Great Barrington, MA Homes

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  /9

  Est $393,998 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft

  148 Hillsdale Rd, Great Barrington, MA 01230

  148 Hillsdale Rd, Great Barrington, MA 01230
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• 

  

  

  /60

  $1,250,000

  • 3 Beds
  • 2.5 Baths
  • 2,204 Sq Ft

  905 West Rd, Great Barrington, MA 01230

  Welcome to Serenity Hill.This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road.

  William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  905 West Rd, Great Barrington, MA 01230
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  /24

  $440,000 Sold Oct 31, 2025

  • 1,500 Sq Ft
  • $293/SF
  • 3 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1900

  3 Benton Ave, Great Barrington, MA 01230

  On the hill overlooking downtown Great Barrington. Minutes away from the center of town. Inside, you'll find four bedrooms, a full bath, and plenty of versatile living space. Whether you're looking for a home office, playroom, or formal dining area, the flexible floor plan allows for endless possibilities. Endless opportunities with a little bit of love. Don't miss this opportunity to own a

  Adam Dingman BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  3 Benton Ave, Great Barrington, MA 01230
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  /20

  Est $346,759 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  9 Forest Row, Great Barrington, MA 01230

  9 Forest Row, Great Barrington, MA 01230
• 

  

  

  /41

  $889,000

  • 4 Beds
  • 2.5 Baths
  • 2,114 Sq Ft

  11 Prospect St, Great Barrington, MA 01230

  Situated on Great Barrington's highly sought after neighborhood of 'The Hill', 11 Prospect delivers on style, convenience and of course, location! This four bedroom home with two and a half baths over three floors and hardwood floors throughout, offers lots of room for family and friends. An oversized screened in porch, attached two car garage and a finished basement are just some of the 'must

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  11 Prospect St, Great Barrington, MA 01230
• 

  

  /40

  $1,200,000 Sold Oct 31, 2025

  • 2,500 Sq Ft
  • $480/SF
  • 146 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2003

  247 Peter Menaker Rd, Great Barrington, MA 01230

  Experience the epitome of luxury and leisure in this exceptional custom-built contemporary home, nestled within a prestigious lakefront community. Sited on over four acres, this property offers exclusive access to a private beach and tennis courts, ensuring a lifestyle of both privacy and recreation. Boasting a sun-filled open floor plan, this residence features three well-appointed bedrooms and

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  247 Peter Menaker Rd, Great Barrington, MA 01230
• 

  

  /46

  Est $984,786 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,078 Sq Ft

  11 Oak St, Great Barrington, MA 01230

  11 Oak St, Great Barrington, MA 01230
• 

  

  /52

  $935,000

  • 4 Beds
  • 2.5 Baths
  • 2,631 Sq Ft

  20 Cooper Rd, Great Barrington, MA 01230

  This is the one you've been waiting for. A classic mid-century home on over 4 private acres, offering the ultimate Berkshire lifestyle. The bright, open-mid century floor plan provides a seamless flow, while two fireplaces add classic comfort. The home features 4 bedrooms, 3 baths, large office and a media room, offering flexibility for family and guests. Outside, your private resort awaits. A

  Tony Segalla LANCE VERMEULEN RE, INC

  20 Cooper Rd, Great Barrington, MA 01230
• 

  

  /10

  $445,000 Sold Oct 31, 2025

  • 1,479 Sq Ft
  • $301/SF
  • 240 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1943

  26 Manville St, Great Barrington, MA 01230

  Charming Updated Cape Style Home in Prime Great Barrington LocationDiscover this beautifully renovated three-bedroom, two-bath Cape style home nestled in a coveted in-town neighborhood of Great Barrington. Thoughtfully updated with modern touches, this inviting residence offers a perfect blend of classic charm and contemporary comfort.Inside, enjoy gleaming hardwood floors throughout the main

  Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  26 Manville St, Great Barrington, MA 01230
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  /4

  Est $739,150 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  1609 County Rd, Great Barrington, MA 01230

  1609 County Rd, Great Barrington, MA 01230
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  /37

  $796,000

  • 2 Beds
  • 2 Baths
  • 1,622 Sq Ft

  324 Park St, Great Barrington, MA 01230

  Architectural gem with lots of glass perched like a treehouse on the backside of Monument Mountain. The open, mid-century modern home was built in 2012 for maximum light, efficiency, and provides glittering views through the trees of the Housatonic River! 2 bedroom, 2 full baths-both ensuite + central AC, and a Scandinavian soapstone wood stove, permit included! Minutes from hiking trails, Taft

