2,598

Chester, VT Homes

Section Image
    • 256 Depot St, Chester, VT 05143
      256 Depot St, Chester, VT 05143
      256 Depot St, Chester, VT 05143
      /25

      Est $317,732

      Not Listed For Sale

      256 Depot St, Chester, VT 05143

      • 3 Beds
      • 3 Baths
      • 1,700 Sq Ft
      • Built 1880
      256 Depot St, Chester, VT 05143

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    • 73 Maple St, Chester, VT 05143
      73 Maple St, Chester, VT 05143
      73 Maple St, Chester, VT 05143
      /26

      Est $409,187

      Not Listed For Sale

      73 Maple St, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 2,382 Sq Ft
      • Built 1862
      73 Maple St, Chester, VT 05143

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    • 191 Depot St, Chester, VT 05143
      191 Depot St, Chester, VT 05143
      191 Depot St, Chester, VT 05143
      /36

      Est $557,645

      Not Listed For Sale

      191 Depot St, Chester, VT 05143

      • 5 Beds
      • 3.5 Baths
      • 2,664 Sq Ft
      • Built 1885
      191 Depot St, Chester, VT 05143

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

    • 63 Highland Ct, Chester, VT 05143
      63 Highland Ct, Chester, VT 05143
      63 Highland Ct, Chester, VT 05143
      /23

      Est $321,471

      Not Listed For Sale

      63 Highland Ct, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,430 Sq Ft
      • Built 1952
      63 Highland Ct, Chester, VT 05143

      Last Sold Summary

      • 6 Days On Market

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

    • 64 Highland Ct, Chester, VT 05143
      64 Highland Ct, Chester, VT 05143
      64 Highland Ct, Chester, VT 05143
      /30

      Est $358,686

      Not Listed For Sale

      64 Highland Ct, Chester, VT 05143

      • 3 Beds
      • 1.5 Baths
      • 1,267 Sq Ft
      • Built 1952
      64 Highland Ct, Chester, VT 05143

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    • 71 Canal St, Chester, VT 05143
      71 Canal St, Chester, VT 05143
      71 Canal St, Chester, VT 05143
      /23

      Est $274,491

      Not Listed For Sale

      71 Canal St, Chester, VT 05143

      • 2 Beds
      • 2 Baths
      • 1,100 Sq Ft
      • Built 1910
      71 Canal St, Chester, VT 05143

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Heather Gleim CENTURY 21 North East

    • 74 Cobleigh St, Chester, VT 05143
      74 Cobleigh St, Chester, VT 05143
      74 Cobleigh St, Chester, VT 05143
      /36

      Est $570,183

      Not Listed For Sale

      74 Cobleigh St, Chester, VT 05143

      • 3 Beds
      • 3 Baths
      • 3,223 Sq Ft
      • Built 1890
      74 Cobleigh St, Chester, VT 05143

      Last Sold Summary

      • 10 Days On Market

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

    • 17 Orcutt Dr, Chester, VT 05143
      17 Orcutt Dr, Chester, VT 05143
      17 Orcutt Dr, Chester, VT 05143
      /18

      Est $334,982

      Not Listed For Sale

      17 Orcutt Dr, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,383 Sq Ft
      • Built 1960
      17 Orcutt Dr, Chester, VT 05143

      Last Sold Summary

      • 2 Days On Market

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

    • 308 Church St, Chester, VT 05143
      308 Church St, Chester, VT 05143
      308 Church St, Chester, VT 05143
      /20

      Est $337,595

      Not Listed For Sale

      308 Church St, Chester, VT 05143

      • 2 Beds
      • 1 Bath
      • 1,354 Sq Ft
      • Built 1900
      308 Church St, Chester, VT 05143

      Last Sold Summary

      • 130 Days On Market

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    • 372 Main St, Chester, VT 05143
      372 Main St, Chester, VT 05143
      372 Main St, Chester, VT 05143
      /38

      Est $536,586

      Not Listed For Sale

      372 Main St, Chester, VT 05143

      • 4 Beds
      • 2 Baths
      • 2,775 Sq Ft
      • Built 1850
      372 Main St, Chester, VT 05143

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Amanda Stearns Barrett and Valley Associates Inc.

