Bennington, VT Homes

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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 $467,160

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  356 Elm St, Bennington, VT 05201
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  /25

  Not Listed For Sale

  86 Ethans Way Unit Lot 86E, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 825 Sq Ft
  • Built 2024

  86 Ethans Way Unit Lot 86E, Bennington, VT 05201

  Last Sold Summary

  • 125 Days On Market

  Last Listing Agent Kate Barry EXP Realty
• 

  

  

  /28

  $209,900

  $15K PRICE DROP Pending

  • 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
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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 $1,456,129

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  16 West Rd, Bennington, VT 05201
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  /56

  Not Listed For Sale

  321 Chester Knoll Dr, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,702 Sq Ft
  • Built 2024

  321 Chester Knoll Dr, Bennington, VT 05201

  Last Sold Summary

  • 156 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate
• 

  

  /50

  $140,000

  $20K 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
• 

  

  /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 $99,715

  Last Listing Agent Zachary Zupan EXP Realty

  109 Evergreen Dr, Bennington, VT 05201
• 

  

  /27

  Est $200,683

  Not Listed For Sale

  731 Main St, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 1,155 Sq Ft
  • Built 1900

  731 Main St, Bennington, VT 05201

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Dana Haley Real Broker LLC
• 

  

  /15

  $162,500

  $7K PRICE DROP

  • 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
• 

  

  /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 $173,053

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

  432 South St Unit B2, Bennington, VT 05201
• 

  

  /60

  Est $327,769

  Not Listed For Sale

  818 Main St, Bennington, VT 05201

  • 4 Beds
  • 3 Baths
  • 1,969 Sq Ft
  • Built 1920

  818 Main St, Bennington, VT 05201

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
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  /6

  $199,900

  • 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
• 

  

  /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 $428,718

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  882 East Rd, Bennington, VT 05201
• 

  

  /35

  Est $281,465

  Not Listed For Sale

  312 School St Unit 314, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 2,184 Sq Ft
  • Built 1908

  312 School St Unit 314, Bennington, VT 05201

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Angela Bevin Maple Leaf Real Estate
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  /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
• 

  

  /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
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  /34

  Est $502,568

  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
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  /44

  $189,900

  Pending

  • 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
• 

  

  /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 $520,140

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

  245 Southshire Dr, Bennington, VT 05201
• 

  

  /39

  Est $596,956

  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
• 

  

  /53

  $1,695,000

  • 3 Beds
  • 2.5 Baths
  • 4,120 Sq Ft

  1944 Monument Ave, Bennington, VT 05201

  Set on 5.63 beautiful acres in one of Bennington's most desirable locations, this exceptional 1880 historic home has been thoughtfully renovated inside and out, blending timeless character with sophisticated modern amenities. The property includes approximately 3,200 square feet in the main residence, an attached two-car garage with a second kitchen, and a separate 1,000-square-foot one-bedroom

  Kelley Mccarthy Mahar McCarthy Real Estate

  1944 Monument Ave, 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 $211,952

  Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

  111 Hicks Ave, Bennington, VT 05201
• 

  

  /38

  Est $691,855

  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
• 

  

  /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
• 

  

  /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 $318,589

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  21 Pageant St, Bennington, VT 05201
• 

  

  /19

  Est $441,140

  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
• 

  

  /32

  $315,000

  • 3 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  314 Chester Knoll Dr, Bennington, VT 05201

  There is something special about a home that has been truly loved, and you can feel it the moment you step inside. Exceptionally clean, beautifully cared for, and thoughtfully maintained, this inviting three-bedroom home is tucked into a peaceful little neighborhood with nearby walking trails and a stream that adds to the sense of calm and community.Inside, the home feels bright, comfortable,

  Faith Rhodes Maple Leaf Real Estate

  314 Chester Knoll Dr, 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 $196,086

  Last Listing Agent Susan Bellville Bellville Realty

  2591 Chapel Rd, Bennington, VT 05201
• 

  

  /21

  Est $193,983

  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
• 

  /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
• 

  

  /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 $285,192

  Last Listing Agent Abi Gregorio

  1808 East Rd, Bennington, VT 05201
• 

  

  /37

  Not Listed For Sale

  73 Woodford City Rd, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1984

  73 Woodford City Rd, Bennington, VT 05201

  Last Sold Summary

  • 73 Days On Market

  Last Listing Agent Abi Gregorio
• 

  

  /34

  $579,000

  • 3 Beds
  • 2 Baths
  • 2,501 Sq Ft

  856 Matteson Rd, Bennington, VT 05201

  Escape to your own private Vermont retreat with this beautiful log home, tucked away in a peaceful, secluded setting surrounded by several acres of thoughtfully landscaped grounds, yet minutes from shopping and dining. From the stamped concrete patio and charming fish pond with waterfall to your very own putting green, this property was designed for enjoying life both indoors and out.Step

  Lilli West Maple Leaf Real Estate

  856 Matteson Rd, Bennington, VT 05201
• 

  

  /17

  $140,500

  Sold Feb 24, 2026

  432 South St Unit C6, Bennington, VT 05201

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

  Last Sold Summary

  • 9% Below List Price
  • $165/SF
  • 181 Days On Market

  Current Estimated Value $150,206

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  432 South St Unit C6, Bennington, VT 05201
• 

  

  /47

  Est $418,130

  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
• 

  

  /52

  $230,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  113 Main St, Bennington, VT 05201

  Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry.Step inside to find gleaming newly upgraded flooring, a warm and inviting

  Lindsey Martin Maple Leaf Real Estate

  113 Main St, Bennington, VT 05201
• 

  

  /50

  $640,000

  Sold Dec 22, 2025

  55 Monument Ave, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 2,675 Sq Ft
  • Built 1787

  Last Sold Summary

  • 2% Below List Price
  • $239/SF
  • 14 Days On Market

  Current Estimated Value $662,890

  Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  55 Monument Ave, Bennington, VT 05201
• 

  

  /57

  Est $286,587

  Not Listed For Sale

  153 Spur Rd Unit PVT, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,224 Sq Ft
  • Built 1978

  153 Spur Rd Unit PVT, Bennington, VT 05201

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Lindsey Martin Maple Leaf Real Estate
• 

  

  /53

  $205,000

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

  305 Weeks St, Bennington, VT 05201

  Experience refined living in this beautifully appointed tri-level townhouse-style condominium, ideally situated just moments from downtown, the hospital, shopping, and dining. Rich in vintage character while thoughtfully updated for modern living, this exceptional residence showcases elegant quartz and butcher block countertops, a designer tile backsplash, and striking marble flooring that create

  Lindsey Martin Maple Leaf Real Estate

  305 Weeks St, Bennington, VT 05201
• 

  

  /4

  $45,000

  Sold Oct 06, 2025

  45 Shady Ln, Bennington, VT 05201

  • 4 Beds
  • 1 Bath
  • 1,142 Sq Ft
  • Built 1948

  Last Sold Summary

  • 25% Below List Price
  • $39/SF
  • 7 Days On Market

  Current Estimated Value $131,516

  Last Listing Agent Erika Floriani Hoffman Real Estate

  45 Shady Ln, Bennington, VT 05201

Showing Results 41 - 80, Page 2 of 18