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: 6.94% last updated on Feb 29, 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.Www.802stateroad.Com

Listed by BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 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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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 of ELYSE HARNEY REAL ESTATE ((860) 435-0120)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 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: 6.94% last updated on Feb 29, 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)

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$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 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$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)

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$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 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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14 Easland Road West Stockbridge MA 01266

West Stockbridge, MA14 Easland Road

Price$2,995,000

Est. Mortgage: $/month

MLS Number 241188

  • Residential
  • Bathroom 8
  • 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 Vashti Poor and Lance Vermeulen of LANCE VERMEULEN RE,INC ((413) 528-6011)

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$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 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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775 Williamstown Road Lanesborough MA 01237

Lanesborough, MA775 Williamstown Road

Price$2,900,000

Est. Mortgage: $/month

MLS Number 235978

  • Residential
  • Bathroom 5
  • Bedrooms 11
  • Square Feet 5,878
  • Acreage 161

Historic berkshire farm gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns. 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, 6 bay carriage barn with second floor for offices, studios., or storage.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 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

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: 6.94% last updated on Feb 29, 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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638 Pitt Hall Road Old Chatham NY 12136

Old Chatham, NY638 Pitt Hall Road

Price$2,600,000

Est. Mortgage: $/month

MLS Number 242267

  • Residential
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 3,609
  • Acreage 168

A setting surrounded by classic columbia county views of rolling hills and bucolic farmland, smack in the middle of old chatham hunt country is the ideal location for this grand, turn of the century five bedroom farmhouse with a in-law suite, guest cottage, in-ground stone pool, pedigree three story barn, a studio outbuilding, and three car garage. A traditional layout prevails throughout with a gracious entrance complete with dutch door, stone flooring and a wood burning fireplace. The large, light filled country kitchen is the heart of the home with expansive views and doors leading to a deck and sublime stone patio, making it ideal for entertaining. The first floor is complete with three more fireplaces and many more rooms for dining, gathering, studying, reading and creating.

Listed by Jennifer Capala of WILLIAM PITT SOTHEBY'S - LENOX ((413) 637-4402)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 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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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: 6.94% last updated on Feb 29, 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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2480 Green River Road Williamstown MA 01267

Williamstown, MA2480 Green River Road

Price$1,900,000

Est. Mortgage: $/month

Pending

MLS Number 241006

  • Residential
  • Bathroom 2
  • Bedrooms 2
  • Square Feet 1,200
  • Acreage 244

Amazing opportunity to own 244 acres of rolling hills, open fields and farmland surrounded by one of the most picturesque views in the berkshires. The green river farm property is comprised of three parcels of land ; the first of which abuts mount hope farm with views of the taconic mountains. This 95 acre parcel is the heart of the property where you will find the farm store fully equipped, cider production facility, greenhouses, dairy barn, horse stable, and 2 bedroom renovated farmhouse. Extending northwest , crossing green river road, lies the second parcel containing 86 acres with 300 blueberry bushes and a 16 acre apple orchard. The third parcel is located across cold spring road (rte. 7) and contains 65 acres. Green river farm is located close to williams college,

Listed by Erin M. Scott of BURNHAM GOLD REAL ESTATE,LLC (kim@burnhamgold.com)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 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 March 4, 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.