Chester, VT

Chester VT Real Estate

42Results

Enjoy style, convenience and serenity in one of our astounding Chester houses. Our Chester listings include granite-made homes in Chester's historic Stone Village, as well as more conventional Chester VT properties with equally unique charm and character. Land for building, commercial space for your small business or alluring rental opportunities all characterize real estate in Chester.

Price High to Low
40 The Common Chester VT 05143

$1,495,000

Chester, VT

40 The Common

  • 1920 Year Built
  • 99 Days on Market
MLS#: 5078509

$1,490,000

Chester, VT

1302 Popple Dungeon Road

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

$1,200,000

Chester, VT

76 Goldthwaite Road

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

$650,000

Chester, VT

3630 Vt Route 103 N

  • 3 Baths
  • 2 Acres
  • 4,324 SqFt
  • 373 Days on Market
MLS#: 5044879

$650,000

Chester, VT

3630 Vt Rt 103 N

  • 1830 Year Built
  • 2 Acres
  • 4,324 SqFt
  • 373 Days on Market
MLS#: 5044894

$649,000

Chester, VT

688 Hidden Heights Road

  • 3 Beds
  • 2 Baths
  • 1.71 Acre
  • 2,205 SqFt
  • 149 Days on Market
MLS#: 5074094
Active Under Contract

$569,000

Chester, VT

147 Pleasant View Lane

  • 3 Beds
  • 2 Baths
  • 3.08 Acres
  • 2,966 SqFt
  • 54 Days on Market
MLS#: 5084462
Active Under Contract

$549,000

Chester, VT

3341 Trebo Road

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

$479,000

Chester, VT

64 Maple Street

  • 3 Beds
  • 3 Baths
  • 2 Acres
  • 2,676 SqFt
  • 38 Days on Market
MLS#: 5087175
Active Under Contract

$474,900

Chester, VT

547 Williams Road

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

$399,000

Chester, VT

40 Fenton Road

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

$390,000

Chester, VT

663 Depot Street

  • 3 Beds
  • 2 Baths
  • 1 Acre
  • 1,304 SqFt
  • 44 Days on Market
MLS#: 5086202
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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 13, 2026 12:52 PM EDT