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! 
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2758 County Rte 9 East Chatham NY 12060

East Chatham, NY2758 County Rte 9 --

Price$1,695,000

Est. Mortgage: $/month

Pending

MLS Number 234095

  • Residential
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 3,290
  • Acreage 92

Historic concord farm. Set back and overlooking 92 acres of rolling fields, this classic 1840 greek revival farmhouse captures that luminous sense of place we call rural life.This authentically restored homestead features 3-4 bedrooms, 3 fireplaces, rocking chair front porch, 9 ft ceilings, large eat-in kitchen with charming kitchen garden, state of the art mechanicals and original hardwood floors.19th century post and beam barn adds additional 3,000 sf of finished space including a workshop/studio with radiant heat on 1st level. On the second level is a private three-room guest space, work-at-home office, or rental.Protected land across from residence ensures view. Farmland suitable for organic farming, horses (4 bay horse barn), or cattle grazing. More land available.

Listed by Nancy Cuddihy of STONE HOUSE PROPERTIES,LLC

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Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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602-606 Hartsville New Marlborough New Marlborough MA 01230

MLS Number 233958

  • Residential
  • Bathroom 8
  • Bedrooms 11
  • Square Feet 11,065
  • Acreage 20

The ultimate family and friends compound with 23 rooms, 11 bedrooms, and 8 baths in 2 houses connected by a 2nd floor porch. The main house was built in the grand gilded age style in 1890 and the second attached home followed in similar style in 1900. Well maintained period details are enhanced by newer mechanicals, fresh paint, and new roofs. The two massive barns with new metal roofs are complemented by an icehouse, garden house, and caretaker home.The views are long range and pastoral overlooking the pastures, stream, and south pond.3rd floor not habitable. The cassilis farm estate offers magnificent homes on a 20-acre beautiful setting less than 10 miles to great barrington. Needs extensive restoration and well worth it!

Listed by Cindy Welch of LANDVEST,INC.

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$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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560 Stockbridge Lee MA 01238

Lee, MA560 Stockbridge Rd

Price$1,470,000

Est. Mortgage: $/month

MLS Number 227991

  • Residential
  • Bathroom 9
  • Bedrooms 7
  • Square Feet 4,695
  • Acreage 7.01

Stunning circa 1850's renovated with seven bedrooms and nine full baths. Classic greek revival with strong lines and lovingly preserved details; three period fireplaces, generous gourmet eat-in cook's kitchen and the comfort and style of today's living in the perfect location just a short drive to tanglewood and in between stockbridge and lenox!! This property offers gracious common spaces and six en-suite guest bedrooms. New first floor guest suite with separate entrance

Listed by Mary Jane White and Cortney K Dupont of COHEN & WHITE ASSOCIATES

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Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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343 West New Lebanon NY 12125

New Lebanon, NY343 West St

Price$1,295,000

Est. Mortgage: $/month

MLS Number 233259

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 5,212
  • Acreage 5.58

West acres....Located in shaker country this stately colonial revival greets you with a circular drive and porte-cochere. Once you enter the foyer you immediately get a sense of openness washed with natural light and high ceilings in the spacious rooms, original moldings and a sweeping view of the valley and berkshire hills beyond. Beautifully sited on a hill surrounded with mature landscaping, gardens and trees on 5 + acres, this property has it all; 5 br main residence with wonderful common rooms, stunning sun room, eat-in country kitchen, 3 br, 2 bath guest house, 4 bay garage/workshop, tennis court and in-ground heated pool w/spa and pool house. Easy access to fine dining, boutique shopping and the cultural and recreational venues in both columbia and berkshire county...A must see!

Listed by Mary Jane White of COHEN & WHITE ASSOCIATES

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$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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102 Castle Hill Great Barrington MA 01230

MLS Number 236360

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1,435
  • Acreage 0.4

A fresh and stylish renovated antique former farmhouse high on the hill in great barrington, within walking distance of lake mansfield and the town center. The sweet home is flooded with light and also warm and cozy. The eat-in kitchen with marble counters and new appliances leads to a large glassed and screened dining porch off the back. There's a full bath on both floors with four bedrooms on the second floor; the smallest of which makes for a great office zoom room, study or nursery. A former garage is now a studio building with french doors leading to a terrace by fruit trees with views to beartown state forest. A very charming home and property in a beautiful, friendly, coveted neighborhood. Furnishings are available.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS,LLC

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$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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94 Dawes Pittsfield MA 01201

Pittsfield, MA94 Dawes Ave

Price$995,000

Est. Mortgage: $/month

Pending

MLS Number 234925

  • Residential
  • Bathroom 6
  • Bedrooms 6
  • Square Feet 7,559
  • Acreage 1.95

Birchwood, a circa 1890's queen anne victorian complete with turrets, has been stewarded with care to renovate for today's lifestyle while preserving all that is unique in this gilded age beauty. Flanked by two gate posts, this stunning mansion is set majestically back from the street where the guest entrance takes you to a port cochre with two acres of lawn with mature trees and perennial gardens, an in-ground pool and pool house and an attached three bay garage. A most special berkshire offering.

