Bennington, VT Homes

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  /41

  $550,000

  Under Contract

  • 5 Beds
  • 2 Baths
  • 1,974 Sq Ft

  971 S Stream Rd, Bennington, VT 05201

  Have you been searching for the Vermont farmhouse that truly feels like home? The one with the land, the barns, the mountain views, the wraparound driveway, the screened in porch, and the beautiful front porch where you can sit and enjoy quiet mornings and peaceful evenings? This is that home.Situated on over 17 acres, this property offers not one but two barns, established fenced pastures,

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  971 S Stream Rd, Bennington, VT 05201
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  /34

  $450,000

  Sold Feb 13, 2026

  356 Elm St, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 2,273 Sq Ft
  • Built 1934

  Last Sold Summary

  • $198/SF
  • 0 Days On Market

  Current Estimated Value $447,099

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  356 Elm St, Bennington, VT 05201
• 

  

  

  /34

  Est $481,290

  Not Listed For Sale

  647 Fox Hill Rd, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 1,901 Sq Ft
  • Built 2008

  647 Fox Hill Rd, Bennington, VT 05201

  Last Sold Summary

  • 133 Days On Market

  Last Listing Agent Erika Floriani Hoffman Real Estate
• 

  

  

  /27

  $209,900

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,075 Sq Ft

  1083 Main St, Bennington, VT 05201

  Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  1083 Main St, Bennington, VT 05201
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  /58

  $1,495,000

  Sold Jul 30, 2026

  16 West Rd, Bennington, VT 05201

  • 7 Beds
  • 5.5 Baths
  • 6,392 Sq Ft
  • Built 1910

  Last Sold Summary

  • $234/SF
  • 65 Days On Market

  Current Estimated Value $1,451,308

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  16 West Rd, Bennington, VT 05201
• 

  

  /39

  Est $586,127

  Not Listed For Sale

  557 Fox Hill Rd, Bennington, VT 05201

  • 4 Beds
  • 3.5 Baths
  • 2,336 Sq Ft
  • Built 2009

  557 Fox Hill Rd, Bennington, VT 05201

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
• 

  

  /11

  $155,000

  Pending

  • 4 Beds
  • 2 Baths
  • 2,643 Sq Ft

  905 County St, Bennington, VT 05201

  Recently this home was a 2 unit (up and down). The current owner has doing work to convert it into a large single family home. Currently 4 bedrooms, 2 bathrooms and many possible room configurations. Also could easily be converted back to a 2 Unit. Many possibilities to put your finishing touches on this property with a lot of square footage.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  905 County St, Bennington, VT 05201
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  /36

  $220,000

  Sold Aug 20, 2025

  1211 Carpenter Hill Rd, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1930

  Last Sold Summary

  • 10% Above List Price
  • $157/SF
  • 4 Days On Market

  Last Listing Agent Peter West BISHOP WEST REAL ESTATE

  1211 Carpenter Hill Rd, Bennington, VT 05201
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  /38

  Est $711,593

  Not Listed For Sale

  3347 West Rd, Bennington, VT 05201

  • 5 Beds
  • 3 Baths
  • 3,266 Sq Ft
  • Built 1969

  3347 West Rd, Bennington, VT 05201

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Margretta Fischer Wohler Realty Group
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  /29

  $250,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,824 Sq Ft

  103 Jennings Brook Dr, Bennington, VT 05201

  Located in the desirable Jennings Brook community, this condominium offers a wonderful opportunity to add your own personal touches while enjoying a convenient Bennington location. The spacious living room features a cozy fireplace, beautiful built-ins, and abundant natural light, while the large dining room provides an ideal setting for gatherings and entertaining. The foyer is currently used as

  Kelley Mccarthy Mahar McCarthy Real Estate

  103 Jennings Brook Dr, Bennington, VT 05201
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  /31

  $77,000

  Sold Aug 04, 2026

  109 Evergreen Dr, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft
  • Built 1940

  Last Sold Summary

  • 38% Below List Price
  • $51/SF
  • 164 Days On Market

  Current Estimated Value $99,517

  Last Listing Agent Zachary Zupan EXP Realty

  109 Evergreen Dr, Bennington, VT 05201
• 

  

