Bennington, VT Homes

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  /21

  $120,000

  Sold Mar 09, 2026

  1319 Vail Rd, Bennington, VT 05201

  • Land
  • 20 Acres
  • $6,000 per Acre

  Last Sold Summary

  • 143 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate

  1319 Vail Rd, Bennington, VT 05201
• 

  

  

  /30

  Est $289,145

  Not Listed For Sale

  221 Grandview St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,042 Sq Ft
  • Built 1948

  221 Grandview St, Bennington, VT 05201

  Last Sold Summary

  • 75 Days On Market

  Last Listing Agent Angela Bevin Maple Leaf Real Estate
• 

  

  

  /22

  $232,500

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft

  903 Gage St, Bennington, VT 05201

  You can make this home your own! With a little TLC, this charming 3 bedroom, 2 bath, Cape has the potential to become the perfect home. Featuring a large, level yard, a two-car, detached garage, with attached outdoor room, mudroom to the kitchen, wood floors, fireplace (condition unknown) and with this central location, it offers endless possibilities. Whether you are looking to renovate,

  Pauline Green

  903 Gage St, Bennington, VT 05201
• 

  

  

  /47

  $240,000

  Sold Sep 24, 2025

  120 Imperial Ave, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 2,404 Sq Ft
  • Built 1895

  Last Sold Summary

  • 20% Below List Price
  • $100/SF
  • 114 Days On Market

  Current Estimated Value $278,592

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  120 Imperial Ave, Bennington, VT 05201
• 

  

  

  /31

  Est $334,786

  Not Listed For Sale

  325 Silver St, Bennington, VT 05201

  • 5 Beds
  • 3 Baths
  • 1,840 Sq Ft
  • Built 1956

  325 Silver St, Bennington, VT 05201

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Derek Greene Derek Greene
• 

  

  /30

  $595,000

  • 3 Beds
  • 2 Baths
  • 2,379 Sq Ft

  1278 Harrington Rd, Bennington, VT 05201

  Nestled on 16.96 picturesque acres, this spacious 3-4 bedroom, 2 full bath home offers the perfect blend of privacy, comfort, and breathtaking Vermont scenery. Built in 1993, the home features a bright, open-concept great room with expansive windows that capture stunning views of the surrounding landscape. The inviting living area is anchored by a beautiful fireplace, creating a warm and

  Kelley Mccarthy Mahar McCarthy Real Estate

  1278 Harrington Rd, Bennington, VT 05201
• 

  

  /36

  $355,000

  Sold May 29, 2026

  695 Dermody Rd, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,748 Sq Ft
  • Built 1978

  Last Sold Summary

  • 5% Below List Price
  • $203/SF
  • 2 Days On Market

  Current Estimated Value $364,868

  Last Listing Agent Monique Geannelis Mahar McCarthy Real Estate

  695 Dermody Rd, Bennington, VT 05201
• 

  

  /22

  Est $313,505

  Not Listed For Sale

  214 Prospect St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,833 Sq Ft
  • Built 1920

  214 Prospect St, Bennington, VT 05201

  Last Sold Summary

  • 93 Days On Market

  Last Listing Agent Lori Hurley Four Corner Properties LLC
• 

  

  /37

  $539,900

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  811 Middle Pownal Rd, Bennington, VT 05201

  Thoughtfully crafted with a distinctive European-inspired character and beautifully updated throughout, this custom-built 4-bedroom, 3-bath home offers the perfect blend of quality craftsmanship, privacy, and convenience on a picturesque, landscaped lot just minutes from downtown Bennington. The bright and inviting interior features a beautifully renovated kitchen, spacious living areas with

  Jeffrey Dorman

  811 Middle Pownal Rd, Bennington, VT 05201
• 

  

  /52

  $740,000

  Sold Oct 10, 2025

  77 Monument Ave, Bennington, VT 05201

  • 4 Beds
  • 3.5 Baths
  • 4,032 Sq Ft
  • Built 1807

  Last Sold Summary

  • 5% Below List Price
  • $184/SF
  • 16 Days On Market

  Current Estimated Value $765,796

  Last Listing Agent Moira Spivey Four Seasons Sotheby's Int'l Realty

  77 Monument Ave, Bennington, VT 05201
• 

  

