2,598

Chester, VT Homes

Section Image
    • 656 Depot St, Chester, VT 05143
      656 Depot St, Chester, VT 05143
      656 Depot St, Chester, VT 05143
      /35

      Est $335,526

      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

      Last Listing Agent Glenn Olney Barrett and Valley Associates Inc.

  • 3466 Vt Route 103 N, Chester, VT 05143
    3466 Vt Route 103 N, 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 $383,229

    Last Listing Agent Betsy Adamovich Real Broker LLC

    3466 Vt Route 103 N, Chester, VT 05143
    • 4150 Trebo Rd, Chester, VT 05143
      4150 Trebo Rd, Chester, VT 05143
      4150 Trebo Rd, Chester, VT 05143
      /42

      Not Listed For Sale

      4150 Trebo Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,566 Sq Ft
      • Built 1995
      4150 Trebo Rd, Chester, VT 05143

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Alexandra Eatmon Kelley Real Estate, Inc.

  • 15 Breezy Ln, Chester, VT 05143
    15 Breezy Ln, Chester, VT 05143
    15 Breezy Ln, 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 $243,282

    Last Listing Agent Julie Buffum Buffum Realty

    15 Breezy Ln, Chester, VT 05143
    • 566 Simonsville Rd, Chester, VT 05143
      566 Simonsville Rd, Chester, VT 05143
      566 Simonsville Rd, Chester, VT 05143
      /53

      Est $605,545

      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

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

  • 246 Putnam Hill Rd, Chester, VT 05143
    246 Putnam Hill Rd, Chester, VT 05143
    246 Putnam Hill Rd, 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
    • 56 Hidden Newton Rd, Chester, VT 05143
      56 Hidden Newton Rd, Chester, VT 05143
      56 Hidden Newton Rd, Chester, VT 05143
      /41

      Est $436,103

      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

      Last Listing Agent Alison Cummings Cummings & Co

  • 918 Lovers Lane Rd, Chester, VT 05143
    918 Lovers Lane Rd, Chester, VT 05143
    918 Lovers Lane 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
    • 2358 N Hill Rd, Chester, VT 05143
      2358 N Hill Rd, Chester, VT 05143
      2358 N Hill Rd, Chester, VT 05143
      /39

      Est $559,971

      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

      Last Listing Agent John Napier TPW Real Estate

  • Lot 3 Mattson Rd, Chester, VT 05143
    Lot 3 Mattson Rd, Chester, VT 05143
    Lot 3 Mattson 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
    • 1767 Rockingham Rd, Chester, VT 05143
      1767 Rockingham Rd, Chester, VT 05143
      1767 Rockingham Rd, Chester, VT 05143
      /24

      Est $309,377

      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

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • 3200 Baltimore Rd, Chester, VT 05143
    3200 Baltimore Rd, Chester, VT 05143
    3200 Baltimore 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 $147,823

    Last Listing Agent Kate Jarvis Williamson Group Sothebys Intl. Realty

    3200 Baltimore Rd, Chester, VT 05143
    • 1328 Chandler Rd, Chester, VT 05143
      1328 Chandler Rd, Chester, VT 05143
      1328 Chandler Rd, Chester, VT 05143
      /52

      Est $1,133,961

      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

      Last Listing Agent Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

  • 1573 Flamstead Rd, Chester, VT 05143
    1573 Flamstead Rd, Chester, VT 05143
    1573 Flamstead 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 $557,987

    Last Listing Agent Jamie Watson BHG Masiello Keene

    1573 Flamstead Rd, Chester, VT 05143
    • 218 Gunderson Rd, Chester, VT 05143
      218 Gunderson Rd, Chester, VT 05143
      218 Gunderson Rd, Chester, VT 05143
      /50

      Est $893,853

      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

      Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

  • 423 Main St, Chester, VT 05143
    423 Main St, Chester, VT 05143
    423 Main St, 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
    • 2401 N Hill Rd, Chester, VT 05143
      2401 N Hill Rd, Chester, VT 05143
      2401 N Hill Rd, Chester, VT 05143
      /38

      Est $752,108

      Not Listed For Sale

      2401 N Hill Rd, Chester, VT 05143

      • 4 Beds
      • 2.5 Baths
      • 2,242 Sq Ft
      • Built 1990
      2401 N Hill Rd, Chester, VT 05143

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Alison Cummings Cummings & Co

  • 231 Richardson Rd, Chester, VT 05143
    231 Richardson 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 $359,017

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

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

      Est $526,020

      Not Listed For Sale

      316 Little Pond Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,456 Sq Ft
      • Built 1975
      316 Little Pond Rd, Chester, VT 05143