  /19

  Est $413,793

  Not Listed For Sale

  1 Division Place, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 975 Sq Ft
  • Built 1895

  1 Division Place, Bennington, VT 05201

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Vicki Wilson Maple Leaf Real Estate
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  /14

  $224,000

  $14K PRICE DROP

  • 1,222 Sq Ft

  117 Putnam St, Bennington, VT 05201

  This beautifully renovated 2-unit home by JDN Properties offers exceptional flexibility for buyers, allowing for a variety of living arrangements to suit your needs. Whether you choose to enjoy it as a spacious two-story single family residence with a luxurious upstairs primary suite and kitchenette, use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize

  Dan Mason Perrott Realty

  117 Putnam St, Bennington, VT 05201
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  /17

  $159,900

  Sold Jun 05, 2026

  432 South St Unit B2, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 852 Sq Ft
  • Built 1989

  Last Sold Summary

  • $188/SF
  • 40 Days On Market

  Current Estimated Value $162,187

  Last Listing Agent Max Squiers KW Vermont - Brenda Jones Real Estate Group

  432 South St Unit B2, Bennington, VT 05201
• 

  

  /21

  Est $173,539

  Not Listed For Sale

  106 Park St Unit 16, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1993

  106 Park St Unit 16, Bennington, VT 05201

  Last Sold Summary

  • 76 Days On Market

  Last Listing Agent Peggy Winchester ACORN REAL ESTATE GROUP LLC
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  /43

  $619,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,692 Sq Ft

  34 Monument Ave, Bennington, VT 05201

  Set along tree-lined Monument Avenue in prestigious and historic Old Bennington, the Spargo House offers a rare opportunity to own a distinctive piece of Vermont history. Dating to circa 1800, this remarkable home was once the longtime residence of noted author, historian and collector John Spargo, founder and longtime director of the Bennington Museum. Just below the Bennington Battle Monument,

  Jeffrey Dorman

  34 Monument Ave, Bennington, VT 05201
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  /41

  $410,000

  Sold Oct 17, 2025

  882 East Rd, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 1,792 Sq Ft
  • Built 2002

  Last Sold Summary

  • 3% Above List Price
  • $229/SF
  • 14 Days On Market

  Current Estimated Value $416,039

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  882 East Rd, Bennington, VT 05201
• 

  

  /29

  Est $544,525

  Not Listed For Sale

  9378 Vt Route 9, Bennington, VT 05201

  • 4 Beds
  • 3 Baths
  • 1,752 Sq Ft
  • Built 1985

  9378 Vt Route 9, Bennington, VT 05201

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Lisa Mirando Deerfield Valley Real Estate
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  /28

  $209,900

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft

  107 Jefferson Ave, Bennington, VT 05201

  Terrific in town location for this 3 bedroom, 2 bathroom home in Bennington. Offering living room, large kitchen, formal dining room and office/study. Covered porch and patio. Privacy bushes and yard. Property is being sold "as-is".

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  107 Jefferson Ave, Bennington, VT 05201
• 

  

  /19

  $89,499

  Sold Jan 21, 2026

  64 Ethans Way, Bennington, VT 05201

  • 2 Beds
  • 1 Bath
  • 746 Sq Ft
  • Built 2024

  Last Sold Summary

  • $120/SF
  • 238 Days On Market

  Last Listing Agent Kate Barry EXP Realty

  64 Ethans Way, Bennington, VT 05201
• 

  

  /47

  Est $433,047

  Not Listed For Sale

  201 Erbs Way, Bennington, VT 05201

  • 3 Beds
  • 3.5 Baths
  • 2,686 Sq Ft
  • Built 1974

  201 Erbs Way, Bennington, VT 05201

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Vicki Wilson Maple Leaf Real Estate
• 

