Great Barrington, MA Homes

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  /22

  Est $588,718 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
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  /46

  $625,000

  • 9 Beds
  • 4 Baths
  • 4,152 Sq Ft

  1057 Main St, Great Barrington, MA 01236

  Great investment opportunity! A very rare property offered for the first time outside the family in over 50 years. This is a well maintained and loved four unit income property that can produce over seventy five thousand dollars per year in rents! Lifetime metal roof, freshly painted exterior, updated units are just a few of the benefits of this investment. In the bustling village of Housatonic,

  Ryan Lane GILCREST PROPERTIES

  1057 Main St, Great Barrington, MA 01236
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  /43

  $435,000 Sold Oct 22, 2025

  272 Park St, Great Barrington, MA 01230

  • 2 Beds
  • 1.5 Baths
  • 1,535 Sq Ft
  • Built 1948

  Last Sold Summary

  • $283/SF
  • 4 Days On Market

  Last Listing Agent Katie Williams STONE HOUSE PROPERTIES, LLC

  272 Park St, Great Barrington, MA 01230
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  /29

  Est $407,572 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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  /36

  $775,000

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

  458 Monterey Rd, Great Barrington, MA 01230

  Located just 1.8 miles from Ski Butternut, this Berkshires retreat is the perfect basecamp for multi-generational gatherings, or groups of friends who want room to spread out. Set on 4.32 private acres on the Great Barrington/Monterey line, this spacious 1958 ranch has grown over the years into an impressive 5,200 sq. ft. haven--ideal for creating lifelong vacation memories.Inside, the home's

  Cortney Dupont COHEN & WHITE ASSOCIATES

  458 Monterey Rd, Great Barrington, MA 01230
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  /28

  $600,000 Sold Dec 05, 2025

  51 Downs Rd, Great Barrington, MA 01230

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  Last Sold Summary

  • 20% Below List Price
  • $400/SF
  • 138 Days On Market

  Last Listing Agent Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  51 Downs Rd, Great Barrington, MA 01230
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  /31

  Est $595,788 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
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  /34

  $589,000

  • 4 Beds
  • 4 Baths
  • 5,044 Sq Ft

  163 Front St, Great Barrington, MA 01230

  Suzann Ward HOUSATONIC REAL ESTATE

  163 Front St, Great Barrington, MA 01230
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  /46

  $685,000 Sold Jul 02, 2025

  120 Maple Ave, Great Barrington, MA 01230

  • 5 Beds
  • 2 Baths
  • 2,765 Sq Ft
  • Built 1835

  Last Sold Summary

  • 2% Below List Price
  • $248/SF
  • 53 Days On Market

  Current Estimated Value $715,011

  Last Listing Agent Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  120 Maple Ave, Great Barrington, MA 01230
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  /7

  Est $843,073 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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  /37

  $455,000

  • 3 Beds
  • 2 Baths
  • 1,992 Sq Ft

  35 Mechanic St, Great Barrington, MA 01230

  Live in the center of Great Barrington with a private backyard of almost 3 acres on the river! This renovated farmhouse has an inviting kitchen with cozy wood stove, first floor primary suite and 2 spacious bedrooms with a shared bath on second floor. Beautiful wide-plank floors and built-ins preserve this home's history. A solar rooftop system brings energy efficiency and electricity credits.

  Christine Martin COMPASS MASSACHUSETTS , LLC GB

  35 Mechanic St, Great Barrington, MA 01230
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  /37

  $465,000 Sold Jul 08, 2025

  5 Grant Ln, Great Barrington, MA 01230

  • 3 Beds
  • 1 Bath
  • 1,260 Sq Ft
  • Built 1951

  Last Sold Summary

  • 11% Below List Price
  • $369/SF
  • 47 Days On Market

  Last Listing Agent Lawrence Reilly THE KINDERHOOK GROUP

  5 Grant Ln, Great Barrington, MA 01230
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  /7

  Est $273,682 Not Listed For Sale

  • 2 Beds

  Unlisted Address

  Unlisted Address
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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
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  /26

