Great Barrington, MA Homes

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  /39

  $595,000

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft

  6 Blue Hill Rd, Great Barrington, MA 01230

  Set on a deep, level one-acre lot, this colonial offers a nice balance of space, privacy, and neighborhood convenience. The front entry opens to an inviting staircase that leads upstairs to three bedrooms and a shared full bath. The main level includes a comfortable living room with a fireplace and back door opening to a covered porch overlooking the fenced backyard and in-ground pool.A bright

  Paige Paluch LANCE VERMEULEN RE, INC

  6 Blue Hill Rd, Great Barrington, MA 01230
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  /34

  $919,000 Sold Oct 03, 2025

  • 1,782 Sq Ft
  • $516/SF
  • 75 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2021

  10 Terra Ferma Dr, Egremont, MA 01230

  Escape the expected and discover the art of effortless living on Terra Ferma Drive. Tucked away on a private dead-end road in coveted South Egremont, this nearly new (built within 5 years) residence redefines one-level luxury. Imagine a home where every detail is designed for comfort and ease - no steps, just seamless flow leading you first to a beautifully appointed kitchen, the true heart of

  Tony Segalla LANCE VERMEULEN RE, INC

  10 Terra Ferma Dr, Egremont, MA 01230
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  /7

  Est $401,907 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,498 Sq Ft

  102 Egremont Plain Rd, Great Barrington, MA 01230

  102 Egremont Plain Rd, Great Barrington, MA 01230
• 

  

  

  /23

  $525,000

  • 4 Beds
  • 2 Baths
  • 1,964 Sq Ft

  41 Pearl St Unit 1-2, Great Barrington, MA 01230

  Welcome to 41 Pearl Street- a 1900s two-family residence nestled on a quiet street just moments from downtown Great Barrington. This spacious 4-bedroom, 2-bathroom (both sides are 2 BR/1 BA) home offers 1,964 square feet of living space on a generous 0.25-acre lot, blending classic charm with modern comfort.Step inside to discover a welcoming floor plan with ample natural light, hardwood floors,

  David Carlson FAIRGROUND REAL ESTATE, INC

  41 Pearl St Unit 1-2, Great Barrington, MA 01230
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  /29

  $550,000 Sold Oct 01, 2025

  • 1,456 Sq Ft
  • $378/SF
  • 9 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1981

  150 Alford Rd, Great Barrington, MA 01230

  Inviting Mid-Century Inspired Berkshire Home with Trails Next Door!Just minutes from downtown Great Barrington, this mid-century inspired deck house offers an inviting retreat with an easy connection to nature. Set into the hillside, the home is surrounded by trees and bordered by the 583-acre Tom Ball Mountain Reserve, where trails, stone walls, and boardwalks lead through forest and wetlands

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  150 Alford Rd, Great Barrington, MA 01230
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  /17

  Est $379,554 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,164 Sq Ft

  359 State Rd, Great Barrington, MA 01230

  359 State Rd, Great Barrington, MA 01230
• 

  

  /70

  $2,250,000

  • 4 Beds
  • 6 Baths
  • 4,846 Sq Ft

  302 Egremont Plain Rd, Great Barrington, MA 01230

  A completely transformed barn renovated into a chic home with every modern convenience. Located in the desirable town of Egremont and just minutes from Great Barrington, this delightful property offers long-range pasture views with the Green River just beyond.Thoughtful living spaces for every walk of life featuring a roomy primary suite on the first floor, an additional primary suite that

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  302 Egremont Plain Rd, Great Barrington, MA 01230
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  /29

  $485,000 Sold Sep 30, 2025

  • 1,444 Sq Ft
  • $336/SF
  • 12 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  1 Stanley Dr, Great Barrington, MA 01230

  Unique Town House that stands alone! Nicely maintained unit with first floor Bedroom & updated Bath, a walk-in shower with bench, and attractive new flooring. Upstairs two Bedrooms share a spacious full bath. Expansive composite deck overlooks a private yard bordered by woods for total privacy. The attached garage affords plenty of extra storage. Nicely landscaped and conveniently located.

