2,722

Chester, VT Homes

Section Image
  • 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
    • 1767 Rockingham Rd, Chester, VT 05143
      1767 Rockingham Rd, Chester, VT 05143
      1767 Rockingham Rd, Chester, VT 05143
      /24

      Est $303,293 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

      • 2% Below List Price
      • $240/SF
      • 116 Days On Market

      Last Sold Price $310,000

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • 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
    • 2401 N Hill Rd, Chester, VT 05143
      2401 N Hill Rd, Chester, VT 05143
      2401 N Hill Rd, Chester, VT 05143
      /38

      Est $759,322 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

      • 1% Above List Price
      • $335/SF
      • 67 Days On Market

      Last Sold Price $750,000

      Last Listing Agent Alison Cummings Cummings & Co

  • 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 $922,718

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    218 Gunderson Rd, Chester, VT 05143
    • 126 Gould Rd, Chester, VT 05143
      126 Gould Rd, Chester, VT 05143
      126 Gould Rd, Chester, VT 05143
      /25

      Est $420,509 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

      • 23% Above List Price
      • $126/SF
      • 12 Days On Market

      Last Sold Price $342,000

      Last Listing Agent Chris Benoit Highland 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
    • 723 Chandler Rd, Chester, VT 05143
      723 Chandler Rd, Chester, VT 05143
      723 Chandler Rd, Chester, VT 05143
      /36

      Est $548,635 Not Listed For Sale

      723 Chandler Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 2,063 Sq Ft
      • Built 1981
      723 Chandler Rd, Chester, VT 05143

      Last Sold Summary

      • 17% Above List Price
      • $227/SF
      • 26 Days On Market

      Last Sold Price $469,000

      Last Listing Agent Suzanne Garvey Mary W. Davis Realtor & Assoc., 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 $381,000

    Last Listing Agent Jessica Citera Cummings & Co

    387 Weston-Andover Rd, 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

      Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  • 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 $565,235

    Last Listing Agent Jamie Watson BHG Masiello Keene

    1573 Flamstead 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

      Last Listing Agent Dia Jenks LandVest, Inc/Woodstock

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

      Est $134,035 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

      • 8% Above List Price
      • $197/SF
      • 6 Days On Market

      Last Sold Price $124,000

      Last Listing Agent Darlene Conca

  • 2240 Baltimore Rd, Chester, VT 05143
    2240 Baltimore Rd, Chester, VT 05143
    2240 Baltimore Rd, Chester, VT 05143
    /39

    $385,000 Sold Mar 20, 2025

    2240 Baltimore Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,518 Sq Ft
    • Built 1986

    Last Sold Summary

    • $254/SF
    • 14 Days On Market

    Current Estimated Value $424,793

    Last Listing Agent Morriah Adams BHG Masiello Brattleboro

    2240 Baltimore Rd, Chester, VT 05143
    • 994 Dodge Rd, Chester, VT 05143
      994 Dodge Rd, Chester, VT 05143
      994 Dodge Rd, Chester, VT 05143
      /40

      Est $677,495 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

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

  • 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
    • 110 Shady Grove Ln, Chester, VT 05143
      110 Shady Grove Ln, Chester, VT 05143
      110 Shady Grove Ln, Chester, VT 05143
      /33

      Est $224,786 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

      • 7% Above List Price
      • $126/SF
      • 47 Days On Market

      Last Sold Price $210,000

      Last Listing Agent Rob Weltz 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 $360,386

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    231 Richardson 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

      Last Listing Agent Alison Cummings Cummings & Co

    • 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

      Last Listing Agent Frank Provance Diamond Realty

    • 1716 Brockway Mills Rd, Chester, VT 05143
      1716 Brockway Mills Rd, Chester, VT 05143
      1716 Brockway Mills Rd, Chester, VT 05143
      /40

      Est $552,184 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

      • 2% Below List Price
      • $295/SF
      • 6 Days On Market

      Last Sold Price $562,725

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

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

      Est $104,502 Not Listed For Sale

      505 Hidden Heights Rd, Chester, VT 05143

      505 Hidden Heights Rd, Chester, VT 05143

      Last Sold Summary

      • 5% Above List Price
      • 8 Days On Market

      Last Sold Price $100,000

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    • 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

      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 $141,849 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

      • 29% Above List Price
      • $156/SF
      • 10 Days On Market

      Last Sold Price $110,000

      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

      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

      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

      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

      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 $225,823 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

      • 8% Above List Price
      • $243/SF
      • 5 Days On Market

      Last Sold Price $210,000

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    • 0 Brookside Dr Unit 4994316, Chester, VT 05143
      0 Brookside Dr Unit 4994316, Chester, VT 05143
      0 Brookside Dr Unit 4994316, Chester, VT 05143
      /25

      Not Listed For Sale

      0 Brookside Dr Unit 4994316, Chester, VT 05143

      0 Brookside Dr Unit 4994316, Chester, VT 05143

      Last Sold Summary

      • 206 Days On Market

      Last Sold Price $107,000

      Last Listing Agent Mike England Michael England Real Estate

    • 4351 Route 11, Chester, VT 05143
      4351 Route 11, Chester, VT 05143
      4351 Route 11, Chester, VT 05143
      /18

      Not Listed For Sale

      4351 Route 11, Chester, VT 05143

      • 2 Beds
      • 1 Bath
      • 980 Sq Ft
      • Built 1968
      4351 Route 11, Chester, VT 05143

      Last Sold Summary

      • $46/SF
      • 8 Days On Market

      Last Sold Price $45,000

      Last Listing Agent Glenn Olney Barrett and Valley Associates Inc.