Listed by Brandon White of COHEN & WHITE ASSOCIATES

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$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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93 Brett Monterey MA 01245

Monterey, MA93 Brett Rd

Price$895,000

Est. Mortgage: $/month

MLS Number 234093

  • Residential
  • Bathroom 3
  • Bedrooms 8
  • Square Feet 3,536
  • Acreage 102

102 glorious monterey acresbordering 12,000 acre beartown state forest on 3 sides10 minutes to great barrington10 miles to stockbridgeinspiring, rare & private land with an ideal combination of open fields & forest. Sloping gradually up the mountain there are superb locations to build your dream home or homes with a sw exposure and the potential for distant views. Even rarer, this colonial-era farm borders what is now 12,000 acre beartown state forest with the appalachian trail, the knox trail, and benedict pond a hike away. Long road frontage equates to opportunity for up to 6 homes, if desired. This historic monterey farm is located in a truly unbeatable location with very low monterey taxes + a rustic original colonial farmhouse & barns. Fiber broadband on the way! Sold 'as is'

Listed by L. Chapin Fish and Jared Kelly of BROCKMAN REAL ESTATE,LLC

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$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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34 Division Great Barrington MA 01230

Great Barrington, MA34 Division St

Price$885,000

Est. Mortgage: $/month

MLS Number 235949

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,612
  • Acreage 4

Rare opportunity to own restored 230 yr old home with new electric, plumbing, windows roof sills and structural supports that is move in and ready for the holidays. Wonderful open kitchen dining great room and second living space to entertain and cook with family and friends. Stunning wood floors throughout. First floor bedroom with private bath. Three additional bedrooms on second floor with private bath. Additional living space could be added to main house. Separate barn in need of renovation could be a studio/office. Nice level flat yard surrounding house, plenty of room for a pool.

Listed by Samantha A. Homeyer and Suzann Laverack Ward of HOUSATONIC REAL ESTATE

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$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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443 Johnson Hill Washington MA 01223

Washington, MA443 Johnson Hill Rd

Price$880,000

Est. Mortgage: $/month

MLS Number 235405

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,034
  • Acreage 9.69

An oasis of peace & privacy awaits, with fields, apple trees, woods, pond, a lovely 3-4br house, barn, guest cottage, spring house, on 9.89a abutting conservation land. Just up the hill from the north becket atheneum & cafe, easily reachable from routes 20 & 8. As you come down the country road to the stone walls where you enter the property, stress melts away. Brew your morning coffee in the updated cook's kitchen & enjoy it on the porch. Enjoy sunrises to the east, sunsets to the west. Stroll a woodland trail to the pond. Welcome guests to the 2br cottage. Get creative in the barn. This venerable property, located in washington, the town james taylor & arlo guthrie call home, traces its history to fdr's grandchildren, & further back to its beginnings as a farm. A country place. Bliss.

Listed by Thom Garvey and Gladys Montgomery of WILLIAM PITT SOTHEBY'S - LENOX

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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59 Main Sheffield MA 01257

Sheffield, MA59 Main St

Price$839,000

Est. Mortgage: $/month

MLS Number 236099

  • Residential
  • Bathroom 9
  • Bedrooms 9
  • Square Feet 5,358
  • Acreage 1

Gracious 1818 colonial in the village of sheffield on a beautifully landscaped acre. Walk to restaurants, library, post office and historical society. Currently a turnkey fully furnished 7 bedroom, 7 bath b&b with a 1600 sq ft open plan owner's quarters with 2 bedrooms and 1.5 baths. Many permitted uses in the village center district. The property is perfect to continue as a b&b or consider other live/work home businesses. Perhaps a family compound. The 40x24 barn with concrete floor and second floor is ideal for workshop, studio, car storage. So many possibilities!

Listed by Sheila Thunfors and Brian Farrell of STONE HOUSE PROPERTIES,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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319 Berkshire School Sheffield MA 01257

MLS Number 236282

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 1,940
  • Acreage 2.57

Beautifully renovated colonial on the schenob brook. Light filled living room takes in east, south and west light, open dining and kitchen with walk in pantry also filled with light. Entry room with fireplace and newly added powder room complete the first floor. Upstairs there are two guest bedrooms and a hall bath with a landing and laundry closet. Primary suite has vaulted ceilings and private balcony overlooking the brook. New roof, new windows, new electrical, new plumbing, new appliances, newer heating system and freshly painted on the exterior and interior.Lovely 2.57 acre lot with access to the brook and nice size barn.

Listed by Jen Harvey of BERKSHIRE PROPERTY AGENTS,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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16 Cottage Great Barrington MA 01230

Great Barrington, MA16 Cottage St

Price$828,000

Est. Mortgage: $/month

Open House

MLS Number 236318

  • Residential
  • Next Open House: Sat 12/4 11:00 am. to 12:30 pm.
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,688

Rare find! Combine country living with 100% urban walkability, plus riverfront!! Completely renovated, this home is pristine, practical & inviting. A beautiful chef's kitchen with walk- in country pantry, and the easy flow of open living. & dining rooms. There is a 1st floor full bath. The view from the kitchen window takes in the fenced & lighted yard extending to the water's edge. Gorgeous finishes throughout. Upstairs a primary bedroom, two guest bedrooms & a well appointed bath with laundry. An additional bonus is the 3rd floor, easily finished off to expand the living or work space. A wrap around porch, deck, custom fencing & a host of seating areas to entertain and enjoy. Walking distance to prairie whale, shops, farmer's market! A must see...

Listed by Helen Mullany of HELEN MULLANY REAL ESTATE,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

Based on information submitted to BCMLS  as of December 3, 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.