2,722

Chester, VT Homes

Section Image
  • 1295 Middletown Rd, Chester, VT 05143
    1295 Middletown Rd, Chester, VT 05143
    /2

    $792,000 Sold Jul 15, 2025

    1295 Middletown Rd, Chester, VT 05143

    • 3 Beds
    • 3.5 Baths
    • 3,614 Sq Ft
    • Built 2012

    Last Sold Summary

    • 7% Below List Price
    • $219/SF
    • 0 Days On Market

    Current Estimated Value $807,084

    Last Listing Agent Sarah Sheehan William Raveis Real Estate Vermont Properties

    1295 Middletown Rd, Chester, VT 05143
    • 242 Mattson Rd, Chester, VT 05143
      242 Mattson Rd, Chester, VT 05143
      242 Mattson Rd, Chester, VT 05143
      /25

      Est $296,440 Not Listed For Sale

      242 Mattson Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 2004
      242 Mattson Rd, Chester, VT 05143

      Last Sold Summary

      • 26% Above List Price
      • $175/SF
      • 9 Days On Market

      Last Sold Price $235,000

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

  • 725 Flamstead Rd, Chester, VT 05143
    725 Flamstead Rd, Chester, VT 05143
    /2

    $800,000 Sold Dec 12, 2025

    725 Flamstead Rd, Chester, VT 05143

    • 4 Beds
    • 3.5 Baths
    • 2,775 Sq Ft
    • Built 2005

    Last Sold Summary

    • 11% Below List Price
    • $288/SF
    • 17 Days On Market

    Current Estimated Value $853,988

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

    725 Flamstead Rd, Chester, VT 05143
    • 199 Maple Ridge Rd, Chester, VT 05143
      199 Maple Ridge Rd, Chester, VT 05143
      199 Maple Ridge Rd, Chester, VT 05143
      /31

      Est $352,986 Not Listed For Sale

      199 Maple Ridge Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,492 Sq Ft
      • Built 1980
      199 Maple Ridge Rd, Chester, VT 05143

      Last Sold Summary

      • 2% Below List Price
      • $241/SF
      • 2 Days On Market

      Last Sold Price $360,000

      Last Listing Agent Heather Gleim CENTURY 21 North East

  • 106 Hall Rd, Chester, VT 05143
    106 Hall Rd, Chester, VT 05143
    106 Hall Rd, Chester, VT 05143
    /27

    $210,000 Sold Nov 20, 2025

    106 Hall Rd, Chester, VT 05143

    • 1 Bed
    • 1 Bath
    • 528 Sq Ft
    • Built 1950

    Last Sold Summary

    • 16% Below List Price
    • $398/SF
    • 33 Days On Market

    Current Estimated Value $213,197

    Last Listing Agent Sandy Reavill Real Broker LLC

    106 Hall Rd, Chester, VT 05143
    • 5051 Vt Route 103 N, Chester, VT 05143
      5051 Vt Route 103 N, Chester, VT 05143
      5051 Vt Route 103 N, Chester, VT 05143
      /8

      Est $215,309 Not Listed For Sale

      5051 Vt Route 103 N, Chester, VT 05143

      • 2 Beds
      • 1 Bath
      • 864 Sq Ft
      • Built 1967
      5051 Vt Route 103 N, Chester, VT 05143

      Last Sold Summary

      • 187% Above List Price
      • $87/SF
      • 30 Days On Market

      Last Sold Price $75,000

      Last Listing Agent Judy Thompson Walnut Hill Realty

  • 302 Davidson Hill Rd, Chester, VT 05143
    302 Davidson Hill Rd, Chester, VT 05143
    /2

    $330,000 Sold Nov 20, 2025

    302 Davidson Hill Rd, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Built 1989

    Last Sold Summary

    • 15% Below List Price
    • $367/SF
    • 114 Days On Market

    Current Estimated Value $332,254

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    302 Davidson Hill Rd, Chester, VT 05143
    • 247 Cavendish Rd, Chester, VT 05143
      247 Cavendish Rd, Chester, VT 05143
      247 Cavendish Rd, Chester, VT 05143
      /20

      Est $323,008 Not Listed For Sale

      247 Cavendish Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft
      • Built 1968
      247 Cavendish Rd, Chester, VT 05143

      Last Sold Summary

      • 8% Above List Price
      • $261/SF
      • 11 Days On Market

      Last Sold Price $299,000

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • 316 Little Pond Rd, Chester, VT 05143
    316 Little Pond Rd, Chester, VT 05143
    316 Little Pond Rd, Chester, VT 05143
    /54

