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.

250 Long Pond Rd Great Barrington MA 01230

Price$8,750,000

Est. Mortgage: $/month

MLS Number 225029

  • Single Family
  • Address 250 Long Pond Rd
  • 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.

Courtesy of Non-member

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Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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20 Berkshire Heights Rd Great Barrington MA 01230

MLS Number 223462

  • Single Family
  • Year Built 1915
  • Bedrooms 6
  • Bathroom 7
  • Total Full Baths 5

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.

Courtesy of BERKSHIRE PROPERTY AGENTS, LLC

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Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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267 Long Pond Rd Great Barrington MA 01230

Price$1,749,000

Est. Mortgage: $/month

MLS Number 226290

  • Single Family
  • Address 267 Long Pond Rd
  • 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.

Courtesy of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

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Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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280 Division St Great Barrington MA 01230

Price$1,550,000

Est. Mortgage: $/month

MLS Number 218213

  • Single Family
  • Address 280 Division St
  • 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.

Courtesy of COHEN & WHITE ASSOCIATES

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Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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14 Monument Valley Rd Great Barrington MA 01230

MLS Number 219997

  • Single Family
  • Year Built 1964
  • Parking Spaces 3
  • Bedrooms 5
  • Bathroom 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

Courtesy of STONE HOUSE PROPERTIES, LLC

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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24 Locust Hill Rd Great Barrington MA 01230

Price$1,350,000

Est. Mortgage: $/month

MLS Number 225834

  • Single Family
  • Address 24 Locust Hill Rd
  • 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.

Courtesy of BERKSHIRE PROPERTY AGENTS, LLC

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Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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10 Haley Rd Great Barrington MA 01230

Price$1,300,000

Est. Mortgage: $/month

MLS Number 223182

  • Single Family
  • Address 10 Haley Rd
  • 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.''

Courtesy of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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6 & 8 Berkshire Heights Rd Great Barrington MA 01230

MLS Number 222829

  • Single Family
  • Year Built 2007
  • Parking Spaces 2
  • Bedrooms 5
  • Bathroom 6

Magnificent Great Barrington turn-key home in coveted ''The Hill'' neighborhood. A rare opportunity to live in a tranquil pastoral setting, in walking distance to vibrant downtown Great Barrington. Spacious1st floor master suite w/ luxurious master bath, state-of-the-art sun filled gourmet eat-in kitchen, spectacular large living room w/ stone fireplace and cathedral ceilings, beautiful finished lower level. Top of the line finishes throughout. Loads of sunlight & open floor plan. Large, level backyard w/ mature plantings, patio & meditation garden. The perfect home for entertaining family & friends or relaxing with your favorite book in front of the fireplace. Close to the Berkshires' premier cultural attractions. Your Berkshires paradise awaits!

Courtesy of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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58 Hollenbeck Ave Great Barrington MA 01230

Price$1,274,998

Est. Mortgage: $/month

MLS Number 222559

  • Single Family
  • Address 58 Hollenbeck Ave
  • Year Built 1918
  • Bedrooms 4
  • Bathroom 3

A Perfect Family Home in Great Barrington 's premiere neighborhood. Minutes to both Ski Butternut and Catamount Ski slopes with amazing ski programs for the entire family, also within walking distance to downtown restaurants and shops and movies. Room for kids to play inside and out. A cooks dream kitchen, plaster walls, 5 fireplaces, sun room, eat in kitchen, formal dining, office, four bedrooms, large family/game/media room and more. Beautiful back yard with stone patio for grilling and family parties, mature gardens and a glass conservatory/greenhouse. It can be used for growing your favorite newly legalized plants or meditation. Some of its extraordinary features: Rocky Mountain bronze hardware and solid kitchen sink, marble counters. This is a truly unique and beautiful home.

Courtesy of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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443 To 454 Monterey Rd Great Barrington MA 01230

MLS Number 221283

  • Single Family
  • List Date 10/31/2017

MOTIVATED SELLER (s) FIVE PARCELS in Gt.Barrington, MA on North & South sides of (Rt#23 E) Monterey Rd. Formerly a campus including housing, classrooms, athletic fields, buildable land & existing fiber connectivity it is zoned residential (R-2) which by right include single family dwellings, government owned or non-profit educational facilities, municipal parks, agricultural uses & swimming pools. Uses allowed by special permit include two-family dwellings, lodging houses, private schools, summer camps, country clubs, and professional buildings. Easily accessible in the heart of Southern Berkshire County three miles from downtown Gt. Barrington this property being sold ''as is''.

Courtesy of BERKSHIRE PROPERTY AGENTS, LLC

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Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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94 West Ave Great Barrington MA 01230

Price$1,200,000

Est. Mortgage: $/month

MLS Number 223931

  • Single Family
  • Address 94 West Ave
  • Year Built 1900
  • Bedrooms 4
  • Bathroom 3

Stately elegance yet classic and comfortable and beautifully restored for the 21st century.

