2,737

Chester, VT Homes

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    • /24

      Est $287,962 Not Listed For Sale

      1369 Flamstead Rd, Chester, VT 05143

      • 3 Beds
      • 1.5 Baths
      • 1,096 Sq Ft
      • Built 1973
      1369 Flamstead Rd, Chester, VT 05143

      Last Sold Summary

      • 25% Above List Price
      • $210/SF
      • 8 Days On Market
      • Last Sold Price $230,000
      • Sep 29, 2023

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • /47

    $569,000

    • 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
  • /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 $314,370

    Last Listing Agent Julie Buffum Buffum Realty

    870 Cummings Rd, Chester, VT 05143
    • /40

      Est $609,511 Not Listed For Sale

      1573 Trebo Rd, Chester, VT 05143

      • 2 Beds
      • 2.5 Baths
      • 1,444 Sq Ft
      • Built 1988
      1573 Trebo Rd, Chester, VT 05143

      Last Sold Summary

      • 6% Below List Price
      • $450/SF
      • 5 Days On Market
      • Last Sold Price $650,000
      • Jun 21, 2024

      Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

  • /22

    $290,000

    • Land
    • 75 Acres
    • $3,867 per Acre

    1175 Quarry Rd, Chester, VT 05143

    An extraordinary potential homesite set in the hills of southern Vermont. This expansive 75-acre parcel offers the perfect blend of privacy, natural beauty, and endless potential. Whether you dream of building a secluded hilltop retreat or preserving land for recreation and conservation, this property invites endless possibilties. Improvements include a septic system, dug well, electricity and a

    Jessica Samples BHG Masiello Keene

    1175 Quarry 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 $337,606

    Last Listing Agent Frank Provance Diamond Realty

    769 Davidson Hill 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

      • $153/SF
      • 27 Days On Market
      • Last Sold Price $130,500
      • Jun 28, 2024

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /21

    $145,000 Under Contract

    • Land
    • 22.23 Acres
    • $6,523 per Acre

    918 Lovers Lane Rd, Chester, VT 05143

    Located only 2 miles from the picturesque Chester Green you will encounter this newly created 22 acre building parcel on scenic Lover's Lane. This property consists of a 2 acre meadow ideal for building and a 20 acre woodlot consisting of pine, hemlock, oak and maple for sugaring. Beautiful fieldstone walls border most of the boundary lines. The surveyed parcel has an approved 4 bedroom State

    Alan Gombosi Northland Real Estate

    918 Lovers Lane Rd, 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 $378,123

    Last Listing Agent Chelsea Bevis KW Vermont Woodstock

    62 Circle Dr, Chester, VT 05143
    • /38

      Est $317,079 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

      • 2% Below List Price
      • $241/SF
      • 119 Days On Market
      • Last Sold Price $325,000
      • Dec 07, 2023

      Last Listing Agent Jessica Citera Cummings & Co

  • /13

    $115,000 Under Contract

    • Land
    • 5 Acres
    • $23,000 per Acre

    3200 Baltimore Rd, Chester, VT 05143

    This lovely open lot offers many possibilities for future use. Facing South, the land is 80% open and bordered by beautiful stonewalls and mature Maple trees. The long range Mountain views are visible from many different locations on the land. A wonderful opportunity to own a piece of Vermont, nestled in the Green Mountains.

    Kate Jarvis Williamson Group Sothebys Intl. Realty

    3200 Baltimore Rd, Chester, VT 05143
  • /26

    $311,688 Sold May 30, 2025

    3590 Vt 103, Chester, VT 05143

    • 4 Beds
    • 2 Baths
    • 2,702 Sq Ft
    • Built 1850

    Last Sold Summary

    • 35% Below List Price
    • $115/SF
    • 387 Days On Market

    Last Listing Agent Jessica Samples BHG Masiello Keene

    3590 Vt 103, Chester, VT 05143
    • /36

      Est $461,233 Not Listed For Sale

      231 Snell Rd, Chester, VT 05143

      • 3 Beds
      • 3 Baths
      • 2,465 Sq Ft
      • Built 1986
      231 Snell Rd, Chester, VT 05143

      Last Sold Summary

      • 8% Above List Price
      • $174/SF
      • 18 Days On Market
      • Last Sold Price $428,000
      • Jun 15, 2023

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /33

    $299,000

    • 2,702 Sq Ft

    41 Vt Route 103 S, Chester, VT 05143

    Here's a great opportunity to own a property on Chester's busy Main Street, Route 103 and Route 11. Situated between the Jiffy Mart and the General Dollar Store, there are many possibilities here for a commercial enterprise. Or you can use one unit for a nice business office and continue to rent the other two existing apartments. There is good road frontage for plenty of parking. Consider the

    Glenn Olney Barrett and Valley Associates Inc.

