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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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310 Old Stockbridge Lenox MA 01240

Lenox, MA310 Old Stockbridge Rd

Price$12,500,000

Est. Mortgage: $/month

MLS Number 232689

  • Residential
  • Bathroom 15
  • Bedrooms 13
  • Square Feet 20,821
  • Acreage 89

The elm court estate retains the title of the largest american shingle style home in the united states. The extraordinary gilded age berkshire cottage was built by william douglas sloane and emily vanderbilt, (granddaughter of cornelius vanderbilt), along with architects peabody & stearns in 1886. The gardens and landscape were designed by frederick law olmsted. In 1919, the elm court talks held at the home ultimately led to the creation of the treaty of versailles and league of nations. Outbuildings include butler and gardener cottages, carriage house & stable, greenhouses & caretaker's house and two barns. Significant renovations were accomplished in the early 2000s and continued work is necessary with an additional 8,000 sq. Ft. Of unrestored living space.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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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2080 Undermountain Sheffield MA 01257

Sheffield, MA2080 Undermountain Rd

Price$12,500,000

Est. Mortgage: $/month

MLS Number 229173

  • Residential
  • Bathroom 7
  • Bedrooms 11
  • Square Feet 7,946
  • Acreage 85

The jewel of new england... Offered for the first time in four decades, this 85 acre berkshire mountainside campus awaits your imagination. This property offers an atmosphere for breakout creative expression with great potential for an enterprise for retreats, wellness center, writers/ artists workshops, educational endeavors or your family's private estate. The property consists of 12 buildings; conference halls, dining/ meeting facilities, lodging accommodations, offices and an historic queen anne manor house sitting on a knoll with breathtaking views. 40 years of stewarding this campus where thousands of participants made life long memories, the owners are ready to pass it on. Let their growth be your opportunity. For details & digital brochure please see jewelinnewengland.Com

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

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$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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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181 Golf Course Craryville NY 12521

Craryville, NY181 Golf Course Rd

Price$9,500,000

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: 2.79% last updated on Jan 14, 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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250 Long Pond Great Barrington MA 01230

Great Barrington, MA250 Long Pond Rd

Price$6,999,900

Est. Mortgage: $/month

Pending

MLS Number 229561

  • Residential
  • Bathroom 10
  • Bedrooms 9
  • Square Feet 14,700
  • Acreage 119.73

Contemporary masterpiece beautifully situated on 120 acres offers privacy, tranquility, and breathtaking views in every season. The main house and the guest house were designed by steven haas, recognized by architectural digest as one of the world's foremost architects. Sorpetaler sliding glass walls and expansive decks create a harmonious interplay with nature. Beautiful 3,000 square foot barn with soaring ceilings adds to the allure of this unique property. Outdoor features include 25-meter heated saltwater lap pool, hot tub, outdoor showers, stone fire pit, exquisite rock outcroppings, sweeping lawn, running and biking trails, and access to williams river trout stream. Quintessential berkshires setting off a private country road just ten minutes from the vibrant town center

Listed by Reciprocal Listing: See Realtor Remarks of NON-MEMBER

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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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101 & 95 Yokun Lenox MA 01240

Lenox, MA101 & 95 Yokun Ave

Price$5,900,000

Est. Mortgage: $/month

MLS Number 232837

  • Residential
  • Bathroom 11
  • Bedrooms 13
  • Square Feet 11,748
  • Acreage 31.19

Set on 31 acres overlooking two mountain ridges, this 26 room, 11,700+ sq. Ft. Stately english manor home is one-of-a-kind in so many ways. Generously proportioned and graceful rooms with exceptional architectural details throughout such as exquisite moldings & period marble carved fireplaces. First floor includes an elegant living room, library paneled in rare purpleheart wood from the amazon rainforest, banquet sized dining room, family room with original faux bois panelling, cocktails room, cooks kitchen, breakfast room, catering kitchen & staff office. 7 principal bedroom suites, most with fireplaces & private baths. 6 additional bedrooms. Perfect for offices, etc. Third floor is generous with several rooms for fun, play or fitness. 2 berm guest house on separate parcel.

