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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! 
2080 Undermountain Rd Sheffield MA 01257

Sheffield, MA2080 Undermountain Rd

Price$16,000,000

Est. Mortgage: $/month

MLS Number 229173

  • Single Family
  • Village Berkshire - South
  • Year Built 1880
  • Bedrooms 11
  • Bathroom 7

The Jewel of New England... Offered for the first time in four decades, this 85 acre Berkshire mountainside campus awaits your imagination. This property offers an atmosphere for breakout creative expression with great potential for an enterprise for retreats, wellness center, writers/ artists workshops, educational endeavors or your family's private estate. The property consists of 12 buildings; conference halls, dining/ meeting facilities, lodging accommodations, offices and an historic Queen Anne manor house sitting on a knoll with breathtaking views. 40 years of stewarding this campus where thousands of participants made life long memories, the owners are ready to pass it on. Let their growth be your opportunity. For details & digital brochure please see jewelinnewengland.com

Listed by COHEN & WHITE ASSOCIATES

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$
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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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3 Ice Glen Rd Stockbridge MA 01262

Stockbridge, MA3 Ice Glen Rd

Price$8,500,000

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

Lenox, MA106 Cliffwood St

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 Mary Jane White of COHEN & WHITE ASSOCIATES

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

Lenox, MA89 Cliffwood St

Price$3,350,000

Est. Mortgage: $/month

MLS Number 230032

  • 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 BERKSHIRE PROPERTY AGENTS, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

Lenox, MA51 Walker St

Price$3,200,000

Est. Mortgage: $/month

MLS Number 230193

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

Perfect Family or Corporate Retreat away from the City. This Iconic Masterpiece in the Heart of Lenox Village in the Berkshires can accommodate the whole gang or team!! 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. The elegant 5 STAR 11 bedroom mansion is a centerpiece and crown jewel of the town and includes a second 3 bedroom home on the property. Impeccably maintained!

Listed by THE KINDERHOOK GROUP - PITTSFIELD

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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 230154

  • Single Family
  • Village Berkshire - South
  • Year Built 1915
  • Parking Spaces 2
  • Bedrooms 6

ONCE IN A LIFETIME IT COMES ALONG: a modern renovation. Every detail is thoughtful, the rooms offer height and grace, its magnitude gives space without being overwhelming. Built on the top of Great Barrington's Hill. Peering down on the town, within walking distance on 3 +acres. Built by a local craftsman and designed with easy living in mind. The open kitchen/great room, has a soaring ceiling, will gather you with family and friends in front of the stone fireplace or relaxing at the granite island while meals are prepared in the chef quality kitchen with Calcutta marble counters. Clean modern lines, meticulously chosen materials, two master suites, a modern open stairway concept with metal balusters, outdoor kitchen, spa pool. Light and Bright in law/Nanny suite. Kosher Kitchen.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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25 Cliffwood St Lenox MA 01240

Lenox, MA25 Cliffwood St

Price$2,600,000

Est. Mortgage: $/month

MLS Number 228145

  • Single Family
  • Address 25 Cliffwood St
  • Village Berkshire - South
  • Year Built 1889
  • Bedrooms 10

Proudly presenting this newly refurbished 10 Bedroom, 9 and half bath, privately owned, walk to town, historic Lenox ''Cottage''. Lovingly named Osceola after the dramatic view of Osceola Mountain on the Yokun Ridge experienced upon entering the columned and balustraded front porch. Osceola Mansion was designed by world renowned architects Rotch and Tilden in 1889 and commissioned by Sarah Pollock Livingston. Today, this comfortable and beautifully appointed home features an entry foyer with a fireplace to warm your hands and toes after a winter's sleigh ride. Enter the Grand Hall which invites you into the Living Room to your right or draws your attention to the unique Oval Dining Room to your left. Straight ahead is the picturesque outdoor covered 80 feet in length Veranda

Listed by BERKSHIRE HOMES AND CONDOS

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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99 Shaker Museum Rd Old Chatham NY 12136

Old Chatham, NY99 Shaker Museum Rd

Price$2,500,000

Est. Mortgage: $/month

Pending

MLS Number 229391

  • Single Family
  • Selling Office Name GILCREST PROPERTIES
  • Selling Agent GILCREST PROPERTIES
  • Address 99 Shaker Museum Rd
  • Year Built 1790

This large historic property available with component pricing:*House with 30+/- acres, all or some accessory buildings/greenhouse @ $2,500,000* 43,000' barn complex on 170+/- acres @$1,950,000* entire 207 acres all buildings and barns @ $3,95,000The Old Chatham Sheepherders Estate dates back to 1790 and is a landmark property in Upper Hudson Valley, only 30 min from Albany Int'l Airport and Hudson's Amtrak. IDEAL AS A FAMILY COMPOUND, AGRICULTURAL ENTERPRISE OR LIVESTOCK/HORSE FARM, The estate includes a grand 12 room Federal home with 5 bedrooms and 5 1/2 baths, large living room w/ FP, den w/ FP, library, hand muraled dining room and bi-level porches. Formerly a Relais&Chateau ( no longer allowed as an inn) all of the systems have been engineered to the highest commercial

Listed by LANDVEST, INC.

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

Egremont, MA46 Bow Wow Rd

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

Stockbridge, MA21 Prospect Hill Rd

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: 3.33% last updated on Apr 2, 2020
* 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

Williamstown, MA222 Ide Rd

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: 3.33% last updated on Apr 2, 2020
* 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

Tyringham, MA137 Jerusalem Rd

Price$2,200,000

Est. Mortgage: $/month

MLS Number 229212

  • 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 history. Overlooking Tyringham valley, Morningside is set on 44 acres with a circa 1800 Manor House originally constructed by the North Family of the Tyringham Shakers. Pool, pool house, swim pond, & stunning gardens. The permanently protected U.S. Appalachian Trail borders the land to the south & east. 16 rooms include a huge kitchen, 7 bedrooms, one a palatial master suite, and 4 full and 2 1/2 baths. A large 3-car carriage barn has a large vaulted room & full bath above. The setting is both spectacular & quiet, without being isolated. You are in the heart of the Berkshires with staggering views. Add'l land & homes available.

Listed by BROCKMAN REAL ESTATE, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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