  /19

  Est $157,112

  Not Listed For Sale

  432 South St Unit C7, Bennington, VT 05201

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

  432 South St Unit C7, Bennington, VT 05201

  Last Sold Summary

  • 46 Days On Market

  Last Listing Agent Abi Gregorio
• 

  

  /14

  $104,900

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 768 Sq Ft

  347 Hickory Rd, Bennington, VT 05201

  Your wait is over—an exceptional opportunity to own in the highly sought-after Woodford Lake Estates! This unique property offers direct access to the beauty of the surrounding Green Mountain National Forest and is ideally located near VAST snowmobile trails, making it a year-round haven for outdoor enthusiasts. Enjoy cross-country skiing just minutes away at Prospect Mountain, along with beach

  William Paquin Maple Leaf Real Estate

  347 Hickory Rd, Bennington, VT 05201
• 

  

  /58

  $1,800,000

  Sold Jul 24, 2026

  1086 West Rd, Bennington, VT 05201

  • 9 Beds
  • 7 Baths
  • 6,956 Sq Ft
  • Built 1866

  Last Sold Summary

  • 8% Below List Price
  • $259/SF
  • 91 Days On Market

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  1086 West Rd, Bennington, VT 05201
• 

  

  /11

  Est $178,821

  Not Listed For Sale

  432 South St Unit C5, Bennington, VT 05201

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

  432 South St Unit C5, Bennington, VT 05201

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
• 

  

  /59

  $210,000

  • 5 Beds
  • 2 Baths
  • 2,200 Sq Ft

  118 Foster Dr, Bennington, VT 05201

  Set on over 5.5 acres of private, natural surroundings, this unique split-level ranch with an auxiliary dwelling unit offers an exceptional opportunity for multi-generational living, rental income, or a private guest retreat. Surrounded by peaceful woodlands, the property provides a tranquil rural setting while remaining just a short drive from town amenities.The main residence features three

  Lindsey Martin Maple Leaf Real Estate

  118 Foster Dr, Bennington, VT 05201
• 

  

  /39

  $250,000

  Sold Oct 14, 2025

  139 Mckinley St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,264 Sq Ft
  • Built 1920

  Last Sold Summary

  • 9% Below List Price
  • $198/SF
  • 25 Days On Market

  Current Estimated Value $255,332

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  139 Mckinley St, Bennington, VT 05201
• 

  

  /36

  Est $184,124

  Not Listed For Sale

  432 South St Unit B5, Bennington, VT 05201

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

  432 South St Unit B5, Bennington, VT 05201

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
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  /3

  $74,900

  • Land
  • 2.25 Acres
  • $33,289 per Acre

  0 Brambley Ln, Bennington, VT 05201

  Expansive 2.25-acre level lot situated on a quiet, private dead-end street. This is an amazing opportunity to build a dream home, a weekend retreat, or a spec house for investment. The property features 306 feet of road frontage, has been perc tested, and includes septic plans for a three-bedroom system. Located on the outskirt of town, but still close proximity to historic downtown Bennington

  Matt Waddington Hoffman Real Estate

  0 Brambley Ln, Bennington, VT 05201
• 

  

  /34

  $399,900

  Sold Oct 06, 2025

  43 Spur Rd, Bennington, VT 05201

  • 2 Beds
  • 3 Baths
  • 1,700 Sq Ft
  • Built 1996

  Last Sold Summary

  • $235/SF
  • 8 Days On Market

  Current Estimated Value $342,829

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

  43 Spur Rd, Bennington, VT 05201
• 

  

  /31

  Est $153,677

  Not Listed For Sale

  432 South St Unit B4, Bennington, VT 05201

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

  432 South St Unit B4, Bennington, VT 05201

  Last Sold Summary

  • 262 Days On Market

  Last Listing Agent Gabrielle Burdge
• 

  

