5,189

Bennington, VT Homes

Section Image
  • 321 Chester Knoll Dr, Bennington, VT 05201
    321 Chester Knoll Dr, Bennington, VT 05201
    321 Chester Knoll Dr, Bennington, VT 05201
    /56

    $385,000

    Sold Sep 23, 2025

    321 Chester Knoll Dr, Bennington, VT 05201

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

    Last Sold Summary

    • 2% Above List Price
    • $226/SF
    • 156 Days On Market

    Last Listing Agent Lilli West Maple Leaf Real Estate

    321 Chester Knoll Dr, Bennington, VT 05201
    • 227 Division St, Bennington, VT 05201
      227 Division St, Bennington, VT 05201
      227 Division St, Bennington, VT 05201
      /38

      Est $275,945

      Not Listed For Sale

      227 Division St, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,620 Sq Ft
      • Built 1900
      227 Division St, Bennington, VT 05201

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman 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 $394,346

    Last Listing Agent Vicki Wilson Maple Leaf Real Estate

    328 Chester Knoll Dr, Bennington, VT 05201
    • 220 Division St, Bennington, VT 05201
      220 Division St, Bennington, VT 05201
      220 Division St, Bennington, VT 05201
      /17

      Est $189,601

      Not Listed For Sale

      220 Division St, Bennington, VT 05201

      • 3 Beds
      • 1.5 Baths
      • 1,056 Sq Ft
      • Built 1900
      220 Division St, Bennington, VT 05201

      Last Sold Summary

      • 72 Days On Market

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

  • 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 $279,366

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    61 Autumn Acres, Bennington, VT 05201
    • 210 Division St, Bennington, VT 05201
      210 Division St, Bennington, VT 05201
      210 Division St, Bennington, VT 05201
      /15

      Est $183,156

      Not Listed For Sale

      210 Division St, Bennington, VT 05201

      • 3 Beds
      • 1 Bath
      • 1,220 Sq Ft
      • Built 1900
      210 Division St, Bennington, VT 05201

      Last Sold Summary

      • 101 Days On Market

      Last Listing Agent Vicki Wilson Maple Leaf 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
    • 810 Gage St, Bennington, VT 05201
      810 Gage St, Bennington, VT 05201
      810 Gage St, Bennington, VT 05201
      /38

      Est $277,068

      Not Listed For Sale

      810 Gage St, Bennington, VT 05201

      • 4 Beds
      • 2 Baths
      • 1,806 Sq Ft
      • Built 1920
      810 Gage St, Bennington, VT 05201

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • 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 $299,958

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    56 Hildur Hill, Bennington, VT 05201
    • 211 Bradford St, Bennington, VT 05201
      211 Bradford St, Bennington, VT 05201
      211 Bradford St, Bennington, VT 05201
      /34

      Est $283,077

      Not Listed For Sale

      211 Bradford St, Bennington, VT 05201

      • 2 Beds
      • 2 Baths
      • 1,372 Sq Ft
      • Built 1894
      211 Bradford St, Bennington, VT 05201

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Justine Curry 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
    • 222 Bradford St, Bennington, VT 05201
      222 Bradford St, Bennington, VT 05201
      222 Bradford St, Bennington, VT 05201
      /35

      Est $279,803

      Not Listed For Sale

      222 Bradford St, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,756 Sq Ft
      • Built 1890
      222 Bradford St, Bennington, VT 05201

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Abi Gregorio

  • 46 Duffy Dr, Bennington, VT 05201
    46 Duffy Dr, Bennington, VT 05201
    46 Duffy Dr, Bennington, VT 05201
    /47

    $375,000

    Sold Aug 26, 2025

    46 Duffy Dr, Bennington, VT 05201

    • 5 Beds
    • 3.5 Baths
    • 3,600 Sq Ft
    • Built 2001

    Last Sold Summary

    • 6% Below List Price
    • $104/SF
    • 35 Days On Market

    Current Estimated Value $405,882

    Last Listing Agent Nick Sicard EXP Realty

    46 Duffy Dr, Bennington, VT 05201
    • 107 Charles St, Bennington, VT 05201
      107 Charles St, Bennington, VT 05201
      107 Charles St, Bennington, VT 05201
      /18