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  1 Stanley Dr, Great Barrington, MA 01230
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  /22

  Est $660,380 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,032 Sq Ft

  10 Ramsey Ave, Great Barrington, MA 01230

  10 Ramsey Ave, Great Barrington, MA 01230
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  /34

  $449,900

  • 2 Beds
  • 1 Bath
  • 1,182 Sq Ft

  245 Long Pond Rd, Great Barrington, MA 01230

  Tucked away on a quiet country road just minutes from downtown Great Barrington, this charming single-level ranch offers the perfect Berkshire retreat. Set on two private acres, the home is surrounded by mature trees and natural beauty- with nearby access to trails. Step inside to a bright interior featuring a spacious living room anchored by a beautiful stone fireplace. The kitchen offers crisp

  Jessica Rizzo LAMACCHIA REALTY, INC

  245 Long Pond Rd, Great Barrington, MA 01230
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  /26

  $625,000 Sold Sep 26, 2025

  • 1,790 Sq Ft
  • $349/SF
  • 117 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2006

  3 Roger Rd, Great Barrington, MA 01230

  Stylish Contemporary Home in a Prime Great Barrington Location! This beautifully maintained 3-bedroom, 2.5-bath Contemporary offers a lot of space and light-filled layout with high ceilings. The open-concept living area features a cathedral ceiling & gas fireplace, creating a warm and inviting atmosphere.Enjoy the convenience of a first-floor primary suite, filled with natural light from

  Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  3 Roger Rd, Great Barrington, MA 01230
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  /38

  Est $1,819,397 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,156 Sq Ft

  9 Round Hill Rd, Great Barrington, MA 01230

  9 Round Hill Rd, Great Barrington, MA 01230
• 

  

  /27

  $449,000

  • 3 Beds
  • 2.5 Baths
  • 1,368 Sq Ft

  2 Rose Ct W Unit B-1, Great Barrington, MA 01230

  EXCEPTIONAL CORNER UNIT! Bright and inviting 3 Bedroom, 2.5 Bath town house offering the perfect place to live, in the heart of Great Barrington. Designed for comfort & style, these light filled rooms showcase a beautiful distant mountain view. With the warmth of wood floors throughout, the spacious open plan is perfect for entertaining, and a new HVAC system has been added for year round

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  2 Rose Ct W Unit B-1, Great Barrington, MA 01230
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  /103

  $3,500,000 Sold Sep 25, 2025

  • 7,000 Sq Ft
  • $500/SF
  • 22 Days On Market

  • 4 Beds
  • 6 Baths
  • Built 2003

  6 Seekonk Cross Rd, Great Barrington, MA 01230

  SPECTACULAR CONTEMPORARY WITH OUTSTANDING VIEWS. This wonderful home has it all. The half mile, tree-lined driveway approach lets you know that something very special lies ahead. Then, the '''Wow Factor''clicks in as this Calvin Tsao and Zack McKown architectural masterpiece comes into view. The massive floor to ceiling windows provide breathe-taking vistas of the beautiful 17+ manicured

  George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  6 Seekonk Cross Rd, Great Barrington, MA 01230
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  /51

  Est $408,766 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,086 Sq Ft

  26 Avery Ln, Great Barrington, MA 01230

  26 Avery Ln, Great Barrington, MA 01230
• 

  

  /27

  $449,000

  • 3 Beds
  • 2.5 Baths
  • 1,368 Sq Ft

  2 Rose Ct W, Great Barrington, MA 01230

  EXCEPTIONAL CORNER UNIT! Bright and inviting 3 Bedroom, 2.5 Bath town house offering the perfect place to live, in the heart of Great Barrington. Designed for comfort & style, these light filled rooms showcase a beautiful distant mountain view. With the warmth of wood floors throughout, the spacious open plan is perfect for entertaining, and a new HVAC system has been added for year round

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  2 Rose Ct W, Great Barrington, MA 01230
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  /52

  $1,100,000 Sold Sep 25, 2025

  • 4,000 Sq Ft
  • $275/SF
  • 156 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1900

  82 West Ave, Great Barrington, MA 01230

  Classic turn-of-the-century Berkshire residence on the Hill. Rich w/ history & ready for new memories, this home is a rare gem in an ideal location. Lovingly maintained by the same family for over 60 yrs. Nestled on 1.6 acres, this 4,000 SF residence offers 5 BRs, 3.5 BAs & an abundance of historic charm. Original wood floors, high ceilings & period details fill the home, while the grand

  Claire Pollart LANCE VERMEULEN RE, INC

  82 West Ave, Great Barrington, MA 01230
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  /11

  Est $506,849 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 895 Sq Ft

  22 High St, Great Barrington, MA 01230

  22 High St, Great Barrington, MA 01230
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  /16

  $725,000

  • 3 Beds
  • 3.5 Baths
  • 2,560 Sq Ft

  78 State Rd, Great Barrington, MA 01230

  Investment Opportunity - 4-Unit Mixed-Use Property in Downtown Great Barrington, MAPrime downtown Great Barrington location! This well-maintained 4-unit mixed-use property includes three 1-bedroom apartments and one street-level commercial space offering excellent visibility and steady foot traffic.Two of the residential units are currently occupied by long-term tenants with strong payment