    41 Vt Route 103 S, 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 $775,610

    Last Listing Agent Sarah Sheehan William Raveis Real Estate Vermont Properties

    1295 Middletown Rd, Chester, VT 05143
    • /25

      Est $315,249 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

      • 34% Above List Price
      • $175/SF
      • 9 Days On Market
      • Last Sold Price $235,000
      • Jul 15, 2024

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

  • /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 $790,254

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

    725 Flamstead Rd, Chester, VT 05143
    • /31

      Est $364,411 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

      • 1% Above List Price
      • $241/SF
      • 2 Days On Market
      • Last Sold Price $360,000
      • Aug 02, 2024

      Last Listing Agent Heather Gleim CENTURY 21 North East

  • /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 $202,758

    Last Listing Agent Sandy Reavill

    106 Hall Rd, Chester, VT 05143
    • /8

      Est $193,882 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

      • 159% Above List Price
      • $87/SF
      • 30 Days On Market
      • Last Sold Price $75,000
      • May 22, 2023

      Last Listing Agent Judy Thompson Walnut Hill Realty

  • /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 $319,936

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

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

      Est $298,484 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

      • $261/SF
      • 11 Days On Market
      • Last Sold Price $299,000
      • May 24, 2024

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • /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 $531,066

    Last Listing Agent Nick Sicard EXP Realty

    316 Little Pond Rd, Chester, VT 05143
    • /29

      Est $273,239 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

      • 2% Below List Price
      • $305/SF
      • 57 Days On Market
      • Last Sold Price $277,500
      • Oct 01, 2024

      Last Listing Agent Jessica Citera Cummings & Co

  • /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
    • /23

      Est $380,354 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

      • 4% Below List Price
      • $270/SF
      • 23 Days On Market
      • Last Sold Price $395,000
      • Jul 19, 2024

      Last Listing Agent Linda Benoit Highland Realty

  • /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
    • /31

      Est $1,612,859 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
      • Dec 10, 2024

      Last Listing Agent Dia Jenks LandVest, Inc/Woodstock

  • /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 $531,099

    Last Listing Agent Tyleen Murray Kelley Real Estate, Inc.

    534 Elm St, Chester, VT 05143
    • /39

      Est $374,964 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

      • 3% Below List Price
      • $254/SF
      • 14 Days On Market
      • Last Sold Price $385,000
      • Mar 20, 2025

      Last Listing Agent Morriah Adams BHG Masiello Brattleboro

  • /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 $1,647,781

    Last Listing Agent Dia Jenks LandVest, Inc/Woodstock

    611 Simmons Rd, Chester, VT 05143
    • /40

      Est $531,600 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

      • 42% Above List Price
      • $121/SF
      • 226 Days On Market
      • Last Sold Price $375,000
      • May 30, 2024

      Last Listing Agent Kim Mastrianni Greenwald Realty Group

  • /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
    • /40

      Est $614,963 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

      • 3% Above List Price
      • $286/SF
      • 55 Days On Market
      • Last Sold Price $595,000
      • Nov 08, 2024

      Last Listing Agent Betty McEnaney Diamond Realty

  • /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 $657,936

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    31 Palmer Rd, Chester, VT 05143
    • /40

      Est $358,353 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

      • 1% Above List Price
      • $327/SF
      • 39 Days On Market
      • Last Sold Price $355,000
      • May 09, 2024

      Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

  • /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 $208,243

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

    841 Farrar Rd, Chester, VT 05143
    • /14

      Est $382,036 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

      • 47% Above List Price
      • $137/SF
      • 107 Days On Market
      • Last Sold Price $260,000
      • Dec 01, 2023

      Last Listing Agent April Shepard Twin State Realty LLC

  • /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
    • /26

      Est $255,689 Not Listed For Sale

      1096 Mattson Rd, Chester, VT 05143

      1096 Mattson Rd, Chester, VT 05143

      Last Sold Summary

      • 9% Above List Price
      • 23 Days On Market
      • Last Sold Price $235,000
      • Jul 20, 2023

      Last Listing Agent Lisa Kelley Cummings & Co

Showing Results 121 - 160, Page 4 of 18

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