  Claudia Laslie LANCE VERMEULEN RE, INC

  324 Park St, Great Barrington, MA 01230
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  /51

  $617,000 Sold Oct 30, 2025

  • 2,885 Sq Ft
  • $214/SF
  • 5 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1956

  69 Welcome St, Great Barrington, MA 01230

  CHARMING, SPACIOUS RANCH walk to town center and Lake Mansfield. Gorgeous Goshen stone staircase leading to 3 season screened in porch. Offering mid-century style open plan filled with natural light. Livingroom with wood burning fireplace and south facing windows to East Mountain. Primary BR is 16 x 20 with ensuite, 3 additional bedrooms and full bath. Cozy wood paneled den. TWO additional rooms

  Rosemary Baumann LANCE VERMEULEN RE, INC

  69 Welcome St, Great Barrington, MA 01230
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  /42

  Est $438,763 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,368 Sq Ft

  685 Stockbridge Rd, Great Barrington, MA 01230

  685 Stockbridge Rd, Great Barrington, MA 01230
• 

  

  /31

  $945,000

  • 2 Beds
  • 2 Baths
  • 1,620 Sq Ft

  18 Creamery Rd, Great Barrington, MA 01230

  Nestled on 6.6 peaceful acres, this beautifully renovated country Cape offers exceptional privacy just minutes from town. Set well back from the road, the home enjoys a quiet, convenient location surrounded by mature trees and gardens.Inside, a spacious dining room features a striking stone fireplace, while the large living room showcases wood floors that extend throughout. Every detail has been

  Allison Rada STONE HOUSE PROPERTIES, LLC

  18 Creamery Rd, Great Barrington, MA 01230
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  /45

  $1,400,000 Sold Oct 27, 2025

  • 2,900 Sq Ft
  • $483/SF
  • 123 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1981

  21 Kalliste Hill, Great Barrington, MA 01230

  SWEEPING MOUNTAIN VIEWS less than 5 minutes to Main Street. Sited on 5+ acres, this stylish contemporary is located in the most desirable section of Great Barrington. The home has an open living/dining/kitchen floor plan with a gas fireplace and huge windows taking in the view. A screened porch is conveniently located off the kitchen. The first floor also has a primary bedroom suite with full

  Tom Lynch COMPASS MASSACHUSETTS , LLC GB

  21 Kalliste Hill, Great Barrington, MA 01230
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  /27

  Est $575,210 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,561 Sq Ft

  24 Manville St, Great Barrington, MA 01230

  24 Manville St, Great Barrington, MA 01230
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  /36

  $775,000

  • 10 Beds
  • 4 Baths
  • 5,293 Sq Ft

  458 Monterey Rd, Great Barrington, MA 01230

  This rare find, located on the Great Barrington/Monterey line, offers the right buyer a unique opportunity to live, work, and play in the heart of the Berkshires. Situated on 4.32 acres, this 1958 ranch-style home has evolved over the years into a sprawling 5,200 square-foot property boasting endless potential. While it currently serves as an owner-operated wellness facility, an expansive

  Cortney Dupont COHEN & WHITE ASSOCIATES

  458 Monterey Rd, Great Barrington, MA 01230
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  /30

  $795,000 Sold Oct 24, 2025

  • 1,881 Sq Ft
  • $423/SF
  • 21 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1985

  80 Taconic Ave Unit 14, Great Barrington, MA 01230

  A stunning condo nestled just minutes from the heart of downtown. This is the largest corner unit, strategically positioned to capture both the vibrant East and serene South-facing views, ensuring an abundance of natural light. Soaring cathedral ceilings that enhance the spaciousness. The entryway features a private mudroom, an updated kitchen that is equipped with modern amenities and a private

  Suzann Ward HOUSATONIC REAL ESTATE

  80 Taconic Ave Unit 14, Great Barrington, MA 01230
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  /41

  Est $483,168 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft

  533 Main St, Great Barrington, MA 01230

  533 Main St, Great Barrington, MA 01230
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  /76

  $950,000

  • 3 Beds
  • 4 Baths
  • 2,900 Sq Ft

  29 Old Village Rd, Great Barrington, MA 01230

  First-time for this treasured dwelling to be available for purchase. This magical setting surrounded by lush gardens and plantings is just the beginning of the enchantment. Distant mountain views to the east brings your viewscape to Butternut Ski & beyond. Inside the dwelling is a large open living space & kitchen on the first floor. Separately, there is a first-floor Ensuite. Abutting the first

  Thomas Doyle, Sr. BISHOP WEST REAL ESTATE

  29 Old Village Rd, Great Barrington, MA 01230
• 

  

