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: 3.05% last updated on Oct 14, 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: 3.05% last updated on Oct 14, 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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775 Williamstown Lanesborough MA 01237

Lanesborough, MA775 Williamstown Rd

Price$4,900,000

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: 3.05% last updated on Oct 14, 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$4,750,000

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 wraparound 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. Golf tee/driving area. Several building lots totaling 15 acres plus an additional garage.

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

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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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: 3.05% last updated on Oct 14, 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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615 Laurel Lee MA 01238

Lee, MA615 Laurel St

Price$3,975,000

Est. Mortgage: $/month

MLS Number 235976

  • Residential
  • Bathroom 18
  • Bedrooms 17
  • Square Feet 7,937
  • Acreage 2

This historic landmark property, which is now known as the lakehouse inn, is situated on a cliff with panoramic views of laurel lake and its famous sunsets. Set on two well-manicured acres with over 500 ft of waterfront, this magnificent property has many outdoor gathering areas, gardens, rock walls, bluestone patios & pathways, outdoor gas fire pit, and a dock area with direct access to the water, perfect for swimming and boating. The property underwent a complete renovation in 2015 with respect for preserving its historic character with period details restored throughout and modernized for today's buyer. With completely new wiring & plumbing; mahogany porch and second floor balcony; commercial kitchen; mini split a/c units in every room; radiant heat throughout the first floor; new

Listed by Maggie Gavin and Cody Gavin of WILLIAM PITT SOTHEBY'S - LENOX

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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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 235967

  • 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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$
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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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: 3.05% last updated on Oct 14, 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$1,895,000

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: 3.05% last updated on Oct 14, 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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8 Prospect Hill Stockbridge MA 01262

Stockbridge, MA8 Prospect Hill Rd

Price$1,865,000

Est. Mortgage: $/month

MLS Number 235913

  • Residential
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 5,765
  • Acreage 1.97

In 1737 ephraim williams chose a special setting on prospect hill to build his home. Through many iterations, windermere has become an exceptional home. Beautiful porches wrap around two sides. The interior is bathed in natural light. The first floor is graced by an entry parlor, living room and fabulous music room. Great updated kitchen has an exceptional butler's pantry and breakfast room. Beautiful formal dining room. 5+ bedrooms, 4 full baths, 2 half-baths. Guest/au pair wing with separate stairs. Central ac. Attached 2 car garage. Gorgeous grounds with specimen trees, gunite swimming pool and patio. Just a mile's walk to main street stockbridge and 2.5 miles to the town beach and under 5 miles to tanglewood.

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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$1,730,000

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

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$
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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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1001 Canaan Southfield New Marlborough MA 01259

MLS Number 216149

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,389
  • Acreage 23.25

The house and landscaping for this home have been lovingly and meticulously restored by the same family for over 30 years. Land is owned on 2 sides of the road with the umpachene river runs through the property. There are 2 ponds with extensive landscaping and one with field-stone steps leading to patio area with fire-pit fountains waterfall. The outside creates a spa like feel with the sound of water.

Listed by BERKSHIRE HATHAWAY HOMESERVICESBARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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 October 17, 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.