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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 Sheffield MA 01257

Sheffield, MA2080 Undermountain Rd

Price$16,000,000

Est. Mortgage: $/month

MLS Number 229173

  • Residential
  • Bathroom 7
  • Bedrooms 11
  • Square Feet 7,946
  • Acreage 85

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 Mary Jane White and Nancy K. Kalodner of COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 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 Stockbridge MA 01262

Stockbridge, MA3 Ice Glen Rd

Price$8,500,000

Est. Mortgage: $/month

MLS Number 225549

  • Residential
  • Bathroom 15
  • Bedrooms 13
  • Square Feet 12,253
  • Acreage 58.8

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 Patrice C. Melluzzo of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 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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66 Willowbrook Hillsdale NY 12529

Hillsdale, NY66 Willowbrook Ln

Price$7,200,000

Est. Mortgage: $/month

MLS Number 230793

  • Residential
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 5,412
  • Acreage 754.95

Amazing opportunity to own a large parcel of land in one of the most desirable towns in columbia county. With frontage on four picturesque roads less than 10mins to great barrington this 1850s barn offers so much; main house has a great room with fireplace and loft above, large dining room off eat-in kitchen and laundry room with ample storage and separate entry, 3 guest rooms all with en suite. The post and beam structure allows for the entire main space to be opened up with southern exposure. Lower level pool area, tower structure ideal for studio and it just keeps going; a 20 acre pond, three additional dwellings, 4 additional barns plus tractor shed, tennis court, original concrete pool and trails taking you back to the frontage along the roe jan.Organically farmed.

Listed by Jen Harvey of BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 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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66 WILLOWBROOK Hillsdale NY 12529

Hillsdale, NY66 WILLOWBROOK Ln

Price$6,250,000

Est. Mortgage: $/month

MLS Number 230794

  • Residential
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 5,412
  • Acreage 617.05

Amazing opportunity to own a large parcel of land in one of the most desirable towns in columbia county. With frontage on four picturesque roads less than 10mins to great barrington this 1850s barn offers so much; main house has a great room with fireplace and loft above, large dining room off eat-in kitchen and laundry room with ample storage and separate entry, 3 guest rooms all with en suite. The post and beam structure allows for the entire main space to be opened up with southern exposure. Lower level pool area, tower structure ideal for studio and it just keeps going; a 20 acre pond, three additional dwellings, 4 additional barns plus tractor shed, tennis court, original concrete pool and trails taking you back to the frontage along the roe jan.Organically farmed.

Listed by Jen Harvey of BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 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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2 Kemble Lenox MA 01240

Lenox, MA2 Kemble St

Price$4,600,000

Est. Mortgage: $/month

MLS Number 230546

  • Residential
  • Bathroom 14
  • Bedrooms 13
  • Square Feet 11,800
  • Acreage 3

Here is your opportunity to own a magnificent berkshire cottage that has been brought back to its original grandeur & fully updated to function as a modern inn or private home in every way.Walking distance to all shops & restaurants,the mount & minutes to tanglewood,the kemble is perfectly located in lovely downtown lenox.Step out onto your wrap around rear veranda w/spectacular mountain views.Rich w/original details throughout,the kemble is a visual feast w/majestic entry hall & winding staircase w/crystal chandelier above along w/gathering areas, media/parlor room & dining room w/ ornate crown molding & exquisitely carved wood fireplace mantels.Each of the 13 bdrms has been tastefully renovated w/historical design in mind,all w/stunning en suite baths & fireplaces. (more in supplement)

Listed by Thom Garvey of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY, LENOX

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 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 Lenox MA 01240

Lenox, MA89 Cliffwood St

Price$3,350,000

Est. Mortgage: $/month

MLS Number 230032

  • Residential
  • Bathroom 7
  • Bedrooms 6
  • Square Feet 10,371
  • Acreage 3.17

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 Selina Lamb of BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 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 Great Barrington MA 01230
Pending

MLS Number 230154

  • Residential
  • Bathroom 7
  • Bedrooms 6
  • Square Feet 6,849
  • Acreage 3.17

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 Maureen White Kirkby of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 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 Lenox MA 01240

Lenox, MA25 Cliffwood St

Price$2,600,000

Est. Mortgage: $/month

MLS Number 228145

  • Residential
  • Bathroom 10
  • Bedrooms 10
  • Square Feet 7,393
  • Acreage 1.22

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 Matthew Marlow and Sheila E. McKenna of BERKSHIRE HOMES AND CONDOS

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 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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78 Interlaken Stockbridge MA 01262

Stockbridge, MA78 Interlaken Rd

Price$2,550,000

Est. Mortgage: $/month

MLS Number 230952

  • Residential
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 3,424
  • Acreage 8

Spacious 1800's colonial tastefully updated on 8 acres of land with 296 ft of waterfront on stockbridge bowl! A private dock for your boat. A secluded flat grass area for picnics and sunbathing. Swim from the sandy water front. The house offers 4 or 5 bedrooms, 4 updated baths, expansive eat in kitchen with butcher block counters, an island, stainless appliances and walk in pantry/laundry room. The kitchen opens to the cozy family room with french doors to a covered porch and views of acres of fields. The living space includes a 25 ft living room with fireplace, large dining room currently being used as a pool room! Time for a game? Enjoy out door living in style; porches, decks, gardens, stone walls, gorgeous lawn and basketball court. More than enough space for pool and or tennis!

Listed by Patrice C. Melluzzo of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 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 Egremont MA 01258

Egremont, MA46 Bow Wow Rd

Price$2,500,000

Est. Mortgage: $/month

MLS Number 221749

  • Residential
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 11,353
  • Acreage 115.82

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 Brandon White and Cortney K Dupont of COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 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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66 Willowbrook Hillsdale NY 12529

Hillsdale, NY66 Willowbrook Ln

Price$2,450,000

Est. Mortgage: $/month

MLS Number 230795

  • Residential
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 5,412
  • Acreage 262.75

Amazing opportunity to own a large parcel of land in one of the most desirable towns in columbia county. With frontage on four picturesque roads less than 10mins to great barrington this 1850s barn offers so much; main house has a great room with fireplace and loft above, large dining room off eat-in kitchen and laundry room with ample storage and separate entry, 3 guest rooms all with en suite. The post and beam structure allows for the entire main space to be opened up with southern exposure. Lower level pool area, tower structure ideal for studio and it just keeps going; a 20 acre pond, tennis court, original concrete pool and trails taking you back to the frontage along the roe jan.Organically farmed.

Listed by Jen Harvey of BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

137 Jerusalem Tyringham MA 01264

Tyringham, MA137 Jerusalem Rd

Price$2,200,000

Est. Mortgage: $/month

Pending

MLS Number 229212

  • Residential
  • Bathroom 7
  • Bedrooms 8
  • Square Feet 7,185
  • Acreage 44.42

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 L. Chapin Fish of BROCKMAN REAL ESTATE, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

Based on information submitted to BCMLS  as of July 9, 2020 . All data is obtained from various sources and has not been, and will not be, verified by broker or BCMLS.  All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.