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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! 
3 Ice Glen Rd Stockbridge MA 01262

Price$10,000,000

Est. Mortgage: $/month

MLS Number 225549

  • Single Family
  • Address 3 Ice Glen Rd
  • Village Berkshire - South
  • Year Built 1915
  • Parking Spaces 2

Built in 1915 believed to be the last of the Berkshire Cottages. This stunning home on 58.8 acres is just minutes to the village of Stockbridge MA. Restored to its original splendor with black and white marble floor entry, curved marble staircase, loggia with painted ceiling and fountain. The library includes book shelves flanking 3 walls and two fireplaces. The room is used as an office/family space with Tv and electronics hidden behind custom doors. Main salon with fireplace and views of the terrace and eastern light. Dining room with fireplace custom table seats 14 easily. Modern kitchen with Corian topped island and comfortable table spaces. A work area as well as tv space off of kitchen. Nine bedrooms. six baths on second and third floors. SEE ADDITIONAL INFO

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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 Cliffwood St Lenox MA 01240

Price$3,600,000

Est. Mortgage: $/month

MLS Number 217523

  • Single Family
  • Address 106 Cliffwood St
  • Village Berkshire - South
  • Year Built 1883
  • Parking Spaces 3

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 COHEN & WHITE ASSOCIATES

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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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$3,350,000

Est. Mortgage: $/month

MLS Number 227001

  • Single Family
  • Address 89 Cliffwood St
  • Village Berkshire - South
  • Year Built 1888
  • Parking Spaces 3

Best of the Berkshires. Truly one of the most gracious homes exquisitely restored for modern life with family and friends. Designed by Boston architects in the 1880's the unparalleled flow and understated charm of this home function as beautifully today as then. In superb condition, with excellent systems throughout. Large, caretaker apartment or home office too. Beautifully sited gunite swimming pool and mature gardens add to the sense of elegance, ease and privacy. , Ideally located in Lenox one can walk to town, Tanglewood or hike in Kennedy Park and the numerous preserved woodlands. See documents for additional information and details.

Listed by STONE HOUSE PROPERTIES, LLC

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%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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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20 Berkshire Heights Rd Great Barrington MA 01230

MLS Number 223462

  • Single Family
  • Village Berkshire - South
  • Year Built 1915
  • Bedrooms 6
  • Bathroom 7

Complete 2012 rebuild and seamless expansion of a gracious home on The Hill in Great Barrington, into a stunning timeless and modern Federal estate, perched on a notable parcel with a barn and private spa pool. No detail was overlooked inside or out from custom everything to geothermal heating and cooling. Too many amenities to list, including central A/C, full house generator, Pella true divided light windows throughout, Rocky Mountain hardware, Lutron lighting, spray foam insulation, double insulated floors, and most all of the house has radiant heated floors and of course state-of-the-art mechanicals. The three acres are beautifully landscaped and include a spa pool with a waterfall and auto cover, bocci court, invisible dog fence, a seasonal stream, and a barn. Walk to town.

Listed by BERKSHIRE PROPERTY AGENTS, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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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51 Walker St Lenox MA 01240

Price$2,995,000

Est. Mortgage: $/month

MLS Number 225630

  • Single Family
  • Address 51 Walker St
  • Village Berkshire - South
  • Year Built 1912
  • Bedrooms 14

Iconic masterpiece in the heart of Lenox village!Built in 1912 as a summer ''cottage'' for Harley Procter, of Procter & Gamble the home has been the site of some of the Berkshires most lavish celebrations hosting everyone from Arthur Fiedler and Yo Yo Ma to Paul Newman and Norman Rockwell.The elegant 5 STAR 11 bedroom mansion is a centerpiece and crown jewel of the town. A rare opportunity to enter the rich cultural heritage of Lenox and the Berkshires. Turn - Key and awaiting your fresh energies and ideas! Expansion potential.Newly built 3 bedroom guest home included.

Listed by THE KINDERHOOK GROUP - STOCKBRIDGE

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$
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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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 221750

  • Single Family
  • Address 2650 Swamp Rd
  • Village Berkshire - Central
  • Year Built 1850
  • Bedrooms 5

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

Listed by STONE HOUSE PROPERTIES, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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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46 Bow Wow Rd Egremont MA 01258

Price$2,500,000

Est. Mortgage: $/month

MLS Number 221749

  • Single Family
  • Address 46 Bow Wow Rd
  • Village Berkshire - South
  • Year Built 1915
  • Bedrooms 5

Applegate Farm...Country residence with both formal and informal common spaces to accommodate a few or many with five fireplaces, two master suites and guest wing with tennis court all overlooking your own lake with a western mountain view for backdrop. 100 + acres of very special land located on the border of Egremont and Sheffield on a back country road.