  /21

  $695,000 Sold Oct 23, 2025

  • 1,680 Sq Ft
  • $414/SF
  • 68 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1949

  111 Castle Hill Ave, Great Barrington, MA 01230

  Just around the corner from lovely Lake Mansfield in Great Barrington this comfortable cape is located in a most desirable site on the 'Hill'. Surrounded by blooming shrubs and trees, this 3 bedroom, two bath home has great classic character. Living room with fireplace, separate dining room, and an unfinished walkout allow potential expansion. Perfect spot to access biking, swimming, kayaking and

  Martha Piper THE KINDERHOOK GROUP

  111 Castle Hill Ave, Great Barrington, MA 01230
• 

  

  /42

  Est $861,335 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 3,372 Sq Ft

  4 Kirk St, Housatonic, MA 01236

  4 Kirk St, Housatonic, MA 01236
• 

  

  /59

  $899,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 4,072 Sq Ft

  311 N Plain Rd, Housatonic, MA 01236

  This historic 4-bedroom 3.5-bath home sits on a beautifully landscaped 1-acre lot surrounded by ornamental trees, vibrant flower gardens and mature plantings. Originally built around 1800, this comfortable well-maintained house features high ceilings, warm wood flooring, and plenty of period charm. The main level welcomes you with a spacious living room accented with Greek Revival moldings, an

  Vashti Poor LANCE VERMEULEN RE, INC

  311 N Plain Rd, Housatonic, MA 01236
• 

  

  /43

  $435,000 Sold Oct 22, 2025

  • 1,535 Sq Ft
  • $283/SF
  • 4 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1948

  272 Park St, Great Barrington, MA 01230

  This charming Cape-style home welcomes you with a spacious, heated mudroom that opens into a bright kitchen and dining area. The living room features a cozy fireplace with a pellet stove insert, built-in shelving, and abundant natural light. The first-floor primary suite includes a large bathroom with a double vanity and soaking tub, while a convenient half bath with laundry completes the main

  Katie Williams STONE HOUSE PROPERTIES, LLC

  272 Park St, Great Barrington, MA 01230
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  /54

  Est $1,122,736 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 2,940 Sq Ft

  16 Seekonk Rd, Great Barrington, MA 01230

  16 Seekonk Rd, Great Barrington, MA 01230
• 

  

  /11

  $829,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 3,808 Sq Ft

  10 Thrushwood Ln, Great Barrington, MA 01230

  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

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  10 Thrushwood Ln, Great Barrington, MA 01230
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  /26

  $495,000 Sold Oct 17, 2025

  • 717 Sq Ft
  • $690/SF
  • 10 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2019

  34 Bridge St Unit 204, Great Barrington, MA 01230

  Discover effortless living in this beautifully appointed 1-bedroom, 1-bath condo located in the heart of Great Barrington. Just steps from shops, restaurants, cafes, and all the charm this vibrant town has to offer, this fully furnished unit is elegant and efficient.Step inside to a bright, open living space featuring high-end finishes and a south-facing Juliette balcony that overlooks peaceful &

  Paige Paluch LANCE VERMEULEN RE, INC

  34 Bridge St Unit 204, Great Barrington, MA 01230
• 

  

  /24

  Est $665,113 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,073 Sq Ft

  163 N Plain Rd, Great Barrington, MA 01230

  163 N Plain Rd, Great Barrington, MA 01230
• 

  

  /38

  $799,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,695 Sq Ft

  6 Lake Buel Rd, Great Barrington, MA 01230

  Welcome to 6 Lake Buel Road--a stunningly renovated 3-bedroom, 2-bathroom home set on 3.5 private acres in one of the Berkshires' most desirable locations. Just 1 minute to Butternut Ski Resort and 7 minutes to downtown Great Barrington, this property offers the perfect balance of peaceful seclusion and year-round convenience.Gutted and fully renovated within the last five years, the home

  Jessie Bennett WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  6 Lake Buel Rd, Great Barrington, MA 01230
• 

  

  /33

  $395,000 Sold Oct 14, 2025

  • 1,425 Sq Ft
  • $277/SF
  • 13 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1949

  375 N Plain Rd, Great Barrington, MA 01230

  Beautiful brick faced Cape situated on a lovely corner lot and conveniently located to Berkshire attractions and the Williams River. This charming property has great natural light, character and inviting outdoor spaces. Gracious living room with fireplace and wood flooring, renovated kitchen with Island, dining area with picture window and first floor bedroom with half bath complete the main

  Cortney Dupont COHEN & WHITE ASSOCIATES

  375 N Plain Rd, Great Barrington, MA 01230
• 

  

