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Berkshire Single Family Properties

Discover single family homes for sale in the Southern Berkshires of Massachusetts. Find homes in Great Barrington, Egremont, Lee, and beyond. Search through a variety of current listings, including lakeside homes, antique luxury homes, and many more! Whether you're looking for multimillion dollar estates or modest cabins and camps, Southern Berkshire homes are truly diverse and offer options for most any homebuyer. Enjoy the mountains, lakes, and the area's many natural wonders from your new home!

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2128 Canaan Southfield New Marlborough MA 01259

MLS Number 237057

  • Residential
  • Bathroom 9
  • Bedrooms 10
  • Square Feet 4,273
  • Acreage 298

Set on a rise of nearly 300 acres of rolling meadows, ponds, forests, and river frontage, vergelegen is a berkshire estate without parallel. Developed by two art historians in collaboration with an award-winning creative team composed of world-class american architect tom kundig, and acclaimed british landscape architect tom stuart-smith, and a berkshires based master builder. This is an iconic modern house which affords vast vistas of the berkshire hills and taconic mountains. With cantilevered decks and entire walls of glass that open mechanically, the house offers matchless indoor/outdoor living. Built around a central fireplace, the living area is open plan with an adjacent dropped-ceiling music room and an innovative public/private kitchen with a hidden galley butler's pantry.

Listed by Kenzie Fields and Elyse Harney Morris of ELYSE HARNEY REAL ESTATE

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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 Under Mountain Lenox MA 01240

Lenox, MA319 Under Mountain Rd

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

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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2080 Undermountain Sheffield MA 01257

Sheffield, MA2080 Undermountain Rd

Price$11,890,000

Est. Mortgage: $/month

MLS Number 234183

  • Residential
  • Bathroom 6
  • Bedrooms 11
  • Square Feet 5,850
  • Acreage 85

This spectacular 85+/- acre property is a destination educational center. It offers a magnificent 1880 manor house, with spectacular distant views, a pond, and 11 additional buildings which house an auditorium, group meeting areas, breakout private offices, a fitness center, pondside cottage, huge dining hall with commercial kitchen, and accommodations in over 56 guest rooms. The land is made up of 70+/- acres in the southern berkshires and 15+/- abutting acres in salisbury, ct - the entire ct side runs along sage's ravine. There are walking trails throughout the land and access to the appalachian trail. You will be smitten by this property and totally taken with the possibilities... Building and property tax details are for the main house only. Please contact agent for more details.

Listed by Juliet Moore and Elyse Harney Morris of ELYSE HARNEY REAL ESTATE

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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30 East Alford MA 01266

Alford, MA30 East Rd

Price$9,750,000

Est. Mortgage: $/month

MLS Number 238100

  • Residential
  • Bathroom 8
  • Bedrooms 5
  • Square Feet 9,280
  • Acreage 71.59

Nestled in the hills of alford, this cotswolds-inspired home is a work of art that comes along once in a lifetime. From the moment you enter the property, the magical setting exudes peace and tranquility. You first see the guest house: a stone-clad english cottage flooded with natural light greets you at the entrance. Romance meets luxury. Your guests will never want to leave. Kitchen with wood burning fireplace. Sitting room with additional fireplace. 2 bedrooms and 2.5 baths. Overlooking fields and pond.Across the way sits a quintessential red barn. Just a few feet away from a raised bed garden. Perfect for the gardener at heart. A mile up the driveway, with the most incredible far reaching views of the alford valley, is the most exquisite and thoughtfully designed

Listed by Nikki Carchedi of STONE HOUSE PROPERTIES,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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181 Golf Course Craryville NY 12521

Craryville, NY181 Golf Course Rd

Price$7,950,000

Est. Mortgage: $/month

MLS Number 231864

  • Residential
  • Bathroom 6
  • Bedrooms 7
  • Square Feet 4,035
  • Acreage 134.39

Unparalleled 134 acre estate fronted on copake lake and adjacent to the copake country club. Spacious, 7 br 6 ba stone & wood home surrounded by dramatic stonework and lush landscaping. Great room with fireplace, chef's kitchen and 4 season sun-room. Grotto-like swimming pool with multi-level terraces and outdoor kitchen. Tennis court is beyond a wooden foot bridge. Past the stocked pond are the horse stables with a fenced in pasture, & a 3,600 square foot heated hangar, perfectly suited for an artist's work space, recording studio or a classic car collection. Several dramatic building sites have been thoughtfully cleared revealing jaw-dropping panoramic views of the hudson valley and the catskills & some w views of lake. 2,200 ft of lake frontage & trails throughout the wooded hillside.

