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

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!

r=1-12
87 Railroad St Great Barrington MA 01230

MLS Number 227431

  • Commercial
  • Bathroom 5
  • Village Berkshire - South
  • Square Feet 3520
  • Year Built 1920

In the heart of downtown great barrington, this investment opportunity features two business storefronts, and four apartment units fully rented. The property also includes a large parking lot being rented as well for added monthly income. The units feature their own separate utilities, electric, gas forced hot air, & individual gas meters. Owner financing available.

Listed by JAN PERRY REALTY & ASSOCIATES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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

920 South Main St Great Barrington MA 01230

MLS Number 228079

  • Single Family
  • Bathroom 2
  • Address 920 South Main St
  • Village Berkshire - South
  • Square Feet 2380

Great opportunity for either commercial or residential . Charming brick built home on 17 acres in town . Open plan living with beautiful fireplace, wood floor and pastoral views in the back. There is an outdoor shower , a beautiful deck and a great barn /workshop . Great possibilities

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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

6 Deer Trail Great Barrington MA 01230

Price$799,000

Est. Mortgage: $/month

Pending

MLS Number 225120

  • Single Family
  • Bathroom 6
  • Address 6 Deer Trail
  • Village Berkshire - South
  • Square Feet 4668

Magnificent 4 plus bedroom home on a quiet country road . The home has a state of the art kitchen with 2 miele dishwashers , wolf range and many other features. New furance and water heater.There are three fireplaces throughout the house. The den is gorgeous and leads to a patio overlooking beautiful gardens.

Listed by STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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

100 West Sheffield Rd Great Barrington MA 01230

MLS Number 225861

  • Single Family
  • Bathroom 5
  • Village Berkshire - South
  • Square Feet 3192
  • Year Built 2000

Much bigger than it looks, this home is ideal for entertaining. Boasting an open kitchen - living- dining area, separate office space, and often sought after first floor master suite. First floor laundry room is adjacent to master bedroom. Bright kitchen with granite countertops, center island and viking stove. Convenient mud room leads to oversized three car garage. The lower level with its own full bathroom, spacious game room, sauna, media room and wet bar is an entertainer's paradise. In addition to the main house, there is also a one bedroom, full bathroom apartment above the garage. This apartment has its own outside entry, as well as indoor access. This property has to be absolutely seen to be fully appreciated. Prepare to fully fall in love with it.

Listed by Joanna Szwyd and Stephen Schoenfeld of STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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

241 North Plain Rd Great Barrington MA 01230

MLS Number 228425

  • Single Family
  • Bathroom 2
  • Address 241 North Plain Rd
  • Village Berkshire - South
  • Square Feet 2456

A rare offering! Main residence with stunning guest cottage. A long, winding driveway slowly reveals the serene, unspoiled elegance of this gracious c. 1840 colonial home: moved to its present location in 1980, the house rests privately far back from the road, nestled among stately trees and sloping lawn, overlooking the williams river. Beautiful antique floors, huge country kitchen with sitting area, stately wood-burning fireplace and spacious screened porch; the guest cottage includes 1200+- sq. Ft of open common spaces, one bedroom, one full bath, an airy loft, and its own screened porch. Elegantly landscaped throughout, with raised beds, mature plantings and in ground pool. Located just minutes from downtown great barrington and all the very best of the berkshires!

Listed by COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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

9 Monument Valley Rd Great Barrington MA 01230

MLS Number 226978

  • Single Family
  • Bathroom 3
  • Address 9 Monument Valley Rd
  • Village Berkshire - South
  • Square Feet 2850

Privately tucked away around the corner from ski butternut and down a long drive, is this quintessential ski lodge that's been expanded over the years to host guests in all seasons. The inviting warm interior calls for group dinners in the dining room overlooking the lawn, pond and woods, then relax after out at the fire pit or in the cathedral living room with a big fireplace and a loft. The later family room addition was built to be a possible first floor master suite, and there's another upstairs, along with guest rooms and baths. The basement was finished for kids to bounce off the walls and to house winter and summer sports equipment - directly accessed from outside. This home has been a beloved gathering place for friends escaping the city, offered for sale due to a big move west.

