Chester, VT

Real Estate for Sale in Chester VT

38Results

Browse all homes for sale in Chester, Vermont. Questions? Contact Vermont Properties online or give us a call at 802-228-8877 to start your search for homes in Okemo Valley. Create an account to save your favorite listings and receive email notifications when similar listings become available.

Newest
New Listing
250 Fenton Road Chester VT 05148

$153,000

Chester, VT

250 Fenton Road

  • Land
  • 4.7 Acres
  • 13 Days on Market
MLS#: 5090458
New Listing

$3,300/month

Chester, VT

735 Main Street

  • 4 Beds
  • 3 Baths
  • 21 Days on Market
MLS#: 5089039
New Listing

$1,200,000

Chester, VT

76 Goldthwaite Road

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

$349,000

Chester, VT

397 River Street

  • 4 Beds
  • 3 Baths
  • 2 Acres
  • 3,332 SqFt
  • 26 Days on Market
MLS#: 5087965
New Listing

$1,490,000

Chester, VT

1302 Popple Dungeon Road

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

$479,000

Chester, VT

64 Maple Street

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

$390,000

Chester, VT

663 Depot Street

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

$549,000

Chester, VT

3341 Trebo Road

  • 4 Beds
  • 3 Baths
  • 2.13 Acres
  • 2,464 SqFt
  • 35 Days on Market
MLS#: 5086105

$474,900

Chester, VT

547 Williams Road

  • 3 Beds
  • 2 Baths
  • 10.86 Acres
  • 1,320 SqFt
  • 41 Days on Market
MLS#: 5085214

$425,000

Chester, VT

176 Meadow Road

  • 5 Beds
  • 2 Baths
  • 0.27 Acres
  • 1,982 SqFt
  • 55 Days on Market
MLS#: 5082995

$120,000

Chester, VT

508 Mattson Road

  • Land
  • 3.24 Acres
  • 57 Days on Market
MLS#: 5082636

$129,000

Chester, VT

Green Mountain Turnpike

  • Land
  • 7.95 Acres
  • 69 Days on Market
MLS#: 5081034

Chester VT Real Estate for Sale

The Chester real estate market features everything from antique homes to newer builds set against scenic backdrops. Its combination of rural beauty and a lively town center makes it one of southern Vermont’s most attractive markets.

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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 4, 2026 12:09 PM EDT