      Est $151,005

      Not Listed For Sale

      107 Charles St, Bennington, VT 05201

      • 3 Beds
      • 1 Bath
      • 1,112 Sq Ft
      • Built 1925
      107 Charles St, Bennington, VT 05201

      Last Sold Summary

      • 224 Days On Market

      Last Listing Agent Lindsey Martin Maple Leaf Real Estate

  • 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 $191,438

    Last Listing Agent Matt Waddington Hoffman Real Estate

    215 Maple St, Bennington, VT 05201
    • 109 Charles St, Bennington, VT 05201
      109 Charles St, Bennington, VT 05201
      109 Charles St, Bennington, VT 05201
      /30

      Est $222,554

      Not Listed For Sale

      109 Charles St, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,000 Sq Ft
      • Built 1920
      109 Charles St, Bennington, VT 05201

      Last Sold Summary

      • 14 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 $278,542

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    218 Union St, Bennington, VT 05201
    • 926 Gage St, Bennington, VT 05201
      926 Gage St, Bennington, VT 05201
      926 Gage St, Bennington, VT 05201
      /21

      Est $293,724

      Not Listed For Sale

      926 Gage St, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,661 Sq Ft
      • Built 1930
      926 Gage St, Bennington, VT 05201

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

  • 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 $59,919

    Last Listing Agent Dan Mason Perrott Realty

    420 Burgess Rd, Bennington, VT 05201
    • 920 Gage St, Bennington, VT 05201
      920 Gage St, Bennington, VT 05201
      920 Gage St, Bennington, VT 05201
      /9

      Est $210,597

      Not Listed For Sale

      920 Gage St, Bennington, VT 05201

      • 3 Beds
      • 1.5 Baths
      • 1,152 Sq Ft
      • Built 1920
      920 Gage St, Bennington, VT 05201

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Matt Waddington Hoffman Real Estate

  • 27 Broken Pines Dr, Bennington, VT 05201
    27 Broken Pines Dr, Bennington, VT 05201
    27 Broken Pines Dr, Bennington, VT 05201
    /58

    $355,000

    Sold Apr 06, 2026

    27 Broken Pines Dr, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,344 Sq Ft
    • Built 1973

    Last Sold Summary

    • 1% Above List Price
    • $264/SF
    • 5 Days On Market

    Current Estimated Value $346,267

    Last Listing Agent Vicki Wilson Maple Leaf Real Estate

    27 Broken Pines Dr, Bennington, VT 05201
    • 211 Branch St, Bennington, VT 05201
      211 Branch St, Bennington, VT 05201
      211 Branch St, Bennington, VT 05201
      /24

      Est $271,418

      Not Listed For Sale

      211 Branch St, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,340 Sq Ft
      • Built 1920
      211 Branch St, Bennington, VT 05201

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Pauline Green Lamacchia Realty, Inc. - Adams

  • 1016 County St, Bennington, VT 05201
    1016 County St, Bennington, VT 05201
    1016 County St, Bennington, VT 05201
    /25

    $250,000

    Sold Dec 15, 2025

    1016 County St, Bennington, VT 05201

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Built 1900

    Last Sold Summary

    • $278/SF
    • 3 Days On Market

    Current Estimated Value $246,405

    Last Listing Agent Abi Gregorio

    1016 County St, Bennington, VT 05201
    • 906 County St, Bennington, VT 05201
      906 County St, Bennington, VT 05201
      906 County St, Bennington, VT 05201
      /40

      Est $224,077

      Not Listed For Sale

      906 County St, Bennington, VT 05201

      • 3 Beds
      • 1 Bath
      • 1,152 Sq Ft
      • Built 1930
      906 County St, Bennington, VT 05201

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • 165 Pippin Knoll, Bennington, VT 05201
    165 Pippin Knoll, Bennington, VT 05201
    165 Pippin Knoll, Bennington, VT 05201
    /48

