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 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: 2.78% last updated on Jul 22, 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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399 Under Mountain Lenox MA 01240

Lenox, MA399 Under Mountain Rd

Price$4,935,000

Est. Mortgage: $/month

MLS Number 233680

  • Residential
  • Bathroom 7
  • Bedrooms 8
  • Square Feet 9,364
  • Acreage 11.45

Highwick farm manor house is nearing its 3 year restoration/renovation in time for the summer of 2021. Meticulously preserving and restoring the magnificent original details of this berkshire cottage from the infrastructure to the doorknobs, while renovating it with only the finest of materials for the sought after amenities of a modern lifestyle today, makes this distinctive lenox home shine in its original grandeur, designed to be luxurious yet cozy and unpretentious. Generously proportioned rooms with walls of windows flooding the house with natural light and taking in the view, with open flow from room to room and the spectacular kitchen/family room not often seen in homes of this era. Perched high above the country road taking in the sweeping southern vista of parsons marsh and

Listed by Mary Jane White and Brandon White of COHEN & WHITE ASSOCIATES

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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17 Prospect Hill Stockbridge MA 01262

Stockbridge, MA17 Prospect Hill Rd

Price$4,850,000

Est. Mortgage: $/month

MLS Number 234293

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 6,000
  • Acreage 15

The property, anchored by a 200 year old copper beech, runs along the crest of prospect hill. Magnificent unspoiled views to the south and west create interest at all hours of the day and at sunset in particular.Rumored to have been the first of the large 'cottages' on prospect hill. A cornerstone dated 1823 still exists although the house has undergone numerous renovations. A three sided glass porch overlooks the walled sunken garden. Three floors of living spaces with almost every room open to the views. Beautiful detailing with marble fireplaces and antique woodwork. Four bedroom and four and a half baths. A large game room with full bath occupies the third floor. There is a gunite pool. Several building lots with more land available.

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

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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20 Jug End Egremont MA 01258

Egremont, MA20 Jug End Rd

Price$4,400,000

Est. Mortgage: $/month

MLS Number 234456

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 3,240
  • Acreage 230

Gracious and stately new england colonial farmhouse on 230 acres.Antique barns and outbuildings, pool with amazing views. A babbling brook runs near the house and into a small pond bringing sound and nature into view. This comfortable home has had numerous additions through the years making it even more appealing to today's living. First floor primary bedroom with double baths. Screened porch overlooking the brook. Flagstone patio. Woodland party cabin reached by a passable 'road' up the mountain. Beautiful views from the house and the possibility of huge views from mountain sites.Blooming shrubs abound throughout the gardens. Maples for sugaring in the woods. Lots of frontage for anyone interested in division. A really magical property that has it all.

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

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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 233840

  • 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: 2.78% last updated on Jul 22, 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 State Richmond MA 01254

Richmond, MA802 State Rd

Price$2,500,000

Est. Mortgage: $/month

MLS Number 233555

  • Residential
  • Bathroom 8
  • Bedrooms 7
  • Square Feet 4,000
  • Acreage 10

Options abound for a lifestyle change at what is now known as the inn at richmond this magnificent property includes a historic colonial era 7 bedroom inn, 3 cottages, and party barn, on 10 pastoral acres. With its casual elegance and charm, this colonial estate will allow your long held passion to blossom whether you use the property as a stunning family compound, or as an event destination. The prime, central berkshire county location will graciously support your new found lifestyle. Two hours from boston, 2.75 form nyc, and easy access from just about anywhere with a municipal airport 5 min away. 15 min to tanglewood and lenox. Be a part of the berkshire renaissance by establishing yourself in the stunning rural landscape of richmond, ma. And enjoy all that this region has to offer.

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

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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22 Cliffwood Lenox MA 01240

Lenox, MA22 Cliffwood St

Price$2,200,000

Est. Mortgage: $/month

Pending

MLS Number 234245

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,472
  • Acreage 0.35

This stunning shingle style victorian with the prominent carriage house create a luxurious in-town residence and display exceptional standards of architecture and craftsmanship. With an outstanding floor plan and attention to details restored, this comfortable property is turnkey in every detail. The main house offers a gourmet kitchen, 3-4 bedrooms, multiple balconies, and central a/c. The carriage house is comprised of a 2 bedroom apartment with great cook's type of kitchen, central a/c and a lovely courtyard patio and would keep any guest delighted. The remaining area is being used as an artist studio and offers a wonderful place for creativity. The grounds and landscaping are lush and offer a casual elegance for berkshire living. Minutes to hiking, dining, and tanglewood.

Listed by Lori J Rose of STONE HOUSE PROPERTIES, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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684 Egremont Great Barrington MA 01230

Great Barrington, MA684 Egremont Rd

Price$1,995,000

Est. Mortgage: $/month

MLS Number 233793

  • Residential
  • Bathroom 20
  • Bedrooms 19
  • Square Feet 17,551
  • Acreage 10.43

The beautiful & historic windflower inn, is a terrific business or lifestyle opportunity. Built in 1850 & meticulously maintained, this rambling colonial with 13 en-suite guest rooms, several with in-room fireplaces, is a top-rated property on trip advisor. The first floor consists of two living rooms & a dining room - all with large fireplaces. The ground-floor accommodations also feature private access to a beautiful wrap-around porch. The screened porch overlooks a small pond & gardens. The 10+ acres includes four perennial gardens, mature blooming trees, & firepit, & meanders to celebrated ''trolly trail'' for walks, cross-country skiing & snowshoeing. A fabulous chicken coop provides fresh eggs for guests. Restaurant kitchen includes a double garland commercial stove, commercial

Listed by Cara Carroll of LANCE VERMEULEN RE, INC

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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$1,985,000

Est. Mortgage: $/month

MLS Number 232860

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,206
  • 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

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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0,183 &185 Pine Otis MA 01253

Otis, MA0,183 &185 Pine Rd

Price$1,750,000

Est. Mortgage: $/month

MLS Number 233964

  • Residential
  • Bathroom 3
  • Bedrooms 6
  • Square Feet 3,416
  • Acreage 1.4

Welcome to the berkshires & otis reservoir -the largest recreational lake in ma at 1085 acres.This listing is all about the land,the location & 150 ft of beautiful waterfront.The property consists of 3 parcels making up a unique, conforming 1.39 acre compound,with 4 well maintained docks, lakeside patio,2 homes and additional lot.Right on the lake is a 4 bedroom seasonal cottage with an indoor wrap-around porch & water views galore.Build your dream home or use as is for a summer of family fun.The 2nd waterfront has a small, quaint,4 season home.A large front deck offers quieter,private lake views.Great for guests,winter getaways or summer rentals.The 3rd parcel is a .47acre lot with potential use as a garage or guest house site. Please enjoy the aerial photos to get a sense of the property

Listed by Kim Bergland of RED HORSE REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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 July 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.