Great Barrington, MA Homes

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  /32

  $399,000 Pending

  • 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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  /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

  Current Estimated Value $448,401

  Last Listing Agent Katie Williams STONE HOUSE PROPERTIES, LLC

  272 Park St, Great Barrington, MA 01230
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  /26

  Est $429,799 Not Listed For Sale

  84 Division St, Great Barrington, MA 01230

  • 3 Beds
  • 1 Bath
  • 1,173 Sq Ft
  • Built 1950

  84 Division St, Great Barrington, MA 01230

  Last Sold Summary

  • 23% Above List Price
  • $298/SF
  • 203 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Helen Mullany HELEN MULLANY REAL ESTATE, LLC
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  /58

  $2,595,000

  • 5 Beds
  • 4.5 Baths
  • 4,305 Sq Ft

  95 Lewis Ave, Great Barrington, MA 01230

  This exquisite single-family home spans an impressive 4,300 square feet, offering an unmatched blend of elegance and modern comfort. With 5 spacious bedrooms and 4.5 beautifully renovated bathrooms, every detail has been meticulously crafted to perfection. Walking distance to downtown Great Barrington's shops and restaurants, the house is in one of the quietest areas of ''The Hill''.12 rooms

  Martin Albert COMPASS MASSACHUSETTS , LLC GB

  95 Lewis Ave, 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

  Current Estimated Value $606,141

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

  51 Downs Rd, Great Barrington, MA 01230
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  /22

  Est $626,185 Not Listed For Sale

  33 Hillside Ave, Great Barrington, MA 01230

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • Built 1988

  33 Hillside Ave, Great Barrington, MA 01230

  Last Sold Summary

  • 11% Above List Price
  • $307/SF
  • 38 Days On Market

  Last Sold Price $565,000

  Last Listing Agent Tom Lynch COMPASS MASSACHUSETTS , LLC GB
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  /5

  $119,000

  • Land
  • 4.85 Acres
  • $24,536 per Acre

  0 Division St, New Marlborou, MA 01230

  A beautiful land offering with a combination of natural features and convenience. This property borders the Housatonic River providing a peaceful setting, some distant southern mountain views create a scenic backdrop. Fairly level, well suited for a variety of potential uses.

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  0 Division St, New Marlborou, 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 $732,393

  Last Listing Agent Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  120 Maple Ave, Great Barrington, MA 01230
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  /29

  Est $403,533 Not Listed For Sale

  147 Maple Ave, Great Barrington, MA 01230

  • 2 Beds
  • 1 Bath
  • 826 Sq Ft
  • Built 1900

  147 Maple Ave, Great Barrington, MA 01230

  Last Sold Summary

  • 20% Above List Price
  • $406/SF
  • 26 Days On Market

  Last Sold Price $335,000

  Last Listing Agent James Nugent THE KINDERHOOK GROUP
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  /32

  $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 WILLIAM RAVEIS - BERKSHIRE

  165 Maple Ave Unit D, 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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  /31

  Est $648,392 Not Listed For Sale

  22 Monument Valley Rd, Great Barrington, MA 01230

  • 3 Beds
  • 2 Baths
  • 1,347 Sq Ft
  • Built 1997

  22 Monument Valley Rd, Great Barrington, MA 01230

  Last Sold Summary

  • 25% Above List Price
  • $386/SF
  • 6 Days On Market

  Last Sold Price $520,000

  Last Listing Agent Timothy Lovett COMPASS MASSACHUSETTS , LLC GB
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  /29

  $1,024,000

  • 4 Beds
  • 3 Baths
  • 2,322 Sq Ft

  97 Brush Hill Rd, Great Barrington, MA 01230

  On 2.65 private acres in the Berkshires this fully renovated 4-BR 3-bath home offers a rare combination of modern luxury w/ direct access to nature. $650K + in renovations have transformed the property into a turnkey retreat for full-time living or a seasonal escape. The outdoor space features private hiking trails, a wraparound deck, upper balcony, a large upper patio & a newly resurfaced

  David White OwnerEntry.com

  97 Brush Hill Rd, Great Barrington, MA 01230
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  /40

  $340,000 Sold Mar 13, 2026

  212 Highland St, Housatonic, MA 01236

  • 3 Beds
  • 2 Baths
  • 1,618 Sq Ft
  • Built 1900

  Last Sold Summary

  • 13% Below List Price
  • $210/SF
  • 168 Days On Market

  Current Estimated Value $389,367

  Last Listing Agent Patricia Andrew STONE HOUSE PROPERTIES, LLC

  212 Highland St, Housatonic, MA 01236
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  /7

  Est $889,566 Not Listed For Sale

  215 Cross Rd, Great Barrington, MA 01230

  • 3 Beds
  • 2 Baths
  • 1,784 Sq Ft
  • Built 1987

  215 Cross Rd, Great Barrington, MA 01230

  Last Sold Summary

  • 19% Above List Price
  • $420/SF
  • 3 Days On Market

  Last Sold Price $750,000

  Last Listing Agent William Morrow William Pitt
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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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  /27

