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 244657

  • 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: 6.89% last updated on Feb 6, 2025
* 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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25 Sheffield Road Egremont MA 01230

Egremont, MA25 Sheffield Road

Price$5,900,000

Est. Mortgage: $/month

MLS Number 243036

  • Residential
  • Bathroom 10
  • Bedrooms 11
  • Square Feet 9,748
  • Acreage 67

Tullar farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of south egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of future for generations to come. Set on 67 +/- park-like acres this property offers 3 unique residences, a mature specimen tree farm, a spring-fed pond, wooded walking trails, and captivating views of the distant mountains all just a stone's throw away to restaurants and shops. At the heart of the estate stands the tullar house; a well-preserved and substantial 6-bedroom 5,000+ sq ft antique dutch gambrel dating back t

Listed by Elyse Harney Morris and Lauren A. Molk of ELYSE HARNEY REAL ESTATE

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$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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 Compass Massachusetts,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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 01258

Egremont, MA19 Mill Road

Price$3,575,000

Est. Mortgage: $/month

MLS Number 244751

  • Residential
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 3,940
  • Acreage 59.6

Escape to your own lakefront sanctuary in the berkshires nestled in the heart of the picturesque berkshires, this enchanting lakefront property offers a rare opportunity to create your dream retreat. With over 500 feet of private waterfront, this expansive estate is a haven for those seeking tranquility and natural beauty. Situated on a sprawling parcel of land, this property is perfectly positioned to offer breathtaking views and serene surroundings. The berkshires are renowned for their stunning landscapes, vibrant cultural scene, and outdoor recreational activities. Expansive living space:** the 4,000-square-foot home features five spacious bedrooms and six bathrooms, providing ample space for family and friends.

Listed by Suzann Laverack Ward and LJ Stark of HOUSATONIC REAL ESTATE

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$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

Pending

MLS Number 242971

  • Residential
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 12,589
  • Acreage 57.71

In 2021, the freeman was transformed utilizing high-quality materials from an aging nineteenth-century estate to a clean and modern getaway and top-performing rental property. The main house, renovated to be 100% carbon-neutral, features six fireplaces, two dining rooms, a library, 1500sqft bluestone deck and more. The freeman sits atop 57 acres of greenery to explore, containing a tennis court, four-acre vineyard, mountain views and a dock to access harman marsh pond. Individuals, wedding parties, and corporate retreats alike have come to the freeman to enjoy its secluded feel while being close to key berkshire attractions like catamount ski area, bash bish falls, and downtown great barrington. This property is just over 100 miles from both boston and new york city.

Listed by Cameron Volastro and Lori J Rose of STONE HOUSE PROPERTIES,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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$3,400,000

Est. Mortgage: $/month

MLS Number 245461

  • Residential
  • Bathroom 8
  • Bedrooms 7
  • Square Feet 4,000
  • Acreage 27.3

Nestled in the heart of the berkshires, this historic richmond compound presents a rare blend of colonial charm and modern equestrian excellence. Spanning 27 bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence, three enchanting cottages, and the region's premier full-service equestrian facility.The main residence, a testament to time-honored craftsmanship, features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. The inn's dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that cater to both intimate family gatherings and grand celebrations. Equestrian enthusiasts will revel in the compound's state-of-the-art amenities

Listed by Diana Bisselle and Leslie G Chesloff of WILLIAM PITT SOTHEBY'S - SALISBURY

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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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349 Old Stockbridge Road Lenox MA 01240

Lenox, MA349 Old Stockbridge Road

Price$3,100,000

Est. Mortgage: $/month

MLS Number 245369

  • Residential
  • Bathroom 30
  • Bedrooms 32
  • Square Feet 38,415
  • Acreage 11.9

A rare, once in a lifetime opportunity to own an original berkshire cottage! This spectacular property is situated on a 12-acre campus in lenox, overleigh was built in 1903 by samuel frothingham. Its history is detailed in the popular coffee table book ''the berkshire cottages-a vanishing era'', by carole owens. This property is located just 1.8 mi. From downtown lenox and within minutes to the most popular berkshire attractions. Designed by adams and warren out of nyc and built by joseph clifford's sons, a firm responsible for several cottage era constructions and renovations in berkshire county. A rare find, this property has deep roots in being used as an academic setting for several diverse private residential schools and has been well maintained throughout the years.