  $235,000 Sold Feb 26, 2025

  11 Fairview Rd, Great Barrington, MA 01230

  • 3 Beds
  • 1 Bath
  • 1,464 Sq Ft
  • Built 1954

  Last Sold Summary

  • 16% Below List Price
  • $161/SF
  • 70 Days On Market

  Current Estimated Value $293,127

  Last Listing Agent Suzann Ward HOUSATONIC REAL ESTATE

  11 Fairview Rd, Great Barrington, MA 01230
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  /33

  Est $1,377,215 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,642 Sq Ft

  97 Corser Hill Rd, Great Barrington, MA 01230

  97 Corser Hill Rd, Great Barrington, MA 01230
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  /27

  $299,000 Open Sat 11:30AM - 1PM

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

  54 Division St, Great Barrington, MA 01230

  PRICE DROP TO 299K IS FIRM.This beautifully renovated 1,792 sq. ft. home offers a unique opportunity for buyers seeking modern updates with the chance to add personal finishing touches. Major renovations including:*New Electrical and plumbing*New Windows*Fresh interior paint*kitchen with cabinets*Fully renovated first-floor bathroom*New 3-bedroom septic system*Primary bathroom with new toilet &

  Judi Panzano HOUSATONIC REAL ESTATE

  54 Division St, Great Barrington, MA 01230
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  /19

  $502,500 Sold Jul 09, 2025

  1 Christian Hill Rd, Great Barrington, MA 01230

  • 3 Beds
  • 2 Baths
  • 2,280 Sq Ft
  • Built 1900

  Last Sold Summary

  • 8% Below List Price
  • $220/SF
  • 9 Days On Market

  Current Estimated Value $504,177

  Last Listing Agent Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  1 Christian Hill Rd, Great Barrington, MA 01230
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  /64

  Est $1,276,216 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,312 Sq Ft

  20 Taconic Ln, Great Barrington, MA 01230

  20 Taconic Ln, Great Barrington, MA 01230
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  /27

  $449,000 Under Contract

  • 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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  /27

  $490,000 Sold Sep 05, 2025

  1068 Main St, Housatonic, MA 01236

  • 4 Beds
  • 2 Baths
  • 1,634 Sq Ft
  • Built 1900

  Last Sold Summary

  • 11% Below List Price
  • $300/SF
  • 262 Days On Market

  Last Listing Agent Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

  1068 Main St, Housatonic, MA 01236
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  /43

  Est $1,100,716 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,416 Sq Ft

  21 Brainard Ave, Great Barrington, MA 01230

  21 Brainard Ave, Great Barrington, MA 01230
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  /63

  $1,330,000

  • 16 Beds
  • 10 Baths
  • 8,870 Sq Ft

  6 Manville St, Great Barrington, MA 01230

  A prime investment opportunity in the heart of downtown Great Barrington. This 10-unit residential property features a desirable mix of six spacious two-bedroom apartments and four one-bedroom units. The two-bedroom apartments are particularly appealing, all offering private balconies and fireplaces, with three of these premium units also including formal dining rooms and Jack-and-Jill style

  Tony Segalla LANCE VERMEULEN RE, INC

  6 Manville St, Great Barrington, MA 01230
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  /43

  $915,000 Sold Dec 19, 2025

  14 Copper Beech Ln, Great Barrington, MA 01230

  • 3 Beds
  • 2.5 Baths
  • 2,062 Sq Ft
  • Built 1998

  Last Sold Summary

  • 1% Below List Price
  • $444/SF
  • 19 Days On Market

  Last Listing Agent Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  14 Copper Beech Ln, Great Barrington, MA 01230
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  /32

  Est $1,113,715 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,400 Sq Ft

  89 Taconic Ave, Great Barrington, MA 01230

  89 Taconic Ave, Great Barrington, MA 01230
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  /17

  $299,000

  • 2,950 Sq Ft

  16 Depot St, Great Barrington, MA 01230

  Prime Commercial / Residential / Multi-Family Space in Downtown Housatonic! A chance to create a central hub for commerce and discover the endless possibilities with a versatile commercial space. Spanning 2,950 square feet, this property offers a unique opportunity to breathe new life into the area and create a thriving business hub. Ready to be transformed into a cozy coffee shop, a vibrant meat