  $325,000 Sold Jan 23, 2026

  58 Sheffield Rd, Great Barrington, MA 01230

  • 3 Beds
  • 1.5 Baths
  • 1,280 Sq Ft
  • Built 1945

  Last Sold Summary

  • 6% Below List Price
  • $254/SF
  • 20 Days On Market

  Current Estimated Value $342,389

  Last Listing Agent Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  58 Sheffield Rd, Great Barrington, MA 01230
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  /7

  Est $278,064 Not Listed For Sale

  Unlisted Address

  • 2 Beds
  • Built 1935

  Unlisted Address

  Last Sold Summary

  • 75% Above List Price
  • $132/SF
  • 594 Days On Market

  Last Sold Price $159,000

  Last Listing Agent Jason Saphire www.HomeZu.com
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  /29

  $649,000

  • 4 Beds
  • 2 Baths
  • 3,000 Sq Ft

  783 Main St, Great Barrington, MA 01230

  Renovated, well-maintained, multi-use building perfect for a live-work situation in prime location! All 4 floors offer opportunity for offices, a studio, storage, retail showroom and more! Highlights include: a large parking lot, handicap accessible ramp, 2 half baths & finished 3rd floor attic. Finished basement w/ vault & video security system. The current retail space is bright & sunny with a

  Claudia Laslie WILLIAM RAVEIS - BERKSHIRE

  783 Main 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 $513,453

  Last Listing Agent Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  1 Christian Hill Rd, Great Barrington, MA 01230
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  /33

  Est $1,500,161 Not Listed For Sale

  97 Corser Hill Rd, Great Barrington, MA 01230

  • 4 Beds
  • 3.5 Baths
  • 3,642 Sq Ft
  • Built 1989

  97 Corser Hill Rd, Great Barrington, MA 01230

  Last Sold Summary

  • 19% Above List Price
  • $347/SF
  • 31 Days On Market

  Last Sold Price $1,262,500

  Last Listing Agent Leslie Chesloff William Pitt
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  /15

  $550,000

  • 4 Beds
  • 2 Baths
  • 2,346 Sq Ft

  88 Main St, Great Barrington, MA 01230

  Building has been used as an antique business for the last 50 years. Seller had previously lived in the upstairs apartment. Located across the street from Mend and Calgary's and .5 miles from downtown Great Barrington. Selling as is, business and inventory for sale separately - negotiable with owner. Near all the cultural events specific to the Berkshires!

  Freddy Friedman Birch Properties

  88 Main St, 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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  /23

  Est $690,938 Not Listed For Sale

  49 Pine St, Great Barrington, MA 01230

  • 5 Beds
  • 2 Baths
  • 1,799 Sq Ft
  • Built 1900

  49 Pine St, Great Barrington, MA 01230

  Last Sold Summary

  • 10% Above List Price
  • $350/SF
  • 112 Days On Market

  Last Sold Price $630,000

  Last Listing Agent Suzann Ward HOUSATONIC REAL ESTATE
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  /26

  $399,900

  • 4 Beds
  • 1 Bath
  • 1,337 Sq Ft

  153 State Rd, Great Barrington, MA 01230

  Neat as a pin cape walking distance to downtown Great Barrington and amenities, this home has been thoughtfully renovated top to bottom. This sweet property, also zoned commercially, has 4 bedrooms, a full bath, and even a partially finished basement. The kitchen, complete with a large pantry, retains the charming mid century details, while appealing to the modern aesthetic. Outside, there is a

  Lauren Rosen WILLIAM RAVEIS - BERKSHIRE

  153 State Rd, 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

  Current Estimated Value $916,165

  Last Listing Agent Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  14 Copper Beech Ln, Great Barrington, MA 01230
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  /64

  Est $1,234,511 Not Listed For Sale

  20 Taconic Ln, Great Barrington, MA 01230

  • 4 Beds
  • 3.5 Baths
  • 3,312 Sq Ft
  • Built 1980

  20 Taconic Ln, Great Barrington, MA 01230

  Last Sold Summary

  • 29% Above List Price
  • $290/SF
  • 4 Days On Market

  Last Sold Price $960,000

  Last Listing Agent Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES
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  /47

