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Berkshire Classic Homes

Looking for a home with some antique and historical charm? Discover beautiful homes with classic charm in the Berkshires. From Victorian homes with acres of land, to Colonial estates with breathtaking views. See something you love? Register with us to save your favorites and to receive notifications when similar properties are listed. Contact us today to see any listed homes below! 
2 Glendale Middle Rd, Stockbridge, MA 01262

Price$6,900,000

Est. Mortgage: $/month

MLS Number 215244

  • Single Family
  • Year Built 1870
  • Bedrooms 8
  • Bathroom 10
  • Total Full Baths 8

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.

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.09% last updated on Jan 19, 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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106 & 114 Cliffwood St, Lenox, MA 01240

Price$4,750,000

Est. Mortgage: $/month

MLS Number 217523

  • Single Family
  • Year Built 1883
  • Parking Spaces 3
  • Bedrooms 8
  • Bathroom 8

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 Nancy Kalodner of BENCHMARK REAL ESTATE

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.09% last updated on Jan 19, 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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151 Walker St, Lenox, MA 01240

Price$4,250,000

Est. Mortgage: $/month

MLS Number 214688

  • Single Family
  • Year Built 1880
  • Bedrooms 10
  • Bathroom 10
  • Total Full Baths 8

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

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.09% last updated on Jan 19, 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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89 Cliffwood St, Lenox, MA 01240

Price$3,950,000

Est. Mortgage: $/month

MLS Number 217574

  • Single Family
  • Year Built 1888
  • Bedrooms 6
  • Bathroom 8
  • Total Full Baths 5

SUPREMELY WELCOMING...One of Lenox's last 19th century Berkshire''cottages'' that has been meticulously restored and updated.

Listed by Deborah Levinson of BERKSHIRE PROPERTY AGENTS

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.09% last updated on Jan 19, 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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575 South St, Pittsfield, MA 01201

Price$3,800,000

Est. Mortgage: $/month

MLS Number 216840

  • Single Family
  • Year Built 1911
  • Bedrooms 6
  • Bathroom 8
  • Total Full Baths 5

The Morewood is a masterpiece of historical restoration, every room draws you in to a place where guests are treated like family. It represents the design influence of the early work of Sir Edwin Lutyens, with architecture adapted from the Elizabethan period, and nestled into its incredible English gardens. A 10, 000+ sq.ft. Tutor style brick main house with 6 bedrooms, 8 bathrooms.

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

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.09% last updated on Jan 19, 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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406 Canaan Valley Rd, New Marlborough, MA 01259

MLS Number 216183

  • Single Family
  • Year Built 1800
  • Parking Spaces 4
  • Bedrooms 8
  • Bathroom 6

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

Listed by Jen Harvey of BERKSHIRE PROPERTY AGENTS

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.09% last updated on Jan 19, 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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, Williamstown, MA 01267

Price$2,950,000

Est. Mortgage: $/month

MLS Number 217915

  • Single Family
  • Year Built 1911
  • Parking Spaces 2
  • Bedrooms 8
  • Bathroom 8

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 eight bedrooms, seven and one-half baths, and 7, 215 square feet of living space. Mature trees, stone walls, beautiful gardens, an in-ground pool and picturesque mountain views complete this rare offering.

Listed by Maureen Dietze and Cheryl Westall of ALTON & WESTALL REAL ESTATE AGENCY, LLC

Barnbrook Realty
27 Housatonic Street
Lenox MA, 01240
Office: 413-528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.09% last updated on Jan 19, 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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165 Litchfield Rd, Norfolk, CT 06058

Price$2,850,000

Est. Mortgage: $/month

MLS Number 217023

  • Single Family
  • Year Built 1903
  • Bedrooms 5
  • Bathroom 6
  • Total Full Baths 5

Inspired by medieval England and his love of Italian architecture, renowned architect- Alfredo Taylor- designed "Moss Hill" in Norfolk, Ct. in 1903. Moss Hill rises three stories with tall gables and bands of windows on all sides, taking full advantage of its elevated site and dramatic views. 5+ bedrooms, beautiful kitchen, greenhouse and pool. Stunning details inside and out.

Listed by Mimi Harson and of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.09% last updated on Jan 19, 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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795 Rannapo Rd, Sheffield, MA 01257

Price$2,800,000

Est. Mortgage: $/month

MLS Number 217224

  • Single Family
  • Year Built 1850
  • Bedrooms 6
  • Bathroom 6
  • Total Full Baths 6

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 Nancy Kalodner and Benchmark Real Estate of BENCHMARK REAL ESTATE

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.09% last updated on Jan 19, 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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22 New Marlboro Rd, Monterey, MA 01245

Price$2,750,000

Est. Mortgage: $/month

MLS Number 215890

  • Single Family
  • Year Built 1766
  • Bedrooms 6
  • Bathroom 6
  • Total Full Baths 5

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.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.09% last updated on Jan 19, 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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137 Jerusalem Rd, Tyringham, MA 01264

Price$2,750,000

Est. Mortgage: $/month

MLS Number 218074

  • Single Family
  • Year Built 1800
  • Parking Spaces 3
  • Bedrooms 8
  • Bathroom 6

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

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.09% last updated on Jan 19, 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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58 Yokun Ave, Lenox, MA 01240

Price$2,599,000

Est. Mortgage: $/month

Pending

MLS Number 215346

  • Single Family
  • Year Built 1880
  • Parking Spaces 3
  • Bedrooms 8
  • Bathroom 8

This grand lady, w/8 bedrooms, 8 fireplaces, 5 full, 3 half baths, tennis, pool/pool house on 6.1 acres in fab walk-to-lenox location. Elegant yet easy, children and adults delight in the open, light-filled rooms that have enchanted since 1879 when ''Shingle Style'' design first came into Vogue. With tasteful modern updates, she is known as Gusty Gables. She is ready to welcome her new residents!

Listed by Claudia Laslie of BARNBROOK REALTY, INC.

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.09% last updated on Jan 19, 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