Listed by Timothy Gallagher of STONE HOUSE PROPERTIES,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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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3 Berkshire Heights Road Great Barrington MA 01230
Pending

MLS Number 243313

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,478
  • Acreage 1.4

Built in 1904 this historic home sits on a beautiful 1.4-acre lot, which offers privacy while being in the most coveted and accessible neighborhood of great barrington. High ceilings and adorned with oak and mahogany woodwork throughout, this home has been tastefully renovated while retaining its period charm. The spacious layout, with 4 bedrooms, 31/2 bathrooms and an expansive porch provide comfort and grace. A fully updated kitchen, new windows, central air and natural gas enhance the living experience with modern ease. The surrounding landscape is adorned with perennial beds, and mature specimen trees. Walkable to town's restaurants, shops and farmers market, this property offers laid-back charm along with convenience and style.

Listed by Martin Albert of Compass Massachusetts,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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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147 New Hartford Road Sandisfield MA 01255

Sandisfield, MA147 New Hartford Road

Price$2,200,000

Est. Mortgage: $/month

Pending

MLS Number 244634

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,547
  • Acreage 23

This quintessential country property is what everyone wants. Located in the southern berkshires close to the towns of great barrington, new marlborough and southfield and norfolk, ct. This sleek historic and beautifully restored home is conveniently located for skiing, hiking, arts and culture, restaurants and all other berkshire offerings. This home is beautifully restored and includes a stunning 'party ' barn, and separate garage/storage shed. The house glows, filled with light and sun. A large living room with fireplace and several seating areas has views to fields and flowers. A cook's kitchen with a counter-height fireplace looks out onto a stone patio with fire pit. The library, tv/ media room and powder room complete the 1st floor.Four.Bedrooms, 2.5 baths. Restored barn.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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$1,980,000

Est. Mortgage: $/month

MLS Number 235978

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

Historic berkshire farm best bargain in the berkshires! Gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns and maintenance building. 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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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 East Street Stockbridge MA 01262

Stockbridge, MA17 East Street

Price$1,925,000

Est. Mortgage: $/month

MLS Number 244472

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 5,469
  • Acreage 13.1

Nestled just north of stockbridge, ma, this elegantly expanded brick federal estate offers a harmonious blend of historic charm and modern design on 13+/- acres (9 conserved.) originally built in the 1830s, the carter estate has been artfully expanded and renovated and boasts over 5,400sf of light-filled, luxurious living space, ideal for those seeking a private yet gracious lifestyle.As you enter through classic stone walls and manicured hedgerows, you'll be welcomed by sweeping meadows and lush gardens. Time slows as you meander along stone pathways that lead to a charming red barn and a quaint stone summer cottage--perfect for painting or relaxing. The estate is oriented towards cultural and natural beauty with walking trails

Listed by Selina Lamb of BIRCH PROPERTIES

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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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1277 Hartsville Mill River Road New Marlborough MA 01230
Pending

MLS Number 244225

  • Residential
  • Bathroom 5
  • Bedrooms 7
  • Square Feet 5,052
  • Acreage 2.9

1790 colonial restored for 2024 living. Located on the well loved konkapot river and on a quiet country road this home has been completely revamped to today's standards. Large recently expanded living room with fireplace, plus large windows to views of beartown mountain. First floor primary suite with private sitting room with fireplace. Gracious formal dining room with adjacent butler's pantry. Spacious eat-in kitchen. Library also on the main floor. The second floor has four bedrooms, two baths plus spaces for additional offices. The property includes a fenced pool, patio and garage. As an extra bonus there is an additional lot at lake buel with a storagegarage and access to a private entry to the lake. Minutes to butternut, shopping and restaurants. A quick trip to inn on the green.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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 February 8, 2025 . 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.