Chester, VT

Homes for Sale in Chester VT

12Results

View the current listings for sale in Chester, Vermont. TIP: To save your favorite listings, create an account and you can get email updates for new properties. For more information, questions, or to schedule a tour, please contact us today!  We are here 7 days a week.

Newest
New Listing
81 Main Street Chester VT 05143

$475,000

Chester, VT

81 Main Street

  • 5 Beds
  • 4 Baths
  • 0.44 Acres
  • 3,865 SqFt
  • 12 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
  • 12 Days on Market
MLS#: 5095486
New Listing

$75,000

Chester, VT

1144 Potash Brook Road

  • 2 Beds
  • 1 Bath
  • 0.6 Acres
  • 620 SqFt
  • 23 Days on Market
MLS#: 5093286

$1,200,000

Chester, VT

76 Goldthwaite Road

  • 4 Beds
  • 3 Baths
  • 7.8 Acres
  • 3,308 SqFt
  • 50 Days on Market
MLS#: 5088175

$1,490,000

Chester, VT

1302 Popple Dungeon Road

  • 5 Beds
  • 5 Baths
  • 18 Acres
  • 5,400 SqFt
  • 53 Days on Market
MLS#: 5087874

$479,000

Chester, VT

64 Maple Street

  • 3 Beds
  • 3 Baths
  • 2 Acres
  • 2,676 SqFt
  • 55 Days on Market
MLS#: 5087175

$390,000

Chester, VT

663 Depot Street

  • 3 Beds
  • 2 Baths
  • 1 Acre
  • 1,304 SqFt
  • 61 Days on Market
MLS#: 5086202

$649,000

Chester, VT

688 Hidden Heights Road

  • 3 Beds
  • 2 Baths
  • 1.71 Acre
  • 2,205 SqFt
  • 166 Days on Market
MLS#: 5074094

$349,000

Chester, VT

1397 Popple Dungeon Road

  • 3 Beds
  • 2 Baths
  • 3.3 Acres
  • 1,788 SqFt
  • 167 Days on Market
MLS#: 5073930

$399,000

Chester, VT

40 Fenton Road

  • 4 Beds
  • 3 Baths
  • 1.5 Acre
  • 2,148 SqFt
  • 175 Days on Market
MLS#: 5073147

$289,000

Chester, VT

106 Contro Road

  • 2 Beds
  • 3 Baths
  • 9 Acres
  • 1,475 SqFt
  • 224 Days on Market
MLS#: 5069928

$169,000

Chester, VT

3019 Popple Dungeon Road

  • 1 Bed
  • 1 Bath
  • 1 Acre
  • 200 SqFt
  • 243 Days on Market
MLS#: 5067929

Chester VT Homes for Sale

Chester is known for its classic Vermont charm, with historic stone houses, inviting green spaces, and a strong sense of community. Homes here often blend traditional architecture with updated comforts, offering a variety of choices for those seeking both character and practicality.

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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 June 29, 2026 11:08 PM EDT