Bennington, VT Homes

• 

  

  

  /53

  $529,000

  $166K PRICE DROP Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,715 Sq Ft

  58 Mount Anthony Rd, Bennington, VT 05201

  Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can

  

  Monique Geannelis

  Mahar McCarthy Real Estate

  58 Mount Anthony Rd, Bennington, VT 05201
• Explore Bennington

• 

  

  

  /3

  Starting at $1,750 Per Month

  • Studio - 2 Beds

  757 Main St, Bennington, VT 05201

  Newly Constructed Luxury Apartments in Bennington, VermontWelcome to 757 Main Street, a newly constructed apartment community offering modern living in a convenient Bennington location. Choose from a variety of thoughtfully designed studio, one-bedroom, and two-bedroom residences created for everyday comfort and easy living.The property is conveniently located near local dining,

  757 Main St, Bennington, VT 05201
• 

  

  

  /48

  $295,000

  Sold Jul 22, 2026

  166 Cardinal Ln, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 2,753 Sq Ft
  • Built 1964

  Last Sold Summary

  • $107/SF
  • 16 Days On Market

  Current Estimated Value $303,218

  Last Listing Agent Monique Geannelis Mahar McCarthy Real Estate

  166 Cardinal Ln, 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
• 

  

  

  /38

  $299,000

  $26K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,829 Sq Ft

  89 Merson St, Woodford, VT 05201

  Welcome to 89 Merson Street! This charming Cape style home offers 3 bedrooms, 1 full bathroom and a half bathroom, and nearly an acre of land on a quiet in town street. Inside, you’ll find beautifully refinished hardwood floors, an updated kitchen, a spacious family room with a fireplace, and a new Weil-McLain boiler installed in February 2026.What truly sets this property apart is its

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  89 Merson St, Woodford, VT 05201
• 

  

  /6

  $1,050 Per Month

  • 1 Bed
  • 1 Bath
  • 450 Sq Ft
  • Condo for Rent

  103 County St Unit 2, Bennington, VT 05201

  Property Id: 810906 1 bedroom apartment is located on second floor.Month to month lease where tenants pay for their utilities such as heat electric etc..

  103 County St Unit 2, Bennington, VT 05201
• 

  

  /30

  $345,750

  Sold Oct 21, 2025

  374 Overlea Rd, North Bennington, VT 05257

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft
  • Built 1948

  Last Sold Summary

  • 5% Below List Price
  • $197/SF
  • 58 Days On Market

  Current Estimated Value $403,722

  Last Listing Agent Gregory Cutler Four Seasons Sotheby's Int'l Realty

  374 Overlea Rd, North Bennington, VT 05257
• 

  

  /14

  Est $292,383

  Not Listed For Sale

  400 South St, Bennington, VT 05201

  • 3 Beds
  • 3 Baths
  • 1,461 Sq Ft
  • Built 1825

  400 South St, Bennington, VT 05201

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent William Paquin Maple Leaf Real Estate
• 

  

  /33

  $279,000

  $20K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,408 Sq Ft

  8 West St, Bennington, VT 05201

  Nestled in the heart of the charming North Bennington community, this lovingly maintained 3 bedroom, 1.5 bath home is ready for its next chapter. Recently refreshed with newly painted interiors, rejuvenated floors, updated electrical, a recently repointed foundation, and repointed chimney, this home blends classic character with thoughtful updates throughout.Enjoy the convenience of first

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  8 West St, Bennington, VT 05201
• 

  /2

  $1,050 Per Month

  • 1 Bed
  • 1 Bath
  • House for Rent

  165 Benmont Ave, Bennington, VT 05201

  Property Id: 1488761 I bed 1 bath small house.The tenants pay their own utilities:heat electric etc…

  165 Benmont Ave, Bennington, VT 05201
• 

  

  /49

  $435,000

  Sold Oct 10, 2025

  458 Fox Hill Rd, Bennington, VT 05201

  • 4 Beds
  • 4 Baths
  • 3,040 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Above List Price
  • $143/SF
  • 7 Days On Market

  Current Estimated Value $469,431

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  458 Fox Hill Rd, Bennington, VT 05201
• 

  

  /22

  Est $88,384

  Not Listed For Sale

  91 Nelson Rd, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 832 Sq Ft
  • Built 1963

  91 Nelson Rd, Bennington, VT 05201

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Brenda Jones KW Vermont - Brenda Jones Real Estate Group
• 

  

  /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
• 

  

  /26

  $1,300

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  172 S Branch St Unit 172, Bennington, VT 05201

  First floor two bedroom- walk to town- living room, dining room, kitchen, full bathroom with shower stall, comes with newer electric stove and fridge, washer/dryer hookups- heat is forced hot air (fuel oil)- rent DOES NOT INCLUDE utilities- I pay for lawncare, plowing and garbage- I take first month's rent, last month's rent and one month's rent as a security deposit (3x

  172 S Branch St Unit 172, Bennington, VT 05201
• 

  

