Great Barrington Real Estate

Great Barrington is the heart of southern Berkshire County. Both a summer resort and home to Ski Butternut, Great Barrington has plenty to do all year long. In 2012, Smithsonian magazine ranked Great Barrington #1 in its list of "The 20 Best Small Towns in America". The town is also home to a vibrant farm-to-table restaurant scene and has also become a major arts and culture destination.

Love what you see? Register with us to save your favorites, and receive notifications when similar Great Barrington properties are listed. Contact us today to with questions or to schedule a showing of any property below!

250 Long Pond Rd Great Barrington MA 01230

Price$8,750,000

Est. Mortgage: $/month

MLS Number 225029

  • Single Family
  • Village Berkshire - South
  • Year Built 2007
  • Parking Spaces 3
  • Bedrooms 9

Contemporary masterpiece beautifully situated on 120 acres offers privacy and breathtaking views in every season. Main House and 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 barn adds to 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, hiking trails and access to Williams River trout stream. Quintessential Berkshires setting off private road just minutes from vibrant town center of Great Barrington, selected in 2012 by Smithsonian Magazine as #1 of The 20 best small towns in America.

Listed by Non-member

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

20 Berkshire Heights Rd Great Barrington MA 01230

MLS Number 223462

  • Single Family
  • Village Berkshire - South
  • Year Built 1915
  • Bedrooms 6
  • Bathroom 7

Complete 2012 rebuild and seamless expansion of a gracious home on The Hill in Great Barrington, into a stunning timeless and modern Federal estate, perched on a notable parcel with a barn and private spa pool. No detail was overlooked inside or out from custom everything to geothermal heating and cooling. Too many amenities to list, including central A/C, full house generator, Pella true divided light windows throughout, Rocky Mountain hardware, Lutron lighting, spray foam insulation, double insulated floors, and most all of the house has radiant heated floors and of course state-of-the-art mechanicals. The three acres are beautifully landscaped and include a spa pool with a waterfall and auto cover, bocci court, invisible dog fence, a seasonal stream, and a barn. Walk to town.

Listed by BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

Great Barrington MA 01230

Price$3,200,000

Est. Mortgage: $/month

MLS Number 226629

  • Single Family
  • Year Built 2006
  • Parking Spaces 2
  • Bedrooms 4
  • Bathroom 5

Wind up the gated drive through the expansive lawn to this private and classic/contemporary residence. From the car park, enter a gracious and welcoming paneled foyer to striking views through the double-height living room overlooking the stone terrace, pool and grounds to Monument Mountain and the hills beyond. Unmatched attention to the creation of this estate by a noted architect and discerning owners is apparent throughout the home with its views, flow of public and private areas, proportion of design, attention to detail, custom finishes and elegant kitchen. Its attention to both comfort and style appeals to discerning buyers of all age groups with easy access to all rooms, as well as elevator to second story and attached garage. Offer includes two adjacent building parcels.

Listed by BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

109 Stockbridge Rd Great Barrington MA 01230

MLS Number 226159

  • Commercial
  • Village Berkshire - South
  • List Date 03/06/2019
  • Zoning Business

**NEW PRICE** Bowling and Family Entertainment Center on prime Route 7 corridor. Well established & popular Berkshire attraction. 24 Bowling Lanes, Indoor Mini-Golf, Arcade Center, Cafe & Bar. 3.69 acres and over 275 feet of frontage. Parking for 109 cars. High traffic area (DOT reported 17,900). Ongoing & profitable business, many upgrades, licenses transfer, turn-key!

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

109 Stockbridge Rd Great Barrington MA 01230

MLS Number 226158

  • Commercial
  • Village Berkshire - South
  • Year Built 1958
  • Square Feet 26,012
  • List Date 03/06/2019

**NEW PRICE** Bowling and family entertainment Center on prime Route 7 corridor. Well established & popular Berkshire attraction. 24 Bowling Lanes, Indoor Mini-Golf, Arcade Center, Cafe & Bar. 3.69 acres and over 275 feet of frontage. Parking for 109 cars. High traffic area (DOT reported 17,900). Ongoing & profitable business, many upgrades, licenses transfer, turn-key!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

267 Long Pond Rd Great Barrington MA 01230

Price$1,749,000

Est. Mortgage: $/month

MLS Number 226290

  • Single Family
  • Village Berkshire - South
  • Year Built 1820
  • Parking Spaces 2
  • Bedrooms 5

A True Berkshire Gem in a Premiere Location Over Looking Long Pond. Wow! Classic farmhouse on nearly 80 acres with a barn, orchard, pool, tennis court, play house, and gardens. All of this over looking open fields, Log Pond and Catamount. This is truly a spectacular setting with a large living/family room, formal dining, large eat-in kitchen and den. Second floor with bedrooms and third floor finished as studio space. Finished lower level room with full bath and outdoor shower for after swimming, tennis, gardening, or just playing. Come put your personal touch on this gem. A bit of work for a lot of gain.In 1987 additional land was purchased for $80,000. House sits on just 4+ acres but the entire lot is nearly 80 acres. Inscription in kitchen beams are from 1820.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