  John Segalla HOUSATONIC REAL ESTATE

  16 Depot St, Great Barrington, MA 01230
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  /37

  $644,000 Sold Aug 01, 2025

  284 Brewer Branch Rd, Great Barrington, MA 01230

  • 3 Beds
  • 2 Baths
  • 1,224 Sq Ft
  • Built 1973

  Last Sold Summary

  • 5% Below List Price
  • $526/SF
  • 21 Days On Market

  Current Estimated Value $637,465

  Last Listing Agent Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  284 Brewer Branch Rd, Great Barrington, MA 01230
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  /31

  Est $833,495 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,304 Sq Ft

  193 East St, Great Barrington, MA 01230

  193 East St, Great Barrington, MA 01230
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  /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
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  /25

  $250,000 Sold Aug 20, 2025

  39 Christian Hill Rd, Great Barrington, MA 01230

  • 3 Beds
  • 1.5 Baths
  • 1,414 Sq Ft
  • Built 1900

  Last Sold Summary

  • 24% Below List Price
  • $177/SF
  • 166 Days On Market

  Current Estimated Value $257,023

  Last Listing Agent Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  39 Christian Hill Rd, Great Barrington, MA 01230
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  /10

  Est $616,075 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,161 Sq Ft

  10 Prospect St, Great Barrington, MA 01230

  10 Prospect 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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  /17

  $375,000 Sold Aug 01, 2025

  75 van Deusenville Rd, Great Barrington, MA 01230

  • 3 Beds
  • 1 Bath
  • 1,691 Sq Ft
  • Built 1958

  Last Sold Summary

  • 6% Below List Price
  • $222/SF
  • 22 Days On Market

  Current Estimated Value $388,750

  Last Listing Agent Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

  75 van Deusenville Rd, Great Barrington, MA 01230
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  /23

  Est $522,873 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,016 Sq Ft

  913 Main St, Great Barrington, MA 01230

  913 Main St, Great Barrington, MA 01230
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  /28

  $1,200,000

  • 5 Beds
  • 3 Baths
  • 3,328 Sq Ft

  3 Pleasant View Dr, Great Barrington, MA 01230

  Rare offering of over six acres ''On the Hill'', sprawling residence with first floor primary, large eat-in kitchen with cozy fireplace.. porch-privacy-garage..open acreage bordered by woods.. walking distance to Main Street, Skiing and Lake Mansfield nearby...Five bedrooms, three baths. Formal living room.Plenty of room for expansion.

  Martha Piper THE KINDERHOOK GROUP

  3 Pleasant View Dr, Great Barrington, MA 01230
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  /18

  $317,000 Sold May 30, 2025

  155 Division St, Great Barrington, MA 01230

  • 1 Bed
  • 1 Bath
  • 760 Sq Ft
  • Built 1965

  Last Sold Summary

  • 6% Above List Price
  • $417/SF
  • 9 Days On Market

  Current Estimated Value $324,769

  Last Listing Agent Lauren Rosen LANCE VERMEULEN RE, INC

  155 Division St, Great Barrington, MA 01230
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  /29

  Est $715,686 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,652 Sq Ft

  6 Berkshire Cir, Great Barrington, MA 01230

  6 Berkshire Cir, Great Barrington, MA 01230
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  /33

  $779,000

  • 3 Beds
  • 2 Baths
  • 1,771 Sq Ft

  165 Maple Ave Unit D, Great Barrington, MA 01230

  Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless

  Tony Segalla LANCE VERMEULEN RE, INC

  165 Maple Ave Unit D, Great Barrington, MA 01230
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  /29

  $445,000 Sold Jul 11, 2025

  2 Emily Ct, Great Barrington, MA 01230

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $294/SF
  • 11 Days On Market

  Current Estimated Value $441,770

  Last Listing Agent Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  2 Emily Ct, Great Barrington, MA 01230
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  /27

  Est $565,140 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft

  103 East St, Great Barrington, MA 01230

  103 East St, Great Barrington, MA 01230

Showing Results 121 - 160, Page 4 of 18