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! 
319 Under Mountain Road Lenox MA 01240

Lenox, MA319 Under Mountain Road

Price$13,500,000

Est. Mortgage: $/month

MLS Number 237753

  • Residential
  • Bathroom 6
  • Bedrooms 7
  • Square Feet 13,261
  • Acreage 218.11

Pine needles built in 1903, this very private berkshire cottage epitomizes the area- past and present. Built in the arts and crafts style, surrounded by hundreds of acres of land, with magnificent southern views, one can enjoy nature, sports, and a relaxed lifestyle. Unspoiled, original detailing in place. Settle right in and be transported back to an earlier age. Paneled public rooms overlook the unspoiled views. Logias beckon to the out of doors. Seven bedrooms and 9 baths, two sleeping porches . The eat in kitchen offers space to gather, cook, enjoy the wildlife. This east wing also contains a butler's pantry, formal dining room, a summer dining room and one of the loggias.

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

$
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%
$/month over payments
Federal 30-year interest rate: 6.32% last updated on Mar 23, 2023
* 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 Street Lenox MA 01240

Lenox, MA2 Kemble Street

Price$5,840,000

Est. Mortgage: $/month

MLS Number 238388

  • Residential
  • Bathroom 14
  • Bedrooms 13
  • Square Feet 9,556
  • Acreage 3

The kemble, a registered ''great estate'' built in 1881 is located within walking distance to the wonderful array of shops and restaurants in downtown lenox. This classic colonial revival building has recently been refreshed with modern furnishings and decor, repurposed as a luxury estate, and is being offered as a turn key property. With grand gathering spaces, a well equipped kitchen, handsome mahogany bar, and 13 en-suite bedrooms, the property can easily accommodate parties and guests of 20+. Property qualifies as a ''great estate'' allowing for special uses in the residential district. When not using the property, enjoy the benefits of short/long term rental. Manicured lawns and gardens, stone walls, breathtaking views to the west, and fully ada compliant.

Listed by Lori J Rose and C. Randolph Thunfors of STONE HOUSE PROPERTIES,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.32% last updated on Mar 23, 2023
* 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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14 Easland Road West Stockbridge MA 01266

West Stockbridge, MA14 Easland Road

Price$4,850,000

Est. Mortgage: $/month

MLS Number 238758

  • Residential
  • Bathroom 8
  • Bedrooms 8
  • Square Feet 5,728
  • Acreage 94.93

Blueberry hill is an historic legacy property enjoyed by four generations and available for the first time since 1938, a secluded retreat yet proximate to popular berkshires attractions. Surrounded by 95 acres of land, its sprawling private footprint makes this estate a coveted berkshires gem. The compound includes four residences that offer space for family, friends, and support staff - a 5 bedroom, 4.5 bath gracious main house, a converted barn 3 bedroom, 3 bath guest house, a 3 bedroom, 2 bath caretakers house with multiple garages for both cars and equipment, and a destination 2 bedroom, 1 bath coveted guest house at the top of the pasture. There are facilities for outdoor activities like tennis, swimming, hiking, a greenhouse and more. (see supplement)

Listed by Timothy Lovett and Fintan T Hanley of BERKSHIRE PROPERTY AGENTS,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.32% last updated on Mar 23, 2023
* 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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775 Williamstown Road Lanesborough MA 01237

Lanesborough, MA775 Williamstown Road

Price$3,900,000

Est. Mortgage: $/month

MLS Number 235978

  • Residential
  • Bathroom 7
  • Bedrooms 12
  • Square Feet 5,878
  • Acreage 161

Terrific lifestyle opportunity. Gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns, and the berkshire's finest 9 hole golf course! 161 acres with stunning views, mountain paths, and jim kelly's stunning giant stonewalls throughout. Gorgeous new england marble stone farmhouse built in 1780, with modern addition featuring vaulted ceiling and massive windows which flood the dining and kitchen area with light. Enormous custom built hearth and fireplace, mahogany full bar, artisan-made bookcases, wrap-around deck. Close to williams college and jiminy peak. The property offers swimming in two private ponds, and potential helipad on site. 6 bay carriage barn with second floor for offices/studios. 184 adjacent acres also available.

Listed by Andy Kelly of Berkshire Business Properties

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$
%
$/month over payments
Federal 30-year interest rate: 6.32% last updated on Mar 23, 2023
* 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 Road Egremont MA 01230

Egremont, MA46 Bow Wow Road

Price$3,750,000

Est. Mortgage: $/month

MLS Number 239490

  • Residential
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 12,589
  • Acreage 41.14

Fully revitalized in 2021, the freeman, with its white washed brick exterior sits like an alsace-lorraine chateau atop an ecologically diverse 40 acres. This southern berkshire estate consists of the main house, a sprawling vineyard, manicured grounds, tennis court, and the picturesque harmon marsh pond. 2.5 hours from the george washington bridge, the freeman is just far enough away to embody the peace, tranquility and natural splendor that defines the berkshires lifestyle while being easily accessible from the north east's major metropolitan areas. For more information, visit www.46bowwowroad.Comassessed at over 12,000 sf, though floor scans are closer to 10,000

Listed by Heather Gallagher and Timothy Gallagher of JAN PERRY REALTY & ASSOCIATES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.32% last updated on Mar 23, 2023
* 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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410 Park Street Great Barrington MA 01236

Great Barrington, MA410 Park Street

Price$3,750,000

Est. Mortgage: $/month

MLS Number 239619

  • Residential
  • Bathroom 5
  • Bedrooms 2
  • Square Feet 13,350
  • Acreage 0.43

Stunning, one-of-a-kind modern and gorgeous historic mill building in the dynamic village of housatonic, ma. Utterly unique in the berkshires. Light-filled, three stories of stunning open space. First floor includes studio, recording studio, kitchen and bath with adjoining private, walled gardens at each side. 2nd floor comprises a large gallery space, living room, primary bedroom suite and guest bedroom with private bath. 3rd floor is fully open loft space. Finished basement. Central ac, all updates systems, commercial grade fire systems, residential or commercial use.

