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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: 4.17% last updated on Apr 18, 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: 4.17% last updated on Apr 18, 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: 4.17% last updated on Apr 18, 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 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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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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: 4.17% last updated on Apr 18, 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: 4.17% last updated on Apr 18, 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: 4.17% last updated on Apr 18, 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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$
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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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: 4.17% last updated on Apr 18, 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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50 Shun Toll Rd Egremont MA 01252

Price$1,895,000

Est. Mortgage: $/month

MLS Number 224990

  • Single Family
  • Village Berkshire - South
  • Year Built 1900
  • Bedrooms 4
  • Bathroom 3

BeBeautifully sited on 57 acres in North Egremont MA, this completely renovated Cape style home was originally built in the early 1900's. Peaceful and private yet less than one mile from the General Store and convenient to restaurants, recreation, and cultural attractions in Great Barrington, Lenox, Northwest Connecticut and NY State. Features include Four Bedrooms, 3.5 Baths, first-floor Master, beautiful kitchen with custom cabinets by William Ohs, office with craftsman-built cabinetry, in-law apartment, heated two car garage, and spacious barns on a 30-acre pasture. Enjoy hiking, abundant wildlife and cross-country skiing without leaving home!

Listed by Elyse Harney Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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101 Green River Rd Alford MA 01230

Price$1,850,000

Est. Mortgage: $/month

MLS Number 221523

  • Single Family
  • Village Berkshire - South
  • Year Built 1835
  • Bedrooms 5
  • Bathroom 3

A Scandinavian-styled renovated modern Farmhouse with luminous light and glowing spaces, inside and out. 5 bedrooms, 3 full baths and 3 floors- completely refinished and refined. The studio is huge and perfect for any number of uses:family, crafts, workspace, art... Gorgeously oiled finished fir and oak floors, custom kitchen with pantry. Oversized library opens out to wrap around porches + 3rd floor attic is finished and available for media room, office, yoga/meditation. Outdoors there is 14+ acres of established flower beds, bi-level barn, greenhouse, 2 hoop houses, fruit and nut trees, berries chicken coops...a spectacular walking woods and 9 acres is protected by a deer fence + additional fencing and gated entry for privacy, protection and ease. This might be the perfect Herb Farm!

Listed by LANCE VERMEULEN RE, INC

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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267 Long Pond Rd Great Barrington MA 01230

Price$1,749,000

Est. Mortgage: $/month

MLS Number 226290

  • Single Family
  • Village Berkshire - South
  • Year Built 1820
  • Parking Spaces 2
  • Bedrooms 5

A True Berkshire Gem in a Premiere Location Over Looking Long Pond. Wow! Classic farmhouse on nearly 80 acres with a barn, orchard, pool, tennis court, play house, and gardens. All of this over looking open fields, Log Pond and Catamount. This is truly a spectacular setting with a large living/family room, formal dining, large eat-in kitchen and den. Second floor with bedrooms and third floor finished as studio space. Finished lower level room with full bath and outdoor shower for after swimming, tennis, gardening, or just playing. Come put your personal touch on this gem. A bit of work for a lot of gain.In 1987 additional land was purchased for $80,000. House sits on just 4+ acres but the entire lot is nearly 80 acres. Inscription in kitchen beams are from 1820.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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