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 ((413) 528-4192)

$
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%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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$5,485,000

Est. Mortgage: $/month

MLS Number 241190

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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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700 Cooper Hill Road Sheffield MA 01257

Sheffield, MA700 Cooper Hill Road

Price$4,499,000

Est. Mortgage: $/month

Pending

MLS Number 240775

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 2,452
  • Acreage 233

Discover an exceptional estate with a recently renovated farmhouse, two expansive barns, and 233 acres of magnificent land. The farmhouse features four spacious bedrooms, four and a half bathrooms, and breathtaking western views. Immerse yourself in the tranquility of this tastefully updated residence. The versatile barns, spanning 16,000 square feet, offer endless possibilities for parties, equestrian pursuits, artistry, or storage. The surrounding acreage showcases lush fields for farming and multiple world-class building sites, allowing you to create your dream home with stunning vistas. Enjoy the convenience of nearby attractions in salisbury, ct, and great barrington, ma, while relishing the serenity of bartholomew's cobble.

Listed by William Melnick and Elyse Harney of ELYSE HARNEY REAL ESTATE ((860) 435-0120)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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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2650 Swamp Road Richmond MA 01254

Richmond, MA2650 Swamp Road

Price$3,985,000

Est. Mortgage: $/month

MLS Number 240523

  • Residential
  • Bathroom 7
  • Bedrooms 5
  • Square Feet 6,022
  • Acreage 5.65

A simply splendid berkshire country estate. April hill, an 1850 greek revival, is the epitome of symmetry, simplicity and elegance, fostering comfortable country living. A classic beauty meticulously restored and upgraded to the highest standard. The compound is comprised of the main house, guest cottage, potting shed/studio and barn. Spectacular views, stone walls, spring fed pond, a heated salt water pool, beautiful manicured lawn and grounds. Rock wool insulation. For full list of amenities and details please see supplement.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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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185 Keyes Hill Road New Marlborough MA 01230

New Marlborough, MA185 Keyes Hill Road

Price$3,785,000

Est. Mortgage: $/month

MLS Number 240472

  • 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 and Fintan T Hanley of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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$3,650,000

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 ((415) 515-3750)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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$3,485,000

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. With an extensive and lucrative rental history, 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 ((413) 442-5550)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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$2,995,000

Est. Mortgage: $/month

MLS Number 241188

  • Residential
  • Bedrooms 8
  • Square Feet 6,255
  • Acreage 32

Welcome to blueberry hill, a generational family estate, nestled in the picturesque berkshire hills. This remarkable property offers an unparalleled combination of luxury, elegance, and natural beauty spread across more than 30 acres. As you step onto this breathtaking estate, you will be captivated by the stunning south-easterly views that stretch as far as the eye can see. The centerpiece is the charming main house, a true masterpiece spanning 3,900+ square feet. With its timeless architecture and superb craftsmanship, this residence is an embodiment of refined living. The main house boasts four fireplaces and comprises five lavishly appointed bedrooms, with three of them being en-suite to ensure privacy and comfort for all family members and guests.

Listed by Antonio M Segalla and Lance Vermeulen of LANCE VERMEULEN RE,INC ((413) 528-6011)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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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1-1a George Canon Road Tyringham MA 01264

Tyringham, MA1-1a George Canon Road

Price$2,950,000

Est. Mortgage: $/month

MLS Number 241140

  • Residential
  • Bathroom 4
  • Bedrooms 8
  • Square Feet 4,952
  • Acreage 150

Four brooks farm, a 150 acre estate offering, owned by the de kay gilder palmer family since 1898, is now available. This exceptional property embodies idyllic country living in the heart of the berkshires. Highlights include the main house, guest house, barns with tack room, roman walled garden with sunrise/sunset window, stonewalls, pastures, trails & views . Ready for restoration to former glory, many recent improvements have been completed. Comprised of five lots, portions of the property may be sold separately, but are in an apr. Rolling meadows, gardens, stone walls and views! Rich in history, with so much potential to be a cherished berkshire retreat. Close proximity to notable area cultural attractions . Reportedly visited by notables such as mark twain and grover cleveland.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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$2,900,000

Est. Mortgage: $/month

MLS Number 235978

  • Residential
  • Bathroom 7
  • Bedrooms 11
  • 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. The property was formerly a horse farm

Listed by Andy Kelly of BERKSHIRE BUSINESS PROPERTIES ((413) 281-2784)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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$2,600,000

Est. Mortgage: $/month

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: 7.31% last updated on Sep 28, 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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15 Franklin Street Lenox MA 01240

Lenox, MA15 Franklin Street

Price$2,450,000

Est. Mortgage: $/month

MLS Number 241012

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 4,424
  • Acreage 0.1

A unique opportunity to own two amazing residential units affording 2 bedrooms and full bath each with gourmet kitchens and soaring vaulted ceilings in walking distance to all things central to lenox. Just 2 miles from tanglewood, rentals would be the obvious choice in an already difficult rental market, or take advantage of an owner/operator dream living and working at the same location with an iconic, upscale italian steakhouse below you. Mixed use and turnkey ready to go, the current family owners are retiring after 35 years and are ready for a new start. Its location is in the robust central part of lenox with an extremely large outdoor dining patio and walking distance to most shopping attractions. 3 hours to nyc, 2.5 hours to boston; 30-60 minutes to most berkshire attractions!

Listed by Jeffrey M. Loholdt of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

Based on information submitted to BCMLS  as of September 30, 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.