5,202

Bennington, VT Homes

Section Image
    • 8 Center St, Bennington, VT 05201
      8 Center St, Bennington, VT 05201
      8 Center St, Bennington, VT 05201
      /38

      Est $361,425

      Not Listed For Sale

      8 Center St, Bennington, VT 05201

      • 4 Beds
      • 2.5 Baths
      • 1,784 Sq Ft
      • Built 1977
      8 Center St, Bennington, VT 05201

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • 113 South St Unit 302, Bennington, VT 05201
    113 South St Unit 302, Bennington, VT 05201
    113 South St Unit 302, Bennington, VT 05201
    /30

    $295,000

    Sold Jul 21, 2026

    113 South St Unit 302, Bennington, VT 05201

    • 1 Bed
    • 1.5 Baths
    • 1,120 Sq Ft
    • Built 1865

    Last Sold Summary

    • 9% Below List Price
    • $263/SF
    • 32 Days On Market

    Current Estimated Value $368,237

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    113 South St Unit 302, Bennington, VT 05201
    • 322 Burgess Rd, Bennington, VT 05201
      322 Burgess Rd, Bennington, VT 05201
      322 Burgess Rd, Bennington, VT 05201
      /60

      Est $254,134

      Not Listed For Sale

      322 Burgess Rd, Bennington, VT 05201

      • 2 Beds
      • 2 Baths
      • 2,004 Sq Ft
      • Built 1958
      322 Burgess Rd, Bennington, VT 05201

      Last Sold Summary

      • 62 Days On Market

      Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  • 24 Cassie Ln, Bennington, VT 05201
    24 Cassie Ln, Bennington, VT 05201
    24 Cassie Ln, Bennington, VT 05201
    /14

    $96,906

    Sold Jan 22, 2026

    24 Cassie Ln, Bennington, VT 05201

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

    Last Sold Summary

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

    Last Listing Agent Kate Barry EXP Realty

    24 Cassie Ln, Bennington, VT 05201
    • 38 Arthurs Dr, Bennington, VT 05201
      38 Arthurs Dr, Bennington, VT 05201
      38 Arthurs Dr, Bennington, VT 05201
      /22

      Est $196,617

      Not Listed For Sale

      38 Arthurs Dr, Bennington, VT 05201

      • 3 Beds
      • 1 Bath
      • 900 Sq Ft
      • Built 1949
      38 Arthurs Dr, Bennington, VT 05201

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  • 149 Jewett Dr, Bennington, VT 05201
    149 Jewett Dr, Bennington, VT 05201
    149 Jewett Dr, Bennington, VT 05201
    /36

    $350,000

    Sold Jun 26, 2026

    149 Jewett Dr, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 2,108 Sq Ft
    • Built 1967

    Last Sold Summary

    • 1% Below List Price
    • $166/SF
    • 20 Days On Market

    Current Estimated Value $376,528

    Last Listing Agent Faith Rhodes Maple Leaf Real Estate

    149 Jewett Dr, Bennington, VT 05201
    • 508 Burgess Rd, Bennington, VT 05201
      508 Burgess Rd, Bennington, VT 05201
      508 Burgess Rd, Bennington, VT 05201
      /36

      Est $273,176

      Not Listed For Sale

      508 Burgess Rd, Bennington, VT 05201

      • 4 Beds
      • 1.5 Baths
      • 1,684 Sq Ft
      • Built 1890
      508 Burgess Rd, Bennington, VT 05201

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Lindsey Martin Maple Leaf Real Estate

  • 1047 East Rd, Bennington, VT 05201
    1047 East Rd, Bennington, VT 05201
    1047 East Rd, Bennington, VT 05201
    /10

    $265,000

    Sold Dec 19, 2025

    1047 East Rd, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,428 Sq Ft
    • Built 1956

    Last Sold Summary

    • 4% Below List Price
    • $186/SF
    • 1 Day On Market

    Current Estimated Value $272,417

    Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate

    1047 East Rd, Bennington, VT 05201
    • 1032 Main St, Bennington, VT 05201
      1032 Main St, Bennington, VT 05201
      1032 Main St, Bennington, VT 05201
      /3

