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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$12,500,000

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: 2.9% last updated on Sep 24, 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: 2.9% last updated on Sep 24, 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: 2.9% last updated on Sep 24, 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: 2.9% last updated on Sep 24, 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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119 Under Mountain Lenox MA 01240

Lenox, MA119 Under Mountain Rd

Price$3,400,000

Est. Mortgage: $/month

MLS Number 231866

  • Residential
  • Bathroom 9
  • Bedrooms 9
  • Square Feet 11,857
  • Acreage 11.2

Spectacular landscaping surrounds the gracious main home of this historic property in lenox. With a sympathetic melding of the old and the new, the original house was built in the 1830's and added to throughout the years. Today it is a large and comfortable home for gathering and entertaining family and friends or just escaping the stress of today's world. Six bedrooms, 5.5 baths. Brick paths meander through lovely gardens , to the artfully converted barn/guest house and the 20'x 40'pool/hot tub area - far enough from the main house for privacy but close enough for conviviality. Highlighted by a fabulous cone-shaped window the 'barn' has large living spaces, a kitchen, bar, three bedrooms, 2.5 baths. A magnificent property.

Listed by Martha Piper of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 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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24 East Alford MA 01230

Alford, MA24 East Rd

Price$2,800,000

Est. Mortgage: $/month

MLS Number 231603

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,413
  • Acreage 32.2

Rare opportunity to own this private, 32-acre estate in the center of alford. Built in 1875, the historic post-and-beam home was completely renovated by famed director dick schneider to create this spacious and comfortable country house perfect for relaxing with friends and family. The main part of the house features a light-filled, eat-in kitchen which leads out to the deck overlooking nature. The living room has a wood-burning fireplace and an adjacent den with attached full bath. Upstairs are 3 bedrooms including a large master suite. The breezeway off the downstairs atrium leads to a 2-car garage above which are located the guest quarters with full bath and which is also ideal for use as an office or home gym. The grounds are simply gorgeous, with the alford brook running through

Listed by Lisa Bouchard Hoe of THE KINDERHOOK GROUP - PITTSFIELD

$
$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 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: 2.9% last updated on Sep 24, 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

Pending

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: 2.9% last updated on Sep 24, 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: 2.9% last updated on Sep 24, 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

454 Main Great Barrington MA 01230

Great Barrington, MA454 Main St

Price$2,400,000

Est. Mortgage: $/month

MLS Number 231623

  • Residential
  • Bathroom 2
  • Square Feet 5,519
  • Acreage 1.26

This unique and majestic property has been originally erected in 1853 as a residence for a local doctor clarkson t. Collins. The american gothic revival style home has been converted many times since and it is currently the home of a renowned local jeweler. It consists of 1940 sq. Ft of the first floor and 1680 sq. Ft of the second floor. With the right mix of creative vision and passion, it can be turned back to that ''one of a kind'' home. Situated right in the heart of great barrington, within walking distance to downtown, it is also only 2+ hours travel from boston or new york. Come take a look, bring your architect and decorator and this incredible property could be yours.See also mls 230288

Listed by Stephen R. Schoenfeld and Joanna Szwyd of STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 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 Williamstown MA 01267

Williamstown, MA222 Ide Rd

Price$2,250,000

Est. Mortgage: $/month

MLS Number 231929

  • Residential
  • Bathroom 8
  • Bedrooms 7
  • Square Feet 7,215
  • Acreage 2.78

An iconic country estate nestled in the northern hills of berkshire county. Boasting early 1900's classic craftsman style architecture yet fully renovated and modernized with gourmet kitchen and freshly redone, heated gunite in ground pool. The main residence offers a master suite and 3 en suites on the second level while all entertaining spaces are on the ground level with access to patios and porches. Connected by your 3-season glass and screened nature-gallery, your guest house awaits. Multi level with workout space, office and 2 bedrooms / 2 full baths. Further guest accommodations are found above the detached garage blending a more contemporary 1 bedroom with living space and sizable full bath. Its rare to find almost 4 acres in such close proximity to all of williamstown.

Listed by Jeffrey M. Loholdt of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 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 Tyringham MA 01264

Tyringham, MA137 Jerusalem Rd

Price$2,200,000

Est. Mortgage: $/month

Pending

MLS Number 229212

  • Residential
  • Bathroom 11
  • Bedrooms 13
  • Square Feet 9,587
  • Acreage 119.56

Morningside, tyringham a spectacular estate dating back to the tyringham shakers. An extraordinary, & unique opportunity to own a part of berkshire history. Overlooking tyringham valley, morningside is set on 120 acres with a c. 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 21/2 baths. A large 3-car carriage barn has a large vaulted room & full bath above. Included in the sale is a tractor barn with a 3br home above and a 2 br guest cottage you are in the heart of the berkshires with staggering views.

Listed by L. Chapin Fish of BROCKMAN REAL ESTATE, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 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 September 28, 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.