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Berkshire County Luxury Homes

Explore all luxury homes 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.

278 Hillsdale, Egremont, MA 01258

Price$6,150,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 220002

  • Listings Residential
  • Village North Egremont
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 7075

Listed by Thomas H McGowan and Elyse Harney Morris of ELYSE HARNEY REAL ESTATE

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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.

106 & 114 Cliffwood, Lenox, MA 01240

Price$4,750,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217523

  • Listings Residential
  • Bedrooms 8
  • Bathroom 8
  • Square Feet 8500
  • Year Built 1883

Unsurpassed 19th Century Queen Anne Style Berkshire Lenox ''Cottage'' restored and reinvented for today's most discriminating family wishing for an understatedly elegant, 'cool' and comfortable Twenty-First Century lifestyle. See attached document for all details. Shown by advance appointment only.

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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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.

185 BEARTOWN MOUNTAIN, Monterey, MA 01245

Price$4,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 220508

  • Listings Residential
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4160
  • Year Built 2004

Casually elegant and beautiful shingled eco-luxury mountaintop home with rare and extraordinary protected southerly long-range views, abutting 12000 acre Beartown State Forest. Carefully and exquisitely crafted, the gracious rooms feature four fireplaces with a hefty stone central core, mahogany windows and doors, and radiant heated wood floors. The horse barn has three generous stalls, a tack room, and caretaker's quarters. Horses enjoy organic pastures and an outdoor arena that could easily be a tennis court. The private setting and views are unmatched in the southern Berkshires, and the quality of construction speaks for itself.

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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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.

89 Cliffwood, Lenox, MA 01240

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

Est. Mortgage: $/month

MLS Number 217574

  • Listings Residential
  • Address 89 Cliffwood St
  • Bedrooms 6
  • Bathroom 8
  • Square Feet 10333

SUPREMELY WELCOMING...One of Lenox's19th century Berkshire''cottages'' that has been meticulously restored and updated. Located on prestigious Cliffwood Street within walking distance of downtown Lenox, this exceptionally welcoming Berkshire "cottage" on 3.17 acres epitomizes gracious living with a porte cochere and sixteen fireplaces . Meticulously restored and updated, the six-bedroom house has many original architectural details such as paneled walls, carved mantelpieces and a two-tier staircase with an oculus on the second floor that overlooks the generous foyer (large enough for a baby grand piano.) The main floor has exceptional flow for a 19th century house: The library and living room with adjoining den (separated by pocket doors) have massive French doors that open onto a large screened porch; the dining room, with built-in corner cabinets, and billiards room are ideal for entertaining; the cook's kitchen with capacious dining and lounge areas opens onto a large deck. The adjacent mudroom, with a contoured entry doors, still has the original "call board" for the servants. In the basement, there's the original ice room and a dumb waiter for transporting firewood to the upper floors. This property has a gracious driveway, mature gardens, a privately situated swimming pavilion and a barn-like garage that can accommodate five cars. One of the few 19th century cottages that has been maintained as a private residence, this is a rare opportunity to live in a park-like setting so close to town.

Listed by Deborah Levinson 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.

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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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.

65 Shun Toll, Egremont, MA 01230

Price$3,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219302

  • Listings Residential
  • Address 65 Shun Toll Rd
  • Village North Egremont
  • Bedrooms 4
  • Bathroom 7

Many dream of converting a historic barn into a country house. A barn tells a story, has a past, and the old beams, posts and boards have a patina and a magic which new construction can never recreate. This 26 acre estate is masterfully designed and crafted from two 18th & 19th century barns on one of the Berkshire's finest country lanes in North Egremont. 65 Shun Toll Road embodies a rustic elegance that will simply captivate you as you gaze across the soaring, yet brilliantly intimate spaces and through the expanses of glass to the inspiring and extraordinary distant views of farmland below and mountains beyond. Offering nearly every luxury imaginable in its 6, 600 square feet, yet in an ultimately comfortable and authentic manner - the perfect Berkshire country home.

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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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.

50 Mount Hunger Estates, Monterey, MA 01245

Price$2,995,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219713

  • Listings Residential
  • Bedrooms 7
  • Bathroom 5
  • Square Feet 5500
  • Year Built 2005

THREE STATE SOUTH WESTERLY VIEW over Lake Garfield to the Catskill range all the way on the other side of the Hudson River. Built on a mountaintop in 2005 down a long gated drive, this seven-bedroom, five-bath, 5700sf Contemporary home in Monterey, MA enjoys ultimate privacy on over 16 acres. Enter a two-story great room and be immediately knocked out by the view, possibly the best from any home in the southern Berkshires. The generous first floor master suite has an office library, and there are two more bedrooms on the main floor. Guests have their own floor with four bedrooms, two baths, and a second kitchen and family room, all with the same panoramic vistas. Four fireplaces, two-car attached garage, and separate two car garage for county and lake toys. The ultimate mountainside lodge.

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

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.

406 CANAAN VALLEY, New Marlborough, MA 01259

Price$2,900,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 216183

  • Listings Residential
  • Address 406 Canaan Valley Rd
  • Bedrooms 8
  • Bathroom 6
  • Square Feet 4420

Whiting ridge; the main house was built in 1860 with an original 'guest cottage' built in 1740, there is a 5 stall horse barn and a newer 4-car barn with huge unfiniished second floor. The main house was completely renovated and added on to in 2009. Gorgeous chefs kitchen with sitting area, fireplace and doors out to heated screened porch/sun room. Sunken den with fireplace and porch overlooking the south western hills of ct. Formal living room with fireplace, dining room and entry boot room complete the first flr. Off the second floor landing there is a lovely master suite complete with fireplace and office, two guest rooms and two baths along with a laundry closet. Third floor has additional office or guest room space as well as finished storage space. Patios, porches, unbelievable western views.

Listed by Jen Harvey of BERKSHIRE PROPERTY AGENTS

{$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.

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.