Great Barrington Luxury Homes

View a list of Great Barrington Massachusetts luxury homes currently for sale below and let us know if you would like to learn more or schedule a tour.  If you would like to save your favorite Great Barrington MA luxury real estate listings, you can register with our site.  You may also be interested in Great Barrington homes or Stockbridge luxury homes.

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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Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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42 Sheffield Great Barrington MA 01230

Great Barrington, MA42 Sheffield Rd

Price$2,495,000

Est. Mortgage: $/month

MLS Number 236981

  • Residential
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 7,000
  • Acreage 19.85

Truly one of a kind home sits on 19.85 acres of woods adjacent to the wyantenuck golf course & has a beautiful half mile long driveway. It's the perfect combination of privacy & accessibility to downtown great barrington. The home boasts over 7,000 sq. Ft. Of living space as well as an over 3,000 sq. Ft. 4 car garage. The house has 5 bedrooms & 3 full baths with two of those bedrooms & one bath located in a separate guest wing. The expansive primary bedroom suite has a separate sitting room & wall to wall windows. Three massive common areas include the living room, theater/game room & family room. Other rooms throughout include 2 offices, meditation tower, workout room, bonus room & indoor pool inside of a solarium. The kitchen is highlighted by a commercial viking range, custom cabinets,

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

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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21 Kalliste Great Barrington MA 01230

Great Barrington, MA21 Kalliste Hill

Price$2,400,000

Est. Mortgage: $/month

MLS Number 234767

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,900
  • Acreage 7.12

Privacy, expansiveness & spectacular views into ct! This contemporary cedar home is an idyllic, private sanctuary in a dream location featuring a hilltop swimming pool w/ stone patio, horse barn & room for horses, koi pond w/ bridge, mature landscaping, and beautiful stonework throughout. Perfectly sited on 7.123 acres, this property includes an extra building lot which would allow the construction of another residence making this the complete family compound! The spacious interior of this light-filled home with soothing earth tones & warm woods includes 3 brs, 2.5 bathrooms, open concept floor plan, office space, central a/c, jetted tub, screened porch, fireplace, skylights, and incredible views both inside & out. Gather year-round with friends & family at this spectacular retreat!

Listed by Douglas M Goudey of WHEELER & TAYLOR REALTY CO.,INC.'

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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21 Kalliste Great Barrington MA 01230

Great Barrington, MA21 Kalliste Hill

Price$1,900,000

Est. Mortgage: $/month

MLS Number 235495

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,900
  • Acreage 5.2

Privacy, expansiveness & spectacular views into ct! This contemporary cedar home is an idyllic, private sanctuary in a dream location featuring a hilltop swimming pool w/ stone patio, horse barn & room for horses, koi pond w/ bridge, mature landscaping, and beautiful stonework throughout. The spacious interior of this light-filled home with soothing earth tones & warm woods includes 3 brs, 2.5 bathrooms, open concept floor plan, office space, central a/c, jetted tub, screened porch, fireplace, skylights, and incredible views both inside & out. Gather year-round with friends & family at this spectacular retreat!

Listed by Douglas M Goudey of WHEELER & TAYLOR REALTY CO.,INC.'

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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684 Egremont Great Barrington MA 01230

Great Barrington, MA684 Egremont Rd

Price$1,695,000

Est. Mortgage: $/month

MLS Number 236863

  • Residential
  • Bathroom 20
  • Bedrooms 20
  • Square Feet 17,551
  • Acreage 10.43

Unique opportunity for the business-minded interested in purchasing a well-established gem of a bed & breakfast in the heart of the berkshires. Located minutes from cultural attractions w/ convenient access to boston/new york. Windflower inn welcomes guests w/ its wraparound porch & manicured grounds. The inn has 13 bedrooms each w/ their own private bath. Blending the charm of the past w/modern-day conveniences. The commercial grade kitchen & laundry meets the demands of a busy bed & breakfast. The kitchen includes double commercial ovens & has the potential for expansion for restaurant purposes. The 3 bedroom 2.5 bath cottage on site adds income potential. Owners also have a 4 bedroom 2 bath home currently used as innkeepers quarters. Potential for events/weddings/family compound.