    $351,000

    Sold Nov 21, 2025

    165 Pippin Knoll, Bennington, VT 05201

    • 4 Beds
    • 3 Baths
    • 2,994 Sq Ft
    • Built 1958

    Last Sold Summary

    • 8% Above List Price
    • $117/SF
    • 7 Days On Market

    Current Estimated Value $379,929

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    165 Pippin Knoll, Bennington, VT 05201
    • 305 Grove St, Bennington, VT 05201
      305 Grove St, Bennington, VT 05201
      305 Grove St, Bennington, VT 05201
      /40

      Est $190,364

      Not Listed For Sale

      305 Grove St, Bennington, VT 05201

      • 1 Bed
      • 1 Bath
      • 800 Sq Ft
      • Built 2016
      305 Grove St, Bennington, VT 05201

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Justine Curry Maple Leaf Real Estate

  • 339 Chester Knoll Dr, Bennington, VT 05201
    339 Chester Knoll Dr, Bennington, VT 05201
    339 Chester Knoll Dr, Bennington, VT 05201
    /21

    $300,000

    Sold Oct 16, 2025

    339 Chester Knoll Dr, Bennington, VT 05201

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

    Last Sold Summary

    • $220/SF
    • 77 Days On Market

    Current Estimated Value $305,301

    Last Listing Agent Lori Hurley Four Corner Properties LLC

    339 Chester Knoll Dr, Bennington, VT 05201
    • 304 Grove St, Bennington, VT 05201
      304 Grove St, Bennington, VT 05201
      304 Grove St, Bennington, VT 05201
      /17

      Not Listed For Sale

      304 Grove St, Bennington, VT 05201

      • 5 Beds
      • 3 Baths
      • 1,810 Sq Ft
      • Built 1900
      304 Grove St, Bennington, VT 05201

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Gabrielle Burdge

  • 106 Park St Unit 1, Bennington, VT 05201
    106 Park St Unit 1, Bennington, VT 05201
    106 Park St Unit 1, Bennington, VT 05201
    /32

    $170,000

    Sold Sep 03, 2025

    106 Park St Unit 1, Bennington, VT 05201

    • 2 Beds
    • 1.5 Baths
    • 1,155 Sq Ft
    • Built 1993

    Last Sold Summary

    • 8% Below List Price
    • $147/SF
    • 66 Days On Market

    Last Listing Agent Faith Rhodes Maple Leaf Real Estate

    106 Park St Unit 1, Bennington, VT 05201
    • 111 Lyons St, Bennington, VT 05201
      111 Lyons St, Bennington, VT 05201
      111 Lyons St, Bennington, VT 05201
      /38

      Est $259,346

      Not Listed For Sale

      111 Lyons St, Bennington, VT 05201

      • 4 Beds
      • 1 Bath
      • 1,476 Sq Ft
      • Built 1915
      111 Lyons St, Bennington, VT 05201

      Last Sold Summary

      • 217 Days On Market

      Last Listing Agent Lilli West Maple Leaf Real Estate

  • 105 Albe Dr, Bennington, VT 05201
    105 Albe Dr, Bennington, VT 05201
    105 Albe Dr, Bennington, VT 05201
    /37

    $300,007

    Sold Jul 09, 2026

    105 Albe Dr, Bennington, VT 05201

    • 3 Beds
    • 2 Baths
    • 1,729 Sq Ft
    • Built 1999

    Last Sold Summary

    • 5% Below List Price
    • $174/SF
    • 3 Days On Market

    Current Estimated Value $316,370

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    105 Albe Dr, Bennington, VT 05201
    • 106 Putnam St, Bennington, VT 05201
      106 Putnam St, Bennington, VT 05201
      106 Putnam St, Bennington, VT 05201
      /32

      Est $349,842

      Not Listed For Sale

      106 Putnam St, Bennington, VT 05201

      • 4 Beds
      • 3 Baths
      • 2,308 Sq Ft
      • Built 1892
      106 Putnam St, Bennington, VT 05201

