2,737

Chester, VT Homes

Section Image
  • 501 Gates Rd, Chester, VT 05143
    501 Gates Rd, Chester, VT 05143
    501 Gates Rd, Chester, VT 05143
    /27

    $165,000 Sold Jul 23, 2025

    501 Gates Rd, Chester, VT 05143

    • 1 Bed
    • 1 Bath
    • 616 Sq Ft
    • Built 2013

    Last Sold Summary

    • 18% Below List Price
    • $268/SF
    • 20 Days On Market

    Last Listing Agent Rebecca Seymour Brattleboro Area Realty

    501 Gates Rd, Chester, VT 05143
    • 656 Depot St, Chester, VT 05143
      656 Depot St, Chester, VT 05143
      656 Depot St, Chester, VT 05143
      /35

      Est $323,458 Not Listed For Sale

      656 Depot St, Chester, VT 05143

      • 3 Beds
      • 3 Baths
      • 2,280 Sq Ft
      • Built 1987
      656 Depot St, Chester, VT 05143

      Last Sold Summary

      • 77% Above List Price
      • $80/SF
      • 13 Days On Market
      • Last Sold Price $183,000
      • Dec 08, 2023

      Last Listing Agent Glenn Olney Barrett and Valley Associates Inc.

  • 358 Maple Ridge Rd, Chester, VT 05143
    358 Maple Ridge Rd, Chester, VT 05143
    358 Maple Ridge Rd, Chester, VT 05143
    /16

    $285,000 Sold Jul 31, 2025

    358 Maple Ridge Rd, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 1,488 Sq Ft
    • Built 1989

    Last Sold Summary

    • $192/SF
    • 2 Days On Market

    Current Estimated Value $290,970

    Last Listing Agent Gale Alger

    358 Maple Ridge Rd, Chester, VT 05143
    • 566 Simonsville Rd, Chester, VT 05143
      566 Simonsville Rd, Chester, VT 05143
      566 Simonsville Rd, Chester, VT 05143
      /53

      Est $625,000 Not Listed For Sale

      566 Simonsville Rd, Chester, VT 05143

      • 3 Beds
      • 2.5 Baths
      • 2,650 Sq Ft
      • Built 1820
      566 Simonsville Rd, Chester, VT 05143

      Last Sold Summary

      • 25% Above List Price
      • $188/SF
      • 229 Days On Market
      • Last Sold Price $499,000
      • Feb 03, 2025

      Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

  • 3619 Baltimore Rd, Chester, VT 05143
    3619 Baltimore Rd, Chester, VT 05143
    3619 Baltimore Rd, Chester, VT 05143
    /55

    $300,000 Sold Jan 16, 2026

    3619 Baltimore Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • Built 1994

    Last Sold Summary

    • 10% Below List Price
    • $189/SF
    • 81 Days On Market

    Last Listing Agent Leila Tarantelli KW Coastal and Lakes & Mountains Realty/Hanover

    3619 Baltimore Rd, Chester, VT 05143
    • 56 Hidden Newton Rd, Chester, VT 05143
      56 Hidden Newton Rd, Chester, VT 05143
      56 Hidden Newton Rd, Chester, VT 05143
      /41

      Est $462,616 Not Listed For Sale

      56 Hidden Newton Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,410 Sq Ft
      • Built 1999
      56 Hidden Newton Rd, Chester, VT 05143

      Last Sold Summary

      • 13% Above List Price
      • $291/SF
      • 44 Days On Market
      • Last Sold Price $410,000
      • Nov 08, 2024

      Last Listing Agent Alison Cummings Cummings & Co

  • 525 Route 103 N, Chester, VT 05143
    525 Route 103 N, Chester, VT 05143
    /2

    $315,000 Sold Dec 10, 2025

    525 Route 103 N, Chester, VT 05143

    • 6 Beds
    • 1 Bath
    • 2,308 Sq Ft
    • Built 1830

    Last Sold Summary

    • 47% Below List Price
    • $136/SF
    • 69 Days On Market

    Last Listing Agent Glenn Olney Barrett and Valley Associates Inc.