11 Londonderry Dr Great Barrington MA 01230

Price$1,650,000

Est. Mortgage: $/month

MLS Number 226719

  • Single Family
  • Village Berkshire - South
  • Year Built 2006
  • Parking Spaces 3
  • Bedrooms 8

Totally secluded with views to Ski Catamount, yet just minutes from Great Barrington center. From the moment you enter, attention to detail is apparent, along with the dramatic wall of glass to the westerly view from the two-story great room. The same view is found from the sumptuous first floor master suite which leads out to a large sun-soaked deck. A virtual resort for country house guests - the kitchen has two of everything, the gorgeous pool area has a pool house and basketball court, the finished walk-out lower level offers exercise, play and workspace for everyone, and there's separate guest wings for fun-filled weekends. The words ''spotless'' and ''well-cared for'' do not do this property justice, as it's triple mint. Attached three-car garage for collectors. Call us for a tour.

Listed by Timothy Lovett and Fintan Hanley of BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

280 Division St Great Barrington MA 01230

Price$1,550,000

Est. Mortgage: $/month

MLS Number 218213

  • Single Family
  • Village Berkshire - South
  • Year Built 1983
  • Parking Spaces 3
  • Bedrooms 7

Affording the perfect combination of privacy and luxury, this fabulous Contemporary is an outstanding choice for the Berkshires. It's stunning interior with 7 bedrooms, 5 baths and powder room, includes a guest wing with separate entrance, UNIQUELY SUITABLE FOR A PROFESSIONAL OFFICE The luxurious master bedroom features his and her bathrooms en suite. Situated on beautiful, professionally landscaped five plus acres, spacious decking and a dramatic gunite pool, this home is just a few short miles from town and is a convenient location for all the Berkshires offers.

Listed by COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

14 Monument Valley Rd Great Barrington MA 01230

MLS Number 219997

  • Single Family
  • Village Berkshire - South
  • Year Built 1964
  • Parking Spaces 3
  • Bedrooms 5

63 incredible acres of forest and ponds surround this home that has been in one family for several generations. The land extends to the top of the mountain where there are cross country skiing and hiking trails. A stream runs almost all year and empties into two ponds. Off the very large kitchen is a screened-in porch and deck. The living room which was the original part of the house and built in an A frame, has great character and leads to a family room overlooking the pool and backyard. The master bedroom is on the first floor and overlooks the pool and deck as well. Two more bedrooms occupy the opposite end of the 1st floor and incorporate a small utility kitchen. The property also includes a two level barn; one part currently is a wood shop, other part was formerly housing horses

Listed by STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

317 Long Pond Rd Great Barrington MA 01230

Price$1,395,000

Est. Mortgage: $/month

MLS Number 226483

  • Single Family
  • Village Berkshire - South
  • Year Built 2015
  • Bedrooms 4
  • Bathroom 3

Designed by award winning Boston architect, Flavin Architects for today's lifestyle. Enter through nine foot door with open staircase designed with custom metal railings, continue to an open floor plan with custom chefs kitchen. Floor to ceiling windows offer spectacular view of private pristine lake complete with dock for launching kayaks. First floor bedrooms, full bath. Take custom floating stairs to two additional second floor en suite bedrooms. A family/media room and full laundry complete all that is needed for life in Great Barrington. Private yet close to downtown. See documents for feature details.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

24 Locust Hill Rd Great Barrington MA 01230

Price$1,350,000

Est. Mortgage: $/month

MLS Number 225834

  • Single Family
  • Village Berkshire - South
  • Year Built 2008
  • Parking Spaces 2
  • Bedrooms 4

LEED rated custom home on a quiet country road with painterly views over rolling sheep pastures to mountains beyond, yet just minutes to downtown Great Barrington. Built on the site of a former farmhouse and created with great thought, spirit and attention to detail, this timeless residence features large windows, high ceilings, reclaimed wood floors and cabinetry, a first floor master, guest suites, a private studio and a second-floor covered loggia with a gas fireplace facing the enchanting view. All possible means of smart eco and conservation practices were employed such as geothermal heat, solar arrays and high R-value panelized construction, to name a few. All while creating a very pretty, warm, comfortable living environment with international style, grounded by ancient trees.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

10 Haley Rd Great Barrington MA 01230

Price$1,300,000

Est. Mortgage: $/month

MLS Number 223182

  • Single Family
  • Village Berkshire - South
  • Year Built 2000
  • Parking Spaces 5
  • Bedrooms 4

Million dollar, protected sunset views, proximity to Great Barrington restaurants, shops, and theaters, and a spacious, comfortable one-of-a-kind home create the perfect Berkshire retreat. Built by the current owners in 2000 and lovingly maintained, this wonderful home features a first-floor open plan with fireplace and four-season porch, cook's kitchen, and master suite, and spacious attached garage, while the walk-out lower level offers three bedrooms. Perfectly sited, on two manicured acres, with westerly views from every room and equipped with radiant-heated floors throughout the first floor, lower level & garage, it combines beauty and practicality as a vacation or primary home in America's ''best small town.''

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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