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! 
310 Old Stockbridge Lenox MA 01240

Lenox, MA310 Old Stockbridge Rd

Price$12,500,000

Est. Mortgage: $/month

MLS Number 232689

  • Residential
  • Bathroom 15
  • Bedrooms 13
  • Square Feet 20,821
  • Acreage 89

The elm court estate retains the title of the largest american shingle style home in the united states. The extraordinary gilded age berkshire cottage was built by william douglas sloane and emily vanderbilt, (granddaughter of cornelius vanderbilt), along with architects peabody & stearns in 1886. The gardens and landscape were designed by frederick law olmsted. In 1919, the elm court talks held at the home ultimately led to the creation of the treaty of versailles and league of nations. Outbuildings include butler and gardener cottages, carriage house & stable, greenhouses & caretaker's house and two barns. Significant renovations were accomplished in the early 2000s and continued work is necessary with an additional 8,000 sq. Ft. Of unrestored living space.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 19, 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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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

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 19, 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: 2.72% last updated on Nov 19, 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: 2.72% last updated on Nov 19, 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: 2.72% last updated on Nov 19, 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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802 MA-41 Richmond MA 01254

Richmond, MA802 MA-41 Rd

Price$4,600,000

Est. Mortgage: $/month

MLS Number 232610

  • Residential
  • Bathroom 8
  • Bedrooms 7
  • Square Feet 4,000
  • Acreage 27

Options abound for a lifestyle change at what is now known as the inn at richmond and the berkshire equestrian center. This magnificent 27 acre property includes a charming colonial era 7 bedroom inn, 5 cottages, 2 event barns, 1 shaker horse barn, 26 horse stalls, 15 grazing paddocks, a 16,000 sf multi-purpose heated indoor arena with offices and a two bed apartment with spa, 1 outdoor arena, and the possibility to develop three building lots. With its casual elegance and charm, this colonial equestrian estate will allow your long held passion to blossom whether you use the property as a stunning family compound, an event destination, and/or a first class equestrian facility. The prime central berkshire county location will graciously support your new found lifestyle,

Listed by Jennifer Capala of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY, LENOX

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 19, 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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1204 Ashley Falls Sheffield MA 01257

Sheffield, MA1204 Ashley Falls Rd

Price$2,750,000

Est. Mortgage: $/month

MLS Number 232592

  • Residential
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 3,970
  • Acreage 2.33

The historic ashley falls mill built in 1737. Inviting and dramatic renovation with contemporary floor plan. The mill sits suspended above the water and features two waterfalls, two lush islands and a large swimming pond. Beautiful details including original hand-hewn beams, reclaimed marble, soaring ceilings and luxury finishes. Finished studio space above two car garage. Meticulously landscaped with masonry and multiple outdoor vignettes. Incredible light and the soothing sound of water make this a unique retreat. Features 5 bedrooms and 4 full baths.

Listed by Karen Climo of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 19, 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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135 Main Lenox MA 01240

Lenox, MA135 Main St

Price$2,750,000

Est. Mortgage: $/month

MLS Number 232864

  • Residential
  • Bathroom 17
  • Bedrooms 16
  • Square Feet 8,722
  • Acreage 4.23

The garden gables, located in the center of lenox on over 4 very private park-like acres with gardens, patios, mature trees and a heated 70' pool, can be the ultimate family compound. Beautifully furnished and tastefully decorated with 16 unique bedrooms all with updated private baths, several with fireplaces and all fully air conditioned.The historic 1780 main building and attached eladesor cottage includes 12 spacious suites. The separate orchard cottage includes 4 ensuite rooms with separate entrances, cathedral ceilings and fireplaces.There are also 2 charming dining areas in the main building in addition to the library/music room and cozy ''sherry room'' both with fireplaces.The kitchen is equipped with updated appliances. An extraordinary opportunity!

Listed by C. Randolph Thunfors and Michael Linden of STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 19, 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: 2.72% last updated on Nov 19, 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: 2.72% last updated on Nov 19, 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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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: 2.72% last updated on Nov 19, 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$2,300,000

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: 2.72% last updated on Nov 19, 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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Based on information submitted to BCMLS  as of November 25, 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.