2,599

Chester, VT Homes

Section Image
  • 159 Lower Bartonsville Rd, Chester, VT 05143
    159 Lower Bartonsville Rd, Chester, VT 05143
    159 Lower Bartonsville Rd, Chester, VT 05143
    /23

    $255,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 1.5 Baths
    • 1,683 Sq Ft

    159 Lower Bartonsville Rd, Chester, VT 05143

    Welcome to 159 Lower Bartonsville Road, a charming carriage house nestled along a scenic country farm road in Rockingham, Vermont, just moments from the picturesque restored Bartonsville covered bridge. This 3 bed, 1.5 bath property features authentic 1830s architecture and timeless rustic character, offering a solid structural foundation with much of its original detail preserved. Seamlessly

    Abby Gerbick Century 21 Highview Realty

    159 Lower Bartonsville Rd, Chester, VT 05143
  • 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 $378,018

    Last Listing Agent Chelsea Bevis KW Vermont Woodstock

    62 Circle Dr, Chester, VT 05143
    • 28 Mineral Spring Rd, Chester, VT 05143
      28 Mineral Spring Rd, Chester, VT 05143
      28 Mineral Spring Rd, Chester, VT 05143
      /13

      Not Listed For Sale

      28 Mineral Spring Rd, Chester, VT 05143

      • 2 Beds
      • 1 Bath
      • 852 Sq Ft
      • Built 1993
      28 Mineral Spring Rd, Chester, VT 05143

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • 1175 Quarry Rd, Chester, VT 05143
    1175 Quarry Rd, Chester, VT 05143
    1175 Quarry Rd, Chester, VT 05143
    /25

    $270,000

    $30K PRICE DROP
    • Land
    • 75 Acres
    • $3,600 per Acre

    1175 Quarry Rd, Chester, VT 05143

    A private Vermont retreat with room to make it your own. Tucked approximately one mile up a quiet, dead-end dirt road in Chester, this expansive parcel offers the kind of space and seclusion that can be hard to find. Mostly wooded with varied, rising terrain, the property offers plenty to explore and possibilities for recreation, a private homestead, hunting camp, or seasonal getaway.Now

    Jessica Samples BHG Masiello Keene

    1175 Quarry Rd, Chester, VT 05143
  • 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 $797,423

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

    725 Flamstead Rd, Chester, VT 05143
    • 616 Mattson Rd, Chester, VT 05143
      616 Mattson Rd, Chester, VT 05143
      616 Mattson Rd, Chester, VT 05143
      /38

      Est $316,420

      Not Listed For Sale

      616 Mattson Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,349 Sq Ft
      • Built 1940
      616 Mattson Rd, Chester, VT 05143

      Last Sold Summary

      • 119 Days On Market

      Last Listing Agent Jessica Citera Cummings & Co

  • 96 Lower Bartonsville Rd, Chester, VT 05143
    96 Lower Bartonsville Rd, Chester, VT 05143
    96 Lower Bartonsville Rd, Chester, VT 05143
    /43

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,312 Sq Ft

    96 Lower Bartonsville Rd, Chester, VT 05143

    This tastefully updated ranch-style home is set on a unique one-acre parcel with a convenient location to the Williams River. Three bedrooms and two baths, thoughtfully updated interior with inviting living spaces and the convenience of one level living. A full basement provides valuable additional space and could be finished to create a family room, home office, recreation area, or even a gym.

    Jessica Citera Cummings & Co

    96 Lower Bartonsville Rd, Chester, VT 05143
  • 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
    • 242 Mattson Rd, Chester, VT 05143
      242 Mattson Rd, Chester, VT 05143
      242 Mattson Rd, Chester, VT 05143
      /25

      Est $310,750

      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

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

  • 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 $208,593

    Last Listing Agent Sandy Reavill

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

      Est $324,470

      Not Listed For Sale

      769 Davidson Hill Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,400 Sq Ft
      • Built 2002
      769 Davidson Hill Rd, Chester, VT 05143

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Frank Provance Diamond Realty

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

      Est $364,873

      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

      Last Listing Agent Heather Gleim CENTURY 21 North East

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

      Est $338,861

      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

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • 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 $557,735

    Last Listing Agent Tyleen Murray Kelley Real Estate, Inc.