    525 Route 103 N, Chester, VT 05143
    • 2358 N Hill Rd, Chester, VT 05143
      2358 N Hill Rd, Chester, VT 05143
      2358 N Hill Rd, Chester, VT 05143
      /39

      Est $509,688 Not Listed For Sale

      2358 N Hill Rd, Chester, VT 05143

      • 4 Beds
      • 3 Baths
      • 2,070 Sq Ft
      • Built 1975
      2358 N Hill Rd, Chester, VT 05143

      Last Sold Summary

      • 5% Above List Price
      • $235/SF
      • 6 Days On Market
      • Last Sold Price $485,500
      • Jul 31, 2024

      Last Listing Agent John Napier TPW Real Estate

  • 3236 Weston-Andover Rd, Chester, VT 05143
    3236 Weston-Andover Rd, Chester, VT 05143
    3236 Weston-Andover Rd, Chester, VT 05143
    /60

    $677,000 Sold Aug 15, 2025

    3236 Weston-Andover Rd, Chester, VT 05143

    • 4 Beds
    • 3 Baths
    • 2,456 Sq Ft
    • Built 1878

    Last Sold Summary

    • 6% Above List Price
    • $276/SF
    • 6 Days On Market

    Current Estimated Value $663,411

    Last Listing Agent Mendi Michael Engel & Völkers Okemo

    3236 Weston-Andover Rd, Chester, VT 05143
    • 1767 Rockingham Rd, Chester, VT 05143
      1767 Rockingham Rd, Chester, VT 05143
      1767 Rockingham Rd, Chester, VT 05143
      /24

      Est $311,463 Not Listed For Sale

      1767 Rockingham Rd, Chester, VT 05143

      • 2 Beds
      • 1.5 Baths
      • 1,293 Sq Ft
      • Built 1988
      1767 Rockingham Rd, Chester, VT 05143

      Last Sold Summary

      • $240/SF
      • 116 Days On Market
      • Last Sold Price $310,000
      • Dec 03, 2024

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • 186 Mountain View, Chester, VT 05143
    186 Mountain View, Chester, VT 05143
    /2

    $250,000 Sold Jul 16, 2025

    186 Mountain View, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 966 Sq Ft
    • Built 1942

    Last Sold Summary

    • $259/SF
    • 40 Days On Market

    Current Estimated Value $251,601

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    186 Mountain View, Chester, VT 05143
    • 2401 N Hill Rd, Chester, VT 05143
      2401 N Hill Rd, Chester, VT 05143
      2401 N Hill Rd, Chester, VT 05143
      /38

      Est $731,682 Not Listed For Sale

      2401 N Hill Rd, Chester, VT 05143

      • 4 Beds
      • 2.5 Baths
      • 2,242 Sq Ft
      • Built 1990
      2401 N Hill Rd, Chester, VT 05143

      Last Sold Summary

      • 2% Below List Price
      • $335/SF
      • 67 Days On Market
      • Last Sold Price $750,000
      • Sep 20, 2024

      Last Listing Agent Alison Cummings Cummings & Co

  • 95 Church St, Chester, VT 05143
    95 Church St, Chester, VT 05143
    95 Church St, Chester, VT 05143
    /52

    $563,000 Sold Apr 13, 2026

    95 Church St, Chester, VT 05143

    • 4 Beds
    • 3 Baths
    • 2,794 Sq Ft
    • Built 1800

    Last Sold Summary

    • 16% Below List Price
    • $202/SF
    • 148 Days On Market

    Current Estimated Value $626,657

    Last Listing Agent McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

    95 Church St, Chester, VT 05143
    • 126 Gould Rd, Chester, VT 05143
      126 Gould Rd, Chester, VT 05143
      126 Gould Rd, Chester, VT 05143
      /25

