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

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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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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 33
  • 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: 2.97% last updated on Feb 25, 2021
* 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 - LENOX

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$
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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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9 Seekonk Great Barrington MA 01230

Great Barrington, MA9 Seekonk Rd

Price$3,750,000

Est. Mortgage: $/month

Pending

MLS Number 233070

  • Residential
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 5,930
  • Acreage 11.66

Surrounded by magnificent pastoral views over protected land, this historic home is a gem. Once part of the adjacent farm, then home to an opera diva, it has been transformed into a wonderful, light-filled sanctuary with a clean, simple aesthetic. Antique character has been highlighted, modern conveniences added, and high-efficiency updates made. Each room is delightful. The sleek eat-in chef's kitchen with access to deck and screened porch. The dining room with antique fireplace, custom bar and wall of built-in shelving. The extraordinary great room, once a barn, now a dramatic space with a fireplace at one end, and spectacular view window on the other. The primary bedroom suite with exquisite bathroom & dressing room. The gracious first floor guest suite with sweet ceiling detail...

Listed by Lance Vermeulen and Barney Stein of LANCE VERMEULEN RE, INC

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$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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 - GT BARRINGTON

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$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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

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$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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

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$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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 3 acres in such close proximity to all of williamstown.

Listed by Jeffrey M. Loholdt of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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36 Main Stockbridge MA 01262

Stockbridge, MA36 Main St

Price$2,200,000

Est. Mortgage: $/month

MLS Number 233139

  • Residential
  • Bathroom 6
  • Bedrooms 2
  • Square Feet 6,392
  • Acreage 0.25

Main street stockbridge historic property - home to williams & sons country store and the picturesque shops in ''the mews'', this building is an adored piece of stockbridge's historic downtown landscape, and one of the few featured in norman rockwell's world renowned 1967 painting - stockbridge main street at christmas. With a total of 10 units, including a well established restaurant, six retail spaces, two apartments, and one office, this property provides consistent and profitable income with a flexible layout. Two of the retail spaces have main street entrances, while the other four and the restaurant are accessed from the mews. With direct access from the mews to the courtyard of the red lion inn, these retail shops have plenty of foot traffic throughout each season.

Listed by Katie Williams of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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83 Hurlburt Great Barrington MA 01230

Great Barrington, MA83 Hurlburt Rd

Price$2,200,000

Est. Mortgage: $/month

MLS Number 232860

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,868
  • Acreage 2.8

This meticulously renovated home on one of great barrington's most desirable roads is perfect for both a full-time home or weekends in the country. Traditional exterior but thoroughly moderized from top to bottom. Graciously sized rooms, high ceilings, large cook's kitchen, attention to every luxurious detail, this home has everything one needs for comfortable living. Three bedrooms, 2 1/2 baths. Separate apartment for staff or guests. Views in several directions.

Listed by Martha Piper of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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$2,100,000

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

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$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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2758 County Rte 9 East Chatham NY 12060

East Chatham, NY2758 County Rte 9 --

Price$1,895,000

Est. Mortgage: $/month

MLS Number 232743

  • Residential
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 3,290
  • Acreage 134

Historic concord farm. Set back and overlooking 134 acres of rolling fields, this classic 1840 greek revival farmhouse captures that luminous sense of place we call rural life.This authentically restored homestead features 3-4 bedrooms, 3 fireplaces, rocking chair front porch, 9 ft ceilings, large eat-in kitchen with charming kitchen garden, state of the art mechanicals and original hardwood floors.19th century post and beam barn adds additional 3,000 sf of finished space including a workshop/studio with radiant heat on 1st level. On the second level is a private three-room guest space, work-at-home office, or rental.Land suitable for organic farming, horses (4 bay horse barn), or cattle grazing (cattle + utility barns). Frontage on 2 roads for possible sub-division.

Listed by Nancy Cuddihy of STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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 February 27, 2021 . 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.