  /28

  $398,350

  Sold Sep 04, 2025

  315 Chester Knoll Dr, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 2025

  Last Sold Summary

  • $246/SF
  • 0 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate

  315 Chester Knoll Dr, Bennington, VT 05201
• 

  

  /37

  Est $246,059

  Not Listed For Sale

  213 Gage St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft
  • Built 1850

  213 Gage St, Bennington, VT 05201

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  

  /33

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,911 Sq Ft

  21 Russett Dr, Bennington, VT 05201

  Tucked into a beautifully maintained neighborhood, 21 Russett Drive is the kind of home that feels welcoming the moment you arrive. Beautiful landscaping, a charming Dutch door, and a thoughtfully cared for yard give this property an almost secret garden feel private, inviting, and full of character.Inside, the versatility of this home truly shines. The main level offers a comfortable living

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  21 Russett Dr, Bennington, VT 05201
• 

  

  /26

  $1,300

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 500 Sq Ft
  • Condo for Rent

  178 S Branch St Unit 178, Bennington, VT 05201

  Second floor two bedroom in quiet neighborhood.- two good sized bedrooms, each with closet- living room- eat in kitchen with new floor- bathroom with shower stall- new windows- newer carpet / newly painted- great quiet neighborhood but still close to downtown- propane heat (tenant pays)- off peak electric hot water (tenant pays)- property owner pays for

  178 S Branch St Unit 178, Bennington, VT 05201
• 

  

  /28

  $265,000

  Sold Dec 15, 2025

  26 Cyr Ct, Bennington, VT 05201

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft
  • Built 2000

  Last Sold Summary

  • $255/SF
  • 5 Days On Market

  Current Estimated Value $271,315

  Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate

  26 Cyr Ct, Bennington, VT 05201
• 

  

  /32

  Est $339,062

  Not Listed For Sale

  169 Bard Rd, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1975

  169 Bard Rd, Bennington, VT 05201

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate
• 

  

  /16

  $249,000

  Under Contract

  • 2,144 Sq Ft

  250 North St, Bennington, VT 05201

  Investment opportunities like this are few and far between! Located in a desirable mixed use district, this well maintained four unit one bedroom apartment building offers an excellent opportunity for both seasoned and first time investors. The property features four one bedroom apartments with full bathrooms, each with its own unique character and appeal. Two of the front/lower units have been

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  250 North St, Bennington, VT 05201
• 

  

  /11

  $2,125

  Total Monthly Price

  • 3 Beds
  • 1.5 Baths
  • 980 Sq Ft
  • House for Rent

  9 Mountain View Rd, Bennington, VT 05201

  Please read instructions below on how to tour or apply. The green "Request To Apply" button will cause a delay in our ability to respond.COMPLETELY RENOVATED 3br MANUFACTURED HOME for rent!*Large 2-CAR Garage!**Desirable Lot*Unit: M-009Apply To: Mountain View CommunityRent: $2125/moBeds/Baths: 3 beds 1.5 bathsSize: 980 square feetPets: Cat & Dog

  9 Mountain View Rd, Bennington, VT 05201
• 

  

  /16

  $96,906

  Sold Jul 18, 2026

  41 Audrey Ln, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Above List Price
  • $125/SF
  • 301 Days On Market

  Last Listing Agent Kate Barry EXP Realty

  41 Audrey Ln, Bennington, VT 05201
• 

  

  /57

  Not Listed For Sale

  115-117 Norton St, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 1,701 Sq Ft
  • Built 1930

  115-117 Norton St, Bennington, VT 05201

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  

  /19

  $179,000

  Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  106 Park St Unit 9, Bennington, VT 05201

  Looking for easy, low maintenance living in a location that puts everything within reach? This inviting first floor condo offers comfort, convenience, and affordability all in one package.Featuring two bedrooms, a bright and welcoming living room filled with natural light, a spacious kitchen with generous counter space, ample storage, and the convenience of having your kitchen, bathroom,

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  106 Park St Unit 9, Bennington, VT 05201
• 

  

  /8

  $1,070 Per Month

  • 1 Bed
  • 1 Bath
  • 460 Sq Ft
  • Condo for Rent

  319 Pleasant St Unit 101 - Front Down, Bennington, VT 05201

  *MANAGED BY CRM, LLC*NO FEES CHARGED AT APPLICATION PROCESS, PLEASE BE AWARE OF SCAMS!This charming apartment offers a cozy and comfortable living space with one bedroom and one bathroom. Immerse yourself in the rich history of Bennington as you explore the vibrant downtown area, just steps away from your doorstep. The apartment boasts a convenient location, allowing you to easily

  319 Pleasant St Unit 101 - Front Down, Bennington, VT 05201
• 

  

  /57

  $190,000

  Sold Sep 16, 2025

  100 Webb St, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,416 Sq Ft
  • Built 1943

  Last Sold Summary

  • 12% Below List Price
  • $134/SF
  • 75 Days On Market

  Current Estimated Value $200,839

  Last Listing Agent Lindsey Martin Maple Leaf Real Estate

  100 Webb St, Bennington, VT 05201
• 

  