      Est $386,498 Not Listed For Sale

      126 Gould Rd, Chester, VT 05143

      • 4 Beds
      • 2 Baths
      • 2,714 Sq Ft
      • Built 1827
      126 Gould Rd, Chester, VT 05143

      Last Sold Summary

      • 13% Above List Price
      • $126/SF
      • 12 Days On Market
      • Last Sold Price $342,000
      • Aug 18, 2023

      Last Listing Agent Chris Benoit Highland Realty

  • 3466 Vt Route 103 N, Chester, VT 05143
    3466 Vt Route 103 N, Chester, VT 05143
    /2

    $379,000 Sold Apr 20, 2026

    3466 Vt Route 103 N, Chester, VT 05143

    • 2 Beds
    • 2 Baths
    • 2,751 Sq Ft
    • Built 1874

    Last Sold Summary

    • 5% Below List Price
    • $138/SF
    • 24 Days On Market

    Current Estimated Value $392,651

    Last Listing Agent Betsy Adamovich Real Broker LLC

    3466 Vt Route 103 N, Chester, VT 05143
    • 0 Gould Rd Unit 5023598, Chester, VT 05143
      0 Gould Rd Unit 5023598, Chester, VT 05143
      0 Gould Rd Unit 5023598, Chester, VT 05143
      /10

      Not Listed For Sale

      0 Gould Rd Unit 5023598, Chester, VT 05143

      0 Gould Rd Unit 5023598, Chester, VT 05143

      Last Sold Summary

      • 17 Days On Market
      • Last Sold Price $35,500
      • Jan 17, 2025

      Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  • 246 Putnam Hill Rd, Chester, VT 05143
    246 Putnam Hill Rd, Chester, VT 05143
    246 Putnam Hill Rd, Chester, VT 05143
    /51

    $550,000 Sold Nov 17, 2025

    246 Putnam Hill Rd, Chester, VT 05143

    • 3 Beds
    • 3.5 Baths
    • 2,256 Sq Ft
    • Built 2004

    Last Sold Summary

    • $244/SF
    • 10 Days On Market

    Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    246 Putnam Hill Rd, Chester, VT 05143
    • 209 Ingraham Hill Rd, Chester, VT 05143
      209 Ingraham Hill Rd, Chester, VT 05143
      209 Ingraham Hill Rd, Chester, VT 05143
      /34

      Not Listed For Sale

      209 Ingraham Hill Rd, Chester, VT 05143

      • 2 Beds
      • 2 Baths
      • 1,918 Sq Ft
      • Built 2004
      209 Ingraham Hill Rd, Chester, VT 05143

      Last Sold Summary

      • $652/SF
      • 27 Days On Market
      • Last Sold Price $1,250,000
      • Dec 05, 2024

      Last Listing Agent Dia Jenks LandVest, Inc/Woodstock

  • 0 Hall Rd, Chester, VT 05143
    0 Hall Rd, Chester, VT 05143
    0 Hall Rd, Chester, VT 05143
    /19

    $85,000 Sold Jul 16, 2025

    0 Hall Rd, Chester, VT 05143

    • Land
    • 46.77 Acres
    • $1,817 per Acre

    Last Sold Summary

    • 29% Below List Price
    • 195 Days On Market

    Last Listing Agent Jessica Samples BHG Masiello Keene

    0 Hall Rd, Chester, VT 05143
    • 22 White Rd, Chester, VT 05143
      22 White Rd, Chester, VT 05143
      22 White Rd, Chester, VT 05143
      /12

      Est $143,674 Not Listed For Sale

      22 White Rd, Chester, VT 05143

      • 1 Bed
      • 1 Bath
      • 630 Sq Ft
      • Built 1940
      22 White Rd, Chester, VT 05143

      Last Sold Summary

      • 16% Above List Price
      • $197/SF
      • 6 Days On Market
      • Last Sold Price $124,000
      • Oct 25, 2024

