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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! 
106 & 114 Cliffwood St, Lenox, MA 01240

Price$4,750,000

Est. Mortgage: $/month

MLS Number 217523

  • Single Family
  • Year Built 1883
  • Parking Spaces 3
  • Bedrooms 8
  • Bathroom 8

Unsurpassed 19th Century Queen Anne Style Berkshire Lenox ''Cottage'' restored and reinvented for today's most discriminating family wishing for an understatedly elegant, 'cool' and comfortable Twenty-First Century lifestyle. See attached document for all details. Shown by advance appointment only.

Listed by Mary Jane White and Nancy Kalodner of COHEN & WHITE ASSOCIATES

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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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68 Van Wyck Ln, Hudson, NY 12534

Price$3,980,000

Est. Mortgage: $/month

MLS Number 221208

  • Single Family
  • Year Built 1840
  • Bedrooms 18
  • Bathroom 14
  • Total Full Baths 13

Hudson Valley Heaven.The Goodfarm, a private 100+ acre gated estate, is located just ten minutes from trending Hudson, NY, known for its antique shops, art galleries, music venues and restaurants. From the restored 1840 main home to the diverse countryside of fields, woods, trails, paddocks, orchard, pond and meandering creek, this compound is the quintessential country property.The centerpiece is the 1840 Center Hall Colonial, with a splash of Federal. This 7 BR, 5.5 BA home has been exquisitely modernized for today's conveniences, while respecting the architecture and features of days gone by. The open kitchen/dining room/family room is surrounded by picture windows, framing the landscaped vistas. Marble counters. A two-sided wood-burning fireplace adds to the ambiance.

Listed by Lindsay LeBrecht of Copake Lake Realty Corp.

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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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450 Monterey Rd, Great Barrington, MA 01230

Price$3,400,000

Est. Mortgage: $/month

MLS Number 221283

  • Single Family
  • Square Feet 40,175
  • List Date 10/31/2017

MOTIVATED SELLER (s) 12 parcels 33 acres in Gt.Barrington, MA on North & South sides of (Rt#23 E) Monterey Rd w/ a combined frontage of 2604 ft. See MLS #221357 for additional parcel. Formerly a campus including housing, classrooms, athletic fields, buildable land & existing fiber connectivity it is zoned residential (R-2) which by right include single family dwellings, government owned or non-profit educational facilities, municipal parks, agricultural uses & swimming pools. Uses allowed by special permit include two-family dwellings, lodging houses, private schools, summer camps, country clubs, and professional buildings. Easily accessible in the heart of Southern Berkshire County three miles from downtown Gt. Barrington this property being sold "as is''.

Listed by Christian Deckert and Deborah Levinson of BERKSHIRE PROPERTY AGENTS

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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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222 Ide Rd, Williamstown, MA 01267

Price$2,950,000

Est. Mortgage: $/month

MLS Number 217915

  • Single Family
  • Year Built 1911
  • Parking Spaces 2
  • Bedrooms 8
  • Bathroom 8

Elegant simplicity is the trademark of this American Craftsman-style residence.Sited on 2.775 acres, this magnificent country home is well-suited to large-scale entertaining with a total of seven to eight bedrooms, seven and one-half baths, and 7,215 square feet of living space.Superb design and the finest quality of materials and workmanship are the defining characteristic of this splendid estate. Bluestone walls, terraces and walkways wind through beautiful gardens in the lovely backyard with its heated pool, rustic outdoor shower, and an array of spaces for dining, including a snack bar which opens from the guest house.The impressive grounds include a circular perennial garden surrounding a flagpole, a small orchard of flowering fruit trees, gorgeous mountain view.See floor plans in documents.