      Est $217,811

      Not Listed For Sale

      1032 Main St, Bennington, VT 05201

      • Studio
      • 2,334 Sq Ft
      • Built 1930
      1032 Main St, Bennington, VT 05201

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Paul Carroccio TPW Real Estate

  • 523 Jennings Brook Dr, Bennington, VT 05201
    523 Jennings Brook Dr, Bennington, VT 05201
    523 Jennings Brook Dr, Bennington, VT 05201
    /4

    $327,000

    Sold Jun 30, 2026

    523 Jennings Brook Dr, Bennington, VT 05201

    • 2 Beds
    • 2 Baths
    • 1,190 Sq Ft
    • Built 2026

    Last Sold Summary

    • 7% Below List Price
    • $275/SF
    • 0 Days On Market

    Last Listing Agent Lilli West Maple Leaf Real Estate

    523 Jennings Brook Dr, Bennington, VT 05201
    • 1004 Main St, Bennington, VT 05201
      1004 Main St, Bennington, VT 05201
      1004 Main St, Bennington, VT 05201
      /28

      Est $240,155

      Not Listed For Sale

      1004 Main St, Bennington, VT 05201

      • 5 Beds
      • 3 Baths
      • 1,872 Sq Ft
      • Built 1920
      1004 Main St, Bennington, VT 05201

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Erica Hale Ridgeline Real Estate

  • 111 Booth Terrace, Bennington, VT 05201
    111 Booth Terrace, Bennington, VT 05201
    111 Booth Terrace, Bennington, VT 05201
    /40

    $265,000

    Sold May 29, 2026

    111 Booth Terrace, Bennington, VT 05201

    • 6 Beds
    • 4 Baths
    • 2,520 Sq Ft
    • Built 1922

    Last Sold Summary

    • 8% Below List Price
    • $105/SF
    • 18 Days On Market

    Current Estimated Value $282,651

    Last Listing Agent Abi Gregorio

    111 Booth Terrace, Bennington, VT 05201
    • 121 Fillmore St, Bennington, VT 05201
      121 Fillmore St, Bennington, VT 05201
      121 Fillmore St, Bennington, VT 05201
      /38

      Est $304,627

      Not Listed For Sale

      121 Fillmore St, Bennington, VT 05201

      • 4 Beds
      • 2 Baths
      • 1,736 Sq Ft
      • Built 1946
      121 Fillmore St, Bennington, VT 05201

      Last Sold Summary

      • 66 Days On Market

      Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  • 115 River St, Bennington, VT 05201
    115 River St, Bennington, VT 05201
    115 River St, Bennington, VT 05201
    /26

    $75,500

    Sold Dec 05, 2025

    115 River St, Bennington, VT 05201

    • 4 Beds
    • 1.5 Baths
    • 1,887 Sq Ft
    • Built 1913

    Last Sold Summary

    • 6% Below List Price
    • $40/SF
    • 134 Days On Market

    Current Estimated Value $181,578

    Last Listing Agent Linda Benoit Highland Realty

    115 River St, Bennington, VT 05201
    • 82 Oakes St, Bennington, VT 05201
      82 Oakes St, Bennington, VT 05201
      82 Oakes St, Bennington, VT 05201
      /36

      Est $273,281

      Not Listed For Sale

      82 Oakes St, Bennington, VT 05201

      • 2 Beds
      • 1 Bath
      • 1,512 Sq Ft
      • Built 1991
      82 Oakes St, Bennington, VT 05201

      Last Sold Summary

      • 57 Days On Market

      Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  • 224 Union St, Bennington, VT 05201
    224 Union St, Bennington, VT 05201
    224 Union St, Bennington, VT 05201
    /34