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Nick Sicard EXP Realty

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

      Not Listed For Sale

      1873 Brockway Mills Rd, Chester, VT 05143

      • 5 Beds
      • 3 Baths
      • 2,752 Sq Ft
      • Built 2024
      1873 Brockway Mills Rd, Chester, VT 05143

      Last Sold Summary

      • 113 Days On Market

      Last Listing Agent Heather Gleim CENTURY 21 North East

    • 0 Gould Rd Unit 5023598, Chester, VT 05143
      0 Gould Rd Unit 5023598, Chester, VT 05143
      0 Gould Rd Unit 5023598, Chester, VT 05143
      /10

      Not Listed For Sale

      0 Gould Rd Unit 5023598, Chester, VT 05143

      0 Gould Rd Unit 5023598, Chester, VT 05143

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    • 0 Hall Rd, Chester, VT 05143
      0 Hall Rd, Chester, VT 05143
      0 Hall Rd, Chester, VT 05143
      /19

      Not Listed For Sale

      0 Hall Rd, Chester, VT 05143

      0 Hall Rd, Chester, VT 05143

      Last Sold Summary

      • 195 Days On Market

      Last Listing Agent Jessica Samples BHG Masiello Keene

    • 358 Maple Ridge Rd, Chester, VT 05143
      358 Maple Ridge Rd, Chester, VT 05143
      358 Maple Ridge Rd, Chester, VT 05143
      /16

      Est $298,603

      Not Listed For Sale

      358 Maple Ridge Rd, Chester, VT 05143

      • 2 Beds
      • 1 Bath
      • 1,488 Sq Ft
      • Built 1989
      358 Maple Ridge Rd, Chester, VT 05143

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Gale Alger

    • 209 Ingraham Hill Rd, Chester, VT 05143
      209 Ingraham Hill Rd, Chester, VT 05143
      209 Ingraham Hill Rd, Chester, VT 05143
      /34

      Not Listed For Sale

      209 Ingraham Hill Rd, Chester, VT 05143

      • 2 Beds
      • 2 Baths
      • 1,918 Sq Ft
      • Built 2004
      209 Ingraham Hill Rd, Chester, VT 05143

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Dia Jenks LandVest, Inc/Woodstock

    • 22 White Rd, Chester, VT 05143
      22 White Rd, Chester, VT 05143
      22 White Rd, Chester, VT 05143
      /12

      Est $138,526

      Not Listed For Sale

      22 White Rd, Chester, VT 05143

      • 1 Bed
      • 1 Bath
      • 630 Sq Ft
      • Built 1940
      22 White Rd, Chester, VT 05143

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Darlene Conca

    • 994 Dodge Rd, Chester, VT 05143
      994 Dodge Rd, Chester, VT 05143
      994 Dodge Rd, Chester, VT 05143
      /40

      Est $648,374

      Not Listed For Sale

      994 Dodge Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,876 Sq Ft
      • Built 2012
      994 Dodge Rd, Chester, VT 05143

      Last Sold Summary

      • 89 Days On Market

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

    • 110 Shady Grove Ln, Chester, VT 05143
      110 Shady Grove Ln, Chester, VT 05143
      110 Shady Grove Ln, Chester, VT 05143
      /33

      Est $276,189

      Not Listed For Sale

      110 Shady Grove Ln, Chester, VT 05143

      • 2 Beds
      • 2 Baths
      • 1,672 Sq Ft
      • Built 2022
      110 Shady Grove Ln, Chester, VT 05143

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Rob Weltz Barrett and Valley Associates Inc.

    • 2253 White Rd, Chester, VT 05143
      2253 White Rd, Chester, VT 05143
      2253 White Rd, Chester, VT 05143
      /38

      Not Listed For Sale

      2253 White Rd, Chester, VT 05143

      • 2 Beds
      • 2 Baths
      • 1,171 Sq Ft
      • Built 1990
      2253 White Rd, Chester, VT 05143

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent Alison Cummings Cummings & Co

    • 0 Remington Rd Unit 12 5001944, Chester, VT 05143
      0 Remington Rd Unit 12 5001944, Chester, VT 05143
      0 Remington Rd Unit 12 5001944, Chester, VT 05143
      /12

      Not Listed For Sale

      0 Remington Rd Unit 12 5001944, Chester, VT 05143

      0 Remington Rd Unit 12 5001944, Chester, VT 05143

      Last Sold Summary

      • 183 Days On Market

      Last Listing Agent Frank Provance Diamond Realty

    • 1716 Brockway Mills Rd, Chester, VT 05143
      1716 Brockway Mills Rd, Chester, VT 05143
      1716 Brockway Mills Rd, Chester, VT 05143
      /40

      Est $564,259

      Not Listed For Sale

      1716 Brockway Mills Rd, Chester, VT 05143

      • 3 Beds
      • 2.5 Baths
      • 1,908 Sq Ft
      • Built 1992
      1716 Brockway Mills Rd, Chester, VT 05143