Listed by Jessica L. Rizzo of BERKSHIRE DREAM HOME,INC.'

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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453 Stockbridge Great Barrington MA 01230

Great Barrington, MA453 Stockbridge Rd

Price$1,390,000

Est. Mortgage: $/month

MLS Number 232573

  • Residential
  • Bathroom 15
  • Bedrooms 14
  • Square Feet 10,302
  • Acreage 2.4

Perfect for large family or other looking to utilize10,000 sf plus of space for dwelling or other mixed-use purposes. Current configuration has 13 guest suites plus the owners' apartment. Full commercial-level kitchen with large dining spaces, bar/tavern area and other spaces for offices, etc.

Listed by Thomas K. Doyle,Sr. of LANCE VERMEULEN RE,INC'

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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34 Castle Hill Great Barrington MA 01230

Great Barrington, MA34 Castle Hill Ave

Price$1,375,000

Est. Mortgage: $/month

MLS Number 237554

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,581
  • Acreage 1.66

This turn of the century victorian home sits pride of place on ''the hill', just a few minutes walk to downtown great barrington. Tastefully updated, the home still displays the fine details and charm of yesteryear. Double pocket doors throughout the first floor allow for a flow from living spaces with wood burning fireplaces through to the kitchen and dining areas. A walkthrough butlers pantry off the kitchen leads you to the perfect office space, and then to the screened in porch. The second floor laundry is perfectly situated for the three bedrooms and two newly renovated full baths, one being the primary. A well maintained attic space with high ceilings and the oversized two floor barn have many possibilities for work spaces or storage, and all this on 1.6 acres.Welcome to castlehill

Listed by Fintan T Hanley of BERKSHIRE PROPERTY AGENTS,LLC'

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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34 Seekonk Cross Great Barrington MA 01230

MLS Number 237915

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,177
  • Acreage 2.03

This magical country lifestyle awaits you! Unspoiled charming new england farmhouse with views across neighboring pasture & barns to the mountains beyond. An 1800's stage coach stop, this cozy home retains many original details, king's boards floors and original fireplaces. Presently a two family house, with a wonderful apartment with separate entrance. The backyard is an oasis to find peace after a busy day. Extensive perennials, vintage peonies, iris, day lilies, vintage roses and a small herb garden, fruit trees and berry patches. Simplicity defined when relaxing on the rocking chair front porch. Detached barn and a workshop. Update or renovate this jewel. Embrace the country life.

Listed by Helen Mullany of HELEN MULLANY REAL ESTATE,LLC'

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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35 Silver Great Barrington MA 01230

Great Barrington, MA35 Silver St

Price$1,195,000

Est. Mortgage: $/month

MLS Number 238036

  • Residential
  • Bathroom 5
  • Bedrooms 10
  • Square Feet 6,832
  • Acreage 4.37

This remarkable property on over four acres near the heart of great barrington offers a serene setting of private ponds and views over agricultural fields. Three units make up over 6000 square feet, each offering individual sun porches, basement spaces and utilities. Unit a offers a first floor primary bedroom, a full bathroom including washer and dryer, and office. Four additional bedrooms and bathroom on the second floor. Units b and c each offer three bedrooms and one bathroom. The property will be unoccupied to allow the future owner an easy transition to their own vision.

Listed by Samantha A. Homeyer and Molly DiGiovanni of HOUSATONIC REAL ESTATE'

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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18 Kalliste Great Barrington MA 01230

Great Barrington, MA18 Kalliste Hill

Price$1,150,000

Est. Mortgage: $/month

MLS Number 238061

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,960
  • Acreage 1.79

Classic ''wellenkamp'' custom built contemporarysurrounded by almost 2 acres of privacy and mature landscaping. Soaring great room with a wall of windows and wood burning fireplace, open to dining/eat-in kitchen and direct access to a fabulous screened porched and expansive decking. Main level primary bedroom with generous sitting area and en suite bath, den/office with a wall of built-ins, two spacious guest bedrooms on the upper level and an attached two car garage complete this special offering minutes from a quiet oasis to the center of great barrington and all the action!