    $540,000 Sold May 23, 2025

    316 Little Pond Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1975

    Last Sold Summary

    • $371/SF
    • 32 Days On Market

    Current Estimated Value $523,664

    Last Listing Agent Nick Sicard EXP Realty

    316 Little Pond Rd, Chester, VT 05143
    • 3483 Popple Dungeon Rd, Chester, VT 05143
      3483 Popple Dungeon Rd, Chester, VT 05143
      3483 Popple Dungeon Rd, Chester, VT 05143
      /29

      Est $253,484 Not Listed For Sale

      3483 Popple Dungeon Rd, Chester, VT 05143

      • 2 Beds
      • 2 Baths
      • 910 Sq Ft
      • Built 1950
      3483 Popple Dungeon Rd, Chester, VT 05143

      Last Sold Summary

      • 9% Below List Price
      • $305/SF
      • 57 Days On Market

      Last Sold Price $277,500

      Last Listing Agent Jessica Citera Cummings & Co

  • 0 Remington Rd Unit 5049898, Chester, VT 05143
    0 Remington Rd Unit 5049898, Chester, VT 05143
    0 Remington Rd Unit 5049898, Chester, VT 05143
    /20

    $80,000 Sold Dec 05, 2025

    0 Remington Rd Unit 5049898, Chester, VT 05143

    • Land
    • 1.82 Acres
    • $43,956 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 122 Days On Market

    Last Listing Agent Frank Provance Diamond Realty

    0 Remington Rd Unit 5049898, Chester, VT 05143
    • 3019 Popple Dungeon Rd, Chester, VT 05143
      3019 Popple Dungeon Rd, Chester, VT 05143
      3019 Popple Dungeon Rd, Chester, VT 05143
      /20

      Not Listed For Sale

      3019 Popple Dungeon Rd, Chester, VT 05143

      • 1 Bed
      • 1 Bath
      • 200 Sq Ft
      • Built 1975
      3019 Popple Dungeon Rd, Chester, VT 05143

      Last Sold Summary

      • $775/SF
      • 4 Days On Market

      Last Sold Price $155,000

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

  • 1950 Anderson Rd, Chester, VT 05143
    1950 Anderson Rd, Chester, VT 05143
    1950 Anderson Rd, Chester, VT 05143
    /24

    $269,000 Sold Dec 15, 2025

    1950 Anderson Rd, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 876 Sq Ft
    • Built 1972

    Last Sold Summary

    • 4% Above List Price
    • $307/SF
    • 5 Days On Market

    Last Listing Agent Wilma Skovinski Berkley & Veller Greenwood Country

    1950 Anderson Rd, Chester, VT 05143
    • 138 Farrar Rd, Chester, VT 05143
      138 Farrar Rd, Chester, VT 05143
      138 Farrar Rd, Chester, VT 05143
      /23

      Est $292,203 Not Listed For Sale

      138 Farrar Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,464 Sq Ft
      • Built 1965
      138 Farrar Rd, Chester, VT 05143

      Last Sold Summary

      • 26% Below List Price
      • $270/SF
      • 23 Days On Market

      Last Sold Price $395,000

      Last Listing Agent Linda Benoit Highland Realty

  • 611 Simmons Rd, Chester, VT 05143
    611 Simmons Rd, Chester, VT 05143
    611 Simmons Rd, Chester, VT 05143
    /32

    $1,510,000 Sold Dec 22, 2025

    611 Simmons Rd, Chester, VT 05143

    • 2 Beds
    • 4 Baths
    • 3,514 Sq Ft
    • Built 1965

    Last Sold Summary

    • 33% Below List Price
    • $430/SF
    • 151 Days On Market

    Current Estimated Value $1,623,319

    Last Listing Agent Dia Jenks LandVest, Inc/Woodstock

    611 Simmons Rd, Chester, VT 05143
    • 231 Christmas Tree Farm Rd, Chester, VT 05143
      231 Christmas Tree Farm Rd, Chester, VT 05143
      231 Christmas Tree Farm Rd, Chester, VT 05143
      /31

      Est $1,606,331 Not Listed For Sale

      231 Christmas Tree Farm Rd, Chester, VT 05143

      • 4 Beds
      • 5 Baths
      • 4,171 Sq Ft
      • Built 1980
      231 Christmas Tree Farm Rd, Chester, VT 05143

      Last Sold Summary

      • 15% Below List Price
      • $456/SF
      • 38 Days On Market

      Last Sold Price $1,900,000

      Last Listing Agent Dia Jenks LandVest, Inc/Woodstock

  • 1873 Brockway Mills Rd, Chester, VT 05143
    1873 Brockway Mills Rd, Chester, VT 05143
    1873 Brockway Mills Rd, Chester, VT 05143
    /40

