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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
  • Village Berkshire - South
  • Year Built 1915
  • Parking Spaces 2
  • Bedrooms 13

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: 4.35% last updated on Feb 21, 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$3,900,000

Est. Mortgage: $/month

MLS Number 217523

  • Single Family
  • Village Berkshire - South
  • Year Built 1883
  • Parking Spaces 3
  • Bedrooms 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 COHEN & WHITE ASSOCIATES

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$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 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: 4.35% last updated on Feb 21, 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$3,500,000

Est. Mortgage: $/month

MLS Number 225630

  • Single Family
  • Village Berkshire - South
  • Year Built 1912
  • Bedrooms 14
  • Bathroom 15

Host and entertain in the embodiment of Gilded Age sophistication w/ the finest details & craftsmanship captured by this 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 elegant celebrations hosting everyone from Arthur Fiedler and Yo Yo Ma to Paul Newman and Norman Rockwell.The elegant 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! Newly built 3 bedroom guest home included.

Listed by THE KINDERHOOK GROUP - STOCKBRIDGE

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$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 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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108 Raup Rd Chatham NY 12037

Price$2,900,000

Est. Mortgage: $/month

MLS Number 224895

  • Single Family
  • Year Built 1792
  • Parking Spaces 6
  • Bedrooms 3
  • Bathroom 4

Day-O Farm is the complete Hudson Valley estate, located in perfect privacy just minutes outside the village of Chatham. Available for the first time in nearly 30 years, Harry Belafonte's former Columbia County retreat is magical at every turn. Grandly sited, the 1792 main house is a purist's dream, and also offers a main floor master wing with fireplace. The adjacent original carriage house offers a guest suite and beamed ceiling game room, in addition to three car bays. Through the gardens, on the hillside overlooking the main house, is the spacious two bedroom guest house with sauna. The terrace overlooks the oversized gunite pool and pond, with path to the tennis court. Follow the trails through the woods to a one bedroom loft-style hunting cabin. Many tax savings options available.

Listed by Non-member

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$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 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
  • Village Berkshire - Central
  • Year Built 1850
  • Bedrooms 5
  • Bathroom 7

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: 4.35% last updated on Feb 21, 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
  • Village Berkshire - South
  • Year Built 1915
  • Bedrooms 5
  • Bathroom 6

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: 4.35% last updated on Feb 21, 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
  • Village Berkshire - Central
  • Year Built 1911
  • Bedrooms 6
  • Bathroom 8

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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$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 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
  • Village Berkshire - South
  • Year Built 1775
  • Bedrooms 5
  • Bathroom 6

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

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$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 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
  • Village Berkshire - South
  • Year Built 1800
  • Parking Spaces 3
  • Bedrooms 8

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

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$
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$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 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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406 Canaan Valley Rd New Marlborough MA 01259

MLS Number 224946

  • Single Family
  • Village Berkshire - South
  • Year Built 1860
  • Parking Spaces 4
  • Bedrooms 5

Whiting Ridge: built in 1860 and renovated in 2009 by renowned AD100 architect and interior designer Daniel Romualdez. Set above the Whiting River on 85 acres, with panoramic southwesterly views, this exquisite estate is the ultimate escape for the most discerning of buyers. A chef's kitchen, beautiful master suite with views and private porch, a stunning screened room with radiant heat, and four wood burning fireplaces offer four-season luxury in a unique Berkshires location. A 1740's three-bedroom historic guesthouse, four-car architect-designed garage with office, and five-stall horse barn complete the estate. Private and exclusive, yet only 10 minutes from the Southfield Store and 22 minutes from Great Barrington. State of the art design, with timeless elegance. A superb property.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 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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604 Hartsville New Marlboro Rd New Marlborough MA 01259

MLS Number 223156

  • Single Family
  • Village Berkshire - South
  • Year Built 1890
  • Bedrooms 12
  • Bathroom 7

Cassilis Farm. This historic New Marlborough landmark consists of two stately homes - one 7,666 square feet, the other 4,776 square feet - connected by a porte cochere, plus historic horse and cow barns, an antique ice house and charming garden house. The grounds of this 18-acre estate offer woods, pasture, sweeping lawns, perennial beds, a babbling brook and a pond. The houses are remarkably authentic, with elegant staircases, handsome paneled parlors and bedrooms--several with fireplaces--period moldings, doors and windows. Front house features an impressive two-story side porch with spectacular views. Mechanicals are updated. Seize this incredible opportunity to bring an iconic property to the next place in its evolution! Property consists of 602 and 604 Hartsville New Marlboro Rd.

Listed by LANCE VERMEULEN RE, INC

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$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 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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