Listed by Robin Kencel of COMPASS CONNECTICUT, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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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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 reknowned 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 INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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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179 Mt Hunger Monterey MA 01245

Monterey, MA179 Mt Hunger Rd

Price$4,850,000

Est. Mortgage: $/month

MLS Number 231972

  • Residential
  • Bathroom 8
  • Bedrooms 5
  • Square Feet 8,374
  • Acreage 5.21

Casa tramonti.....House of the sunset...Life's reminder that whatever happens every day can end beautifully, says it all for this sophisticated contemporary, built by one of berkshire's premier builders. Offered for the first time, it has the necessary amenities of broadband fiber optic & great cell phone service. From the approach this home captures stunning westerly views to the catskills, keeping the viewer mesmerized with walls of glass. The sleek & sophisticated design of a most comfortable and ''livable'' space features open common living, decking for 80*, 5 br's en suite, an amazing sunroom & screened porch with waterfall sounds. A home theatre, gym & specimen plantings, organic vegetable garden, a multiple fruit orchard & fire pit to gather around.....Reason to never leave home!!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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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802 MA-41 Richmond MA 01254

Richmond, MA802 MA-41 Rd

Price$4,600,000

Est. Mortgage: $/month

MLS Number 232610

  • Residential
  • Bathroom 8
  • Bedrooms 7
  • Square Feet 4,000
  • Acreage 27

Options abound for a lifestyle change at what is now known as the inn at richmond and the berkshire equestrian center. This magnificent 27 acre property includes a charming colonial era 7 bedroom inn, 5 cottages, 2 event barns, 1 shaker horse barn, 26 horse stalls, 15 grazing paddocks, a 16,000 sf multi-purpose heated indoor arena with offices and a two bed apartment with spa, 1 outdoor arena, and the possibility to develop three building lots. With its casual elegance and charm, this colonial equestrian estate will allow your long held passion to blossom whether you use the property as a stunning family compound, an event destination, and/or a first class equestrian facility. The prime central berkshire county location will graciously support your new found lifestyle,

Listed by Jennifer Capala of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY, LENOX

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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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84 A Undermountain Egremont MA 01230

Egremont, MA84 A Undermountain Rd

Price$3,895,000

Est. Mortgage: $/month

MLS Number 230583

  • Residential
  • Bathroom 8
  • Bedrooms 5
  • Square Feet 6,000
  • Acreage 20.2

The birches.......Welcome to your new oasis in the berkshires where every season is memorable. This magical family compound has all the modern amenities a buyer wants to live, play, relax and work from, surrounded by twenty plus acres of privacy and far reaching views in all directions. Architecturally redesigned and renovated using the finest materials this stunning contemporary has big open common areas for gathering, first floor master en suite, guest bedrooms en suite and a private two bedroom guest quarters with kitchenette, all offering plenty of space for a large crowd or intimacy for a few. Just arrive with your suitcase and enjoy all this impeccably maintained estate has to offer; beautiful gunite heated pool with waterfall surrounded by expansive stone patio

Listed by Mary Jane White of COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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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9 Seekonk Great Barrington MA 01230

Great Barrington, MA9 Seekonk Rd

Price$3,750,000

Est. Mortgage: $/month

MLS Number 233070

  • Residential
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 5,930
  • Acreage 11.66

Surrounded by magnificent pastoral views over protected land, this historic home is a gem. Once part of the adjacent farm, then home to an opera diva, it has been transformed into a wonderful, light-filled sanctuary with a clean, simple aesthetic. Antique character has been highlighted, modern conveniences added, and high-efficiency updates made. Each room is delightful. The sleek eat-in chef's kitchen with access to deck and screened porch. The dining room with antique fireplace, custom bar and wall of built-in shelving. The extraordinary great room, once a barn, now a dramatic space with a fireplace at one end, and spectacular view window on the other. The primary bedroom suite with exquisite bathroom & dressing room. The gracious first floor guest suite with sweet ceiling detail...

Listed by Lance Vermeulen and Barney Stein of LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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 January 20, 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.