2,722

Chester, VT Homes

Section Image
    • 342 Marshall Rd, Chester, VT 05143
      342 Marshall Rd, Chester, VT 05143
      342 Marshall Rd, Chester, VT 05143
      /16

      Est $247,224 Not Listed For Sale

      342 Marshall Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 768 Sq Ft
      • Built 1956
      342 Marshall Rd, Chester, VT 05143

      Last Sold Summary

      • 98% Above List Price
      • $163/SF
      • 38 Days On Market

      Last Sold Price $125,000

      Last Listing Agent Amanda Stearns Barrett and Valley Associates Inc.

    • 3546 E Hill Rd, Chester, VT 05143
      3546 E Hill Rd, Chester, VT 05143
      3546 E Hill Rd, Chester, VT 05143
      /13

      Not Listed For Sale

      3546 E Hill Rd, Chester, VT 05143

      • 3 Beds
      • 1.5 Baths
      • 1,300 Sq Ft
      • Built 1950
      3546 E Hill Rd, Chester, VT 05143

      Last Sold Summary

      • $196/SF
      • 20 Days On Market

      Last Sold Price $255,000

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

    • 58 The Common, Chester, VT 05143
      58 The Common, Chester, VT 05143
      /2

      Est $326,593 Not Listed For Sale

      58 The Common, Chester, VT 05143

      • 2 Beds
      • 2 Baths
      • 1,580 Sq Ft
      • Built 1880
      58 The Common, Chester, VT 05143

      Last Sold Summary

      Last Listing Agent Joan Morey Barrett and Valley Associates Inc.

    • 470 Spruce Dr, Chester, VT 05143
      470 Spruce Dr, Chester, VT 05143
      470 Spruce Dr, Chester, VT 05143
      /24

      Est $478,127 Not Listed For Sale

      470 Spruce Dr, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,800 Sq Ft
      • Built 1979
      470 Spruce Dr, Chester, VT 05143

      Last Sold Summary

      • 55% Above List Price
      • $172/SF
      • 5 Days On Market

      Last Sold Price $309,000

      Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    • 2092 Vt Route 11 W, Chester, VT 05143
      2092 Vt Route 11 W, Chester, VT 05143
      2092 Vt Route 11 W, Chester, VT 05143
      /15

      Est $318,422 Not Listed For Sale

      2092 Vt Route 11 W, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,160 Sq Ft
      • Built 1959
      2092 Vt Route 11 W, Chester, VT 05143

      Last Sold Summary

      • 97% Above List Price
      • $140/SF
      • 50 Days On Market

      Last Sold Price $162,000

      Last Listing Agent Paul Benson Bean Group / Vermont

    • 2208 Popple Dungeon Rd, Chester, VT 05143
      2208 Popple Dungeon Rd, Chester, VT 05143
      2208 Popple Dungeon Rd, Chester, VT 05143
      /18

      Est $235,758 Not Listed For Sale

      2208 Popple Dungeon Rd, Chester, VT 05143

      • 1 Bed
      • 0.5 Baths
      • 240 Sq Ft
      • Built 1960
      2208 Popple Dungeon Rd, Chester, VT 05143

      Last Sold Summary

      • 555% Above List Price
      • $150/SF
      • 7 Days On Market

      Last Sold Price $36,000

      Last Listing Agent Philip Atwood Barrett and Valley Associates Inc.

    • 257 Edson Rd, Chester, VT 05143
      257 Edson Rd, Chester, VT 05143
      257 Edson Rd, Chester, VT 05143
      /29

      Est $558,550 Not Listed For Sale

      257 Edson Rd, Chester, VT 05143

      • 2 Beds
      • 2.5 Baths
      • 1,246 Sq Ft
      • Built 1972
      257 Edson Rd, Chester, VT 05143

      Last Sold Summary

      • 141% Above List Price
      • $186/SF
      • 26 Days On Market

      Last Sold Price $232,000

      Last Listing Agent Christiane Carroccio TPW Real Estate

    • 188 S Main St, Chester, VT 05143
      188 S Main St, Chester, VT 05143
      /2

      Est $409,235 Not Listed For Sale

      188 S Main St, Chester, VT 05143

      • 2 Beds
      • 2 Baths
      • 1,300 Sq Ft
      • Built 1960
      188 S Main St, Chester, VT 05143

      Last Sold Summary

      Last Listing Agent Joan Morey Barrett and Valley Associates Inc.

