5,202

Bennington, VT Homes

Section Image
    • /38

      Est $232,087

      Not Listed For Sale

      134 Imperial Ave, Bennington, VT 05201

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1915
      134 Imperial Ave, Bennington, VT 05201

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Angela Bevin Maple Leaf Real Estate

  • /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
  • /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 $136,045

    Last Listing Agent Catherine Cairns Maple Leaf Real Estate

    273 Union St, Bennington, VT 05201
    • /33

      Est $176,959

      Not Listed For Sale

      105 Booth Terrace, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 840 Sq Ft
      • Built 1880
      105 Booth Terrace, Bennington, VT 05201

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Dan Mason Perrott Realty

  • /39

    $179,900

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 462 Sq Ft

    301 Beech St, Bennington, VT 05201

    Cute, cozy, and move-in ready! This freshly renovated 2-bedroom, 1-bath home has been updated from the ground up and offers comfortable, low-maintenance living in a convenient Bennington location. Recent improvements include a brand-new kitchen and bathroom, new flooring, fresh paint, new baseboards, new roof, front porch and expanded driveway. The home features electric baseboard heat along with

    Floyd Amidon Maple Leaf Real Estate

    301 Beech St, 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
    • /40

      Est $315,961

      Not Listed For Sale

      100 Booth Terrace, Bennington, VT 05201

      • 3 Beds
      • 2.5 Baths
      • 1,568 Sq Ft
      • Built 1905
      100 Booth Terrace, Bennington, VT 05201

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Justine Curry Maple Leaf Real Estate

  • /59

    $190,000

    $20K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,200 Sq Ft

    118 Foster Dr, Bennington, VT 05201

    Invest in the potential with this unique split-level ranch and guest house. This property presents an exceptional opportunity for anyone looking to roll up their sleeves and bring a property back to life. Set on expansive acreage surrounded by peaceful woodlands, the property offers a tranquil rural setting while remaining just a short drive from town amenities.The main residence features

    Lindsey Martin Maple Leaf Real Estate

    118 Foster 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
    • /23

      Est $278,318

      Not Listed For Sale

      101 Barber St, Bennington, VT 05201

      • 3 Beds
      • 1.5 Baths
      • 1,574 Sq Ft
      • Built 1920
      101 Barber St, Bennington, VT 05201

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent William Paquin Maple Leaf Real Estate

  • /59

    $199,900

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,132 Sq Ft

    12 Hurley Ln, Bennington, VT 05201

    Discover the potential of this charming 3-bedroom, 1-bath cabin situated on 2.17 private acres. Offering a peaceful and secluded setting while still conveniently located close to town, this property provides the best of both worlds. The property also includes a barn, providing additional space for storage, hobbies, or other possibilities. The home is served by an existing well and septic system,

    Floyd Amidon Maple Leaf Real Estate

    12 Hurley Ln, Bennington, VT 05201
  • /38

    $303,000

    Sold Sep 04, 2026

    2 Pine Rd, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,900 Sq Ft
    • Built 1948

    Last Sold Summary

    • 7% Below List Price
    • $159/SF
    • 93 Days On Market

    Current Estimated Value $309,450

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

    2 Pine Rd, Bennington, VT 05201
    • /34

      Est $264,023

      Not Listed For Sale

      99 Barber St, Bennington, VT 05201

      • 3 Beds
      • 1 Bath
      • 936 Sq Ft
      • Built 1965
      99 Barber St, Bennington, VT 05201

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  • /3

    $69,900

    $5K PRICE DROP
    • Land
    • 2.25 Acres
    • $31,067 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
  • /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 $389,230

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    231 Washington Ave, Bennington, VT 05201
    • /30

      Est $291,907

      Not Listed For Sale

      228 Grandview St, Bennington, VT 05201

      • 2 Beds
      • 1 Bath
      • 1,092 Sq Ft
      • Built 1933
      228 Grandview St, Bennington, VT 05201

      Last Sold Summary

      • 108 Days On Market

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

  • /33

    $389,900

    Under Contract
    • 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
  • /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 $345,565

