2,743

Chester, VT Homes

Section Image
    • 242 Mattson Rd, Chester, VT 05143
      242 Mattson Rd, Chester, VT 05143
      242 Mattson Rd, Chester, VT 05143
      /25

      Est $308,518

      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

      • 9 Days On Market

  • 3341 Trebo Rd, Chester, VT 05143
    3341 Trebo Rd, Chester, VT 05143
    3341 Trebo Rd, Chester, VT 05143
    /47

    $549,000

    $20K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,464 Sq Ft

    3341 Trebo Rd, Chester, VT 05143

    Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and Vermont charm. The open-concept layout features high ceilings and abundant natural light, creating a warm, airy feel throughout. A spacious primary suite includes a jetted tub and walk-in closet, providing a true retreat at day’s end. Step outside to a sunny, open lot with a

    Daire Gibney Barrett and Valley Associates Inc.

    3341 Trebo Rd, Chester, VT 05143
  • 87 Kevadus Cir, Chester, VT 05143
    87 Kevadus Cir, Chester, VT 05143
    /2

    $229,000

    Sold Aug 29, 2025

    87 Kevadus Cir, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 840 Sq Ft
    • Built 1968

    Last Sold Summary

    • 7% Above List Price
    • $273/SF
    • 2 Days On Market

    Current Estimated Value $239,089

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    87 Kevadus Cir, 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 $377,691

      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 Days On Market

  • 1175 Quarry Rd, Chester, VT 05143
    1175 Quarry Rd, Chester, VT 05143
    1175 Quarry Rd, Chester, VT 05143
    /20

    $290,000

    $10K PRICE DROP
    • Land
    • 75 Acres
    • $3,867 per Acre

    1175 Quarry Rd, Chester, VT 05143

    Discover the true meaning of "getting away from it all" at 1175 Quarry Road. This expansive 75 acre parcel is tucked away a full mile up a quiet, dead end dirt road in the desirable town of Chester. Mostly wooded with rising topography.It’s an ideal canvas for a private homestead, a hunting camp, or a seasonal getaway. You get the peace of a dead end road with the convenience of being near

    Jessica Samples BHG Masiello Keene

    1175 Quarry Rd, Chester, VT 05143
  • 870 Cummings Rd, Chester, VT 05143
    870 Cummings Rd, Chester, VT 05143
    870 Cummings Rd, Chester, VT 05143
    /21

    $320,000

    Sold Dec 18, 2025

    870 Cummings Rd, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 1,525 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Below List Price
    • $210/SF
    • 30 Days On Market

    Current Estimated Value $322,358

    Last Listing Agent Julie Buffum Buffum Realty

    870 Cummings Rd, Chester, VT 05143
    • 247 Cavendish Rd, Chester, VT 05143
      247 Cavendish Rd, Chester, VT 05143
      247 Cavendish Rd, Chester, VT 05143
      /20

      Est $308,143

      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

      • 11 Days On Market

  • 769 Davidson Hill Rd, Chester, VT 05143
    769 Davidson Hill Rd, Chester, VT 05143
    769 Davidson Hill Rd, Chester, VT 05143
    /41

    $327,500

    Sold Aug 21, 2025

    769 Davidson Hill Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2002

    Last Sold Summary

    • 2% Below List Price
    • $234/SF
    • 7 Days On Market

    Current Estimated Value $343,072

    Last Listing Agent Frank Provance Diamond Realty

    769 Davidson Hill 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 $286,410

      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

      • 57 Days On Market

  • 62 Circle Dr, Chester, VT 05143
    62 Circle Dr, Chester, VT 05143
    62 Circle Dr, Chester, VT 05143
    /37

    $389,000

    Sold Sep 22, 2025

    62 Circle Dr, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft
    • Built 1945

    Last Sold Summary

    • $325/SF
    • 6 Days On Market

    Current Estimated Value $389,270

    Last Listing Agent Chelsea Bevis KW Vermont Woodstock

    62 Circle Dr, Chester, VT 05143
    • 138 Farrar Rd, Chester, VT 05143
      138 Farrar Rd, Chester, VT 05143
      138 Farrar Rd, Chester, VT 05143
      /23

      Est $348,928

      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

      • 23 Days On Market

  • 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 $773,345

    Last Listing Agent Sarah Sheehan William Raveis Real Estate Vermont Properties

    1295 Middletown 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 $1,550,270

      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

      • 38 Days On Market

  • 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 $810,218

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

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

      Est $379,741

      Not Listed For Sale

      2240 Baltimore Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,518 Sq Ft
      • Built 1986
      2240 Baltimore Rd, Chester, VT 05143

      Last Sold Summary

      • 14 Days On Market

  • 419 Coach Rd, Chester, VT 05143
    419 Coach Rd, Chester, VT 05143
    419 Coach Rd, Chester, VT 05143
    /12

