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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$6,875,000

Est. Mortgage: $/month

Pending

MLS Number 215244

  • Single Family
  • Selling Office Name LANDVEST, INC.
  • Selling Agent LANDVEST, INC.
  • Year Built 1870
  • Bedrooms 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, , 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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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: 3.94% last updated on May 25, 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 Mary Jane White and Nancy Kalodner of COHEN & WHITE ASSOCIATES

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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: 3.94% last updated on May 25, 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's19th century Berkshire''cottages'' that has been meticulously restored and updated.

Listed by Deborah Levinson of BERKSHIRE PROPERTY AGENTS

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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: 3.94% last updated on May 25, 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 Rd, 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 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 Dietze and Cheryl Westall of ALTON & WESTALL REAL ESTATE AGENCY, LLC

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Barnbrook Realty
27 Housatonic Street
Lenox MA, 01240
Office: 413-637-9897

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$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on May 25, 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

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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: 3.94% last updated on May 25, 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 Mary Jane White and Nancy Kalodner of COHEN & WHITE ASSOCIATES

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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: 3.94% last updated on May 25, 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

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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: 3.94% last updated on May 25, 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. 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 radi

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS

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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: 3.94% last updated on May 25, 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 Rd, Richmond, MA 01254

Price$2,550,000

Est. Mortgage: $/month

MLS Number 220874

  • Single Family
  • Year Built 1850
  • Bedrooms 5
  • Bathroom 7
  • Total Full Baths 6

April Hill, a meticulously restored Greek Revival with privacy, guest house, swimming pool and spectacular views. See the supplement for details.

Listed by Scott Sawyer of STONE HOUSE PROPERTIES, LLC

{$agent->Name}

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: 3.94% last updated on May 25, 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

75-77 Main Rd, Tyringham, MA 01264

Price$2,390,000

Est. Mortgage: $/month

MLS Number 219423

  • Single Family
  • Year Built 1750
  • Parking Spaces 1
  • Bedrooms 7
  • Bathroom 6

''Fairy tale'' Residential & Commercial country retreat, nestled in the luscious green hillsides of the Berkshires. Reside in it's beautiful Cottage, and continue the tradition of sharing the 'Gingerbread House' as a Banquet Hall (leased for weddings, retreats and corporate events) and B&B (currently generating over $200K in income). Santarella is steeped in history, dating back to the 1750's. With just under four acres of lush landscaped gardens, bridges, brooks and beautiful blossoms, this is truly a magical, mystical wonderland and a once-in-a-lifetime offering.

Listed by Steven Weisz and Maggie Merelle of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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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: 3.94% last updated on May 25, 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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907 Norfolk Rd, New Marlborough, MA 01259

Price$2,375,000

Est. Mortgage: $/month

MLS Number 213350

  • Single Family
  • Year Built 1760
  • Bedrooms 7
  • Bathroom 7
  • Total Full Baths 6

Set on 52 pastoral acres, this country estate includes original farmhouse, guesthouse, horse barn, pond, an additional building lot, orchards, hiking & riding trails & wonderful views. Main farmhouse is from 1760 & was meticulously restored to its original grandeur in 2015. Located minutes from Southfield Store & downtown Norfolk, Connecticut & close to Ski Butternut & downtown Great Barrington.

Listed by Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

{$agent->Name}

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: 3.94% last updated on May 25, 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 St, Lenox, MA 01240

Price$2,295,000

Est. Mortgage: $/month

Pending

MLS Number 217903

  • Single Family
  • Selling Office Name PIRETTI REAL ESTATE
  • Selling Agent PIRETTI REAL ESTATE
  • Year Built 1805
  • Bedrooms 6

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

Listed by Suzanne Crerar of STONE HOUSE PROPERTIES, LLC

{$agent->Name}

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: 3.94% last updated on May 25, 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