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 Lenox MA 01240

Lenox, MA319 Under Mountain Rd

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: 5.7% last updated on Jun 30, 2022
* 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 West Stockbridge MA 01266

West Stockbridge, MA14 Easland Rd

Price$5,500,000

Est. Mortgage: $/month

MLS Number 237939

  • Residential
  • Bathroom 11
  • Bedrooms 12
  • Square Feet 7,826
  • Acreage 94.93

Blueberry hill is an historic estate on 95+ acres with 4 houses to comfortably host a 3-generation family. From the high land settings where the main house, silo home, guest house, ''gazebo 2 bed cottage '' and developable building lots are sited, the views looking out over alford valley to mtn tom ball and everett are stunning. Walk the marked hiking trails through the blueberry fields to the highest peak or enjoy a game of tennis on your own court. Cool off with a swim in your pool. With only 5 miles to gt barrington and 8 miles to tanglewood, fine dining and music are minutes away. Note: the data herein pertains to one or all of the 4 houses as blueberry hill is being sold as an entirety.

Listed by Cindy Welch and Keith Ross of LANDVEST,INC.

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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: 5.7% last updated on Jun 30, 2022
* 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$4,450,000

Est. Mortgage: $/month

MLS Number 236486

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 6,000
  • Acreage 15.6

Enjoy all the berkshire seasons. Winter brings sledding, cross country skiing, access to downhill runs or enjoy the fire pit or get cozy by one of thefour fireplaces. Magnificent unspoiled views to the south and west create interest at all hours of the day and at sunset in particular. Thought to be one the first of the large 'cottages' on prospect hill. 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. Minutes from tanglewood . May be purchased without the building lot for 4,150,000.

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

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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: 5.7% last updated on Jun 30, 2022
* 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 Ancram NY 12502

Ancram, NY51 Hall Hill Rd

Price$3,900,000

Est. Mortgage: $/month

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

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$
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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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 01230

Egremont, MA46 Bow Wow Rd

Price$3,850,000

Est. Mortgage: $/month

MLS Number 236337

  • 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 Billy Keane of JAN PERRY REALTY & ASSOCIATES,LLC

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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 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

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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108 Interlaken Stockbridge MA 01262

Stockbridge, MA108 Interlaken Rd

Price$2,500,000

Est. Mortgage: $/month

MLS Number 236514

  • Residential
  • Square Feet 500
  • Acreage 1.34

279' of frontage on stockbridge bowl. A long groomed driveway leads to this large, gorgeous parcel of lakefront. Wide, stunning southeasterly views of the lake with mountains beyond. A boathouse at the waters edge, scarce for lakefront. A victorian cottage (no water or utilities) deemed historic. A rustic storage barn provides a footprint with potential. Septic fields in. Drilled well. Utilities easily accessible. Design plans for a 5,000+ square foot home with garage available. A rare opportunity to own a large parcel of land with frontage on deep lakefront on stockbridge bowl.

Listed by Tom Lynch of BERKSHIRE PROPERTY AGENTS,LLC

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$
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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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30 East Stockbridge MA 01262

Stockbridge, MA30 East St

Price$2,450,000

Est. Mortgage: $/month

MLS Number 237413

  • Residential
  • Bathroom 17
  • Bedrooms 16
  • Square Feet 9,337
  • Acreage 6.98

Move right in and take over this successful well established business in the heart of the berkshires. This beautiful property is complete with a heated in-ground pool, mature landscaping, and distant mountain views. The private location is perfectly situated between the picturesque towns of lenox, stockbridge and lee, close to tanglewood and many other berkshire attractions.This property would also be perfect for a large family compound.

Listed by Lauren Rosen and Lance Vermeulen of LANCE VERMEULEN RE,INC

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$
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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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185-0-183 Pine Otis MA 01253

Otis, MA185-0-183 Pine Rd

Price$2,100,000

Est. Mortgage: $/month

MLS Number 237749

  • Residential
  • Bathroom 3
  • Bedrooms 6
  • Square Feet 3,416
  • Acreage 1.49

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 a new roof,wrap around porch & big water views. 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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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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160 High Lee MA 01238

Lee, MA160 High St

Price$1,950,000

Est. Mortgage: $/month

MLS Number 236754

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 6,385
  • Acreage 0.71

This airy, architect-designed new construction in a sky high early 20th century structure with soaring ceilings, floating staircases and numerous high-end features inspires the imagination and lifts your spirits. Ideally situated on nearly 3/4 acre next to an 18-acre nature reserve, access the great downtown lee shops and restaurants, the mass pike, or tanglewood in a flash. Construction is nearly complete on the first space (4,000 sq. Ft., 5 baths, 4 br). The second space, with massive stained glass windows and 30 foot lofty ceilings is under construction and ready for your customization. Pictures shown include renditions and actual photographs. This property can be your dream home with flexibility for a massive work/studio space or second dwelling unit for additional rental income.

Listed by Jason Saphire of www.HomeZu.com

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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 2, 2022 . 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.