Chester, VT

Homes for Sale in Chester VT

15Results

Browse the current homes for sale in Chester, Vermont. Contact Brattleboro Area Realty to learn more about a listing, and make sure to create an account to save your favorites. 

Chester VT Homes for Sale

Newest
New Listing
76 Goldthwaite Road Chester VT 05143

$1,200,000

Chester, VT

76 Goldthwaite Road

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

$349,000

Chester, VT

397 River Street

  • 4 Beds
  • 3 Baths
  • 2 Acres
  • 3,332 SqFt
  • 25 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
  • 26 Days on Market
MLS#: 5087874
New Listing

$479,000

Chester, VT

64 Maple Street

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

$390,000

Chester, VT

663 Depot Street

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

$549,000

Chester, VT

3341 Trebo Road

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

$474,900

Chester, VT

547 Williams Road

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

$425,000

Chester, VT

176 Meadow Road

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

$649,000

Chester, VT

688 Hidden Heights Road

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

$349,000

Chester, VT

1397 Popple Dungeon Road

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

$399,000

Chester, VT

40 Fenton Road

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

$289,000

Chester, VT

106 Contro Road

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

Homes for sale in Chester, Vermont combine historic character with modern comforts. The town offers easy access to local shops, dining, and outdoor activities, with nearby ski areas for year-round recreation. Chester’s location also provides convenient connections to regional roads, blending small-town living with accessibility.

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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 3, 2026 4:24 PM EDT