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! 
11 Hawthorne Street Stockbridge MA 01262

Stockbridge, MA11 Hawthorne Street

Price$15,000,000

Est. Mortgage: $/month

MLS Number 243138

  • Residential
  • Bathroom 23
  • Bedrooms 19
  • Square Feet 22,000
  • Acreage 21

Wheatleigh is the perfect marriage of the grandeur of a 16th century florentine palazzo and the comfort and elegance of the twenty first century. Imagine living in desirable lenox on 22 acres overlooking stockbridge bowl and the mountains and being within a short stroll to tanglewood! Henry cook in 1893 commissioned peabody and sterns to construct this italianate style home. It has since been updated by famed architects tsao and mckown for contemporary living. The 19 suites, guest rooms and baths set a new standard of style and sophistication and can accommodate many friends, business guests and family. Each of the bedrooms have high speed internet and bang and olufsen tv's . The state of the art fitness center, heated pool, and tennis court keep every one active.

Listed by Cindy Welch of LANDVEST,INC. ((978) 544-5767)

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$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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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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 ((413) 528-4192)

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$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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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764 East Hill Road New Marlborough MA 01259

New Marlborough, MA764 East Hill Road

Price$6,390,000

Est. Mortgage: $/month

MLS Number 243869

  • Residential
  • Bathroom 13
  • Bedrooms 14
  • Square Feet 11,670
  • Acreage 232

On the crest of woodruff mountain, moments from the southfield store, york lake, and area amenities, a classic country estate awaits. Its centerpiece is a stately 5br, 5000sf, c. 1798, georgian-federal home, set on a 232-acre property encompassing a 3,550sf historic barn, smaller barns & run-ins, gardens & green house, gunite pool & pool house, tennis court, fields, pastures, stream, mile-long trail abutting sandisfield state forest, and 5-acre spring-fed pond, all arranged for maximum livability and delight. You'll be pleased with the elevator, generator, & other mod cons, and charmed by historic details, stunning vistas, & untrammeled view of the star-studded night sky. Not enough? A 6,000sf guest house with four apartments suggests myriad uses for guests or income. Perfectly beautiful.

Listed by Gladys Montgomery of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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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18 Main Street Stockbridge MA 01262

Stockbridge, MA18 Main Street

Price$6,200,000

Est. Mortgage: $/month

MLS Number 243879

  • Residential
  • Bathroom 15
  • Bedrooms 11
  • Square Feet 13,426
  • Acreage 2.7

Houses like this do not come along often! Two magnificent houses on 2.7 acres of serenity. The 17 room mansion boasts victorian architecture with modern luxuries. Named the taggart house, this property has hosted celebrities and guests for many years. Almost 9000 square feet including a ballroom! Continue operating the business or live in it as your dream home. The rear guest house is a 4,500 square foot modern post and beam farmhouse built in 2006 with many beautiful recent renovations. Kayak from your private beach on the housatonic river, stroll into town and all that stockbridge has to offer.

Listed by Dina B Browne of NEPONSET VALLEY REAL ESTATE,INC. ((508) 561-4448)

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$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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 Sheffield Road Egremont MA 01230

Egremont, MA25 Sheffield Road

Price$5,900,000

Est. Mortgage: $/month

MLS Number 243036

  • Residential
  • Bathroom 6
  • Bedrooms 6
  • Square Feet 5,468
  • Acreage 67

Listed by Elyse Harney Morris and Lauren A. Molk of ELYSE HARNEY REAL ESTATE ((860) 435-0120)

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%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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$5,485,000

Est. Mortgage: $/month

MLS Number 242956

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

The kemble, a registered ''great estate'' built in 1881 is located in the heart of the thriving downtown lenox business district. This classic colonial revival building has recently been refreshed with modern furnishings and decor, repurposed as a luxury rental property, and is being offered as a turn key operation. With grand gathering spaces, a well equipped kitchen, handsome mahogany bar, and 13 en-suite bedrooms, the property can easily accommodate groups of 20+ and is frequently rented to wedding parties, corporate retreat groups, and multi-generational family retreats. Stays can vary from a weekend to month or longer. Guests can choose to bring in cooks, bartenders, and waitstaff, if desired. Manicured lawns and gardens. Breathtaking views to the west. Fully ada compliant.

Listed by Cameron Volastro and Lori J Rose of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

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$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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 State Road Richmond MA 01254

Richmond, MA802 State Road

Price$4,850,000

Est. Mortgage: $/month

MLS Number 242497

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

A stunning compound located in the picturesque new england town of richmond. A one-of-a-kind combination of a legendary and historic c1776 home integrated with the berkshires premiere full-service equestrian facility, including indoor and outdoor rings. This compound has rich history. With 27 pastoral acres views are abundant. The home offers 7 bedrooms, 7.5 baths, three cottages, a gorgeous barn for events, 5 paddocks, 6000 square foot heated arena with an owners luxury apartment and viewing area, an outdoor arena, a jump field, 3 barns with 26 stalls, 2 tack rooms. Equidistant from new york city and boston, easy access to international airports or take advantage of private flights from the pittsfield airport.