  

  /50

  $150,000

  $10K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,575 Sq Ft

  127 Dewey St, Bennington, VT 05201

  Opportunity awaits with this spacious property offering incredible potential for investors, renovators, or buyers looking to create their dream home. Currently configured as a single family residence, this home features 5 bedrooms and 2 bathrooms. At one point it was a 2 unit home and could potentially be again.Inside, you'll find generous living space ready for your vision and updates. A

  Lindsey Martin Maple Leaf Real Estate

  127 Dewey St, Bennington, VT 05201
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  /41

  $480,000

  Sold Dec 22, 2025

  245 Southshire Dr, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 2,116 Sq Ft
  • Built 1984

  Last Sold Summary

  • 9% Below List Price
  • $227/SF
  • 145 Days On Market

  Current Estimated Value $520,344

  Last Listing Agent Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

  245 Southshire Dr, Bennington, VT 05201
• 

  

  /40

  Est $368,562

  Not Listed For Sale

  505 Cross Rd, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft
  • Built 2003

  505 Cross Rd, Bennington, VT 05201

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Vicki Wilson Maple Leaf Real Estate
• 

  

  /15

  $169,900

  • 2 Beds
  • 1.5 Baths
  • 819 Sq Ft

  432 South St Unit A11, Bennington, VT 05201

  Enjoy easy first-floor, one-level living in this two-bedroom, one-and-a-half-bath condominium in Bennington’s Nathaniel Court community. The comfortable layout features an open living and dining area, a functional brand-new stainless steel kitchen appliances, laminate flooring, and plenty of natural light throughout. Both bedrooms offer inviting spaces, while the in-unit washer and dryer add

  Colt Hazell Flex Realty

  432 South St Unit A11, Bennington, VT 05201
• 

  

  /15

  $199,900

  Sold Jan 16, 2026

  111 Hicks Ave, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft
  • Built 1936

  Last Sold Summary

  • $160/SF
  • 13 Days On Market

  Current Estimated Value $203,292

  Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

  111 Hicks Ave, Bennington, VT 05201
• 

  

  /40

  Est $602,316

  Not Listed For Sale

  260 Tower Rd, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 3,976 Sq Ft
  • Built 1981

  260 Tower Rd, Bennington, VT 05201

  Last Sold Summary

  • 115 Days On Market

  Last Listing Agent Allison Pacelli Pacelli Zepka Corporation
• 

  

  /6

  $199,900

  Pending

  • 1,176 Sq Ft

  2 Hamlin Ave, Bennington, VT 05201

  2-Unit Multi-Family with Professional-Grade Workshop!Versatile property with high-yield setup, perfect for a contractor, carpenter, or owner-occupant. The standout feature is a professional-grade workshop fully optimized for year-round productivity with radiant heat, bright lighting, and the added convenience of an existing sink and toilet. Whether utilized for a trade, automotive enthusiast,

  Lori Hurley Four Corner Properties LLC

  2 Hamlin Ave, Bennington, VT 05201
• 

  

  /19

  $225,000

  Sold Aug 29, 2025

  1801 S Stream Rd, Bennington, VT 05201

  • Land
  • 16.68 Acres
  • $13,489 per Acre

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  1801 S Stream Rd, Bennington, VT 05201
• 

  

  /40

  Est $444,008

  Not Listed For Sale

  42 Maple Grove Rd, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 2,163 Sq Ft
  • Built 1960

  42 Maple Grove Rd, Bennington, VT 05201

  Last Sold Summary

  • 87 Days On Market

  Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate
• 

  

  /12

  $49,000

  • Land
  • 9,147 Sq Ft
  • $233,333 per Acre

  2 Belvedere St, Bennington, VT 05201

  Here is the blank slate for your Vermont home, offering beautiful views of the Green Mountains and a location that is just steps from a 160-acre wildlife preserve with numerous hiking trails, wetland viewing platforms, and abundant wildlife. This cute corner lot is mostly level, cleared, and ready to build, with town water and sewer available at the street. Bring your imagination and come and