Listed by Maureen Dietze and Cheryl Westall of ALTON & WESTALL REAL ESTATE AGENCY, LLC

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Barnbrook Realty
27 Housatonic Street
Lenox MA, 01240
Office: 413-637-9897

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$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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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406 Canaan Valley Rd, New Marlborough, MA 01259

MLS Number 216183

  • Single Family
  • Year Built 1800
  • Parking Spaces 4
  • Bedrooms 8
  • Bathroom 6

Whiting ridge; the main house was built in 1860 with an original 'guest cottage' built in 1740, there is a 5 stall horse barn and a newer 4-car barn with huge unfiniished second floor. The main house was completely renovated and added on to in 2009. Gorgeous chefs kitchen with sitting area, fireplace and doors out to heated screened porch/sun room. Sunken den with fireplace and porch overlooking the south western hills of ct. Formal living room with fireplace, dining room and entry boot room complete the first flr. Off the second floor landing there is a lovely master suite complete with fireplace and office, two guest rooms and two baths along w

Listed by Jen Harvey of BERKSHIRE PROPERTY AGENTS

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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 Rd, Richmond, MA 01254

Price$2,550,000

Est. Mortgage: $/month

MLS Number 221750

  • Single Family
  • Year Built 1850
  • Bedrooms 5
  • Bathroom 7
  • Total Full Baths 6

Listed by Scott Sawyer of STONE HOUSE PROPERTIES, LLC

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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 Rd, Egremont, MA 01258

Price$2,500,000

Est. Mortgage: $/month

MLS Number 221749

  • Single Family
  • Year Built 1915
  • Bedrooms 5
  • Bathroom 6
  • Total Full Baths 5

Applegate Farm...Country residence with both formal and informal common spaces to accommodate a few or many with five fireplaces, two master suites and guest wing with tennis court all overlooking your own lake with a western mountain view for backdrop. 100 + acres of very special land located on the border of Egremont and Sheffield on a back country road.

Listed by Brandon White and Cortney Dupont of COHEN & WHITE ASSOCIATES

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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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165 Kemble St St, Lenox, MA 01240

Price$2,300,000

Est. Mortgage: $/month

MLS Number 216337

  • Condominium Residential - Condo/Townhouse
  • Elementary School Morris
  • Co Listing Office Id 110139
  • Address 165 Kemble St # 17
  • Middle School Lenox Memorial

Enjoy the ultimate luxury of the wellness lifestyle in this residence at Canyon Ranch, Lenox, one of the nation's premier spas. One of only 19 units, it features a spacious great room, master suite, kitchen, two fireplaces, private patio. Mandatory annual resort membership affords access to its unparalleled facilities, close to the cultural, culinary, and outdoor amenities in the Berkshires. Now you can live in luxury at Canyon Ranch® in Lenox, Massachusetts, and enhance your life with greater health and vigor and longevity. There are only 19 beautifully appointed residences, currently under construction at the Canyon Ranch Residences at Bellefontaine. By living on the property, homeowners get full access every day of the year to the active, all-healthy environment that is the hallmark of the world's most celebrated wellness resort, Canyon Ranch. The nineteen residences are comprised of six different open floor plans with high ceilings and eco-friendly materials. Depending on the unit, there are beautiful terraces or balconies to enjoy the fresh country air. The residences feature hardwood flooring, gas fireplaces, custom designed cabinetry, spacious closets, and tile and stone baths. Connected to the resort via an enclosed walkway, there is climate-controlled underground parking and 24-hour security with a staffed, gated entrance. About Canyon Ranch in Lenox Make each day as action-packed, leisurely or inspiring as you need it to be. You'll have access to top Canyon Ranch fitness and health specialists, and spend your days surrounded by natural beauty. Plus just outside the gates lay the charming town of Lenox and rich cultural life of the Berkshires. Homeowners must purchase a membership package to the resort, and can customize their services. The Art of Relaxation: With nearly 100 spa services to choose among, booking a Canyon Ranch body wrap, facial, manicure, or your favorite salon service couldn't be easier. From Healing Energy for mind-body balance to massages and neuromuscular therapy to ease aches and pains, the therapeutic offerings will help you de-stress, reenergize and treat your body right. Personalized Medical Care: Pursue your healthiest life with the help of Canyon Ranch professionals right next door. The Canyon Ranch integrative health care approach encompasses your body, mind and spirit. The diverse wellness team inc...