      Last Listing Agent Darlene Conca

  • 218 Gunderson Rd, Chester, VT 05143
    218 Gunderson Rd, Chester, VT 05143
    218 Gunderson Rd, Chester, VT 05143
    /50

    $950,000 Sold May 30, 2025

    218 Gunderson Rd, Chester, VT 05143

    • 5 Beds
    • 2.5 Baths
    • 3,175 Sq Ft
    • Built 1907

    Last Sold Summary

    • 24% Below List Price
    • $299/SF
    • 263 Days On Market

    Current Estimated Value $901,197

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    218 Gunderson Rd, Chester, VT 05143
    • 994 Dodge Rd, Chester, VT 05143
      994 Dodge Rd, Chester, VT 05143
      994 Dodge Rd, Chester, VT 05143
      /40

      Est $682,103 Not Listed For Sale

      994 Dodge Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,876 Sq Ft
      • Built 2012
      994 Dodge Rd, Chester, VT 05143

      Last Sold Summary

      • 7% Above List Price
      • $338/SF
      • 89 Days On Market
      • Last Sold Price $635,000
      • Dec 06, 2024

      Last Listing Agent Gary Coger Four Seasons Sotheby's Int'l Realty

  • Lot 3 Mattson Rd, Chester, VT 05143
    Lot 3 Mattson Rd, Chester, VT 05143
    Lot 3 Mattson Rd, Chester, VT 05143
    /15

    $95,000 Sold Nov 17, 2025

    Lot 3 Mattson Rd, Chester, VT 05143

    • Land
    • 3.24 Acres
    • $29,321 per Acre

    Last Sold Summary

    • 26% Below List Price
    • 129 Days On Market

    Last Listing Agent Jessica Citera Cummings & Co

    Lot 3 Mattson Rd, Chester, VT 05143
    • 110 Shady Grove Ln, Chester, VT 05143
      110 Shady Grove Ln, Chester, VT 05143
      110 Shady Grove Ln, Chester, VT 05143
      /33

      Est $237,480 Not Listed For Sale

      110 Shady Grove Ln, Chester, VT 05143

      • 2 Beds
      • 2 Baths
      • 1,672 Sq Ft
      • Built 2022
      110 Shady Grove Ln, Chester, VT 05143

      Last Sold Summary

      • 13% Above List Price
      • $126/SF
      • 47 Days On Market
      • Last Sold Price $210,000
      • Jan 21, 2025

      Last Listing Agent Rob Weltz Barrett and Valley Associates Inc.

  • 387 Weston-Andover Rd, Chester, VT 05143
    387 Weston-Andover Rd, Chester, VT 05143
    387 Weston-Andover Rd, Chester, VT 05143
    /57

    $399,000 Sold Jul 31, 2025

    387 Weston-Andover Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,402 Sq Ft
    • Built 1974

    Last Sold Summary

    • $285/SF
    • 22 Days On Market

    Current Estimated Value $398,000

    Last Listing Agent Jessica Citera Cummings & Co

    387 Weston-Andover Rd, Chester, VT 05143
    • 2253 White Rd, Chester, VT 05143
      2253 White Rd, Chester, VT 05143
      2253 White Rd, Chester, VT 05143
      /38

      Not Listed For Sale

      2253 White Rd, Chester, VT 05143

      • 2 Beds
      • 2 Baths
      • 1,171 Sq Ft
      • Built 1990
      2253 White Rd, Chester, VT 05143

      Last Sold Summary

      • $581/SF
      • 53 Days On Market
      • Last Sold Price $680,000
      • Oct 17, 2024

      Last Listing Agent Alison Cummings Cummings & Co

  • 1573 Flamstead Rd, Chester, VT 05143
    1573 Flamstead Rd, Chester, VT 05143
    1573 Flamstead Rd, Chester, VT 05143
    /39

