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Berkshire County Homes with Pools

Explore all homes with pools for sale in Berkshire County, MA. Contact us if you have questions or would like to schedule a showing.

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2 Glendale Middle, Stockbridge, MA 01262

Price$6,900,000The price has recently decreased

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.

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Hillsdale, Egremont, MA 01258

Price$6,190,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 216806

  • Listings Residential
  • Address Hillsdale Rd
  • Village South Egremont
  • Bedrooms 8
  • Bathroom 10

A residential or private retreat compound for any discreet buyer. Built on a pleasant ridge with multi-directional views of 50 miles plus. Most convenient access to NYC, Boston and airports/train stations. Two structures with elevators, four fireplaces, two wood burning stoves. Radiant heating on all ground floors. Enviroshake roofing, hardiplank siding along with vast flower gardens and pool!

Listed by Thomas K. Doyle, Sr. of GATEWAY BERKSHIRE REAL ESTATE & SERVICES, LLC.

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

151 Walker, Lenox, MA 01240

Price$4,250,000The price has recently decreased

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

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1 Pinecroft Drive, Lenox, MA 01240

Price$3,950,000The price has recently decreased

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

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

390&399 Under Mountain, Lenox, MA 01240

Price$3,650,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219053

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

Magnificent, superbly located 106-Acre Lenox estate property--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 the way is an additional 95 acres, providing gorgeous open views of fields & mountains to the south. Abutting future Berkshire Natural Resources conservation land, this parcel contains several buildings: a stable (2BR, 1BA groom's quarters), a barn converted to residences (5BR, 2BA), and a one-story cottage (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

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

44 & 46 Lake, Stockbridge, MA 01262

Price$2,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 216723

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

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

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

795 Rannapo, Sheffield, MA 01257

Price$2,800,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217224

  • Listings Residential
  • Address 795 Rannapo Rd
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 6315

A true American treasure, beautifully expanded yet perfectly preserved, might grace our market once in a lifetime: Such a treasure is the Gen. John Ashley House(c.1762, renov. 1857, 1984, 1992). Upon a bucolic bend of the gentle Housatonic, this historic estate hosts elegant luxuries-- 6 BR, 6 bath, pool & pool house, sauna, summer porch, dining arbor, guest wing, +/- 8.5 sheltered acres & much more!

Listed by Mary Jane White and Nancy Kalodner of COHEN & WHITE ASSOCIATES

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

137 Jerusalem, Tyringham, MA 01264

Price$2,750,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218074

  • Listings Residential
  • Address 137 Jerusalem Rd
  • Bedrooms 8
  • Bathroom 6
  • Square Feet 7185

Morningside: an iconic berkshire estateset on 44 acres adjacent to the appalachian trail, with possibly the berkshire's finest views. The home was a part of the tyringham shaker settlement. Hand-crafted details lend character to the inherent beauty, simplicity and elegance of the home. 8 bedrooms including a guest suite, pool, & swim pond, see suppl please see supplement for complete detail

Listed by L. Chapin Fish of BROCKMAN REAL ESTATE, LLC

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

, Monterey, MA 01245

Price$2,450,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218286

  • Listings Residential
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 5463
  • Year Built 1983

Nestled in a welcoming private setting off of one of Monterey's loveliest roads, Living Waters Farm is an exquisitely crafted & spacious hand-joined oak post-and-beam Main House featuring 5+ BR/5 1/2 baths, 3 bay 2 level post-and-beam garage carriage house with attached guest apartment, 3 bedroom/2 bath 19th century roadside farmhouse, small horse barn, and a spacious studio/workshop with half bath. For those wishing to maximize a family compound, an abutting 2 bedroom/2 bath guest house with pool and garage is available for sale as well. 400 feet of road frontage and 80+ acres of meadow and forest, it has limitless possibilities.

Listed by Mary Jane White and Nancy Kalodner of COHEN & WHITE ASSOCIATES

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

21 Prospect Hill, Stockbridge, MA 01262

Price$2,250,000The price has recently decreased

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

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.