  /21

  Not Listed For Sale

  0 Sunset Dr Unit 5005504, Bennington, VT 05201

  0 Sunset Dr Unit 5005504, Bennington, VT 05201

  Last Sold Summary

  • 297 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate
• 

  

  /7

  $55,000

  • Land
  • 22,215 Sq Ft
  • $107,843 per Acre

  24 Asa Way, Bennington, VT 05257

  Build your future in the heart of North Bennington at 24 Asa's Way. This 0.51 acre corner lot offers a rare opportunity to create a custom home in a well established neighborhood surrounded by beautifully maintained properties. With mountain views and underground utilities already in place, the setting combines natural beauty with modern convenience.Public water and sewer are available,

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  24 Asa Way, Bennington, VT 05257
• 

  

  /6

  $1,025 Per Month

  • 1 Bed
  • 1 Bath
  • 441 Sq Ft
  • 111/113 Gage St

  111-113-113 Gage St Unit 111 #2, Bennington, VT 05201

  *MANAGED BY CRM, LLC*NO FEES CHARGED AT APPLICATION PROCESS, PLEASE BE AWARE OF SCAMS!Charming one-bedroom unit nestled in the heart of our beautiful town. Modern and cozy. Conveniently located for easy access to local amenities, including unique local shops and a relaxed, small-town atmosphere. Your ideal home for enjoying the simplicity of small-town living.For additional

  111-113-113 Gage St Unit 111 #2, Bennington, VT 05201
• 

  

  /36

  $300,000

  Sold Apr 02, 2026

  318 Chester Knoll Dr, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,865 Sq Ft
  • Built 2006

  Last Sold Summary

  • $161/SF
  • 5 Days On Market

  Current Estimated Value $312,085

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  318 Chester Knoll Dr, Bennington, VT 05201
• 

  

  /27

  Est $197,550

  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
• 

  

  /5

  $55,000

  • Land
  • 20,908 Sq Ft
  • $114,583 per Acre

  29 Asa Way, Bennington, VT 05257

  Build your dream home at 29 Asa's Way, ideally situated at the top of the hill in a desirable North Bennington neighborhood. This 0.48 acre lot offers a level, build friendly setting with beautiful mountain views, providing the perfect backdrop for your future home.Public water and sewer are available, along with underground utilities, making for a smooth and efficient building process.

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  29 Asa Way, Bennington, VT 05257
• 

  

  /11

  $1,700 Per Month

  • 3 Beds
  • 1 Bath
  • 1,130 Sq Ft
  • Condo for Rent

  207 Maple St Unit 1, Bennington, VT 05201

  *MANAGED BY CRM, LLC*NO FEES CHARGED AT APPLICATION PROCESS, PLEASE BE AWARE OF SCAMS!Spacious 3 bedroom unit located in downtown Bennington. A spacious apartment with front and back entrance. Walking distance to stores, restaurants, and many more! Experience the charm of Bennington and all it has to offer from the comfort of your new home. Don't miss out on this opportunity to live

  207 Maple St Unit 1, Bennington, VT 05201
• 

  

  /46

  $290,000

  Sold Apr 10, 2026

  112 Norton St, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 1,564 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Below List Price
  • $185/SF
  • 8 Days On Market

  Current Estimated Value $298,265

  Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  112 Norton St, Bennington, VT 05201
• 

  

  /60

  Est $315,800

  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
• 

  

  /32

  $595,000

  • Land
  • 23.62 Acres
  • $25,191 per Acre

  3213 West Rd, Bennington, VT 05201

  Some properties offer acreage, some offer breathtaking views, very few offer both along with a rich history worth preserving and a future waiting to be imagined. For generations, this rare south-facing farm has looked across the valley enjoying sunlight from dawn until dusk & panoramic views that are exceptional! More than productive farmland, it became a place where neighbors and families

  

  Monique Geannelis

  Mahar McCarthy Real Estate

  3213 West Rd, Bennington, VT 05201
• 

  

  /6

  $1,400 Per Month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • 133/135 Dewey St

  133-135 Dewey St Unit 133 #1, Woodford, VT 05201

  *MANAGED BY CRM, LLC*NO FEES CHARGED AT APPLICATION PROCESS, PLEASE BE AWARE OF SCAMS!Charming two-bedroom unit nestled in the heart of our cozy town. Modern and spacious. Conveniently located for easy access to local amenities, including unique local shops and a relaxed, small-town atmosphere. Your ideal home for enjoying the simplicity of small-town living.For additional

  133-135 Dewey St Unit 133 #1, Woodford, VT 05201
• 

  

  /41

  $141,000

  Sold Apr 01, 2026

  235 Maple St, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 1,060 Sq Ft
  • Built 1915

  Last Sold Summary

  • 5% Below List Price
  • $133/SF
  • 13 Days On Market

  Current Estimated Value $150,582

  Last Listing Agent Lindsey Martin Maple Leaf Real Estate

  235 Maple St, Bennington, VT 05201
• 

  

  /35

  Est $279,680

  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

Showing Results 1 - 40, Page 1 of 18