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

    • 505 Hidden Heights Rd, Chester, VT 05143
      505 Hidden Heights Rd, Chester, VT 05143
      505 Hidden Heights Rd, Chester, VT 05143
      /26

      Est $103,382

      Not Listed For Sale

      505 Hidden Heights Rd, Chester, VT 05143

      505 Hidden Heights Rd, Chester, VT 05143

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    • 0 Route 103 Unit 4999744, Chester, VT 05143
      0 Route 103 Unit 4999744, Chester, VT 05143
      0 Route 103 Unit 4999744, Chester, VT 05143
      /14

      Not Listed For Sale

      0 Route 103 Unit 4999744, Chester, VT 05143

      0 Route 103 Unit 4999744, Chester, VT 05143

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Leila Tarantelli KW Coastal and Lakes & Mountains Realty/Hanover

    • 1291 Potash Brook Rd, Chester, VT 05143
      1291 Potash Brook Rd, Chester, VT 05143
      1291 Potash Brook Rd, Chester, VT 05143
      /35

      Est $118,946

      Not Listed For Sale

      1291 Potash Brook Rd, Chester, VT 05143

      • 1 Bed
      • 1 Bath
      • 704 Sq Ft
      • Built 1960
      1291 Potash Brook Rd, Chester, VT 05143

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Frank Provance Diamond Realty

    • 0 Remington Rd Unit 9 4997325, Chester, VT 05143
      0 Remington Rd Unit 9 4997325, Chester, VT 05143
      0 Remington Rd Unit 9 4997325, Chester, VT 05143
      /5

      Not Listed For Sale

      0 Remington Rd Unit 9 4997325, Chester, VT 05143

      0 Remington Rd Unit 9 4997325, Chester, VT 05143

      Last Sold Summary

      • 211 Days On Market

      Last Listing Agent Frank Provance Diamond Realty

    • 0 Remington Rd Unit 6 4996522, Chester, VT 05143
      0 Remington Rd Unit 6 4996522, Chester, VT 05143
      0 Remington Rd Unit 6 4996522, Chester, VT 05143
      /5

      Not Listed For Sale

      0 Remington Rd Unit 6 4996522, Chester, VT 05143

      0 Remington Rd Unit 6 4996522, Chester, VT 05143

      Last Sold Summary

      • 207 Days On Market

      Last Listing Agent Frank Provance Diamond Realty

    • 0 Remington Rd Unit 8 4996410, Chester, VT 05143
      0 Remington Rd Unit 8 4996410, Chester, VT 05143
      0 Remington Rd Unit 8 4996410, Chester, VT 05143
      /6

      Not Listed For Sale

      0 Remington Rd Unit 8 4996410, Chester, VT 05143

      0 Remington Rd Unit 8 4996410, Chester, VT 05143

      Last Sold Summary

      • 215 Days On Market

      Last Listing Agent Frank Provance Diamond Realty

    • 3610 Vt Route 103 N Unit 50003, Chester, VT 03602
      3610 Vt Route 103 N Unit 50003, Chester, VT 03602
      3610 Vt Route 103 N Unit 50003, Chester, VT 03602
      /8

      Not Listed For Sale

      3610 Vt Route 103 N Unit 50003, Chester, VT 03602

      3610 Vt Route 103 N Unit 50003, Chester, VT 03602

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Kimberly Dubois Matson KW Realty

    • 222 Peck Rd, Chester, VT 05143
      222 Peck Rd, Chester, VT 05143
      222 Peck Rd, Chester, VT 05143
      /20

      Est $231,295

      Not Listed For Sale

      222 Peck Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 864 Sq Ft
      • Built 1973
      222 Peck Rd, Chester, VT 05143

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    • 0 Brookside Dr Unit 4994316, Chester, VT 05143
      0 Brookside Dr Unit 4994316, Chester, VT 05143
      0 Brookside Dr Unit 4994316, Chester, VT 05143
      /25

      Not Listed For Sale

      0 Brookside Dr Unit 4994316, Chester, VT 05143

      0 Brookside Dr Unit 4994316, Chester, VT 05143

      Last Sold Summary

      • 206 Days On Market

      Last Listing Agent Mike England Michael England Real Estate

    • 4351 Route 11, Chester, VT 05143
      4351 Route 11, Chester, VT 05143
      4351 Route 11, Chester, VT 05143
      /18

      Not Listed For Sale

      4351 Route 11, Chester, VT 05143

      • 2 Beds
      • 1 Bath
      • 980 Sq Ft
      • Built 1968
      4351 Route 11, Chester, VT 05143

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Glenn Olney Barrett and Valley Associates Inc.

Showing Results 161 - 200, Page 5 of 18

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