    $560,000 Sold Nov 25, 2025

    1573 Flamstead Rd, Chester, VT 05143

    • 4 Beds
    • 3 Baths
    • 2,689 Sq Ft
    • Built 1840

    Last Sold Summary

    • 7% Below List Price
    • $208/SF
    • 43 Days On Market

    Current Estimated Value $544,653

    Last Listing Agent Jamie Watson BHG Masiello Keene

    1573 Flamstead Rd, Chester, VT 05143
    • 0 Remington Rd Unit 12 5001944, Chester, VT 05143
      0 Remington Rd Unit 12 5001944, Chester, VT 05143
      0 Remington Rd Unit 12 5001944, Chester, VT 05143
      /12

      Not Listed For Sale

      0 Remington Rd Unit 12 5001944, Chester, VT 05143

      0 Remington Rd Unit 12 5001944, Chester, VT 05143

      Last Sold Summary

      • 183 Days On Market
      • Last Sold Price $19,000
      • Nov 29, 2024

      Last Listing Agent Frank Provance Diamond Realty

  • 423 Main St, Chester, VT 05143
    423 Main St, Chester, VT 05143
    423 Main St, Chester, VT 05143
    /36

    $425,000 Sold Dec 18, 2025

    423 Main St, Chester, VT 05143

    • 6 Beds
    • 5 Baths
    • 3,217 Sq Ft
    • Built 1850

    Last Sold Summary

    • 30% Below List Price
    • $132/SF
    • 211 Days On Market

    Last Listing Agent Betty McEnaney Diamond Realty

    423 Main St, Chester, VT 05143
    • 1716 Brockway Mills Rd, Chester, VT 05143
      1716 Brockway Mills Rd, Chester, VT 05143
      1716 Brockway Mills Rd, Chester, VT 05143
      /40

      Est $577,128 Not Listed For Sale

      1716 Brockway Mills Rd, Chester, VT 05143

      • 3 Beds
      • 2.5 Baths
      • 1,908 Sq Ft
      • Built 1992
      1716 Brockway Mills Rd, Chester, VT 05143

      Last Sold Summary

      • 3% Above List Price
      • $295/SF
      • 6 Days On Market
      • Last Sold Price $562,725
      • Aug 15, 2024

      Last Listing Agent Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  • 350 Farrar Rd, Chester, VT 05143
    350 Farrar Rd, Chester, VT 05143
    350 Farrar Rd, Chester, VT 05143
    /31

    $600,000 Sold Aug 18, 2025

    350 Farrar Rd, Chester, VT 05143

    • 4 Beds
    • 2.5 Baths
    • 2,747 Sq Ft
    • Built 1998

    Last Sold Summary

    • 14% Below List Price
    • $218/SF
    • 71 Days On Market

    Last Listing Agent Linda Benoit Highland Realty

    350 Farrar Rd, Chester, VT 05143
    • 505 Hidden Heights Rd, Chester, VT 05143
      505 Hidden Heights Rd, Chester, VT 05143
      505 Hidden Heights Rd, Chester, VT 05143
      /26

      Est $100,399 Not Listed For Sale

      505 Hidden Heights Rd, Chester, VT 05143

      505 Hidden Heights Rd, Chester, VT 05143

      Last Sold Summary

      • 8 Days On Market
      • Last Sold Price $100,000
      • Aug 09, 2024

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • 231 Richardson Rd, Chester, VT 05143
    231 Richardson Rd, Chester, VT 05143
    /2

    $360,000 Sold Oct 28, 2025

    231 Richardson Rd, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 1,304 Sq Ft
    • Built 1979

    Last Sold Summary

    • 7% Below List Price
    • $276/SF
    • 41 Days On Market

    Current Estimated Value $356,092

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    231 Richardson Rd, Chester, VT 05143
    • 0 Route 103 Unit 4999744, Chester, VT 05143
      0 Route 103 Unit 4999744, Chester, VT 05143
      0 Route 103 Unit 4999744, Chester, VT 05143
      /14