Listed by BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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

Burning Tree Rd # 29 Great Barrington MA 01230

MLS Number 228635

  • Condominium Residential - Condo/Townhouse
  • Address Burning Tree Rd # 29
  • Middle School Monument Valley Reg.
  • High School Monument Mountain
  • Village Berkshire - South

Inviting entry brings one in to a light filled open living plan with mountain views, high ceilings...Easy living. This perfectly cared for condo spans two floors with first floor master and master bath a guest room with full bath, another room for office/tv room or extra sleeping; all with large closets. The laundry room is off the kitchen and an attached two car garage. The kitchen blends perfectly in to the open living layout and a screened porch brings one even closer to unimpeded views of the changing seasons. The lower floor has unending options with a large open main room, two bedrooms, full bath and lots of additional storage space. Others have used the space for guest visits, gym/exercise setup, entertainment center, office space and more.

Listed by BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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

44 Bridge St # 104, 204, 304 Great Barrington MA 01230

MLS Number 218550

  • Condominium Residential - Condo/Townhouse
  • Middle School Monument Valley Reg.
  • High School Monument Mountain
  • Village Berkshire - South
  • Elementary School Muddy Brook Reg.

Brand new condominiums in the heart of downtown great barrington. Twenty-seven condos conveniently located near the expanded co-op market. This is an excellent investment in the ''boom town'' of the berkshires! Don't miss out on this opportunity to purchase a two bedroom, two and half bath unit with a gas fireplace, underground parking and balcony. Construction expected to begin winter 2017, with an expected delivery of winter 2018. We expect these units will sell out quickly. Pricing, layout and availability are subject to change.

Listed by BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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

81 Division St Great Barrington MA 01230

Price$774,900

Est. Mortgage: $/month

MLS Number 226980

  • Single Family
  • Bathroom 3
  • Address 81 Division St
  • Village Berkshire - South
  • Square Feet 2375

Farmhouse chic on the williams river. Completely renovated. Large farm style kitchen with room to dine and relax, comfortable living room with room for the family. Office and full bath on the main level. Huge enclosed porch on the front and stone patio over looking the river in the back. New master suite with river views, lovely bath and walk-in closet. Three additional bedrooms and hall bath. A detached garage and barn round out the property.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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

445-449 Monterey Rd Great Barrington MA 01230

MLS Number 221507

  • Single Family
  • Address 445-449 Monterey Rd
  • Village Berkshire - South
  • Square Feet 18157
  • Year Built 2003

The gymnasium (2003) and original administrative building (1959)are being sold together with 2+ acres across the street where the leach field is located on a combined 000 acreage. The taxes are on three parcels combined.Read 'more' for extensive information on both buildings.

Listed by BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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

215 Long Pond Rd Great Barrington MA 01230

MLS Number 223040

  • Single Family
  • Bathroom 4
  • Address 215 Long Pond Rd
  • Village Berkshire - South
  • Square Feet 3133

*new price* rare opportunity to own the historic ''beasley'' house in the heart of the berkshires. 7+ acres, in-ground pool & tennis court. Restored farmhouse with modern amenities. 6 bedrooms, 4 baths, includes apartment with private entry. Field stone fireplace, large screened-in porch. Bucolic grounds, out buildings, large shade trees.Close to all berkshire attractions.Room for everyone, steps to everywhere. A true gem!

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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

44 Bridge St # 100, 102, 200, 202, 300, 302 Great Barrington MA 01230

MLS Number 217570

  • Condominium Residential - Condo/Townhouse
  • Middle School Monument Valley Reg.
  • High School Monument Mountain
  • Village Berkshire - South
  • Elementary School Muddy Brook Reg.

Brand new condominiums in the heart of downtown great barrington. Twenty-seven condos conveniently located near the expanded co-op market. This is an excellent investment in the ''boom town'' of the berkshires! Don't miss out on this opportunity to purchase a two bedroom, two and half bath unit with a gas fireplace, underground parking and balcony. Construction expected to begin winter 2017, with an expected delivery of winter 2018. We expect these units will sell out quickly. Pricing, layout and availability are subject to change.

Listed by Tom Lynch and Timothy Lovett of BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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