    $270,000

    Sold Mar 20, 2026

    224 Union St, Bennington, VT 05201

    • 2,754 Sq Ft
    • Built 1920

    Last Sold Summary

    • $98/SF
    • 2 Days On Market

    Current Estimated Value $283,069

    Last Listing Agent Melissa Nebelski Real Broker LLC

    224 Union St, Bennington, VT 05201
    • 4 Gage Place, Bennington, VT 05201
      4 Gage Place, Bennington, VT 05201
      4 Gage Place, Bennington, VT 05201
      /18

      Est $207,802

      Not Listed For Sale

      4 Gage Place, Bennington, VT 05201

      • 3 Beds
      • 1 Bath
      • 948 Sq Ft
      • Built 1925
      4 Gage Place, Bennington, VT 05201

      Last Sold Summary

      • 105 Days On Market

      Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  • 341 Chester Knoll Dr, Bennington, VT 05201
    341 Chester Knoll Dr, Bennington, VT 05201
    341 Chester Knoll Dr, Bennington, VT 05201
    /58

    $285,500

    Sold Jun 12, 2026

    341 Chester Knoll Dr, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,365 Sq Ft
    • Built 1988

    Last Sold Summary

    • 3% Below List Price
    • $209/SF
    • 4 Days On Market

    Current Estimated Value $291,939

    Last Listing Agent Catherine Cairns Maple Leaf Real Estate

    341 Chester Knoll Dr, Bennington, VT 05201
    • 125 Beech St, Bennington, VT 05201
      125 Beech St, Bennington, VT 05201
      125 Beech St, Bennington, VT 05201
      /37

      Est $268,544

      Not Listed For Sale

      125 Beech St, Bennington, VT 05201

      • 4 Beds
      • 2 Baths
      • 1,380 Sq Ft
      • Built 1931
      125 Beech St, Bennington, VT 05201

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • 115 Grandview St, Bennington, VT 05201
    115 Grandview St, Bennington, VT 05201
    115 Grandview St, Bennington, VT 05201
    /35

    $435,000

    Sold Dec 11, 2025

    115 Grandview St, Bennington, VT 05201

    • 5 Beds
    • 2.5 Baths
    • 2,104 Sq Ft
    • Built 1899

    Last Sold Summary

    • 8% Below List Price
    • $207/SF
    • 58 Days On Market

    Current Estimated Value $446,000

    Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate

    115 Grandview St, Bennington, VT 05201
    • 120 Beech St, Bennington, VT 05201
      120 Beech St, Bennington, VT 05201
      120 Beech St, Bennington, VT 05201
      /36

      Est $257,856

      Not Listed For Sale

      120 Beech St, Bennington, VT 05201

      • 3 Beds
      • 1.5 Baths
      • 1,531 Sq Ft
      • Built 1880
      120 Beech St, Bennington, VT 05201

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Floyd Amidon Maple Leaf Real Estate

  • 682 Fox Hill Rd, Bennington, VT 05201
    682 Fox Hill Rd, Bennington, VT 05201
    682 Fox Hill Rd, Bennington, VT 05201
    /21

    $838,500

    Sold May 29, 2026

    682 Fox Hill Rd, Bennington, VT 05201

    • 3 Beds
    • 2.5 Baths
    • 1,728 Sq Ft

    Last Sold Summary

    • $485/SF
    • 0 Days On Market

    Current Estimated Value $821,000

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    682 Fox Hill Rd, Bennington, VT 05201
    • 130 Beech St, Bennington, VT 05201
      130 Beech St, Bennington, VT 05201
      130 Beech St, Bennington, VT 05201
      /38

      Est $236,878

      Not Listed For Sale

      130 Beech St, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,416 Sq Ft
      • Built 1940
      130 Beech St, Bennington, VT 05201

      Last Sold Summary

      • 103 Days On Market

      Last Listing Agent Justine Curry Maple Leaf Real Estate

  • 328 Chester Knoll Dr, Bennington, VT 05201
    328 Chester Knoll Dr, Bennington, VT 05201
    328 Chester Knoll Dr, Bennington, VT 05201
    /54