Listed by BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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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19 Mill Road Egremont MA 01230

Egremont, MA19 Mill Road

Price$4,250,000

Est. Mortgage: $/month

MLS Number 242023

  • Residential
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 3,940
  • Acreage 59.6

''roll away hill'', a rare berkshire oasis! Waterfront on prospect lake, an incredible property and one of a kind. With over 500' of waterfront on 59 acres, this property boasts scenic lake & mountain views. Trails meander past stone walls and through the trees to the water's edge. Relax on the expansive front porch. A lodge like home with rooms of considerable size, offering casual comfort for daily living, entertaining and summer fun. Nestled up a private drive, there is total seclusion where you can immerse yourself in the natural surroundings. Five bedrooms, 4.5 baths, two fireplaces. The charm of yesteryear remains intact. Enjoy berkshire living at its finest in this truly magnificent setting. So much potential!

Listed by Helen Mullany of HELEN MULLANY REAL ESTATE,LLC ((413) 429-7733)

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$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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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185 Keyes Hill Road New Marlborough MA 01230

New Marlborough, MA185 Keyes Hill Road

Price$3,785,000

Est. Mortgage: $/month

MLS Number 242397

  • Residential
  • Bathroom 3
  • Bedrooms 7
  • Square Feet 4,386
  • Acreage 249

Blue hill farm: an 1820 center hall colonial farm and farmhouse in excellent condition on 249 high acres with organic hay meadows and pastureland, an apple orchard, woodlands, gardens, tennis court, a 1970's caretaker/farmer's house and multiple barns. The main house has 6/7 bedrooms and three baths, along with a three-car attached garage. The property consists of seven parcels of contiguous land surrounded by the umpachene river on three sides. There are long views to the west of the taconic range from inside and outside of the home, and a grouping of supportive barns to the south across a very rarely traveled, narrow dirt road. Offered for the first time since 1967, this is truly an unusual and rare offering with development possibilities featuring extraordinary views.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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$3,485,000

Est. Mortgage: $/month

MLS Number 242971

  • Residential
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 12,589
  • Acreage 57.71

In 2021, the freeman was transformed utilizing high-quality materials from an aging nineteenth-century estate to a clean and modern getaway and top-performing rental property. The main house, renovated to be 100% carbon-neutral, features six fireplaces, two dining rooms, a library, 1500sqft bluestone deck and more. The freeman sits atop 40 acres of greenery to explore, containing a tennis court, four-acre vineyard, mountain views and a dock to access harman marsh pond. Individuals, wedding parties, and corporate retreats alike have come to the freeman to enjoy its secluded feel while being close to key berkshire attractions like catamount ski area, bash bish falls, and downtown great barrington. This property is just over 100 miles from both boston and new york city.

Listed by Cameron Volastro and Lori J Rose of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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$2,750,000

Est. Mortgage: $/month

MLS Number 239619

  • Residential
  • Bathroom 3
  • Bedrooms 2
  • Square Feet 13,350
  • Acreage 0.43

Now under $3m! Calling all creative minds - artists, musicians, recording artists, producers, makers, and lovers of historic mill building restorations! Stunning, one-of-a-kind, modern and historic mill building in the dynamic village of housatonic, ma is the place for you to make art | make music | live life in the heart of the berkshires. Seize the moment to make this extraordinary property yours! Utterly unique in the berkshires. Light-filled, three stories of open space. 1st flr includes studio, recording studio, kitchen and bath w adjoining private, walled gardens at each side. 2nd flr comprises gallery space, living room, primary bedroom suite and guest bedroom with private bath. 3rd flr is fully open loft space. Finished basement. Central ac. Residential and comm possible.

Listed by Selina Lamb of BIRCH PROPERTIES ((415) 515-3750)

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$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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$2,600,000

Est. Mortgage: $/month

Pending

MLS Number 237252

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

The garden gables inn is ideally located in the center of lenox on over 4+ private park-like acres with gardens, patios, mature trees and a heated 70' pool. Beautifully furnished and tastefully decorated, the inn consists of 15 unique rooms all with updated private baths, several with fireplaces and all fully air conditioned. The historic 1780 main building and attached cottage includes 9 guest rooms and 2 spacious suites. The separate orchard cottage includes 4 ensuite rooms with separate entrances, cathedral ceilings and fireplaces. There are 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 well equipped with updated appliances and adjoins the private innkeeper's quarters.

Listed by C. Randolph Thunfors and Katie Soules of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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 July 21, 2024 . 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.