    $210,000

    Sold May 13, 2026

    419 Coach Rd, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft
    • Built 1968

    Last Sold Summary

    • 19% Below List Price
    • $146/SF
    • 252 Days On Market

    Last Listing Agent Amy Carson Lowe's Real Estate, LLC

    419 Coach Rd, Chester, VT 05143
    • 870 Baltimore Rd, Chester, VT 05143
      870 Baltimore Rd, Chester, VT 05143
      870 Baltimore Rd, Chester, VT 05143
      /40

      Est $458,127

      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

      • 226 Days On Market

  • 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 $209,775

    Last Listing Agent Sandy Reavill

    106 Hall 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 $627,147

      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

      • 55 Days On Market

  • 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 $331,817

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    302 Davidson Hill Rd, Chester, VT 05143
    • 42 Cobb Rd, Chester, VT 05143
      42 Cobb Rd, Chester, VT 05143
      42 Cobb Rd, Chester, VT 05143
      /40

      Est $361,347

      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

      • 39 Days On Market

  • 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
    • 135 Lower Bartonsville Rd, Chester, VT 05143
      135 Lower Bartonsville Rd, Chester, VT 05143
      135 Lower Bartonsville Rd, Chester, VT 05143
      /14

      Est $378,974

      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

      • 107 Days On Market

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

      Est $260,761

      Not Listed For Sale

      1096 Mattson Rd, Chester, VT 05143

      1096 Mattson Rd, Chester, VT 05143

      Last Sold Summary

      • 23 Days On Market

  • 534 Elm St, Chester, VT 05143
    534 Elm St, Chester, VT 05143
    534 Elm St, Chester, VT 05143
    /58

    $550,000

    Sold Apr 02, 2026

    534 Elm St, Chester, VT 05143

    • 3,850 Sq Ft
    • Built 1868

    Last Sold Summary

    • 8% Below List Price
    • $143/SF
    • 154 Days On Market

    Current Estimated Value $562,761

    Last Listing Agent Tyleen Murray Kelley Real Estate, Inc.

    534 Elm St, Chester, VT 05143
    • 656 Depot St, Chester, VT 05143
      656 Depot St, Chester, VT 05143
      656 Depot St, Chester, VT 05143
      /35

      Est $261,224

      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

      • 13 Days On Market

  • 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 $1,536,480

    Last Listing Agent Dia Jenks LandVest, Inc/Woodstock

    611 Simmons Rd, Chester, VT 05143
    • 566 Simonsville Rd, Chester, VT 05143
      566 Simonsville Rd, Chester, VT 05143
      566 Simonsville Rd, Chester, VT 05143
      /53

      Est $554,934

      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

      • 229 Days On Market

  • 514 1st Ave, Chester, VT 05143
    514 1st Ave, Chester, VT 05143
    514 1st Ave, Chester, VT 05143
    /37

    $515,000

    Sold Jun 02, 2026

    514 1st Ave, Chester, VT 05143

    • 5 Beds
    • 5 Baths
    • 3,880 Sq Ft
    • Built 1803

    Last Sold Summary

    • 3% Below List Price
    • $133/SF
    • 143 Days On Market

    Current Estimated Value $526,353

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    514 1st Ave, 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 $457,113

      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

      • 44 Days On Market

  • 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 $676,123

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    31 Palmer Rd, 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 $491,916

      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

      • 6 Days On Market

  • 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 $209,458

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

    841 Farrar Rd, Chester, VT 05143
    • 1767 Rockingham Rd, Chester, VT 05143
      1767 Rockingham Rd, Chester, VT 05143
      1767 Rockingham Rd, Chester, VT 05143
      /24

      Est $317,124

      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

      • 116 Days On Market

  • 818 Davidson Hill Rd, Chester, VT 05143
    818 Davidson Hill Rd, Chester, VT 05143
    818 Davidson Hill Rd, Chester, VT 05143
    /40

    $261,500

    Sold Mar 27, 2026

    818 Davidson Hill Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 1980

    Last Sold Summary

    • 7% Below List Price
    • $210/SF
    • 8 Days On Market

    Last Listing Agent John Tolosky Barrett and Valley Associates Inc.

    818 Davidson Hill Rd, Chester, VT 05143
    • 1328 Chandler Rd, Chester, VT 05143
      1328 Chandler Rd, Chester, VT 05143
      1328 Chandler Rd, Chester, VT 05143
      /52

      Est $1,113,144

      Not Listed For Sale

      1328 Chandler Rd, Chester, VT 05143

      • 4 Beds
      • 3.5 Baths
      • 3,779 Sq Ft
      • Built 1972
      1328 Chandler Rd, Chester, VT 05143

      Last Sold Summary

      • 220 Days On Market

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

      Est $862,216

      Not Listed For Sale

      218 Gunderson Rd, Chester, VT 05143

      • 5 Beds
      • 2.5 Baths
      • 3,175 Sq Ft
      • Built 1907
      218 Gunderson Rd, Chester, VT 05143

      Last Sold Summary

      • 263 Days On Market

  • 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 $291,521

    Last Listing Agent Gale Alger

    358 Maple Ridge Rd, Chester, VT 05143

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