and narrow your search. If you have fewer than 200 results, you can save your search.

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!

Love what you see? Register with us to save your favorites, and receive notifications when similar properties are listed. Contact us today to with your any home below!

r=1-10
2080 Undermountain Rd Sheffield MA 01257

Sheffield, MA2080 Undermountain Rd

Price$16,000,000

Est. Mortgage: $/month

MLS Number 229173

  • Single Family
  • Village Berkshire - South
  • Year Built 1880
  • Bedrooms 11
  • Bathroom 7

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 COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

3 Ice Glen Rd Stockbridge MA 01262

Stockbridge, MA3 Ice Glen Rd

Price$8,500,000

Est. Mortgage: $/month

MLS Number 225549

  • Single Family
  • Address 3 Ice Glen Rd
  • Village Berkshire - South
  • Year Built 1915
  • Parking Spaces 2

Built in 1915 believed to be the last of the Berkshire Cottages. This stunning home on 58.8 acres is just minutes to the village of Stockbridge MA. Restored to its original splendor with black and white marble floor entry, curved marble staircase, loggia with painted ceiling and fountain. The library includes book shelves flanking 3 walls and two fireplaces. The room is used as an office/family space with Tv and electronics hidden behind custom doors. Main salon with fireplace and views of the terrace and eastern light. Dining room with fireplace custom table seats 14 easily. Modern kitchen with Corian topped island and comfortable table spaces. A work area as well as tv space off of kitchen. Nine bedrooms. six baths on second and third floors. SEE ADDITIONAL INFO

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

250 Long Pond Rd Great Barrington MA 01230

Great Barrington, MA250 Long Pond Rd

Price$6,999,900

Est. Mortgage: $/month

MLS Number 229561

  • Single Family
  • Address 250 Long Pond Rd
  • Village Berkshire - South
  • Year Built 2009
  • Parking Spaces 3

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 Non-member

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

119 West Center Rd West Stockbridge MA 01266

West Stockbridge, MA119 West Center Rd

Price$5,950,000

Est. Mortgage: $/month

MLS Number 227174

  • Single Family
  • Address 119 West Center Rd
  • Village Berkshire - South
  • Year Built 2007
  • Bedrooms 6

When New England Hall of Fame Interior Designer Dalia Tamari decided to devote 3 years to designing and building this 6,700+/- sq.ft. European influenced country home, her first step was to select the best of settings in the heart of the Berkshires, MA. The chosen 68+/- acres, accessed by a long and winding drive leads to a hilltop with commanding views and privacy. Exceptionally designed, the home is both grand and family friendly. The kitchen, by the famed designer herself, is a prime gathering area to cook together, set against an elevated field stone fireplace. This magnificent property offers a 1st floor master and 5 add't bedrooms upstairs, all with baths ensuite. The pool is adjacent to a pool house with full scale kitchen and laundry. All set on beautifully landscaped grounds.

Listed by LANDVEST, INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

40 Millard Rd Egremont MA 01230

Egremont, MA40 Millard Rd

Price$4,999,000

Est. Mortgage: $/month

MLS Number 226848

  • Single Family
  • Address 40 Millard Rd
  • Village Berkshire - South
  • Year Built 1995
  • Parking Spaces 3

Breathtaking Tri-State views from this light filled, 12,000 sq. ft masterpiece featuring gourmet kitchen, huge library, wine cellar, indoor pool with sauna and steam room, as well as an elevator connecting all the levels. This stunning property has been designed by NY architect Michael Schmitt and completely renovated by Peter Whitehead.Private guest wing with three bedrooms and two bathrooms. Fiber Connect for Internet. Close to 90 acres of privacy on one of the most sought after roads in Southern Berkshires.

