Chester, VT Homes For Sale
43 listings. Live MLS data, refreshed nightly. Chester market overview
Chester, VT
Get alerts on new listings
We'll email you when new homes match these filters. No spam, unsubscribe anytime.
Loading map…
Listings
$1,495,000
40 The Common
Chester, 05143
159 days on market
Listed by Patrick Kelley, Real Broker LLC
$1,490,000
1302 Popple Dungeon Road
Chester, 05143
5 bd·1 ba
96 days on market
Listed by Gary Coger, Four Seasons Sotheby's Int'l Realty
$1,200,000
76 Goldthwaite Road
Chester, 05143
4 bd·1 ba
93 days on market
Listed by Gary Coger, Four Seasons Sotheby's Int'l Realty
$900,000
1470 Popple Dungeon Road
Chester, 05143
5 bd·1.5 ba
31 days on market
Listed by Joseph Karl, William Raveis Real Estate Vermont Properties
$789,000
223 Coach Road
Chester, 05143
5 bd·3 ba
42 days on market
Listed by Daire Gibney, Barrett and Valley Associates Inc.
Pending
$750,000
955 Smokeshire Road
Chester, 05143
3 bd·1 ba
14 days on market
Waterfront
Listed by Katherine K Burns, William Raveis Real Estate Vermont Properties
$650,000
3630 Vt Route 103 N
Chester, 05143
432 days on market
Listed by Gary Coger, Four Seasons Sotheby's Int'l Realty
$650,000
3630 VT RT 103 N
Chester, 05143
432 days on market
Listed by Gary Coger, Four Seasons Sotheby's Int'l Realty
$649,000
168 Chandler Road
Chester, 05143
3 bd
43 days on market
Listed by Diane Rousseau, Four Seasons Sotheby's Int'l Realty
Pending
$549,000
3341 Trebo Road
Chester, 05143
4 bd·2.5 ba
33 days on market
Listed by Daire Gibney, Barrett and Valley Associates Inc.
Pending
$495,000
3078 VT Route 10
Chester, 05143
3 bd·1 ba
6 days on market
Listed by Tyleen Murray, Kelley Real Estate, Inc.
Pending
$489,000
3208 Green Mountain Turnpike
Chester, 05143
3 bd·2 ba
49 days on market
Listed by Geralyn Donohue, Four Seasons Sotheby's Int'l Realty
Pending
$469,000
64 Maple Street
Chester, 05143
3 bd·1 ba
92 days on market
Listed by Betsy Adamovich, Real Broker LLC
$450,000
81 Main Street
Chester, 05143
5 bd·2 ba
55 days on market
Listed by Betsy Adamovich, Real Broker LLC
$419,900
176 Meadow Road
Chester, 05143
5 bd·2 ba
45 days on market
Listed by Lauren Behm, Berkshire Hathaway HomeServices Stratton Home
$399,000
40 Fenton Road
Chester, 05143
4 bd·1.5 ba
218 days on market
Waterfront
Listed by John M Napier, TPW Real Estate
Pending
$390,000
663 Depot Street
Chester, 05143
3 bd
81 days on market
Listed by Betsy Adamovich, Real Broker LLC
$385,000
145 South Main Street
Chester, 05143
43 days on market
Listed by The Nancy Jenkins Team, Nancy Jenkins Real Estate
$354,000
302 Davidson Hill Road
Chester, 05143
2 bd
14 days on market
Listed by Tyler Buswell, Vermont Real Estate Company
Pending
$299,000
1397 Popple Dungeon Road
Chester, 05143
3 bd·1 ba
195 days on market
Listed by Daire Gibney, Barrett and Valley Associates Inc.
New
$289,000
447 Elm Street
Chester, 05143
3 bd·1 ba
1 day on market
Listed by Jim Bialowski, BHG Masiello Keene
$285,000
39 S Main Street
Chester, 05143
26 days on market
Listed by Joseph Karl, William Raveis Real Estate Vermont Properties
$270,000
1175 Quarry Road
Chester, 05143
349 days on market
Listed by Jessica Samples, BHG Masiello Keene
$250,000
3781 Flamstead Road
Chester, 05143
15 days on market
Listed by Amy Hill, EXP Realty
Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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. Data last updated 07/10/26.