    • 6905 Popple Dungeon Rd, Chester, VT 05143
      6905 Popple Dungeon Rd, Chester, VT 05143
      6905 Popple Dungeon Rd, Chester, VT 05143
      /25

      Est $508,354 Not Listed For Sale

      6905 Popple Dungeon Rd, Chester, VT 05143

      • 4 Beds
      • 3 Baths
      • 2,000 Sq Ft
      • Built 2004
      6905 Popple Dungeon Rd, Chester, VT 05143

      Last Sold Summary

      • 59% Above List Price
      • $160/SF
      • 834 Days On Market

      Last Sold Price $320,000

      Last Listing Agent Alison Cummings Cummings & Co

    • 833 Lovers Lane Rd, Chester, VT 05143
      833 Lovers Lane Rd, Chester, VT 05143
      833 Lovers Lane Rd, Chester, VT 05143
      /32

      Est $456,267 Not Listed For Sale

      833 Lovers Lane Rd, Chester, VT 05143

      • 3 Beds
      • 2.5 Baths
      • 1,100 Sq Ft
      • Built 1976
      833 Lovers Lane Rd, Chester, VT 05143

      Last Sold Summary

      • 148% Above List Price
      • $167/SF
      • 435 Days On Market

      Last Sold Price $184,000

      Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    • 906 Vt Route 103 S, Chester, VT 05143
      906 Vt Route 103 S, Chester, VT 05143
      906 Vt Route 103 S, Chester, VT 05143
      /16

      Est $248,811 Not Listed For Sale

      906 Vt Route 103 S, Chester, VT 05143

      • 2 Beds
      • 1 Bath
      • 1,000 Sq Ft
      • Built 1968
      906 Vt Route 103 S, Chester, VT 05143

      Last Sold Summary

      • 99% Above List Price
      • $125/SF
      • 4 Days On Market

      Last Sold Price $125,000

      Last Listing Agent Joan Morey Barrett and Valley Associates Inc.

    • 168 Willies Ln, Chester, VT 05143
      168 Willies Ln, Chester, VT 05143
      168 Willies Ln, Chester, VT 05143
      /33

      Est $381,081 Not Listed For Sale

      168 Willies Ln, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,210 Sq Ft
      • Built 1972
      168 Willies Ln, Chester, VT 05143

      Last Sold Summary

      • 86% Above List Price
      • $169/SF
      • 111 Days On Market

      Last Sold Price $205,000

      Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    • 1143 Stigers Rd, Chester, VT 05143
      1143 Stigers Rd, Chester, VT 05143
      1143 Stigers Rd, Chester, VT 05143
      /40

      Est $917,000 Not Listed For Sale

      1143 Stigers Rd, Chester, VT 05143

      • 5 Beds
      • 3 Baths
      • 3,005 Sq Ft
      • Built 2012
      1143 Stigers Rd, Chester, VT 05143

      Last Sold Summary

      • 62% Above List Price
      • $188/SF
      • 210 Days On Market

      Last Sold Price $565,000

      Last Listing Agent Claudia Harris Mary Mitchell Miller Real Estate

    • 102 Main St, Chester, VT 05143
      102 Main St, Chester, VT 05143
      102 Main St, Chester, VT 05143
      /31

      Est $491,819 Not Listed For Sale

      102 Main St, Chester, VT 05143

      • 4 Beds
      • 2 Baths
      • 2,668 Sq Ft
      • Built 1850
      102 Main St, Chester, VT 05143