    • 346 1st Ave, Chester, VT 05143
      346 1st Ave, Chester, VT 05143
      346 1st Ave, Chester, VT 05143
      /34

      Est $308,432

      Not Listed For Sale

      346 1st Ave, Chester, VT 05143

      • 4 Beds
      • 2 Baths
      • 1,610 Sq Ft
      • Built 1830
      346 1st Ave, Chester, VT 05143

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Lisa Kelley Cummings & Co

    • 38 Vt Route 11 W, Chester, VT 05143
      38 Vt Route 11 W, Chester, VT 05143
      38 Vt Route 11 W, Chester, VT 05143
      /40

      Est $814,684

      Not Listed For Sale

      38 Vt Route 11 W, Chester, VT 05143

      • 12 Beds
      • 5 Baths
      • 5,976 Sq Ft
      • Built 1904
      38 Vt Route 11 W, Chester, VT 05143

      Last Sold Summary

      • 139 Days On Market

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

    • 501 Main St, Chester, VT 05143
      501 Main St, Chester, VT 05143
      501 Main St, Chester, VT 05143
      /40

      Est $520,537

      Not Listed For Sale

      501 Main St, Chester, VT 05143

      • 5 Beds
      • 3 Baths
      • 2,687 Sq Ft
      • Built 1810
      501 Main St, Chester, VT 05143

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    • 479 Main St, Chester, VT 05143
      479 Main St, Chester, VT 05143
      479 Main St, Chester, VT 05143
      /38

      Est $480,392

      Not Listed For Sale

      479 Main St, Chester, VT 05143

      • 5 Beds
      • 5 Baths
      • 3,238 Sq Ft
      • Built 1799
      479 Main St, Chester, VT 05143

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    • 683 Church St, Chester, VT 05143
      683 Church St, Chester, VT 05143
      683 Church St, Chester, VT 05143
      /40

      Est $1,327,558

      Not Listed For Sale

      683 Church St, Chester, VT 05143

      • 7 Beds
      • 6 Baths
      • 5,566 Sq Ft
      • Built 1801
      683 Church St, Chester, VT 05143

      Last Sold Summary

      • 236 Days On Market

      Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    • 604 Church St, Chester, VT 05143
      604 Church St, Chester, VT 05143
      604 Church St, Chester, VT 05143
      /40

      Est $659,979

      Not Listed For Sale

      604 Church St, Chester, VT 05143

      • 3 Beds
      • 3 Baths
      • 3,099 Sq Ft
      • Built 1958
      604 Church St, Chester, VT 05143

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    • 312 North St, Chester, VT 05143
      312 North St, Chester, VT 05143
      312 North St, Chester, VT 05143
      /39

      Est $373,139

      Not Listed For Sale

      312 North St, Chester, VT 05143

      • 4 Beds
      • 1 Bath
      • 2,090 Sq Ft
      • Built 1850
      312 North St, Chester, VT 05143

      Last Sold Summary

      • 150 Days On Market

      Last Listing Agent Heather Gleim CENTURY 21 North East

    • 435 Marcs Dr, Chester, VT 05143
      435 Marcs Dr, Chester, VT 05143
      435 Marcs Dr, Chester, VT 05143
      /36

      Est $441,124

      Not Listed For Sale

      435 Marcs Dr, Chester, VT 05143

      • 3 Beds
      • 1.5 Baths
      • 2,019 Sq Ft
      • Built 1986
      435 Marcs Dr, Chester, VT 05143

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Joan Morey Barrett and Valley Associates Inc.

    • 332 Marcs Dr, Chester, VT 05143
      332 Marcs Dr, Chester, VT 05143
      332 Marcs Dr, Chester, VT 05143
      /37

      Est $655,337

      Not Listed For Sale

      332 Marcs Dr, Chester, VT 05143

      • 4 Beds
      • 3.5 Baths
      • 2,795 Sq Ft
      • Built 1988
      332 Marcs Dr, Chester, VT 05143

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    • 498 Marcs Dr, Chester, VT 05143
      498 Marcs Dr, Chester, VT 05143
      498 Marcs Dr, Chester, VT 05143
      /40

      Est $577,064

      Not Listed For Sale

      498 Marcs Dr, Chester, VT 05143

      • 4 Beds
      • 2.5 Baths
      • 2,564 Sq Ft
      • Built 1986
      498 Marcs Dr, Chester, VT 05143

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Heather Gleim CENTURY 21 North East

    • 784 Vt Route 103 N, Chester, VT 05143
      784 Vt Route 103 N, Chester, VT 05143
      784 Vt Route 103 N, Chester, VT 05143
      /10

      Est $338,082

      Not Listed For Sale

      784 Vt Route 103 N, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,214 Sq Ft
      • Built 1972
      784 Vt Route 103 N, Chester, VT 05143