    $640,000 Sold May 16, 2025

    1873 Brockway Mills Rd, Chester, VT 05143

    • 5 Beds
    • 3 Baths
    • 2,752 Sq Ft
    • Built 2024

    Last Sold Summary

    • 15% Below List Price
    • $233/SF
    • 113 Days On Market

    Last Listing Agent Heather Gleim CENTURY 21 North East

    1873 Brockway Mills Rd, Chester, VT 05143
    • 2370 Baltimore Rd, Chester, VT 05143
      2370 Baltimore Rd, Chester, VT 05143
      2370 Baltimore Rd, Chester, VT 05143
      /23

      Est $173,171 Not Listed For Sale

      2370 Baltimore Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,124 Sq Ft
      • Built 1952
      2370 Baltimore Rd, Chester, VT 05143

      Last Sold Summary

      • 35% Above List Price
      • $114/SF
      • 90 Days On Market

      Last Sold Price $128,000

      Last Listing Agent Lori Muse Muse and Associates Real Estate

  • 31 Palmer Rd, Chester, VT 05143
    31 Palmer Rd, Chester, VT 05143
    /2

    $669,000 Sold Sep 04, 2025

    31 Palmer Rd, Chester, VT 05143

    • 3 Beds
    • 2.5 Baths
    • 2,605 Sq Ft
    • Built 1980

    Last Sold Summary

    • $257/SF
    • 7 Days On Market

    Current Estimated Value $668,212

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    31 Palmer Rd, Chester, VT 05143
    • 1248 Baltimore Rd, Chester, VT 05143
      1248 Baltimore Rd, Chester, VT 05143
      1248 Baltimore Rd, Chester, VT 05143
      /18

      Est $179,691 Not Listed For Sale

      1248 Baltimore Rd, Chester, VT 05143

      • 2 Beds
      • 1 Bath
      • 600 Sq Ft
      • Built 1965
      1248 Baltimore Rd, Chester, VT 05143

      Last Sold Summary

      • 40% Above List Price
      • $213/SF
      • 58 Days On Market

      Last Sold Price $128,000

      Last Listing Agent Julie Buffum Buffum Realty

  • 117 S Main St, Chester, VT 05143
    117 S Main St, Chester, VT 05143
    /2

    $330,000 Sold Apr 22, 2025

    117 S Main St, Chester, VT 05143

    • 4 Beds
    • 3 Baths
    • 2,008 Sq Ft
    • Built 1850

    Last Sold Summary

    • 12% Below List Price
    • $164/SF
    • 318 Days On Market

    Current Estimated Value $333,277

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    117 S Main St, Chester, VT 05143
    • 870 Baltimore Rd, Chester, VT 05143
      870 Baltimore Rd, Chester, VT 05143
      870 Baltimore Rd, Chester, VT 05143
      /40

      Est $467,058 Not Listed For Sale

      870 Baltimore Rd, Chester, VT 05143

      • 3 Beds
      • 3.5 Baths
      • 3,100 Sq Ft
      • Built 2004
      870 Baltimore Rd, Chester, VT 05143

      Last Sold Summary

      • 25% Above List Price
      • $121/SF
      • 226 Days On Market

      Last Sold Price $375,000

      Last Listing Agent Kim Mastrianni Greenwald Realty Group

  • 841 Farrar Rd, Chester, VT 05143
    841 Farrar Rd, Chester, VT 05143
    841 Farrar Rd, Chester, VT 05143
    /35

    $190,000 Sold Sep 26, 2025

    841 Farrar Rd, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 1,322 Sq Ft
    • Built 1965

    Last Sold Summary

    • 5% Below List Price
    • $144/SF
    • 78 Days On Market

    Current Estimated Value $212,511

    Last Listing Agent Taylor Medeiros-Batey KW Coastal and Lakes & Mountains Realty/Hanover

    841 Farrar Rd, Chester, VT 05143
    • 2656 Weston-Andover Rd, Chester, VT 05143
      2656 Weston-Andover Rd, Chester, VT 05143
      2656 Weston-Andover Rd, Chester, VT 05143
      /40

      Est $589,622 Not Listed For Sale

      2656 Weston-Andover Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 2,080 Sq Ft
      • Built 2004
      2656 Weston-Andover Rd, Chester, VT 05143

      Last Sold Summary

      • 1% Below List Price
      • $286/SF
      • 55 Days On Market

      Last Sold Price $595,000

      Last Listing Agent Betty McEnaney Diamond Realty

  • 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
    • 42 Cobb Rd, Chester, VT 05143
      42 Cobb Rd, Chester, VT 05143
      42 Cobb Rd, Chester, VT 05143
      /40