      Not Listed For Sale

      0 Route 103 Unit 4999744, Chester, VT 05143

      0 Route 103 Unit 4999744, Chester, VT 05143

      Last Sold Summary

      • 8 Days On Market
      • Last Sold Price $55,000
      • Jul 03, 2024

      Last Listing Agent Leila Tarantelli KW Coastal and Lakes & Mountains Realty/Hanover

    • 1291 Potash Brook Rd, Chester, VT 05143
      1291 Potash Brook Rd, Chester, VT 05143
      1291 Potash Brook Rd, Chester, VT 05143
      /35

      Est $137,978 Not Listed For Sale

      1291 Potash Brook Rd, Chester, VT 05143

      • 1 Bed
      • 1 Bath
      • 704 Sq Ft
      • Built 1960
      1291 Potash Brook Rd, Chester, VT 05143

      Last Sold Summary

      • 25% Above List Price
      • $156/SF
      • 10 Days On Market
      • Last Sold Price $110,000
      • Aug 09, 2024

      Last Listing Agent Frank Provance Diamond Realty

    • 0 Remington Rd Unit 9 4997325, Chester, VT 05143
      0 Remington Rd Unit 9 4997325, Chester, VT 05143
      0 Remington Rd Unit 9 4997325, Chester, VT 05143
      /5

      Not Listed For Sale

      0 Remington Rd Unit 9 4997325, Chester, VT 05143

      0 Remington Rd Unit 9 4997325, Chester, VT 05143

      Last Sold Summary

      • 211 Days On Market
      • Last Sold Price $22,000
      • Jan 31, 2025

      Last Listing Agent Frank Provance Diamond Realty

    • 0 Remington Rd Unit 6 4996522, Chester, VT 05143
      0 Remington Rd Unit 6 4996522, Chester, VT 05143
      0 Remington Rd Unit 6 4996522, Chester, VT 05143
      /5

      Not Listed For Sale

      0 Remington Rd Unit 6 4996522, Chester, VT 05143

      0 Remington Rd Unit 6 4996522, Chester, VT 05143

      Last Sold Summary

      • 207 Days On Market
      • Last Sold Price $20,000
      • Jan 30, 2025

      Last Listing Agent Frank Provance Diamond Realty

    • 0 Remington Rd Unit 8 4996410, Chester, VT 05143
      0 Remington Rd Unit 8 4996410, Chester, VT 05143
      0 Remington Rd Unit 8 4996410, Chester, VT 05143
      /6

      Not Listed For Sale

      0 Remington Rd Unit 8 4996410, Chester, VT 05143

      0 Remington Rd Unit 8 4996410, Chester, VT 05143

      Last Sold Summary

      • 215 Days On Market
      • Last Sold Price $23,000
      • Jan 31, 2025

      Last Listing Agent Frank Provance Diamond Realty

    • 3610 Vt Route 103 N Unit 50003, Chester, VT 03602
      3610 Vt Route 103 N Unit 50003, Chester, VT 03602
      3610 Vt Route 103 N Unit 50003, Chester, VT 03602
      /8

      Not Listed For Sale

      3610 Vt Route 103 N Unit 50003, Chester, VT 03602

      3610 Vt Route 103 N Unit 50003, Chester, VT 03602

      Last Sold Summary

      • 26 Days On Market
      • Last Sold Price $25,475
      • Jul 31, 2024

      Last Listing Agent Kimberly Dubois Matson KW Realty

    • 222 Peck Rd, Chester, VT 05143
      222 Peck Rd, Chester, VT 05143
      222 Peck Rd, Chester, VT 05143
      /20

      Est $228,721 Not Listed For Sale

      222 Peck Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 864 Sq Ft
      • Built 1973
      222 Peck Rd, Chester, VT 05143

      Last Sold Summary

      • 9% Above List Price
      • $243/SF
      • 5 Days On Market
      • Last Sold Price $210,000
      • Jul 24, 2024

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

Showing Results 161 - 200, Page 5 of 18

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