Courtesy of LANCE VERMEULEN RE, INC

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Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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13 East Mountain Rd Great Barrington MA 01230

MLS Number 225201

  • Single Family
  • Address 13 East Mountain Rd
  • Year Built 1995
  • Parking Spaces 2
  • Bedrooms 3

Beautiful Contemporary home on a quiet private road, within the reach of Butternut Ski Area. Country cherry floors and plenty of light throughout. Open kitchen/ family room area, separate dining room. Mountain views from Living/ Dining and Master Bedroom. Two sided wood burning fireplace between family and living rooms. Wet bar in the family room. Large bedrooms with their own private bathrooms and walk in closets.Screened In Porch in front and a private patio in the rear of the property create an additional entertainment space.

Courtesy of STONE HOUSE PROPERTIES, LLC

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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170 Christian Hill Rd Great Barrington MA 01230

MLS Number 221876

  • Single Family
  • Year Built 1984
  • Parking Spaces 3
  • Bedrooms 4
  • Bathroom 4

Country living not far from town, a long drive leads to a private 4000+ sf, 4 bedroom, 4 bath home surrounded by 15 acres of sunny lawn, 20-tree orchard, pastures, and a woodland trail in the forest. Both the large living room and eat-in kitchen great room open to a south-facing stone terrace; one with a fireplace and the other a wood stove. A unique screened porch is in a restored corn silo - a most unique place to entertain guests. Also on the first floor are a den/office, a mud room for winter wear and sports equipment, along with a laundry and caretaker office. A large master suite with a fireplace, and three guest bedrooms and bath are on the second floor. The lower level holds media and

Courtesy of BERKSHIRE PROPERTY AGENTS, LLC

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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44 Bridge St # 1/2/303, 1/2/305, 110/210/310 Great Barrington MA 01230

MLS Number 217571

  • Condominium Residential - Condo/Townhouse
  • Elementary School Muddy Brook Reg.
  • Co Listing Office Id 486
  • Middle School Monument Valley Reg.
  • High School Monument Mountain

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 study, 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.

Courtesy of BERKSHIRE PROPERTY AGENTS, LLC

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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4 East Mountain Rd Great Barrington MA 01230

MLS Number 223259

  • Single Family
  • Address 4 East Mountain Rd
  • Year Built 2006
  • Parking Spaces 2
  • Bedrooms 4

Spacious, light-filled Arts & Crafts Contemporary in a private setting, minutes from Butternut Ski Resort, Great Barrington restaurants & shops, cultural venues, and outdoor recreation. Custom Arts & Crafts details enhance interiors throughout this supremely comfortable home. The main level comprises a spacious master suite, living room with stone fireplace & cathedral ceiling, cook's kitchen with granite countertops, dining area, and deck. Upstairs, is a comfortable arrangement of three bedrooms, including a second master, and laundry. The walk-out lower level features a family room with home entertainment area, space for billiard/ping pong table, and compact home gym or office space. Tucked into a pretty woods threaded with mountain laurel, and discrete mountain views.

Courtesy of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$
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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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6 Deer Trail Great Barrington MA 01230

Price$899,000

Est. Mortgage: $/month

MLS Number 225120

  • Single Family
  • Address 6 Deer Trail
  • Year Built 1983
  • Parking Spaces 2
  • Bedrooms 4

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.

Courtesy of STONE HOUSE PROPERTIES, LLC

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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44 Bridge St # 101, 201, 301 Great Barrington MA 01230

MLS Number 218549

  • Condominium Residential - Condo/Townhouse
  • Elementary School Muddy Brook Reg.
  • Co Listing Office Id 486
  • Middle School Monument Valley Reg.
  • High School Monument Mountain

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.

Courtesy of BERKSHIRE PROPERTY AGENTS, LLC

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$
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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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154 Division St Great Barrington MA 01230

Price$875,000

Est. Mortgage: $/month

MLS Number 224992

  • Single Family
  • Address 154 Division St
  • Year Built 1986
  • Parking Spaces 2
  • Bedrooms 4

Architecturally designed by a local builder. This home has everything one would need. A wonderful floor plan to entertain. Home offers a 1st floor master bedroom/bath. 2 wood burning fireplaces for warmth and atmosphere in living room and great room. Gorgeous wood floors throughout. An eat in cook's kitchen with formal Dining room. Full AC throughout. 3 additional bedrooms and bath on 2nd floor. Relax on the back deck and patio which overlooks beautiful gardens and a small pond. Enjoy a private hot tub off master bedroom deck area.

Courtesy of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

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$
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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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20 Wright Ln Great Barrington MA 01230

Price$875,000

Est. Mortgage: $/month

MLS Number 223632

  • Single Family
  • Address 20 Wright Ln
  • Year Built 1974
  • Bedrooms 4
  • Bathroom 3

This one-level contemporary home will transport you to a peaceful enclave with easy access to downtown Great Barrington. Set on 20 enchanting, private acres with lush greenery, a deck leading to secluded frontage on the Williams River, the open, sunny, floor plan has vaulted ceilings, a great room with fireplace, master suite with fireplace, second bedroom with fireplace and two additional bedrooms. Enjoy the private heated pool, patio and three unique outbuildings, in addition, to a small guest cottage/studio, enchanting custom tree house, and walking paths throughout the property.An absolutely magical place, truly one of a kind.

Courtesy of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$
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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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100 West Sheffield Rd Great Barrington MA 01230

MLS Number 225861

  • Single Family
  • Year Built 2000
  • Parking Spaces 3
  • Bedrooms 4
  • Bathroom 5

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.

Courtesy of STONE HOUSE PROPERTIES, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

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