  /28

  Est $487,698 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  29 Commonwealth Ave, Great Barrington, MA 01230

  29 Commonwealth Ave, Great Barrington, MA 01230
• 

  

  /43

  $925,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,062 Sq Ft

  14 Copper Beech Ln, Great Barrington, MA 01230

  The Country Village Condominiums on Copper Beech Lane remain Great Barrington's premier townhouse condos. Rarely available for sale, Unit 14 is one of few with a two-car garage and a wraparound deck facing south and west. This light-filled end unit offers privacy and three exposures. The kitchen features generous counter space and a bright breakfast area, while the living/dining room opens to the

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  14 Copper Beech Ln, Great Barrington, MA 01230
• 

  

  /61

  $949,000 Sold Oct 14, 2025

  • 3,802 Sq Ft
  • $250/SF
  • 20 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2000

  69 Corser Hill Rd, Great Barrington, MA 01230

  Stunning Contemporary Colonial with Panoramic Views of the Berkshire Hills.Experience the magic of the Berkshires from this immaculate Colonial home, nestled in a lush, green landscape with breathtaking, unobstructed views. Located in low-tax New Marlborough and just under 15 minutes to downtown Great Barrington, this home offers the perfect balance of tranquility and convenience. Inside, you'll

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  69 Corser Hill Rd, Great Barrington, MA 01230
• 

  

  /30

  Est $377,435 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 812 Sq Ft

  27 Blue Hill Rd, Great Barrington, MA 01230

  27 Blue Hill Rd, Great Barrington, MA 01230
• 

  

  /36

  $845,000 Under Contract

  • 4 Beds
  • 1.5 Baths
  • 1,952 Sq Ft

  115 Baldwin Hill Rd S, Great Barrington, MA 01230

  Beautifully appointed four-bedroom, one-and-a-half-bath contemporary New England farmhouse, perfectly situated in Egremont's most desirable location, Baldwin Hill. This thoughtfully designed residence blends timeless farmhouse charm with light filled rooms, delivering a serene retreat with spectacular Berkshire views. Protected land both front and rear ensure these views are protected for

  Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  115 Baldwin Hill Rd S, Great Barrington, MA 01230
• 

  

  /22

  $495,000 Sold Oct 10, 2025

  • 711 Sq Ft
  • $696/SF
  • 75 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2019

  34 Bridge St Unit 202, Great Barrington, MA 01230

  Located in the coveted Powerhouse Square, this stylish 1-bedroom, 1-bath condo offers modern, carefree living right in the center of downtown Great Barrington. Built in 2019 and perched just above the Berkshire Food Co-op, this upscale unit is part of a premium 22-residence community with elevator access, secure entry, and designated parking.Step inside to an open-concept kitchen and living area,

  Paige Paluch LANCE VERMEULEN RE, INC

  34 Bridge St Unit 202, Great Barrington, MA 01230
• 

  

  /19

  Est $477,815 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft

  14 Humphrey St, Great Barrington, MA 01230

  14 Humphrey St, Great Barrington, MA 01230
• 

  

  /58

  $1,995,000

  • 6 Beds
  • 2.5 Baths
  • 4,138 Sq Ft

  32 Benton Ave, Great Barrington, MA 01230

  Spectacular 1896 Victorian on The Hill, completely and stylishly renovated in 2025! This six-bedroom beauty seamlessly blends original floors and grand woodwork with all-new, high-efficiency systems. Key 2025 updates include full insulation, exterior paint and two new upstairs luxury baths. 2024 brought fully ducted Air Source Heat Pumps (central AC/heating) and new windows. A 2023 heat pump

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  32 Benton Ave, Great Barrington, MA 01230
• 

  

  /16

  $125,000 Sold Oct 10, 2025

  • 1,092 Sq Ft
  • $114/SF
  • 18 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1936

  386 N Plain Rd, Great Barrington, MA 01230

  Charming 1930s Bungalow with Privacy and Potential! Tucked away on nearly an acre (.93 acres) of land with direct access to the scenic Rail Trail, this classic 1930s bungalow is an opportunity for investors, contractors, or anyone looking to restore a gem. Terrific bones and a tranquil setting--perfect for a weekend retreat or full-time residence. Located within walking distance to the heart of

  John Segalla HOUSATONIC REAL ESTATE

  386 N Plain Rd, Great Barrington, MA 01230
• 

  

  /37

  Est $1,027,918 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,499 Sq Ft

  225 Long Pond Rd, Great Barrington, MA 01230

  225 Long Pond Rd, Great Barrington, MA 01230

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