      Last Sold Summary

      • 124 Days On Market

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

    • 445 Trebo Rd, Chester, VT 05143
      445 Trebo Rd, Chester, VT 05143
      445 Trebo Rd, Chester, VT 05143
      /40

      Est $870,943

      Not Listed For Sale

      445 Trebo Rd, Chester, VT 05143

      • 6 Beds
      • 4 Baths
      • 2,762 Sq Ft
      • Built 2007
      445 Trebo Rd, Chester, VT 05143

      Last Sold Summary

      • 131 Days On Market

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

    • 3590 Vt Route 103 N, Chester, VT 05143
      3590 Vt Route 103 N, Chester, VT 05143
      3590 Vt Route 103 N, Chester, VT 05143
      /39

      Est $394,641

      Not Listed For Sale

      3590 Vt Route 103 N, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 2,090 Sq Ft
      • Built 1850
      3590 Vt Route 103 N, Chester, VT 05143

      Last Sold Summary

      • 108 Days On Market

      Last Listing Agent Kristen Fehrenbach Engel & Völkers Okemo

    • 668 Grafton Rd, Chester, VT 05143
      668 Grafton Rd, Chester, VT 05143
      668 Grafton Rd, Chester, VT 05143
      /30

      Est $483,345

      Not Listed For Sale

      668 Grafton Rd, Chester, VT 05143

      • 2 Beds
      • 2 Baths
      • 1,688 Sq Ft
      • Built 1840
      668 Grafton Rd, Chester, VT 05143

      Last Sold Summary

      • 6 Days On Market

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

    • 837 Vt Route 11 W, Chester, VT 05143
      837 Vt Route 11 W, Chester, VT 05143
      837 Vt Route 11 W, Chester, VT 05143
      /27

      Est $405,782

      Not Listed For Sale

      837 Vt Route 11 W, Chester, VT 05143

      • 4 Beds
      • 2 Baths
      • 2,412 Sq Ft
      • Built 1987
      837 Vt Route 11 W, Chester, VT 05143

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    • 1010 Vt Route 11 W, Chester, VT 05143
      1010 Vt Route 11 W, Chester, VT 05143
      1010 Vt Route 11 W, Chester, VT 05143
      /37

      Est $261,752

      Not Listed For Sale

      1010 Vt Route 11 W, Chester, VT 05143

      • 2 Beds
      • 1 Bath
      • 884 Sq Ft
      • Built 1960
      1010 Vt Route 11 W, Chester, VT 05143

      Last Sold Summary

      • 9 Days On Market

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

    • 308 Adams Rd, Chester, VT 05143
      308 Adams Rd, Chester, VT 05143
      308 Adams Rd, Chester, VT 05143
      /30

      Est $1,068,497

      Not Listed For Sale

      308 Adams Rd, Chester, VT 05143

      • 3 Beds
      • 2.5 Baths
      • 1,788 Sq Ft
      • Built 2013
      308 Adams Rd, Chester, VT 05143

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Story Jenks LandVest, Inc/Woodstock

    • 110 Linquist Rd, Chester, VT 05143
      110 Linquist Rd, Chester, VT 05143
      110 Linquist Rd, Chester, VT 05143
      /11

      Est $298,333

      Not Listed For Sale

      110 Linquist Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,767 Sq Ft
      • Built 2002
      110 Linquist Rd, Chester, VT 05143

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Samantha Kelley Tranzon Auction Properties

    • 146 Logan Dr, Chester, VT 05143
      146 Logan Dr, Chester, VT 05143
      146 Logan Dr, Chester, VT 05143
      /3

      Est $244,998

      Not Listed For Sale

      146 Logan Dr, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,746 Sq Ft
      • Built 1971
      146 Logan Dr, Chester, VT 05143

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    • 100 Fletcher Hill Rd, Chester, VT 05143
      100 Fletcher Hill Rd, Chester, VT 05143
      100 Fletcher Hill Rd, Chester, VT 05143
      /19

      Est $368,485

      Not Listed For Sale

      100 Fletcher Hill Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,551 Sq Ft
      • Built 1974
      100 Fletcher Hill Rd, Chester, VT 05143

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    • 289 Fletcher Hill Rd, Chester, VT 05143
      289 Fletcher Hill Rd, Chester, VT 05143
      289 Fletcher Hill Rd, Chester, VT 05143
      /21