      Last Sold Summary

      • 114% Above List Price
      • $86/SF
      • 637 Days On Market

      Last Sold Price $230,000

      Last Listing Agent Jessica Citera Cummings & Co

    • 1404 Andover Ridge Rd, Chester, VT 05143
      1404 Andover Ridge Rd, Chester, VT 05143
      1404 Andover Ridge Rd, Chester, VT 05143
      /25

      Est $624,077 Not Listed For Sale

      1404 Andover Ridge Rd, Chester, VT 05143

      • 3 Beds
      • 2.5 Baths
      • 1,704 Sq Ft
      • Built 2002
      1404 Andover Ridge Rd, Chester, VT 05143

      Last Sold Summary

      • 147% Above List Price
      • $148/SF
      • 93 Days On Market

      Last Sold Price $252,500

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

    • 1024 Middletown Rd, Chester, VT 05143
      1024 Middletown Rd, Chester, VT 05143
      1024 Middletown Rd, Chester, VT 05143
      /28

      Est $846,988 Not Listed For Sale

      1024 Middletown Rd, Chester, VT 05143

      • 3 Beds
      • 2.5 Baths
      • 2,366 Sq Ft
      • Built 1990
      1024 Middletown Rd, Chester, VT 05143

      Last Sold Summary

      • 86% Above List Price
      • $192/SF
      • 19 Days On Market

      Last Sold Price $455,000

      Last Listing Agent Nancy Perry Four Seasons Sotheby's Int'l Realty

    • 301 Remington Rd, Chester, VT 05143
      301 Remington Rd, Chester, VT 05143
      301 Remington Rd, Chester, VT 05143
      /21

      Est $562,454 Not Listed For Sale

      301 Remington Rd, Chester, VT 05143

      • 3 Beds
      • 2.5 Baths
      • 1,944 Sq Ft
      • Built 2008
      301 Remington Rd, Chester, VT 05143

      Last Sold Summary

      • 102% Above List Price
      • $144/SF
      • 145 Days On Market

      Last Sold Price $279,000

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

    • 857 Church St, Chester, VT 05143
      857 Church St, Chester, VT 05143
      857 Church St, Chester, VT 05143
      /37

      Est $264,562 Not Listed For Sale

      857 Church St, Chester, VT 05143

      • 2 Beds
      • 1.5 Baths
      • 944 Sq Ft
      • Built 1940
      857 Church St, Chester, VT 05143

      Last Sold Summary

      • 82% Above List Price
      • $154/SF
      • 105 Days On Market

      Last Sold Price $145,000

      Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    • 273 Depot St, Chester, VT 05143
      273 Depot St, Chester, VT 05143
      273 Depot St, Chester, VT 05143
      /35

      Est $318,209 Not Listed For Sale

      273 Depot St, Chester, VT 05143

      • 3 Beds
      • 3 Baths
      • 2,005 Sq Ft
      • Built 1850
      273 Depot St, Chester, VT 05143

      Last Sold Summary

      • 147% Above List Price
      • $64/SF
      • 84 Days On Market

      Last Sold Price $129,000

      Last Listing Agent Amanda Stearns Barrett and Valley Associates Inc.

    • 206 Heald Rd, Chester, VT 05143
      206 Heald Rd, Chester, VT 05143
      206 Heald Rd, Chester, VT 05143
      /24

      Est $1,397,516 Not Listed For Sale

      206 Heald Rd, Chester, VT 05143

      • 5 Beds
      • 3.5 Baths
      • 3,825 Sq Ft
      • Built 1789
      206 Heald Rd, Chester, VT 05143

      Last Sold Summary

      • 60% Above List Price
      • $228/SF
      • 1,133 Days On Market

      Last Sold Price $872,500

      Last Listing Agent Dia Jenks LandVest, Inc/Woodstock

Showing Results 681 - 720, Page 18 of 18

Vermont Windsor County Chester

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group