  Dan Mason Perrott Realty

  2 Belvedere St, Bennington, VT 05201
• 

  

  /32

  $325,000

  Sold Jul 29, 2026

  21 Pageant St, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,443 Sq Ft
  • Built 1950

  Last Sold Summary

  • $225/SF
  • 23 Days On Market

  Current Estimated Value $320,091

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  21 Pageant St, Bennington, VT 05201
• 

  

  /38

  Est $381,997

  Not Listed For Sale

  1063 Middle Pownal Rd, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 1987

  1063 Middle Pownal Rd, Bennington, VT 05201

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Angela Bevin Maple Leaf Real Estate
• 

  

  /44

  $189,900

  • 3 Beds
  • 1 Bath
  • 1,206 Sq Ft

  232 Depot St, Bennington, VT 05201

  Charming in-town 3-bedroom, 1-bath home situated on a low-maintenance 0.09-acre lot. Enjoy a private, fully fenced backyard with views of Mt Anthony, which is perfect for relaxing, entertaining, or pets. Shared driveway with off-street parking. Conveniently located within walking distance to shopping, restaurants, parks, and local amenities. This home offers the perfect blend of comfort and

  Floyd Amidon Maple Leaf Real Estate

  232 Depot St, Bennington, VT 05201
• 

  

  /21

  $175,000

  Sold Dec 23, 2025

  2591 Chapel Rd, Bennington, VT 05201

  • 2 Beds
  • 1 Bath
  • 880 Sq Ft
  • Built 1972

  Last Sold Summary

  • 5% Below List Price
  • $199/SF
  • 11 Days On Market

  Current Estimated Value $190,160

  Last Listing Agent Susan Bellville Bellville Realty

  2591 Chapel Rd, Bennington, VT 05201
• 

  

  /40

  Est $196,249

  Not Listed For Sale

  276 Finley Dr, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 1,866 Sq Ft
  • Built 1987

  276 Finley Dr, Bennington, VT 05201

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate
• 

  

  /36

  $259,000

  Under Contract

  • 4 Beds
  • 2 Baths
  • 1,768 Sq Ft

  549 Houran Rd, Bennington, VT 05201

  Well maintained and thoughtfully updated, this 4-bedroom, 2-bath home offers the ease of single-level living on a beautiful level one-acre lot in Bennington's desirable west end. Enjoy stunning mountain views from the spacious back deck or sip your morning coffee on the covered front porch. Inside, you'll find an updated kitchen, refreshed bathrooms, a cozy fireplace, central air conditioning, a

  Abi Gregorio

  549 Houran Rd, Bennington, VT 05201
• 

  

  /34

  $275,000

  Sold May 22, 2026

  1808 East Rd, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1977

  Last Sold Summary

  • 6% Above List Price
  • $260/SF
  • 7 Days On Market

  Current Estimated Value $273,983

  Last Listing Agent Abi Gregorio

  1808 East Rd, Bennington, VT 05201
• 

  

  /40

  Est $512,052

  Not Listed For Sale

  402 Middle Pownal Rd, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 2,706 Sq Ft
  • Built 1880

  402 Middle Pownal Rd, Bennington, VT 05201

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  /2

  $75,000

  • Land
  • 11.2 Acres
  • $6,696 per Acre

  0 Mount Anthony Rd, Bennington, VT 05201

  A beautiful opportunity awaits on Mount Anthony Road in Bennington, Vermont-11.2 acres of wooded land nestled along a quiet, scenic dirt road. This property offers the perfect blend of seclusion and convenience, giving you the best of both worlds. Currently wooded, the land can be selectively cleared to reveal potential stunning views of the surrounding Vermont landscape. Imagine building a camp

  Kelley Mccarthy Mahar McCarthy Real Estate

  0 Mount Anthony Rd, Bennington, VT 05201

Showing Results 41 - 80, Page 2 of 18