Chester, VT

Chester VT Real Estate

38Results

Chester VTScroll down to browse homes for sale in Chester, Vermont. Contact us to schedule a showing of your favorite Chester properties for sale or if you have any questions. Register with us to save your favorite Chester real estate listings and to receive email notifications when similar properties become available. 

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
MLS#: 5099745
New Listing

$229,000

Chester, VT

00 Quarry Road

  • Land
  • 27.8 Acres
  • 10 Days on Market
MLS#: 5098347
Pending

$199,000

Chester, VT

1372 Potash Brook Road

  • 2 Beds
  • 1 Bath
  • 18 Acres
  • 732 SqFt
  • 13 Days on Market
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
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
MLS#: 5097722
New Listing

$249,500

Chester, VT

3668 Vt Route 103 North

  • 3 Baths
  • 2 Acres
  • 1,922 SqFt
  • 15 Days on Market
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
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
MLS#: 5097600
New Listing

$460,000

Chester, VT

81 Main Street

  • 5 Beds
  • 4 Baths
  • 0.44 Acres
  • 3,865 SqFt
  • 28 Days on Market
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
MLS#: 5095486
Active Under Contract

$495,000

Chester, VT

3078 Vt Route 10

  • 3 Beds
  • 2 Baths
  • 2 Acres
  • 1,800 SqFt
  • 28 Days on Market
MLS#: 5095371

$87,500

Chester, VT

00 Snell Road

  • Land
  • 10.4 Acres
  • 35 Days on Market
MLS#: 5094246

Chester, Vermont is a charming small town tucked away in the Green Mountains. From its quaint buildings to its tranquil rivers and lakes, this beautiful town has something for everyone. Spend an afternoon wandering through the picturesque downtown area and local businesses, take a peaceful stroll through the surrounding countryside, or simply sit back and marvel at the magnificent mountain views – no matter what you choose to do, Chester will offer an unparalleled experience!

Learn More About Chester VT

Chester VT Real Estate for Sale

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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 6:24 PM EDT