    534 Elm St, 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 $300,286

      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

      Last Listing Agent Jessica Citera Cummings & Co

  • 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 $1,549,039

    Last Listing Agent Dia Jenks LandVest, Inc/Woodstock

    611 Simmons Rd, Chester, VT 05143
    • 138 Farrar Rd, Chester, VT 05143
      138 Farrar Rd, Chester, VT 05143
      138 Farrar Rd, Chester, VT 05143
      /23

      Est $382,155

      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

      Last Listing Agent Linda Benoit Highland Realty

  • 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 $514,773

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    514 1st Ave, 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 $1,544,600

      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

      Last Listing Agent Dia Jenks LandVest, Inc/Woodstock

  • 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 $723,028

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    31 Palmer Rd, Chester, VT 05143
    • 354 Miner Rd, Chester, VT 05143
      354 Miner Rd, Chester, VT 05143
      354 Miner Rd, Chester, VT 05143
      /37

      Not Listed For Sale

      354 Miner Rd, Chester, VT 05143

      • 3 Beds
      • 4 Baths
      • 2,941 Sq Ft
      • Built 2008
      354 Miner Rd, Chester, VT 05143

      Last Sold Summary

      • 114 Days On Market

      Last Listing Agent Dia Jenks LandVest, Inc/Woodstock

  • 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 $206,001

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

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

      Est $411,139

      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

      Last Listing Agent Morriah Adams BHG Masiello Brattleboro

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

      Est $444,302

      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

      Last Listing Agent Kim Mastrianni Greenwald Realty Group

  • 641 Depot St, Chester, VT 05143
    641 Depot St, Chester, VT 05143
    641 Depot St, Chester, VT 05143
    /18

    $180,000

    Sold Aug 10, 2026

    641 Depot St, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 1,379 Sq Ft
    • Built 1860

    Last Sold Summary

    • 3% Above List Price
    • $131/SF
    • 2 Days On Market

    Current Estimated Value $284,672

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

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

      Est $358,205

      Not Listed For Sale

      387 Weston-Andover Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,402 Sq Ft
      • Built 1974
      387 Weston-Andover Rd, Chester, VT 05143

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Jessica Citera Cummings & Co

  • 3078 Vt Route 10, Chester, VT 05143
    3078 Vt Route 10, Chester, VT 05143
    3078 Vt Route 10, Chester, VT 05143
    /60

    $480,000

    Sold Aug 14, 2026

    3078 Vt Route 10, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Built 1993

    Last Sold Summary

    • 3% Below List Price
    • $267/SF
    • 5 Days On Market

    Current Estimated Value $490,615

    Last Listing Agent Tyleen Murray Kelley Real Estate, Inc.

    3078 Vt Route 10, 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 $635,327

      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

      Last Listing Agent Betty McEnaney Diamond Realty

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

      Est $677,757

      Not Listed For Sale

      3236 Weston-Andover Rd, Chester, VT 05143

      • 4 Beds
      • 3 Baths
      • 2,456 Sq Ft
      • Built 1878
      3236 Weston-Andover Rd, Chester, VT 05143

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Mendi Michael Engel & Völkers Okemo

  • 35 Upper Bartonsville Rd, Chester, VT 05143
    35 Upper Bartonsville Rd, Chester, VT 05143
    35 Upper Bartonsville Rd, Chester, VT 05143
    /60

    $510,000

    Sold Aug 12, 2026

    35 Upper Bartonsville Rd, Chester, VT 05143

    • 2 Beds
    • 2 Baths
    • 2,016 Sq Ft
    • Built 2010

    Last Sold Summary

    • 13% Below List Price
    • $253/SF
    • 136 Days On Market

    Current Estimated Value $535,871

    Last Listing Agent Erin Kendall EXP Realty

    35 Upper Bartonsville Rd, Chester, VT 05143
    • 42 Cobb Rd, Chester, VT 05143
      42 Cobb Rd, Chester, VT 05143
      42 Cobb Rd, Chester, VT 05143
      /40

      Est $387,214

      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

      Last Listing Agent Geralyn Donohue Four Seasons Sotheby's Int'l Realty

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

      Est $404,983

      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

      Last Listing Agent April Shepard Twin State Realty LLC

  • 127 Trombley Rd, Chester, VT 05143
    127 Trombley Rd, Chester, VT 05143
    127 Trombley Rd, Chester, VT 05143
    /20

    $385,000

    Sold Aug 25, 2026

    127 Trombley Rd, Chester, VT 05143

    • 5 Beds
    • 1 Bath
    • 2,856 Sq Ft
    • Built 1850

    Last Sold Summary

    • 14% Below List Price
    • $135/SF
    • 215 Days On Market

    Current Estimated Value $434,325

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    127 Trombley Rd, Chester, VT 05143
    • 501 Gates Rd, Chester, VT 05143
      501 Gates Rd, Chester, VT 05143
      501 Gates Rd, Chester, VT 05143
      /27

      Not Listed For Sale

      501 Gates Rd, Chester, VT 05143

      • 1 Bed
      • 1 Bath
      • 616 Sq Ft
      • Built 2013
      501 Gates Rd, Chester, VT 05143

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Rebecca Seymour Brattleboro Area Realty

  • 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 $585,508

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

    95 Church St, Chester, VT 05143

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