  Timothy Dunn VENTURE REAL ESTATE, INC

  78 State Rd, Great Barrington, MA 01230
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  /34

  $703,000 Sold Sep 23, 2025

  • 1,125 Sq Ft
  • $625/SF
  • 6 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1941

  26 Prospect St, Great Barrington, MA 01230

  PERFECT ''ON THE HILL'' NEIGHBORHOOD SETTING! Charming well maintained and beautifully updated home, wood floors, living room with fireplace, 2 bedrooms, kitchen with Thermador & Bosch appliances, quartz counters, a new full bath with decorative Pewabic tile, & marble flooring. A/C/ heat units, and a rocking chair front porch. The yard is both fenced and gated. Nicely landscaped, perennial

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  26 Prospect St, Great Barrington, MA 01230
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  /36

  Est $563,914 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  6 Parley St, Great Barrington, MA 01230

  6 Parley St, Great Barrington, MA 01230
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  /32

  $425,000

  • 4 Beds
  • 3 Baths
  • 1,360 Sq Ft

  1592 County Rd, Great Barrington, MA 01230

  Wonderful location, 3 bedroom, 3 bath split level. Minutes to the downtowns of Sheffield and Great Barrington. Primary with en suite bath, finished lower level with family room, artists studio plus a two car garage.

  Michael Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  1592 County Rd, Great Barrington, MA 01230
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  /27

  $388,000 Sold Sep 19, 2025

  • 1,192 Sq Ft
  • $326/SF
  • 53 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  370 Park St, Great Barrington, MA 01230

  Charming New England farmhouse featuring some modern updates and newer mechanical systems. Enjoy the perfect blend of rustic character and warmth of country living with modern conveniences in this delightful home. New full house insulation, Heat/ AC splits, updated electrical system. Large open backyard offers endless possibilities of outdoor activities and enjoyment. With a Berkshire Mountain

  Stephen Schoenfeld WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  370 Park St, Great Barrington, MA 01230
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  /26

  Est $419,381 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,173 Sq Ft

  84 Division St, Great Barrington, MA 01230

  84 Division St, Great Barrington, MA 01230
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  /55

  $3,500,000

  • 5 Beds
  • 6.5 Baths
  • 6,088 Sq Ft

  110 Alford Rd, Great Barrington, MA 01230

  Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure.Inside,

  Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  110 Alford Rd, Great Barrington, MA 01230
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  /48

  $938,250 Sold Sep 17, 2025

  • 2,998 Sq Ft
  • $313/SF
  • 126 Days On Market

  • 7 Beds
  • 4 Baths
  • Built 1863

  49 South St, Great Barrington, MA 01230

  Immaculate home on ''The Hill'' with stunning hardwood floors and abundant natural light from its many large windows. This versatile three-level property is currently enjoyed as a stately single-family residence, but can seamlessly be divided into two separate apartments, offering a range of layout options and rental income potential. The ground floor features a bright, modern kitchen, a spacious

  Kate Lascar COMPASS MASSACHUSETTS , LLC GB

  49 South St, Great Barrington, MA 01230
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  /22

  Est $591,545 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft

  33 Hillside Ave, Great Barrington, MA 01230

  33 Hillside Ave, Great Barrington, MA 01230
• 

  

  /19

  $525,000

  • 4 Beds
  • 3.5 Baths
  • 2,184 Sq Ft

  5 Seekonk Rd, Great Barrington, MA 01230

  This is a spacious house with generously sized rooms 5 minutes from town. 4 bedrooms with 1 full bath, 2 3/4 baths and one powder room. First floor has kitchen, living room, dining room, pantry, laundry and a generous master suite with sitting area, office space and full bath. Second floor has 3 bedrooms, one with ensuite 3/4 bath. Lots of closets and plenty of storage space with basement storage

  Jason Saphire www.HomeZu.com

  5 Seekonk Rd, Great Barrington, MA 01230
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  /13

  $310,000 Sold Sep 12, 2025

  • Land
  • 9.6 Acres
  • $32,292 per Acre

  • 216 Days On Market

  297 N Plain Rd, Housatonic, MA 01236

  Perfect for a very private family compound. GB zoning allows three dwelling units to be built by right. Cleared one acre level house site with driveway and underground utilities brought in. Over $44,000 in site improvements plus survey and perc testing. 700' of frontage on the lovely clear, Williams River including three islands. Bathe, swim, fish, tube, cold plunge, let your imagination run

  Claudia Crane COMPASS MASSACHUSETTS , LLC GB

  297 N Plain Rd, Housatonic, MA 01236
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  /29

  Est $395,036 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 826 Sq Ft

  147 Maple Ave, Great Barrington, MA 01230

  147 Maple Ave, Great Barrington, MA 01230
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  /8

  $465,000

  • 3 Beds
  • 3 Baths
  • 2,480 Sq Ft

  497 S Main St, Great Barrington, MA 01230

  Multi-family in a convenient location, walking distance to town and shopping, bus line nearby.Well maintained. The perfect location, walking distance to restaurants and shopping, public transportation nearby.