      Last Sold Summary

      • 212 Days On Market

      Last Listing Agent Kristin Comeau TPW Real Estate

  • 105 Nelson Rd, Bennington, VT 05201
    105 Nelson Rd, Bennington, VT 05201
    /2

    $41,000

    Sold May 04, 2026

    105 Nelson Rd, Bennington, VT 05201

    • Land
    • 2.21 Acres
    • $18,552 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 15 Days On Market

    Current Estimated Value $41,624

    Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

    105 Nelson Rd, Bennington, VT 05201
    • 120 Elm St, Bennington, VT 05201
      120 Elm St, Bennington, VT 05201
      120 Elm St, Bennington, VT 05201
      /32

      Est $345,260

      Not Listed For Sale

      120 Elm St, Bennington, VT 05201

      • 5 Beds
      • 2.5 Baths
      • 2,942 Sq Ft
      • Built 1930
      120 Elm St, Bennington, VT 05201

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

  • 508 Barney Rd, Bennington, VT 05201
    508 Barney Rd, Bennington, VT 05201
    508 Barney Rd, Bennington, VT 05201
    /60

    $260,000

    Sold Jul 17, 2026

    508 Barney Rd, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,934 Sq Ft
    • Built 1930

    Last Sold Summary

    • 3% Below List Price
    • $134/SF
    • 49 Days On Market

    Current Estimated Value $267,041

    Last Listing Agent Dan Mason Perrott Realty

    508 Barney Rd, Bennington, VT 05201
    • 215 School St, Bennington, VT 05201
      215 School St, Bennington, VT 05201
      215 School St, Bennington, VT 05201
      /39

      Est $216,280

      Not Listed For Sale

      215 School St, Bennington, VT 05201

      • 4 Beds
      • 2 Baths
      • 1,718 Sq Ft
      • Built 1920
      215 School St, Bennington, VT 05201

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • 1758 East Rd, Bennington, VT 05201
    1758 East Rd, Bennington, VT 05201
    1758 East Rd, Bennington, VT 05201
    /33

    $250,000

    Sold Apr 15, 2026

    1758 East Rd, Bennington, VT 05201

    • 2 Beds
    • 1 Bath
    • 1,064 Sq Ft
    • Built 1978

    Last Sold Summary

    • 6% Below List Price
    • $235/SF
    • 12 Days On Market

    Current Estimated Value $261,004

    Last Listing Agent Morriah Adams BHG Masiello Brattleboro

    1758 East Rd, Bennington, VT 05201
    • 106 Park St Unit 8, Bennington, VT 05201
      106 Park St Unit 8, Bennington, VT 05201
      106 Park St Unit 8, Bennington, VT 05201
      /34

      Est $189,993

      Not Listed For Sale

      106 Park St Unit 8, Bennington, VT 05201

      • 2 Beds
      • 1.5 Baths
      • 1,056 Sq Ft
      • Built 1993
      106 Park St Unit 8, Bennington, VT 05201

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  • 20 Rockwood St, Bennington, VT 05201
    20 Rockwood St, Bennington, VT 05201
    20 Rockwood St, Bennington, VT 05201
    /19

    $241,000

    Sold Sep 25, 2025

    20 Rockwood St, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,070 Sq Ft
    • Built 1990

    Last Sold Summary

    • 4% Below List Price
    • $225/SF
    • 4 Days On Market

    Current Estimated Value $244,547

    Last Listing Agent Vicki Wilson Maple Leaf Real Estate

    20 Rockwood St, Bennington, VT 05201
    • 216 Union St, Bennington, VT 05201
      216 Union St, Bennington, VT 05201
      216 Union St, Bennington, VT 05201
      /40

      Est $194,301

      Not Listed For Sale

      216 Union St, Bennington, VT 05201

      • 4 Beds
      • 3 Baths
      • 1,887 Sq Ft
      • Built 1890
      216 Union St, Bennington, VT 05201

      Last Sold Summary

      • 206 Days On Market

      Last Listing Agent Lilli West Maple Leaf Real Estate

Showing Results 321 - 360, Page 9 of 18

Vermont Bennington County

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