Listed by Leslie Chesloff and Gladys Montgomery of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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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21 Prospect Hill Rd, Stockbridge, MA 01262

Price$2,250,000

Est. Mortgage: $/month

MLS Number 222499

  • Single Family
  • Year Built 1775
  • Bedrooms 5
  • Bathroom 6
  • Total Full Baths 5

Exquisitely renovated late 1700 antique home w/ perfect proportions & amazing grounds. High ceilings, multiple fireplaces & historic details, flooded with light. Beautifully sited on over 9 acres on one of the most prestigious roads in the county. Barn, apple orchard, specimen trees, masterful stonework. Secluded and private heated Gunite pool w/ classic pool house & adventurous boardwalk.

Listed by Christian Deckert of BERKSHIRE PROPERTY AGENTS

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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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50 Shun Toll Rd, Egremont, MA 01252

Price$2,250,000

Est. Mortgage: $/month

MLS Number 217584

  • Single Family
  • Year Built 1900
  • Bedrooms 5
  • Bathroom 5
  • Total Full Baths 4

Shun Toll Farm.Rarely does a property come on the market in the Berkshires like this special residence on one of the most beautiful country lanes in the area. Architecturally renovated the casual, but elegant, home has an eat-in country kitchen with hand crafted cabinetry, spacious enough for everyone to gather, a formal dining room with direct access to the flag stone patio for easy indoor/outdoor dining, both a formal living room and a great room where all can watch the Super Bowl, a private office/study, a first floor master bedroom en suite and a screened porch where all you see is a pastoral view and all you can hear is quiet. Three second story guest bedrooms house your family or guests. Private suite w/br/lr & kitchenette offer endless possibilities for guests, family or in-laws. Fifty plus acres of rolling meadows and mature trees, all untouched by chemicals, make the perfect earth for whatever your passion may by from gardening, organic farming, vineyard or the floor for your animals or children to roam. A two story classic bar

Listed by Mary Jane White and Brandon White of COHEN & WHITE ASSOCIATES

{$agent->Name}

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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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907 Norfolk Rd, New Marlborough, MA 01259

Price$2,195,000

Est. Mortgage: $/month

MLS Number 222233

  • Single Family
  • Year Built 1760
  • Bedrooms 7
  • Bathroom 7
  • Total Full Baths 6

A pastoral paradise abutting conservation land, this country estate includes original farmhouse, guesthouse, horse barn, pond, an additional building lot, orchards, hiking & riding trails & wonderful views. Main farmhouse is from 1760 & was meticulously restored to its original grandeur in 2015. Located minutes from Southfield Store & downtown Norfolk, Connecticut & close to Ski Butternut & downtown Great Barrington.

Listed by Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

{$agent->Name}

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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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75-77 Main Rd, Tyringham, MA 01264

Price$2,190,000

Est. Mortgage: $/month

MLS Number 219423

  • Single Family
  • Year Built 1750
  • Parking Spaces 1
  • Bedrooms 7
  • Bathroom 6

''Fairy tale'' Residential & Commercial country retreat, nestled in the luscious green hillsides of the Berkshires. Reside in it's beautiful Cottage, and continue the tradition of sharing the 'Gingerbread House' as a Banquet Hall (leased for weddings, retreats and corporate events) and B&B (currently generating over $200K in income). Santarella is steeped in history, dating back to the 1750's. With just under four acres of lush landscaped gardens, bridges, brooks and beautiful blossoms, this is truly a magical, mystical wonderland and a once-in-a-lifetime offering.

Listed by Steven Weisz and Maggie Merelle of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

{$agent->Name}

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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 A VisitAsk A QuestionMore Details