      Est $355,014 Not Listed For Sale

      42 Cobb Rd, Chester, VT 05143

      • 3 Beds
      • 1.5 Baths
      • 1,087 Sq Ft
      • Built 1965
      42 Cobb Rd, Chester, VT 05143

      Last Sold Summary

      • $327/SF
      • 39 Days On Market

      Last Sold Price $355,000

      Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

  • 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 $312,078

    Last Listing Agent Gale Alger Alger Real Estate Agency

    358 Maple Ridge Rd, Chester, VT 05143
    • 135 Lower Bartonsville Rd, Chester, VT 05143
      135 Lower Bartonsville Rd, Chester, VT 05143
      135 Lower Bartonsville Rd, Chester, VT 05143
      /14

      Est $347,280 Not Listed For Sale

      135 Lower Bartonsville Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,904 Sq Ft
      • Built 1977
      135 Lower Bartonsville Rd, Chester, VT 05143

      Last Sold Summary

      • 34% Above List Price
      • $137/SF
      • 107 Days On Market

      Last Sold Price $260,000

      Last Listing Agent April Shepard Twin State Realty LLC

  • 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
    • 234 Athens Rd, Chester, VT 05143
      234 Athens Rd, Chester, VT 05143
      234 Athens Rd, Chester, VT 05143
      /37

      Not Listed For Sale

      234 Athens Rd, Chester, VT 05143

      • 3 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 1850
      234 Athens Rd, Chester, VT 05143

      Last Sold Summary

      • 49% Below List Price
      • $222/SF
      • 19 Days On Market

      Last Sold Price $399,900

      Last Listing Agent Susan LeCours Barrett & Valley Assoc. Inc

  • 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
    • 1096 Mattson Rd, Chester, VT 05143
      1096 Mattson Rd, Chester, VT 05143
      1096 Mattson Rd, Chester, VT 05143
      /26

      Est $266,138 Not Listed For Sale

      1096 Mattson Rd, Chester, VT 05143

      1096 Mattson Rd, Chester, VT 05143

      Last Sold Summary

      • 13% Above List Price
      • 23 Days On Market

      Last Sold Price $235,000

      Last Listing Agent Lisa Kelley Cummings & Co

  • 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 $699,373

    Last Listing Agent Mendi Michael Engel & Völkers Okemo

    3236 Weston-Andover Rd, Chester, VT 05143
    • 656 Depot St, Chester, VT 05143
      656 Depot St, Chester, VT 05143
      656 Depot St, Chester, VT 05143
      /35

      Est $294,234 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

      • 61% Above List Price
      • $80/SF
      • 13 Days On Market

      Last Sold Price $183,000

      Last Listing Agent Glenn Olney 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 $269,277

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    186 Mountain View, Chester, VT 05143
    • 566 Simonsville Rd, Chester, VT 05143
      566 Simonsville Rd, Chester, VT 05143
      566 Simonsville Rd, Chester, VT 05143
      /53

      Est $596,912 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

      • 20% Above List Price
      • $188/SF
      • 229 Days On Market

      Last Sold Price $499,000

      Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

  • 102 Church St, Chester, VT 05143
    102 Church St, Chester, VT 05143
    102 Church St, Chester, VT 05143
    /48

    $412,000 Sold Apr 30, 2025

    102 Church St, Chester, VT 05143

    • 4 Beds
    • 2 Baths
    • 1,990 Sq Ft
    • Built 1895

    Last Sold Summary

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

    Current Estimated Value $404,493

    Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    102 Church St, 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 $460,470 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

      • 12% Above List Price
      • $291/SF
      • 44 Days On Market

      Last Sold Price $410,000

      Last Listing Agent Alison Cummings Cummings & Co

  • 489 Main St, Chester, VT 05143
    489 Main St, Chester, VT 05143
    489 Main St, Chester, VT 05143
    /34

    $340,000 Sold Mar 27, 2025

    489 Main St, Chester, VT 05143

    • 4 Beds
    • 2 Baths
    • 2,220 Sq Ft
    • Built 1860

    Last Sold Summary

    • 3% Below List Price
    • $153/SF
    • 10 Days On Market

    Current Estimated Value $387,925

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

    489 Main St, 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 $498,558 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

      • 3% Above List Price
      • $235/SF
      • 6 Days On Market

      Last Sold Price $485,500

      Last Listing Agent John Napier TPW Real Estate

Showing Results 121 - 160, Page 4 of 18

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