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

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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Lot 7 Thrushwood Great Barrington MA 01230
Pending

MLS Number 233428

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 3,808
  • Acreage 1.46

Pool community: build your dream home: open plan living with, first floor master, fireplace, screened porch, high ceilings, two car garage, community pool. Hoa covers all lawn maintenance, plowing, shoveling up to the front door. Quality new construction. This price cannot be matched. 10 months to move into your beautiful new home. Photos are from a similar home with the same floor plan in the community, with upgrades. Build your dream home on one of the other beautiful lots. Single level with 2100 square feet or as large as 3800 square feet. 3-5 bedrooms.

Listed by Maureen White Kirkby and Michael Harrigan of BERKSHIRE HATHAWAY HOMESERVICESBARNBROOK REALTY'

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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Lot 9 Thrushwood Great Barrington MA 01230
Pending

MLS Number 233442

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 3,808
  • Acreage 1.46

Pool community: build your dream home: open plan living with, first floor master, fireplace, screened porch, high ceilings, two car garage, community pool. Hoa covers all lawn maintenance, plowing, shoveling up to the front door. Quality new construction. This price cannot be matched. 10 months to move into your beautiful new home. Photos are from a similar home with the same floor plan in the community, with upgrades. Build your dream home on one of the other beautiful lots. Single level with 2100 square feet or as large as 3800 square feet. 3-5 bedrooms with prices beginning at $689,000.

Listed by Maureen White Kirkby and Michael Harrigan of BERKSHIRE HATHAWAY HOMESERVICESBARNBROOK REALTY'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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Lot 10 Thrushwood Great Barrington MA 01230
Pending

MLS Number 233069

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 3,808
  • Acreage 1.46

Pool community: build your dream home: open plan living with, first floor master, fireplace, screened porch, high ceilings, two car garage, community pool. Hoa covers all lawn maintenance, plowing, shoveling up to the front door. Quality new construction. This price cannot be matched. 10 months to move into your beautiful new home. Photos are from a similar home with the same floor plan in the community, with upgrades. Build your dream home on one of the other beautiful lots. Single level with 2100 square feet or as large as 3800 square feet. 3-5 bedrooms with prices beginning at $689,000.

Listed by Maureen White Kirkby and Michael Harrigan of BERKSHIRE HATHAWAY HOMESERVICESBARNBROOK REALTY'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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Lot 8 Thrushwood Great Barrington MA 01230
Pending

MLS Number 233429

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 3,808
  • Acreage 1.46

Pool community: build your dream home: open plan living with, first floor master, fireplace, screened porch, high ceilings, two car garage, community pool. Hoa covers all lawn maintenance, plowing, shoveling up to the front door. Quality new construction. This price cannot be matched. 10 months to move into your beautiful new home. Photos are from a similar home with the same floor plan in the community, with upgrades. Build your dream home on one of the other beautiful lots. Single level with 2100 square feet or as large as 3800 square feet. 3-5 bedrooms with prices beginning at $689,000.

Listed by Maureen White Kirkby and Michael Harrigan of BERKSHIRE HATHAWAY HOMESERVICESBARNBROOK REALTY'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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118 Hollenbeck Great Barrington MA 01230
Pending

MLS Number 236715

  • Residential
  • Bathroom 3
  • Bedrooms 6
  • Square Feet 3,132
  • Acreage 0.42

Just a short distance from town, find all the space you are looking for! This beautiful home is located on castle hill and central to all things great barrington. This home boasts a spacious interior with endless possibilities. There are two lovely porches and a large back patio for hosting and relaxing. The backyard offers serine privacy right in town. This property is located 1/10 of a mile from lake mansfield. With six bedrooms and an office, there is room for everyone! There is a two-car garage and sizable driveway to provide ample parking. This rare find on the hill will only be available once! Come take a look today!

Listed by India Ward of NON-MEMBER: Reciprocal'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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 June 30, 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.