  /33

  $389,900

  • 3 Beds
  • 2 Baths
  • 2,098 Sq Ft

  185 Jewett Dr, Bennington, VT 05201

  Welcome home to this 3-bedroom, 2-bath raised ranch nestled on 1.72 beautifully landscaped acres in a peaceful neighborhood. The picturesque property is adorned with a variety of mature fruit trees and offers stunning mountain views. A spacious back deck overlooks the above-ground pool, making it the perfect setting for relaxing, entertaining, or taking in the scenery.Inside, you'll find

  Julie Glover Mahar McCarthy Real Estate

  185 Jewett Dr, Bennington, VT 05201
• 

  

  /44

  $40,000

  Sold Oct 31, 2025

  273 Union St, Bennington, VT 05201

  • 5 Beds
  • 1 Bath
  • 1,952 Sq Ft
  • Built 1910

  Last Sold Summary

  • 60% Below List Price
  • $20/SF
  • 108 Days On Market

  Current Estimated Value $136,348

  Last Listing Agent Catherine Cairns Maple Leaf Real Estate

  273 Union St, Bennington, VT 05201
• 

  

  /26

  Est $181,452

  Not Listed For Sale

  432 South St Unit A2, Bennington, VT 05201

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

  432 South St Unit A2, Bennington, VT 05201

  Last Sold Summary

  • 142 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate
• 

  

  /3

  $475,000

  • Land
  • 12.82 Acres
  • $37,051 per Acre

  22 Morse Rd, Bennington, VT 05201

  Positioned in the heart of Bennington’s commercial corridor on 12.82 open acres, 22 Morse Road present a prime development opportunity. Offering excellent visibility and accessibility along one of the area’s primary commercial arteries, the property is ideally situated for a variety of commercial, retail, service, mixed-use, or redevelopment possibilities. The location provides convenient access

  Paul Carroccio TPW Real Estate

  22 Morse Rd, Bennington, VT 05201
• 

  

  /15

  $325,000

  Sold Jul 21, 2026

  1803 Harwood Hill Rd, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,496 Sq Ft
  • Built 1970

  Last Sold Summary

  • 9% Above List Price
  • $217/SF
  • 12 Days On Market

  Current Estimated Value $300,340

  Last Listing Agent Lori Hurley Four Corner Properties LLC

  1803 Harwood Hill Rd, Bennington, VT 05201
• 

  

  /4

  Not Listed For Sale

  406 South St, Bennington, VT 05201

  • 6 Beds
  • 6 Baths
  • 2,690 Sq Ft
  • Built 1900

  406 South St, Bennington, VT 05201

  Last Sold Summary

  • 27 Days On Market

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

  

  /4

  $350,000

  New Construction Under Contract

  • 2 Beds
  • 2 Baths
  • 1,190 Sq Ft

  524 Jennings Brook Dr, Bennington, VT 05201

  Brand new 2026 construction offering the ease of single-level living with thoughtful, ADA-compliant design throughout. This energy-efficient home features 2 bedrooms and 2 full bathrooms, including a well-designed primary suite, plus convenient in-unit laundry. The open-concept layout is highlighted by a spacious kitchen and a cathedral ceiling that brings in abundant natural light and an airy

  Lilli West Maple Leaf Real Estate

  524 Jennings Brook Dr, Bennington, VT 05201
• 

  

  /27

  $274,000

  Sold Jan 22, 2026

  26 Sage St, Bennington, VT 05257

  • 9 Beds
  • 3 Baths
  • 3,176 Sq Ft
  • Built 1820

  Last Sold Summary

  • 8% Below List Price
  • $86/SF
  • 55 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate

  26 Sage St, Bennington, VT 05257
• 

  

  /32

  Est $243,165

  Not Listed For Sale

  402 South St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 2,262 Sq Ft
  • Built 1940

  402 South St, Bennington, VT 05201

  Last Sold Summary

  • 721 Days On Market

  Last Listing Agent Phil Lewis Mahar McCarthy Real Estate
• 

  