Listed by STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

84a North Undermountain Rd Egremont MA 01258

Egremont, MA84a North Undermountain Rd

Price$3,895,000

Est. Mortgage: $/month

MLS Number 229193

  • Single Family
  • Village Berkshire - South
  • Year Built 1986
  • Parking Spaces 3
  • Bedrooms 5

Nestled on a ridge offering magnificent views of the mountains both to the east and west this quietly elegant contemporary home has been fully renovated, restored and expanded to the highest standards. Encompassing over 20-acres, the long drive leads to both formal and family entries. Gorgeous gardens and terraces abound, including organic vegetable gardens and orchard. Pool area offers a pool house with kitchenette & 1/2 bath and is a destination in itself - exquisitely landscaped and perfectly relaxing. The main house flows graciously throughout. Every room on the first floor offers views intimate and large, beautifully framed as well as access to the outdoors at every turn. Flawlessly constructed and maintained with meticulous attention to every detail. Gorgeous Egremont home.

Listed by STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

239a Island Dr Craryville NY 12521

Craryville, NY239a Island Dr

Price$3,750,000

Est. Mortgage: $/month

MLS Number 229490

  • Single Family
  • Address 239a Island Dr
  • Year Built 2013
  • Parking Spaces 2
  • Bedrooms 6

Welcome to White Oak on the exclusive, gated Island at Copake Lake. This 6700+ sf Adirondack style home on 1.27 waterfront acres was designed to comfortably host family and friends. There are six bedrooms, four of them en-suites. Let's take a tour. The entrance perfectly aligns with the oversized windows and transoms, which frame the lake's beauty and your pathway to the water's edge. The main level is where you will find the great room with a floor-to-ceiling fireplace and bespoke iron and rope chandeliers. The open floor plan allows the kitchen, dining area and great rooms to blend into one. The kitchen has Caesarstone counters with custom white oak cabinetry and top-of-the-line appliances. There are two en-suites with lofts and a powder room on this floor as well. Adj

Listed by Copake Lake Realty Corp.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

106 Cliffwood St Lenox MA 01240

Lenox, MA106 Cliffwood St

Price$3,600,000

Est. Mortgage: $/month

MLS Number 217523

  • Single Family
  • Address 106 Cliffwood St
  • Village Berkshire - South
  • Year Built 1883
  • Parking Spaces 3

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 of COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

82 Interlaken Rd Stockbridge MA 01262

Stockbridge, MA82 Interlaken Rd

Price$3,500,000

Est. Mortgage: $/month

MLS Number 222056

  • Single Family
  • Address 82 Interlaken Rd
  • Village Berkshire - South
  • Year Built 1959
  • Bedrooms 3

RARE WATERFRONT OPPORTUNITY ON THE STOCKBRIDGE BOWL: A PARADISE FOR YOUR FAMILY. 11 Acres on the beautiful Bowl. Over 400 feet of pristine lake frontage looking across the ''belly'' of the Bowl. Two beautiful site specific modern style plans have been drawn with walls of windows from every room facing the lake. Amazing mountain and water views in every season. Build one private home or a family compound. Three home sites with existing structure for rare opportunity to have your dream home within 71 feet of the lake. Minutes to Tanglewood, Kripalu, and Canyon Ranch.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

89 Cliffwood St Lenox MA 01240

Lenox, MA89 Cliffwood St

Price$3,350,000

Est. Mortgage: $/month

MLS Number 230032

  • Single Family
  • Address 89 Cliffwood St
  • Village Berkshire - South
  • Year Built 1888
  • Parking Spaces 3

Best of the Berkshires. Truly one of the most gracious homes exquisitely restored for modern life with family and friends. Designed by Boston architects in the 1880's the unparalleled flow and understated charm of this home function as beautifully today as then. In superb condition, with excellent systems throughout. Large, caretaker apartment or home office too. Beautifully sited gunite swimming pool and mature gardens add to the sense of elegance, ease and privacy. , Ideally located in Lenox one can walk to town, Tanglewood or hike in Kennedy Park and the numerous preserved woodlands. See documents for additional information and details.

Listed by BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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