      Est $442,110

      Not Listed For Sale

      289 Fletcher Hill Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,848 Sq Ft
      • Built 1990
      289 Fletcher Hill Rd, Chester, VT 05143

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    • 1687 Vt Route 11 E, Chester, VT 05143
      1687 Vt Route 11 E, Chester, VT 05143
      1687 Vt Route 11 E, Chester, VT 05143
      /35

      Est $381,743

      Not Listed For Sale

      1687 Vt Route 11 E, Chester, VT 05143

      • 4 Beds
      • 2 Baths
      • 944 Sq Ft
      • Built 1971
      1687 Vt Route 11 E, Chester, VT 05143

      Last Sold Summary

      • 43 Days On Market

      Last Listing Agent Amanda Stearns Barrett and Valley Associates Inc.

    • 1824 Vt Route 11 E, Chester, VT 05143
      1824 Vt Route 11 E, Chester, VT 05143
      1824 Vt Route 11 E, Chester, VT 05143
      /40

      Est $377,151

      Not Listed For Sale

      1824 Vt Route 11 E, Chester, VT 05143

      • 2 Beds
      • 2 Baths
      • 1,212 Sq Ft
      • Built 1850
      1824 Vt Route 11 E, Chester, VT 05143

      Last Sold Summary

      • 123 Days On Market

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

    • 13 Logan Dr, Chester, VT 05143
      13 Logan Dr, Chester, VT 05143
      13 Logan Dr, Chester, VT 05143
      /38

      Est $337,954

      Not Listed For Sale

      13 Logan Dr, Chester, VT 05143

      • 6 Beds
      • 3 Baths
      • 2,426 Sq Ft
      • Built 1840
      13 Logan Dr, Chester, VT 05143

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Jamie Watson BHG Masiello Keene

    • 690 Trebo Rd, Chester, VT 05143
      690 Trebo Rd, Chester, VT 05143
      690 Trebo Rd, Chester, VT 05143
      /40

      Est $590,482

      Not Listed For Sale

      690 Trebo Rd, Chester, VT 05143

      • 4 Beds
      • 2.5 Baths
      • 2,112 Sq Ft
      • Built 1988
      690 Trebo Rd, Chester, VT 05143

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Sarah Sheehan William Raveis Real Estate Vermont Properties

    • 1187 Potash Brook Rd, Chester, VT 05143
      1187 Potash Brook Rd, Chester, VT 05143
      1187 Potash Brook Rd, Chester, VT 05143
      /40

      Est $477,363

      Not Listed For Sale

      1187 Potash Brook Rd, Chester, VT 05143

      • 4 Beds
      • 4 Baths
      • 3,264 Sq Ft
      • Built 1977
      1187 Potash Brook Rd, Chester, VT 05143

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Chelsea Richardson Barrett and Valley Associates Inc.

    • 165 Snell Rd, Chester, VT 05143
      165 Snell Rd, Chester, VT 05143
      165 Snell Rd, Chester, VT 05143
      /40

      Est $222,358

      Not Listed For Sale

      165 Snell Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 963 Sq Ft
      • Built 1957
      165 Snell Rd, Chester, VT 05143

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Julie Buffum Buffum Realty

    • 231 Snell Rd, Chester, VT 05143
      231 Snell Rd, Chester, VT 05143
      231 Snell Rd, Chester, VT 05143
      /36

      Est $473,447

      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

      • 18 Days On Market

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    • 23 Davidson Hill Rd, Chester, VT 05143
      23 Davidson Hill Rd, Chester, VT 05143
      23 Davidson Hill Rd, Chester, VT 05143
      /19

      Est $396,347

      Not Listed For Sale

      23 Davidson Hill Rd, Chester, VT 05143

      • 2 Beds
      • 2 Baths
      • 1,460 Sq Ft
      • Built 1930
      23 Davidson Hill Rd, Chester, VT 05143

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Richard Spanjian Dark Horse Realty

    • 40 Amsden Hill Rd, Chester, VT 05143
      40 Amsden Hill Rd, Chester, VT 05143
      40 Amsden Hill Rd, Chester, VT 05143
      /26

      Est $262,320

      Not Listed For Sale

      40 Amsden Hill Rd, Chester, VT 05143

      • 4 Beds
      • 2 Baths
      • 1,444 Sq Ft
      • Built 1980
      40 Amsden Hill Rd, Chester, VT 05143

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Amanda Stearns Barrett and Valley Associates Inc.

Showing Results 241 - 280, Page 7 of 18

Vermont Windsor County

Real Estate & Homes

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

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