  /32

  $265,000

  $10K PRICE DROP

  • 1,680 Sq Ft

  318 North St, Bennington, VT 05201

  Versatile mixed-use property with strong potential as a duplex or owner-occupied investment in a highly visible downtown North Street location. Currently configured with a beautifully renovated 1-bedroom, 1-bath apartment on the second floor and a spacious first-floor commercial unit, this property offers multiple paths for income and future use. Zoning supports multi-family, single-family, and a

  Jenifer Prouty Hoffman Hoffman Real Estate

  318 North St, Bennington, VT 05201
• 

  

  /33

  $355,000

  Sold Sep 19, 2025

  60 Knoll Crest Ln, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 2,072 Sq Ft
  • Built 1948

  Last Sold Summary

  • $171/SF
  • 22 Days On Market

  Current Estimated Value $364,597

  Last Listing Agent Moira Spivey Four Seasons Sotheby's Int'l Realty

  60 Knoll Crest Ln, Bennington, VT 05201
• 

  

  /38

  Est $162,859

  Not Listed For Sale

  314 Weeks St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,301 Sq Ft
  • Built 1920

  314 Weeks St, Bennington, VT 05201

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Floyd Amidon Maple Leaf Real Estate
• 

  

  /15

  $269,000

  Pending

  • 2,500 Sq Ft

  626 Main St, Bennington, VT 05201

  Prime Mixed-Use Building on Main Street-Bennington, Vermont. Located in the heart of downtown Bennington, this versatile mixed-use property offers an excellent opportunity for both investors and owner-occupants. The main level features a spacious, adaptable commercial space ideal for retail, office, or service-based businesses. With its high visibility and foot traffic on Main Street, this is a

  Kelley Mccarthy Mahar McCarthy Real Estate

  626 Main St, Bennington, VT 05201
• 

  

  /29

  $398,000

  Sold Jul 21, 2026

  231 Washington Ave, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,556 Sq Ft
  • Built 1932

  Last Sold Summary

  • 1% Above List Price
  • $256/SF
  • 4 Days On Market

  Current Estimated Value $387,907

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  231 Washington Ave, Bennington, VT 05201
• 

  

  /34

  Est $422,741

  Not Listed For Sale

  103 Francis St, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 2,138 Sq Ft
  • Built 1968

  103 Francis St, Bennington, VT 05201

  Last Sold Summary

  • 172 Days On Market

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

  

  /16

  $96,406

  New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  32 Cassie Ln, Bennington, VT 05201

  Welcome to 32 Cassie Lane, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  32 Cassie Ln, Bennington, VT 05201
• 

  

  /33

  $353,000

  Sold May 01, 2026

  308 Elm St, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 2,218 Sq Ft
  • Built 1923

  Last Sold Summary

  • 1% Above List Price
  • $159/SF
  • 12 Days On Market

  Current Estimated Value $346,500

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  308 Elm St, Bennington, VT 05201
• 

  

  /38

  Est $345,107

  Not Listed For Sale

  127 Jefferson Ave, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft
  • Built 1925

  127 Jefferson Ave, Bennington, VT 05201

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Lindsey Martin Maple Leaf Real Estate
• 

  

  /28

  $265,000

  Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,688 Sq Ft

  128 Northside Dr, Bennington, VT 05201

  Welcome to this 3 bedroom, 1.5 bath Cape style home located in a planned commercial zone. Offering 1,688 square feet of well-designed living space on a manageable 0.26-acre lot, this inviting residence is perfect for comfortable family living.Offers beautiful hardwood floors gracing the upstairs bedrooms, as well as the spacious living and dining rooms—ideal for gathering with loved ones.

  Timothy Corcoran Mahar McCarthy Real Estate

  128 Northside Dr, Bennington, VT 05201
• 

  

  /58

  $258,000

  Sold Mar 25, 2026

  341 Dewey St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft
  • Built 1900

  Last Sold Summary

  • 1% Below List Price
  • $180/SF
  • 6 Days On Market

  Current Estimated Value $265,316

  Last Listing Agent Justine Curry Maple Leaf Real Estate

  341 Dewey St, Bennington, VT 05201

Showing Results 201 - 240, Page 6 of 18