    • 2105 White Rd, Chester, VT 05143
      2105 White Rd, Chester, VT 05143
      2105 White Rd, Chester, VT 05143
      /37

      Not Listed For Sale

      2105 White Rd, Chester, VT 05143

      • 4 Beds
      • 2 Baths
      • 2,466 Sq Ft
      • Built 1802
      2105 White Rd, Chester, VT 05143

      Last Sold Summary

      • $235/SF
      • 159 Days On Market

      Last Sold Price $580,000

      Last Listing Agent Claudia Harris Mary Mitchell Miller Real Estate

    • 341 Whitmore Brook Rd, Chester, VT 05143
      341 Whitmore Brook Rd, Chester, VT 05143
      341 Whitmore Brook Rd, Chester, VT 05143
      /39

      Est $726,488 Not Listed For Sale

      341 Whitmore Brook Rd, Chester, VT 05143

      • 3 Beds
      • 3 Baths
      • 2,400 Sq Ft
      • Built 2004
      341 Whitmore Brook Rd, Chester, VT 05143

      Last Sold Summary

      • 21% Above List Price
      • $250/SF
      • 125 Days On Market

      Last Sold Price $600,000

      Last Listing Agent Frank Provance Diamond Realty

    • 0 Smokeshire Rd, Ludlow, VT 05149
      0 Smokeshire Rd, Ludlow, VT 05149
      0 Smokeshire Rd, Ludlow, VT 05149
      /16

      Not Listed For Sale

      0 Smokeshire Rd, Ludlow, VT 05149

      0 Smokeshire Rd, Ludlow, VT 05149

      Last Sold Summary

      • 7 Days On Market

      Last Sold Price $81,000

      Last Listing Agent Sarah Sheehan William Raveis Real Estate Vermont Properties

    • 50 Grafton St, Chester, VT 05143
      50 Grafton St, Chester, VT 05143
      50 Grafton St, Chester, VT 05143
      /3

      Est $373,677 Not Listed For Sale

      50 Grafton St, Chester, VT 05143

      • 4 Beds
      • 3 Baths
      • 2,351 Sq Ft
      • Built 1890
      50 Grafton St, Chester, VT 05143

      Last Sold Summary

      • 18% Above List Price
      • $135/SF
      • 56 Days On Market

      Last Sold Price $317,500

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    • 252 Davidson Hill Rd, Chester, VT 05143
      252 Davidson Hill Rd, Chester, VT 05143
      252 Davidson Hill Rd, Chester, VT 05143
      /38

      Est $736,210 Not Listed For Sale

      252 Davidson Hill Rd, Chester, VT 05143

      • 3 Beds
      • 2.5 Baths
      • 4,070 Sq Ft
      • Built 2002
      252 Davidson Hill Rd, Chester, VT 05143

      Last Sold Summary

      • 6% Above List Price
      • $170/SF
      • 22 Days On Market

      Last Sold Price $693,500

      Last Listing Agent Cassandra Ehrlich BHG Masiello Brattleboro

    • 0 Whitmore Brook Rd, Chester, VT 05143
      0 Whitmore Brook Rd, Chester, VT 05143
      0 Whitmore Brook Rd, Chester, VT 05143
      /6

      Not Listed For Sale

      0 Whitmore Brook Rd, Chester, VT 05143

      0 Whitmore Brook Rd, Chester, VT 05143

      Last Sold Summary

      • 98 Days On Market

      Last Sold Price $60,000

      Last Listing Agent Frank Provance Diamond Realty

    • 64 Maple St, Chester, VT 05143
      64 Maple St, Chester, VT 05143
      64 Maple St, Chester, VT 05143
      /40

      Est $456,558 Not Listed For Sale

      64 Maple St, Chester, VT 05143

      • 4 Beds
      • 3 Baths
      • 2,430 Sq Ft
      • Built 1951
      64 Maple St, Chester, VT 05143

      Last Sold Summary

      • 19% Above List Price
      • $158/SF
      • 8 Days On Market

      Last Sold Price $385,000

      Last Listing Agent Frank Provance Diamond Realty

    • 1458 Vt Route 103 S, Chester, VT 05143
      1458 Vt Route 103 S, Chester, VT 05143
      1458 Vt Route 103 S, Chester, VT 05143
      /27

      Est $267,676 Not Listed For Sale

      1458 Vt Route 103 S, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,080 Sq Ft
      • Built 1964
      1458 Vt Route 103 S, Chester, VT 05143

      Last Sold Summary

      • 4% Below List Price
      • $259/SF
      • 2 Days On Market

      Last Sold Price $280,000

      Last Listing Agent Margretta Fischer Wohler Realty Group

Showing Results 161 - 200, Page 5 of 18

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