76

Recently Sold Chester, VT Homes

Section Image
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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 $682,093

    Last Listing Agent Mendi Michael Engel & Völkers Okemo

    3236 Weston-Andover Rd, 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 $256,932

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    186 Mountain View, 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 $593,908

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

    95 Church St, Chester, VT 05143
  • /2

    $379,000

    Sold Apr 20, 2026

    3466 Vt Route 103 N, Chester, VT 05143

    • 2 Beds
    • 2 Baths
    • 2,751 Sq Ft
    • Built 1874

    Last Sold Summary

    • 5% Below List Price
    • $138/SF
    • 24 Days On Market

    Current Estimated Value $383,649

    Last Listing Agent Betsy Adamovich Real Broker LLC

    3466 Vt Route 103 N, Chester, VT 05143
  • /37

    $239,000

    Sold Jun 01, 2026

    15 Breezy Ln, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 1,026 Sq Ft
    • Built 1953

    Last Sold Summary

    • 11% Below List Price
    • $233/SF
    • 2 Days On Market

    Current Estimated Value $262,070

    Last Listing Agent Julie Buffum Buffum Realty

    15 Breezy Ln, 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 Four Seasons Sotheby's Int'l Realty

    246 Putnam Hill 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
  • /21

    $135,000

    Sold Jun 11, 2026

    918 Lovers Lane Rd, Chester, VT 05143

    • Land
    • 22.23 Acres
    • $6,073 per Acre

    Last Sold Summary

    • 7% Below List Price
    • 160 Days On Market

    Last Listing Agent Alan Gombosi Northland Real Estate

    918 Lovers Lane 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
  • /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 $390,000

    Last Listing Agent Jessica Citera Cummings & Co

    387 Weston-Andover Rd, Chester, VT 05143
  • /13

    $113,000

    Sold Jun 04, 2026

    3200 Baltimore Rd, Chester, VT 05143

    • Land
    • 5 Acres
    • $22,600 per Acre

    Last Sold Summary

    • 2% Below List Price
    • 23 Days On Market

    Current Estimated Value $112,700

    Last Listing Agent Kate Jarvis Williamson Group Sothebys Intl. Realty

    3200 Baltimore 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 $555,622

    Last Listing Agent Jamie Watson BHG Masiello Keene

    1573 Flamstead Rd, 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
  • /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
  • /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 $360,441

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    231 Richardson Rd, Chester, VT 05143
  • /2

    $475,000

    Sold Oct 18, 2025

    2026 Stagecoach Rd, Grafton, VT 05146

    • 3 Beds
    • 2.5 Baths
    • 2,342 Sq Ft
    • Built 1963

    Last Sold Summary

    • 10% Below List Price
    • $203/SF
    • 34 Days On Market

    Current Estimated Value $458,732

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    2026 Stagecoach Rd, Grafton, VT 05146
  • /35

    $675,000

    Sold Apr 03, 2026

    320 Pennell Rd, Cavendish, VT 05142

    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft
    • Built 1977

    Last Sold Summary

    • $307/SF
    • 6 Days On Market

    Current Estimated Value $675,667

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

    320 Pennell Rd, Cavendish, VT 05142

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