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    308 Elm St, Bennington, VT 05201
    • /30

      Est $276,857

      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

  • /25

    $325,000

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

    171 Garbrooke Dr, Bennington, VT 05201

    Welcome to this inviting Cape-style home offering 3 bedrooms, 2 baths and a comfortable layout designed for both everyday living and entertaining. The main level features an open-concept kitchen and dining area that flows directly onto a huge back deck—an ideal spot for summer dinners, gatherings or simply relaxing while overlooking the secluded, wooded backyard. With both a living room and

    Lilli West Maple Leaf Real Estate

    171 Garbrooke 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 $273,030

    Last Listing Agent Justine Curry Maple Leaf Real Estate

    341 Dewey St, Bennington, VT 05201
    • /31

      Est $337,291

      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

  • /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
  • /47

    $525,000

    Sold Apr 09, 2026

    706 Jefferson Heights, Bennington, VT 05201

    • 5 Beds
    • 4 Baths
    • 2,244 Sq Ft
    • Built 1956

    Last Sold Summary

    • $234/SF
    • 4 Days On Market

    Current Estimated Value $547,285

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    706 Jefferson Heights, Bennington, VT 05201
    • /22

      Est $314,101

      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

  • /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
  • /30

    $171,000

    Sold Oct 17, 2025

    14 Pace Rd, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,724 Sq Ft
    • Built 1979

    Last Sold Summary

    • 2% Below List Price
    • $99/SF
    • 177 Days On Market

    Current Estimated Value $225,509

    Last Listing Agent Dick Thackston R.H. Thackston & Company

    14 Pace Rd, Bennington, VT 05201
    • /19

      Est $160,618

      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

  • /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
  • /47

    $304,500

    Sold Oct 24, 2025

    174 Morgan St, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,687 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Above List Price
    • $180/SF
    • 10 Days On Market

    Current Estimated Value $318,595

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    174 Morgan St, Bennington, VT 05201
    • /31

      Est $161,947

      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

  • /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
  • /31

    $329,000

    Sold Jun 05, 2026

    103 Norton St, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 1930

    Last Sold Summary

    • 3% Below List Price
    • $190/SF
    • 191 Days On Market

    Current Estimated Value $331,839

    Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

    103 Norton St, Bennington, VT 05201
    • /19

      Est $167,526

      Not Listed For Sale

      432 South St Unit A7, Bennington, VT 05201

      • 2 Beds
      • 1.5 Baths
      • 819 Sq Ft
      • Built 1989
      432 South St Unit A7, Bennington, VT 05201

      Last Sold Summary

      • 11 Days On Market

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

  • /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
  • /44

    $199,000

    Sold Jun 16, 2026

    106 Park St Unit 2, Bennington, VT 05201

    • 2 Beds
    • 2.5 Baths
    • 1,156 Sq Ft
    • Built 1993

    Last Sold Summary

    • $172/SF
    • 43 Days On Market

    Last Listing Agent Vicki Wilson Maple Leaf Real Estate

    106 Park St Unit 2, Bennington, VT 05201
    • /26

      Est $183,077

      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

  • /37

    $249,500

    • 3 Beds
    • 2 Baths
    • 1,271 Sq Ft

    230 Beech St, Bennington, VT 05201

    Conveniently located in the heart of Bennington, this charming 3-bedroom, 2-bath Cape offers a wonderful combination of comfort, privacy, and walkability. Set along a newly paved road with sidewalks, you can leave the car at home and head downtown for a meal or enjoy some of Bennington’s favorite local events. Easy highway access is nearby, yet the home feels surprisingly tucked away with its

    Mary Beth French Hoffman Real Estate

    230 Beech St, Bennington, VT 05201
  • /16

    $245,000

    Sold Sep 18, 2026

    250 North St, Bennington, VT 05201

    • 2,144 Sq Ft
    • Built 1920

    Last Sold Summary

    • 2% Below List Price
    • $114/SF
    • 6 Days On Market

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    250 North St, 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

Showing Results 201 - 240, Page 6 of 18

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