Chester, VT

Chester, VT Real Estate

46Results

Chester, VT is a great family community, close to all your favorite ski areas like Killington, Okemo, and Stratton. Enjoy the mountain views, and the peaceful tranquility of Chester's scenic beauty. Contact our Hanover, NH real estate office at 603-643-6406 or our Quechee, VT real estate office at 802-332-6830 for any questions you may have about Chester, VT real estate listings.

Chester, VT Town Website
Town of Chester
556 Elm Street ~ PO Box 370
Chester, VT 05143

Real Estate In Nearby Towns: Ludlow, VT, Springfield, VT, Charlestown, NH, Weston, VT, Cavendish, VT (Zoom out on map to view location of nearby towns)

Newest
New Listing
1470 Popple Dungeon Road Chester VT 05143

$925,000

Chester, VT

1470 Popple Dungeon Road

  • 5 Beds
  • 3 Baths
  • 14.1 Acres
  • 2,850 SqFt
  • 2 Days on Market
Listed by Joseph Karl of William Raveis Real Estate Vermont Properties
MLS#: 5099745
New Listing

$229,000

Chester, VT

00 Quarry Road

  • Land
  • 27.8 Acres
  • 10 Days on Market
Listed by Geralyn Donohue of Four Seasons Sotheby's Int'l Realty
MLS#: 5098347
Pending

$199,000

Chester, VT

1372 Potash Brook Road

  • 2 Beds
  • 1 Bath
  • 18 Acres
  • 732 SqFt
  • 13 Days on Market
Listed by Daire Gibney of Barrett and Valley Associates Inc.
MLS#: 5098053
Open House

$649,000

Chester, VT

168 Chandler Road

NEXT OPEN HOUSE:

Fri 7/17 3:00 PM to 6:00 PM

  • 3 Beds
  • 2 Baths
  • 1 Acre
  • 2,204 SqFt
  • 15 Days on Market
Listed by Diane Rousseau of Four Seasons Sotheby's Int'l Realty
MLS#: 5097737
Active Under Contract

$750,000

Chester, VT

955 Smokeshire Road

  • 3 Beds
  • 2 Baths
  • 6.03 Acres
  • 1,695 SqFt
  • 15 Days on Market
Listed by Katherine Burns of William Raveis Real Estate Vermont Properties
MLS#: 5097722
New Listing

$249,500

Chester, VT

3668 Vt Route 103 North

  • 3 Baths
  • 2 Acres
  • 1,922 SqFt
  • 15 Days on Market
Listed by Dan Vigeant of Mary W. Davis Realtor & Assoc.,Inc.
MLS#: 5097621
New Listing

$249,500

Chester, VT

3668 Vt Route 103 North

  • 4 Beds
  • 3 Baths
  • 2 Acres
  • 1,922 SqFt
  • 15 Days on Market
Listed by Dan Vigeant of Mary W. Davis Realtor & Assoc.,Inc.
MLS#: 5097620
New Listing

$849,000

Chester, VT

223 Coach Road

  • 5 Beds
  • 3 Baths
  • 11.24 Acres
  • 4,388 SqFt
  • 15 Days on Market
Listed by Daire Gibney of Barrett and Valley Associates Inc.
MLS#: 5097600
New Listing

$465,000

Chester, VT

34 School Street

  • 1880 Year Built
  • 0.07 Acres
  • 3,940 SqFt
  • 16 Days on Market
Listed by The Nancy Jenkins Team of Nancy Jenkins Real Estate
MLS#: 5097413
New Listing

$385,000

Chester, VT

145 South Main Street

  • 1880 Year Built
  • 0.8 Acres
  • 3,608 SqFt
  • 16 Days on Market
Listed by The Nancy Jenkins Team of Nancy Jenkins Real Estate
MLS#: 5097411
New Listing

$460,000

Chester, VT

81 Main Street

  • 5 Beds
  • 4 Baths
  • 0.44 Acres
  • 3,865 SqFt
  • 28 Days on Market
Listed by Betsy Adamovich of Real Broker LLC
MLS#: 5095551
New Listing

$489,000

Chester, VT

3208 Green Mountain Turnpike

  • 3 Beds
  • 2 Baths
  • 0.33 Acres
  • 1,626 SqFt
  • 28 Days on Market
Listed by Geralyn Donohue of Four Seasons Sotheby's Int'l Realty
MLS#: 5095486
 
Quechee, VT, Homes and Real Estate




   QUECHEE OFFICE
   Service Area
 
   NEW HAMPSHIRE TOWNS
 
   Enfield Hanover Lebanon
   Lyme Plainfield  
 
   VERMONT TOWNS
 
   Barnard  Cavendish  Chester
   Hartford  Hartland Killington
   Mount Holly  Ludlow Norwich
   Plymouth  Pomfret Reading
   Quechee     Sharon Springfield
   Thetford   Weston Weathersfield
   Woodstock  Windsor  
Broker Reciprocity 

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. Data last updated July 16, 2026 6:09 PM EDT