  $7,250,000 New Construction

  • 6 Beds
  • 7 Baths
  • 13,175 Sq Ft

  209 Blue Hill Rd, Great Barrington, MA 01230

  A rare French Manor estate gracing one of South Berkshire's most scenic and sought-after country roads, this extraordinary 45+/- acre sanctuary offers unmatched privacy, panoramic mountain views, and a setting of timeless beauty. Bordering protected state forest, the property unfolds across rolling meadows, tranquil ponds, and a gently flowing brook—creating a secluded retreat that feels worlds

  Mauren White-Kirkby Berkshire Hathaway Homeservice

  209 Blue Hill Rd, 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 $653,611

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

  284 Brewer Branch Rd, Great Barrington, MA 01230
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  /43

  Est $1,151,292 Not Listed For Sale

  21 Brainard Ave, Great Barrington, MA 01230

  • 4 Beds
  • 3 Baths
  • 2,416 Sq Ft
  • Built 1893

  21 Brainard Ave, Great Barrington, MA 01230

  Last Sold Summary

  • $476/SF
  • 30 Days On Market

  Last Sold Price $1,150,000

  Last Listing Agent Claudia Laslie WILLIAM RAVEIS - BERKSHIRE
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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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  /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 $263,652

  Last Listing Agent Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  39 Christian Hill Rd, Great Barrington, MA 01230
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  /32

  Est $1,158,741 Not Listed For Sale

  89 Taconic Ave, Great Barrington, MA 01230

  • 5 Beds
  • 4 Baths
  • 3,400 Sq Ft
  • Built 1898

  89 Taconic Ave, Great Barrington, MA 01230

  Last Sold Summary

  • 46% Above List Price
  • $234/SF
  • 186 Days On Market

  Last Sold Price $795,000

  Last Listing Agent Karen Climo William Pitt
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  /28

  $1,050,000 Pending

  • 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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  /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 $418,799

  Last Listing Agent Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

  75 van Deusenville Rd, Great Barrington, MA 01230
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  /42

  Est $887,810 Not Listed For Sale

  19 Pleasant St, Great Barrington, MA 01230

  • 4 Beds
  • 3 Baths
  • 2,873 Sq Ft
  • Built 1900

  19 Pleasant St, Great Barrington, MA 01230

  Last Sold Summary

  • 15% Above List Price
  • $269/SF
  • 17 Days On Market

  Last Sold Price $774,000

  Last Listing Agent Nancy Cuddihy Stone House Properties, LLC
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  /28

  $785,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,898 Sq Ft

  80 Taconic Ave Unit 13, Great Barrington, MA 01230

  Oakwood Condominium near the hospital. This 3 bedroom 2 bath has been recently up dated. East facing with mountain views. The lighting is beautiful. 1st floor primary with walk in closet and bath. Wood burning fireplace that can be converted to a gas insert. Stackable laundry in unit. Also includes a single car garage. Privately situated in ground pool with plenty of outdoor space to enjoy. Also

  Suzann Ward HOUSATONIC REAL ESTATE

  80 Taconic Ave Unit 13, 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 $340,574

  Last Listing Agent Lauren Rosen WILLIAM RAVEIS - BERKSHIRE

  155 Division St, Great Barrington, MA 01230
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  /45

  Est $806,997 Not Listed For Sale

  48 Quarry St, Great Barrington, MA 01230

  • 4 Beds
  • 2.5 Baths
  • 2,352 Sq Ft
  • Built 2001

  48 Quarry St, Great Barrington, MA 01230

  Last Sold Summary

  • 13% Above List Price
  • $304/SF
  • 138 Days On Market

  Last Sold Price $715,000

  Last Listing Agent Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
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  /24

  $695,000

  • 2 Beds
  • 2 Baths
  • 1,308 Sq Ft

  80 Taconic Ave Unit 3, Great Barrington, MA 01230

  Welcome to Oakwood Condominium. A one car garage comes with unit. Plenty of additional parking. Lovely inground well manicured pool. Beautiful outdoor landscaping and sitting area. Private deck attached to unit for outdoor entertaining. This unit has been renovated over the years with updated kitchen with eat in nook area. All new windows and sliding doors. Gorgeous primary bathroom with radiant

  Suzann Ward HOUSATONIC REAL ESTATE

  80 Taconic Ave Unit 3, Great Barrington, MA 01230

Showing Results 121 - 160, Page 4 of 18