    $386,000

    Sold Apr 30, 2026

    328 Chester Knoll Dr, Bennington, VT 05201

    • 3 Beds
    • 3.5 Baths
    • 2,148 Sq Ft
    • Built 2005

    Last Sold Summary

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

    Current Estimated Value $409,409

    Last Listing Agent Vicki Wilson Maple Leaf Real Estate

    328 Chester Knoll Dr, Bennington, VT 05201
    • 210 Beech St, Bennington, VT 05201
      210 Beech St, Bennington, VT 05201
      210 Beech St, Bennington, VT 05201
      /40

      Est $251,019

      Not Listed For Sale

      210 Beech St, Bennington, VT 05201

      • 6 Beds
      • 3 Baths
      • 2,240 Sq Ft
      • Built 1890
      210 Beech St, Bennington, VT 05201

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Erica Hale Ridgeline Real Estate

  • 61 Autumn Acres, Bennington, VT 05201
    61 Autumn Acres, Bennington, VT 05201
    61 Autumn Acres, Bennington, VT 05201
    /36

    $275,000

    Sold Dec 16, 2025

    61 Autumn Acres, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,169 Sq Ft
    • Built 1970

    Last Sold Summary

    • $235/SF
    • 3 Days On Market

    Current Estimated Value $285,157

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    61 Autumn Acres, Bennington, VT 05201
    • 112 Rollin St, Bennington, VT 05201
      112 Rollin St, Bennington, VT 05201
      112 Rollin St, Bennington, VT 05201
      /33

      Est $273,373

      Not Listed For Sale

      112 Rollin St, Bennington, VT 05201

      • 4 Beds
      • 1 Bath
      • 1,620 Sq Ft
      • Built 1945
      112 Rollin St, Bennington, VT 05201

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate

  • 2288 East Rd, Bennington, VT 05201
    2288 East Rd, Bennington, VT 05201
    2288 East Rd, Bennington, VT 05201
    /24

    $250,000

    Sold Jan 09, 2026

    2288 East Rd, Bennington, VT 05201

    • 5 Beds
    • 3 Baths
    • 3,164 Sq Ft
    • Built 1967

    Last Sold Summary

    • 11% Below List Price
    • $79/SF
    • 64 Days On Market

    Current Estimated Value $259,376

    Last Listing Agent William Paquin Maple Leaf Real Estate

    2288 East Rd, Bennington, VT 05201
    • 129 Webb St, Bennington, VT 05201
      129 Webb St, Bennington, VT 05201
      129 Webb St, Bennington, VT 05201
      /10

      Not Listed For Sale

      129 Webb St, Bennington, VT 05201

      • 12 Beds
      • 4 Baths
      • 5,400 Sq Ft
      • Built 1890
      129 Webb St, Bennington, VT 05201

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Gabrielle Burdge

  • 56 Hildur Hill, Bennington, VT 05201
    56 Hildur Hill, Bennington, VT 05201
    56 Hildur Hill, Bennington, VT 05201
    /32

    $302,000

    Sold Jun 25, 2026

    56 Hildur Hill, Bennington, VT 05201

    • 3 Beds
    • 2 Baths
    • 1,640 Sq Ft
    • Built 1992

    Last Sold Summary

    • 1% Above List Price
    • $184/SF
    • 6 Days On Market

    Current Estimated Value $319,444

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    56 Hildur Hill, Bennington, VT 05201
    • 807 Main St, Bennington, VT 05201
      807 Main St, Bennington, VT 05201
      807 Main St, Bennington, VT 05201
      /37

      Est $204,522

      Not Listed For Sale

      807 Main St, Bennington, VT 05201

      • 3 Beds
      • 1.5 Baths
      • 1,444 Sq Ft
      • Built 1900
      807 Main St, Bennington, VT 05201

      Last Sold Summary

      • 88 Days On Market

      Last Listing Agent Floyd Amidon Maple Leaf Real Estate

  • 123 Bradford St, Bennington, VT 05201
    123 Bradford St, Bennington, VT 05201
    123 Bradford St, Bennington, VT 05201
    /4

