached garage. The three primary living areas merge together beautifully to create an unrivaled Williamstown retreat on 11.7 glorious Berkshire acres where you can start every morning and end every evening enjoying the breathtaking views that are the very heart of this property. The sprawling main residence, together with the guest house, offer over 11,000 generous square feet of living and entertainment spaces and intimate gathering areas with stunning views from almost every room and a total of 7 bedrooms, 7 full and 3 half baths, soaring living spaces with ample windows and French doors that spill out to multiple stone patios and terraces and anchored by large natural stone fireplaces, chef's kitchens, butler's pantry, wine cellar and proper storage areas. With enticing outdoor spaces and unobstructed views, one is hard pressed to find a more engaging environment in which to live the mountain lifestyle. Designed locally and built by master tradesmen, the unique and appropriate architectural details mimic the property's natural setting with extensive stone work and lush landscaping that complement the natural color and visual texture of the Mt. Greylock and Taconic Mountain ranges. An ideal location, minutes from the Clark Art Institute, Williamstown Theatre Festival, Williams College and many local attractions for lovers of nature, culture, and athletic pursuits. Exceptional living, likely never to be duplicated!

Listed by Nick Geranios and Steven J. Weisz of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY, LENOX

{$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 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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9 Cliffwood, Lenox, MA 01240

Price$2,295,000

Est. Mortgage: $/month

Pending

MLS Number 217903

  • Listings Residential
  • Address 9 Cliffwood St
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 5102

This gracious home exemplifies New England village living at it's best. Impeccably restored in 2008, this c.1805 center hall Colonial is just steps from every convenience. An extensive landscaping plan has created a completely private backyard oasis. Rare combination of privacy and in-town living. There are high ceilings in every room, wood floors throughout, 4 fireplaces & 6 spacious bedrooms with en suite baths. The 2008 renovation included new heat, central ac, electric, insulation, a great mudroom and a wonderfully enticing 3 season screened porch. A new oversized 2 car garage with second floor storage also serves as pool storage. Other additions include a wet bar in the formal living room, a spacious second floor laundry and a private guest suite on the 3rd floor. All bathrooms have been exquisitely redone. The sound system extends throughout the first floor and screened porch.

Listed by Suzanne Crerar 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 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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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 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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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

{$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 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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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 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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11 Londonderry, Great Barrington, MA 01230

Price$2,190,000

Est. Mortgage: $/month

MLS Number 218034

  • Listings Residential
  • Address 11 Londonderry Dr
  • Bedrooms 7
  • Bathroom 9
  • Square Feet 7500

Gracious open floor plan perfect for both casual and formal entertaining. Extensive windows to the view bathe the interior with light. Excellent kitchen. Exceptional first floor master suite. Second floor with 4 bedrooms, 4 baths and gathering room. Separate guest wing with 2 bedrooms and bath. Lower level with game room, gym, billiard room, office and 2 full baths. Custom pool and pool house with full bath surrounded by patio, gorgeous stonework and lush landscaping. Perfectly detailed and outfitted throughout. Spaces and activities for everyone. There is even a basketball court. 3-bay garage with built-in storage..

Listed by C. Randolph Thunfors 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 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