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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$6,875,000The price has recently decreased

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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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 2017-07-13

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

{$agent->Name}

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 2017-07-13

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

50 East, Alford, MA 01230

Price$3,300,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 212774

  • Listings Residential
  • Address 50 East Rd
  • Bedrooms 4
  • Bathroom 8
  • Square Feet 11800

A meandering drive through a hardwood forest leads to this 11, 800 sq ft family retreat in the Berkshires. The wood shingled home was built in 2003 on a ridge near the center of the quaint village of Alford. The home offers great privacy with sunset views, yet is only a 20 minute drive to Tanglewood and other cultural amenities offered in the area. A 2,400 sq ft studio and 800 sq ft pool cabana are next to the house. Beautiful gardens are woven through dramatic rock features and flagstone paths. The four-bedroom home offers large rooms for entertaining as well as more intimate spaces. Custom stained glass windows frame the forests and views from the breakfast room adjacent to the gourmet kitchen, and from the expansive living room with fieldstone fireplace and bar. A mural featuring local historic places showcases the grand staircase. The master bedroom features his and hers bathrooms and dressing rooms, as well as a kitchenette. A home theater, game room, bedroom/workout room, and wine cellar are located on the basement floor. The home is handicap accessible, with an elevator, wide doors throughout, and a ramped entry. This offering includes 26.9± acres and improvements at 50 East Road as well as an additional 8.7± acre lot.

Listed by Keith Ross of LANDVEST, INC.

{$agent->Name}

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 2017-07-13

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

42 Alford, West Stockbridge, MA 01266

Price$2,850,000The price has recently decreased

Est. Mortgage: $/month

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}

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

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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! A true historic treasure, beautifully expanded yet perfectly preserved, might grace our market once or twice in a lifetime: such a treasure is the Maj. General John Ashley House (c. 1740, renov. 1762, 1857, 1984, 1992). Upon a bucolic bend of the gentle Housatonic, this elegant Colonial country estate reminds us that the real luxuries are timeless— cozy rooms filled with family and friends, summer evenings dining under the stars, fireplaces flickering and ember-warm through the night. The home's impeccable Colonial style matches its pedigree: built by a participant in the American Revolution who was later instrumental in putting down Shay's Rebellion (in whose final battle, a scant 7 miles down the road near the eponymous village of Ashley Falls, Maj. Gen. Ashley was to play a decisive role), the estate is remarkable for both its elegant Greek Revival touches and for its thorough, sensitive, and superbly executed modern renovations. Expansive and welcoming, the full estate comprises both a guest wing and a main house, with no fewer than 6 bedrooms, 6 full baths and a sauna, 5 fireplaces, 3 kitchens and 2 cast-iron stoves between them ... and that's not to mention the 2 office / media rooms, 2 screened porches, the outdoor pool and its palatial poolhouse, the garage/barn, the play-house, and, not at all least, the restful patio under the arbor, where one may dine al fresco surrounded by topiaries, hanging flowers, and the placid beauty of another perfect country day! Beautifully landscaped, embraced by woods and fields, this is a private sort of estate filled with quiet charms and sudden delights. From the restful screened porches and the many high windows the Housatonic bends gently by, while soft wide lawns invite the laughter of outdoor games, and offer the quiet of a stroll under evening stars. Every room speaks of its history, with original Colonial painted panelled walls, mouldings and cornices all attesting to the solid craftsmanship wh...

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

{$agent->Name}

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 2017-07-13

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

22 New Marlboro, Monterey, MA 01245

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

Est. Mortgage: $/month

MLS Number 215890

  • Listings Residential
  • Address 22 New Marlboro Rd
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 5885

BROOKMEAD FARM. On a quiet, scenic road within walking distance of the Monterey General Store and Lake Garfield Town Beach, this rambling 18th century farmhouse with six bedrooms on 84 acres has open views of its own extensive property. The original house has been painstakingly renovated from stem to stern, preserving its antique charm with important updates. The living room, dining room and study all have working fireplaces. The new wing includes a family room and an eat-in kitchen with a Sub-Zero refrigerator and Viking range; both open through French doors onto the heated swimming pool terrace and have radiant-heat wide plank floors that match those in the older section of the house. A screened porch has a romantic pastoral view over a rolling landscape, much of it in conservation with the Monterey Preservation Land Trust and Berkshire Natural Resources Council, where the current owner allows a local farmer to graze cows. The second floor features a master suite with a large outdoor balcony from where one can survey their domain, and three additional sunny bedrooms that share two baths. The third floor has a guest suite with two bedrooms and a bath - a terrific spot for a home office. The enormous lower level has a media room, home gym and a new 2,000 bottle wine cellar large enough to host tasting dinners. Known as Brookmead Farm, the picture-postcard property has a well-maintained Har-Tru tennis court and a fully restored three-story barn with cement floors, metal roof, hand-hewn beams and the original hay crane rail running the entire length. The grounds include access to a secluded spot on the Konkapot River with the remains of a large stone dam. This is the rare opportunity to purchase an immaculate farmhouse estate with everything on your country house checklist, in an area of large land holdings.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS

{$agent->Name}

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

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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 An iconic Berkshire estate, Morningside combines a central location with superb natural beauty overlooking Tyringham valley, with a rich Shaker and Gilded Age history. Morningside is set on 44 acres (potentially available with over 115 acres) with a circa 1800 Manor House originally constructed by the North Family of the unique Tyringham Shaker community, pool, pool house, swim pond, extensive stonework and stunning perennial gardens. The permanently protected U.S. Appalachian Trail borders the land to the south. The setting is both spectacular and blissfully quiet without being isolated. You are in the very heart of the Berkshires and Tanglewood is only ten miles away. The Manor House dates back to the turn of the 19th century, almost twenty years years after the Tyringham Shakers were established in 1782. The double entry doors, one for the Shaker Brothers and one for the Sisters, stand as testaments to the rich history of the home and the property. While there are numerous luxuries, there is both beauty and simplicity in the inherent elegance of the home. Period, hand-crafted details throughout the home include rich wood floors, exposed post and beam old-growth timbers, colonial-era hardware and woodwork, and millwork. The sixteen rooms include a large kitchen that has evolved into a keeping room, seven bedrooms, one a palatial master suite, and four full and two half baths. A large three-car carriage barn has a guest suite (8th bedroom) above. The library features a hand-painted wall mural evoking the history of the property and the character of the Berkshires, the breakfast room has French doors opening to a stone terrace, and the master suite with a marvelously high ceiling, antique beams, wood-burning fireplace, sitting room, office and expansive bath. Morningside was extensively renovated in 2005 to bring the home soundly into the twenty-first century in order to ensure that it lasts for another two hundred years. Examples of reno...

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

{$agent->Name}

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
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Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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

53 White's Hill, Egremont, MA 01230

Price$2,650,000The price has recently decreased

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}

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 2017-07-13

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

{$agent->Name}

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

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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

9 Cliffwood, Lenox, MA 01240

Price$2,295,000The price has recently decreased

Est. Mortgage: $/month

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}

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

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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