Listed by Selina Lamb of Birch Properties

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$
%
$/month over payments
Federal 30-year interest rate: 6.32% last updated on Mar 23, 2023
* 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 Hall Hill Road Ancram NY 12502

Ancram, NY51 Hall Hill Road

Price$3,500,000

Est. Mortgage: $/month

Pending

MLS Number 237667

  • Residential
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 2,380
  • Acreage 546.59

Make these 500+ acres of prized columbia county farmland the beginning of your next chapter. The possibilities are many given that the land is unencumbered by agricultural or conservation easements and provides an exciting mix of captivating views, fields, croplands, woodlands, ponds, barns both old and new, two farmsteads and even a stretch of the fabled roeliff jansen kill. With many desirable home sites and frontage on three country roads development opportunities abound. Located close to millerton, ancram, and pine plains which will offer you fine dining, shopping, entertainment, and access to a vast playground of outdoor activities. If you need access to a train, 30 minutes to both wassaic and hudson check that box.

Listed by Jennifer Capala of WILLIAM PITT SOTHEBY'S - LENOX

$
$
%
$/month over payments
Federal 30-year interest rate: 6.32% last updated on Mar 23, 2023
* 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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14 Easland Road West Stockbridge MA 01266

West Stockbridge, MA14 Easland Road

Price$3,500,000

Est. Mortgage: $/month

MLS Number 239057

  • Residential
  • Bathroom 8
  • Bedrooms 8
  • Square Feet 5,728
  • Acreage 63.23

Blueberry hill is an historic legacy property enjoyed by four generations and available for the first time since 1938, a secluded retreat yet proximate to popular berkshires attractions. Surrounded by 63 acres of land, its sprawling private footprint makes this estate a coveted berkshires gem. The compound includes three residences that offer space for family, friends, and support staff - a five bedroom, four and a half bath gracious main house, a converted barn-style three bedroom, three bath guest house, and a three bedroom, two bath caretakers house with multiple garage bays for both cars and equipment. There are facilities for outdoor activities such as tennis, swimming, hiking, fishing and a greenhouse. A newer solar array services the property. Spectrum internet and cell service.

Listed by Timothy Lovett and Fintan T Hanley of BERKSHIRE PROPERTY AGENTS,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.32% last updated on Mar 23, 2023
* 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 Street Lenox MA 01240

Lenox, MA135 Main Street

Price$2,750,000

Est. Mortgage: $/month

MLS Number 237252

  • Residential
  • Bathroom 17
  • Bedrooms 16
  • Square Feet 8,688
  • 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: 6.32% last updated on Mar 23, 2023
* 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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739 Center Hill Road Copake NY 12516

Copake, NY739 Center Hill Road

Price$2,495,000

Est. Mortgage: $/month

MLS Number 239582

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,499
  • Acreage 24.56

The farm on center hill awaits. Located in the southeast corner of columbia county, it is thoughtfully curated & turnkey. 1850s greek revival farmhouse immaculately restored and meticulously maintained. 3 bedrooms. 2.5 baths. Extensive cutting gardens. Vineyard. Pastures for goats, sheep, ducks, pigs, and chickens. Multiple barns and sheds throughout. Guest house. In-ground, heated pool with adjacent firepit. Large pond. 24.56 fully-fenced acres. Stroll to the high pasture for stunning views down the oblong valley and of the taconic range.

Listed by Scot Cohen of SCOT COHEN REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 6.32% last updated on Mar 23, 2023
* 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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600 Bee Hill Road Williamstown MA 01267

Williamstown, MA600 Bee Hill Road

Price$2,300,000

Est. Mortgage: $/month

MLS Number 238282

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 5,774
  • Acreage 15.83

Offered for the first time ever, high mowing, is a magical williamstown estate spread over fifteen glorious acres, and nestled in the hills less than 5 minutes from williams college. This exquisitely welcoming home is different from any other property in the berkshires, and it seamlessly integrates beautiful nature and sophisticated culture in an incomparable and eclectic way. The property has been meticulously developed with an artist's eye and a craftsman's hand to blend perfectly with its environment, complementing the colors and textures of surrounding fields, woods, and mountains, exposed under the huge open sky of day and starry nights.

Listed by Carrie Lobovits Wright of JAN PERRY REALTY & ASSOCIATES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.32% last updated on Mar 23, 2023
* 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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13 Cliffwood Street Lenox MA 01240

Lenox, MA13 Cliffwood Street

Price$1,999,900

Est. Mortgage: $/month

MLS Number 239233

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,396
  • Acreage 0.51

In town lenox historical treasure the worthington house circa 1815. Live in one of lenox's most sought after neighborhoods on cliffwood street. Exceptional location is steps to lenox art, shopping and dining district as well as a walk to kennedy park hiking. Just minutes to tanglewood for the ideal berkshire setting. Incredible private retreat is created with mature landscaping surrounding the expansive rear yard and wrap around porch and rear mahogany deck. Experience the charm and history in the federal simple style antique kitchen, den and first of three fireplaces. Enter into formal living and dining fireplaced rooms with bold and vibrant colors. Floor to ceiling original windows fill the room with natural sunlight. Dr wothingtons heir bequest house to the church on the hill.

Listed by Tonia L. Scalise of WILLIAM PITT SOTHEBY'S - LENOX

$
$
%
$/month over payments
Federal 30-year interest rate: 6.32% last updated on Mar 23, 2023
* 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 April 1, 2023 . 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.