Listed by Russ Stein of BERKSHIRE PROPERTY AGENTS,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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 West Stockbridge MA 01266

West Stockbridge, MA14 Easland Rd

Price$5,500,000

Est. Mortgage: $/month

MLS Number 237939

  • Residential
  • Bathroom 11
  • Bedrooms 12
  • Square Feet 7,826
  • Acreage 94.93

Blueberry hill is an historic estate on 95+ acres with 4 houses to comfortably host a 3-generation family. From the high land settings where the main house, silo home, guest house, ''gazebo 2 bed cottage '' and developable building lots are sited, the views looking out over alford valley to mtn tom ball and everett are stunning. Walk the marked hiking trails through the blueberry fields to the highest peak or enjoy a game of tennis on your own court. Cool off with a swim in your pool. With only 5 miles to gt barrington and 8 miles to tanglewood, fine dining and music are minutes away. Note: the data herein pertains to one or all of the 4 houses as blueberry hill is being sold as an entirety.

Listed by Cindy Welch and Keith Ross of LANDVEST,INC.

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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24 & 30 Berkshire Heights Great Barrington MA 01230

MLS Number 232672

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 6,240
  • Acreage 46.25

A rare estate offering in the berkshires. Breathtaking southern and western views from this historically important great barrington estate. Designed by charles platt for charles freer of the renowned freer gallery in dc, and constructed of stone quarried from the property, this one floor layout was well ahead of its time. The main house has a large, comfortable living room with views from massive windows, a library, a gracious dining room, all with fireplaces. The property encompasses a stable and riding ring, pool, orchard, vineyard and two fully equipped guest houses and a caretaker's home. This is a rare opportunity to own a unique nearly 50 acre estate with magnificent views - all close to great barrington.

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

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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 Lanesborough MA 01237

Lanesborough, MA775 Williamstown Rd

Price$4,900,000

Est. Mortgage: $/month

MLS Number 235978

  • Residential
  • Bathroom 7
  • Bedrooms 12
  • 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. 184 adjacent acres also available.

Listed by Andy Kelly of Berkshire Business Properties

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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55 & 0 Maple Hill West Stockbridge MA 01266

MLS Number 238141

  • Residential
  • Bathroom 9
  • Bedrooms 6
  • Square Feet 9,564
  • Acreage 68.6

Dragonfly manor....This stunning berkshire estate on 68+ acres in west stockbridge has recently been renovated and refreshed by custom designing and curated for this special home in a french country with bohemian vintage farmhouse flair for today's lifestyle. Inviting center hall entrance, spacious common rooms, both formal and informal dining, six bedrooms, 7 1/2 baths, study, two sun porches, separate guest apartment, ''pub'' room and library all overlooking stone patios, rolling lawns, a two acre spring fed swimming pond with dock, established landscaping, gardens and specimen orchards, barn with stable & paddock surrounded by privacy and abutting hundreds of acres of protected land in a most convenient location minutes to all things wonderful in the berkshires!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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164 Peter Menaker New Marlborough MA 01230

MLS Number 237795

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,434
  • Acreage 2.95

Rare opportunity to own a spectacular contemporary lakefront home with private beach and dock.This beautiful home features five bedrooms, four full and one half bath. The main level encompasses a bedroom and full bath along with an office, gourmet kitchen, dining room, screened porch and large family room with wood burning fireplace. The expansive lake view deck features a stone fireplace and hot tub, perfect for entertaining. There is also a private association with tennis. The second level features three en-suite bedrooms and bonus/gym, lake views, and ample closet space. This breathtaking resort-style home offers unparalleled craftsmanship, exceptional amenities, and is sure to impress the most discerning buyer.

Listed by Leslie G Chesloff of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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 July 2, 2022 . 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.