    $220,000

    Sold Jul 17, 2026

    123 Bradford St, Bennington, VT 05201

    • 2,080 Sq Ft
    • Built 1920

    Last Sold Summary

    • 12% Below List Price
    • $106/SF
    • 7 Days On Market

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

    123 Bradford St, Bennington, VT 05201
    • 133 Webb St, Bennington, VT 05201
      133 Webb St, Bennington, VT 05201
      133 Webb St, Bennington, VT 05201
      /23

      Not Listed For Sale

      133 Webb St, Bennington, VT 05201

      • 7 Beds
      • 4 Baths
      • 4,264 Sq Ft
      • Built 1850
      133 Webb St, Bennington, VT 05201

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Gabrielle Burdge

  • 215 Maple St, Bennington, VT 05201
    215 Maple St, Bennington, VT 05201
    215 Maple St, Bennington, VT 05201
    /26

    $191,500

    Sold Feb 26, 2026

    215 Maple St, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 1,278 Sq Ft
    • Built 1900

    Last Sold Summary

    • 23% Below List Price
    • $150/SF
    • 128 Days On Market

    Current Estimated Value $195,672

    Last Listing Agent Matt Waddington Hoffman Real Estate

    215 Maple St, Bennington, VT 05201
    • 111 Safford St, Bennington, VT 05201
      111 Safford St, Bennington, VT 05201
      111 Safford St, Bennington, VT 05201
      /40

      Est $292,079

      Not Listed For Sale

      111 Safford St, Bennington, VT 05201

      • 4 Beds
      • 1.5 Baths
      • 1,680 Sq Ft
      • Built 1924
      111 Safford St, Bennington, VT 05201

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • 106 Park St Unit 9, Bennington, VT 05201
    106 Park St Unit 9, Bennington, VT 05201
    106 Park St Unit 9, Bennington, VT 05201
    /19

    $179,000

    Sold Aug 17, 2026

    106 Park St Unit 9, Bennington, VT 05201

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

    Last Sold Summary

    • $170/SF
    • 18 Days On Market

    Current Estimated Value $180,966

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    106 Park St Unit 9, Bennington, VT 05201
    • 809 Gage St, Bennington, VT 05201
      809 Gage St, Bennington, VT 05201
      809 Gage St, Bennington, VT 05201
      /29

      Est $202,344

      Not Listed For Sale

      809 Gage St, Bennington, VT 05201

      • 2 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1930
      809 Gage St, Bennington, VT 05201

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Dan Mason Perrott Realty

  • 218 Union St, Bennington, VT 05201
    218 Union St, Bennington, VT 05201
    218 Union St, Bennington, VT 05201
    /39

    $277,500

    Sold Feb 20, 2026

    218 Union St, Bennington, VT 05201

    • 5 Beds
    • 2 Baths
    • 2,294 Sq Ft
    • Built 1900

    Last Sold Summary

    • 7% Below List Price
    • $121/SF
    • 269 Days On Market

    Current Estimated Value $288,334

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    218 Union St, Bennington, VT 05201
    • 121 Bradford St, Bennington, VT 05201
      121 Bradford St, Bennington, VT 05201
      121 Bradford St, Bennington, VT 05201
      /3

      Est $285,461

      Not Listed For Sale

      121 Bradford St, Bennington, VT 05201

      • 3 Beds
      • 2,178 Sq Ft
      • Built 1878
      121 Bradford St, Bennington, VT 05201

      Last Sold Summary

      • 166 Days On Market

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

  • 420 Burgess Rd, Bennington, VT 05201
    420 Burgess Rd, Bennington, VT 05201
    420 Burgess Rd, Bennington, VT 05201
    /8

    $40,000

    Sold Jul 24, 2026

    420 Burgess Rd, Bennington, VT 05201

    • Land
    • 12,632 Sq Ft
    • $137,931 per Acre

    Last Sold Summary

    • 32% Below List Price
    • 315 Days On Market

    Current Estimated Value $56,366

    Last Listing Agent Dan Mason Perrott Realty

    420 Burgess Rd, Bennington, VT 05201

Showing Results 281 - 320, Page 8 of 18

Vermont Bennington County

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group