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  497 S Main St, Great Barrington, MA 01230
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  /27

  $490,000 Sold Sep 05, 2025

  • 1,634 Sq Ft
  • $300/SF
  • 262 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1900

  1068 Main St, Housatonic, MA 01236

  Very unique duplex in the heart of Housatonic! This very cool house combines antique charm, contemporary style, and a convenient village location to suit many uses and lifestyles. Currently configured as two leased 2 br/1ba apartments, it could easily be converted back to a single-family residence or provide income to an owner-occupant. Each unit offers a bright & cheery eat-in kitchen, living

  Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

  1068 Main St, Housatonic, MA 01236
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  /31

  Est $613,797 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,347 Sq Ft

  22 Monument Valley Rd, Great Barrington, MA 01230

  22 Monument Valley Rd, Great Barrington, MA 01230
• 

  

  /35

  $525,000

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft

  6 Locust St, Great Barrington, MA 01230

  Tucked away in a walkable east-side neighborhood of Great Barrington, this custom 3-bedroom bungalow is anything but ordinary. From the moment you step inside, the care and creativity in every corner are impossible to miss--handcrafted woodwork, thoughtful built-ins, and artful finishes infuse the home with a personality all of its own.The inviting and cozy open floor plan make everyday living

  Paige Paluch LANCE VERMEULEN RE, INC

  6 Locust St, Great Barrington, MA 01230
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  /24

  $775,000 Sold Sep 03, 2025

  • 1,898 Sq Ft
  • $408/SF
  • 11 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1997

  2 Copper Beech Ln, Great Barrington, MA 01230

  Immaculate and well maintained this condo is an easy in town ownership. Main floor has an open living and dining room with small office, large kitchen area with wood burning fireplace, sliders to a nice back deck, powder room, laundry room and access to the attached 1-car garage. Upstairs there are two guest rooms with a hall bath and a primary suite with separate tub/shower, a walk-in closet

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  2 Copper Beech Ln, Great Barrington, MA 01230
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  /7

  Est $874,681 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,784 Sq Ft

  215 Cross Rd, Great Barrington, MA 01230

  215 Cross Rd, Great Barrington, MA 01230
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  /3

  $95,000

  • Land
  • 2.92 Acres
  • $32,534 per Acre

  0 Hemlock Hill Rd, Great Barrington, MA 01230

  PREMIERE LOCATION JUST FIVE MINUTES FROM MAIN STREET. Good percs. Building site cleared. Rough driveway in. Electricity easily accessible. An excellent investment in the ''boom town'' of the Berkshires.

  Tom Lynch COMPASS MASSACHUSETTS , LLC GB

  0 Hemlock Hill Rd, Great Barrington, MA 01230
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  /32

  $660,000 Sold Sep 03, 2025

  • 2,060 Sq Ft
  • $320/SF
  • 113 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1858

  57 South St, Great Barrington, MA 01230

  A charming historic home nestled in the heart of Great Barrington, moved to it's location from Main Street in 1858. This delightful detached residence boasts 2,060 square feet of living space across 10 rooms. The living area features a wood-burning fireplace and space for formal dining. The eat-in kitchen, complete with built-ins, adds character. With four bedrooms and two baths, there's ample

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  57 South St, Great Barrington, MA 01230
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  /7

  Est $274,438 Not Listed For Sale

  • 2 Beds

  Unlisted Address

  Unlisted Address
• 

  

  /20

  $595,000

  • Land
  • 8.1 Acres
  • $73,457 per Acre

  11 Roger Rd, Great Barrington, MA 01230

  A rare opportunity to own a versatile 8+ acre parcel in a prime Great Barrington location. Accessed by an established roadway, this property presents a unique canvas for a private estate, a multi-home development, or a commercial enterprise. The property features a substantial 3,000 square foot building with radiant heat. With three large garage bays, an office, and a loft, it can serve as the

  Tony Segalla LANCE VERMEULEN RE, INC

  11 Roger Rd, Great Barrington, MA 01230

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