Listed by COHEN & WHITE ASSOCIATES

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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$2,490,000

Est. Mortgage: $/month

MLS Number 222925

  • Single Family
  • Address 575 South St
  • Village Berkshire - Central
  • Year Built 1911
  • Bedrooms 6

Description: This gilded age mansion on the gateway to Pittsfield, the Berkshires' major commercial center, has been restored to Museum quality. With large common rooms and 4 levels of living space, Morewood could easily serve as a Cultural Center, Wellness Facility, Medical Spa (with possible ties to Berkshire Medical Center, Kripaulu, and Canyon Ranch) Assisted Living, Educational Facility, and even a golf and dinner club as Morewood adjoins the Pittsfield Country Club. The property is in pristine condition and ready for a new journey. The 10,000+ sq.ft. Tutor style brick mansion has 6 bedrooms, 8 bathrooms, and is in the heart of the Berkshires Pittsfield business and cultural center. Grand gardens looking over the golf course to the lake. Ideal residential other commercial venture

Listed by LANDVEST, INC.

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$
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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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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327 River Rd Florida MA 01247

Price$2,300,000

Est. Mortgage: $/month

MLS Number 227135

  • Single Family
  • Address 327 River Rd
  • Village Berkshire - North
  • Year Built 1900
  • Parking Spaces 2

Imagine relaxing on your back porch, gazing out over the mountains and fields that surround you while watching the deer and turkey meander through the yard. Walk the many hiking trails through your property or head across the street to the Deerfield River to enjoy kayaking, fishing and tubing on this regulated, time released waterway. The home has been taken down to the studs and features a custom kitchen that is sure to make cooking and entertaining a joy. When it is time to turn in for the night, you will be lulled to sleep by the sound of the running river.

Listed by Keller Williams Berkshire

$
$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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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21 Prospect Hill Rd Stockbridge MA 01262

Price$2,250,000

Est. Mortgage: $/month

MLS Number 222499

  • Single Family
  • Address 21 Prospect Hill Rd
  • Village Berkshire - South
  • Year Built 1775
  • Bedrooms 5

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. Please check out the virtual tour.

Listed by BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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$2,250,000

Est. Mortgage: $/month

MLS Number 227158

  • Single Family
  • Address 222 Ide Rd
  • Village Berkshire - North
  • Year Built 1911
  • Parking Spaces 2

A stunning renovation and restoration has elevated this historic Arts & Crafts home to a new level, where elegance and simplicity reign. Sited on 2.78 acres, this magnificent country compound is an alchemy of superb design and the finest quality materials and workmanship. Ideally suited to large-scale entertaining, it totals 7,215sf of living space in the main house, guest house, and suite over the garage, and offers seven to eight bedrooms, seven and one-half baths, a gourmet kitchen, spacious light-filled rooms for large parties, intimate fireplace rooms for quiet conversation, a colonnaded terrace with a glorious mountain view, and a generous three-season room that overlooks a lovely landscaped patio and heated in-ground pool. Beyond the pool and patio, bluestone walls and walkways

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY, LENOX

$
$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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$2,200,000

Est. Mortgage: $/month

MLS Number 225619

  • Single Family
  • Address 137 Jerusalem Rd
  • Village Berkshire - South
  • Year Built 1800
  • Parking Spaces 3

MORNINGSIDE, TYRINGHAM A spectacular estate dating back to the Tyringham Shakers. This is an extraordinary, & unique opportunity to own a part of Berkshire. Overlooking Tyringham valley, Morningside is set on 44 acres with a circa 1800 Manor House originally constructed by the North Family of the Tyringham Shaker community, pool, pool house, swim pond, & stunning gardens. The permanently protected U.S. Appalachian Trail borders the land to the south. 16 rooms include a large kitchen, 7 bedrooms, one a palatial master suite, and 4 full and 2 half baths. A large 3-car carriage barn has a large vaulted room and full bath above. The setting is both spectacular & quiet, without being isolated. You are in the heart of the Berkshires with Tanglewood only 10 miles away. Add'l land & homes avail.

Listed by BROCKMAN REAL ESTATE, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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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