Chester, VT

Chester VT Real Estate

426Results

Nestled in the Deerfield Valley of Vermont, Chester is a small town known for its old-world charm and hospitality in Windham County. This picturesque community boasts numerous attractions such as Grafton Village Cheese Factory, Southern Vermont Arts Center, and Silver Lake State Park. Visitors can explore local history at sites like Old Fort West or visit the Basketville store to purchase unique handmade crafts. With plenty of restaurants, cafes and pubs to choose from, Chester offers something for everyone. Whether you're looking for a romantic getaway or simply an enjoyable place to spend time with family and friends, Chester is sure to deliver an unforgettable experience.

Newest
New Listing
1144 Potash Brook Road Chester VT 05143

$75,000

Chester, VT

1144 Potash Brook Road

  • 2 Beds
  • 1 Bath
  • 0.6 Acres
  • 620 SqFt
  • 10 Days on Market
Listed by Julie Buffum of Buffum Realty
MLS#: 5093286
Active Under Contract

$250,000

Chester, VT

202 Mountain View

  • 3 Beds
  • 2 Baths
  • 0.25 Acres
  • 1,140 SqFt
  • 35 Days on Market
Listed by Daire Gibney of Barrett and Valley Associates Inc.
MLS#: 5088678

$1,200,000

Chester, VT

76 Goldthwaite Road

  • 4 Beds
  • 3 Baths
  • 7.8 Acres
  • 3,308 SqFt
  • 37 Days on Market
Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty
MLS#: 5088175

$325,000

Chester, VT

397 River Street

  • 4 Beds
  • 3 Baths
  • 2 Acres
  • 3,332 SqFt
  • 39 Days on Market
Listed by Lisa Kelley of Cummings & Co
MLS#: 5087965

$1,490,000

Chester, VT

1302 Popple Dungeon Road

  • 5 Beds
  • 5 Baths
  • 18 Acres
  • 5,400 SqFt
  • 40 Days on Market
Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty
MLS#: 5087874

$479,000

Chester, VT

64 Maple Street

  • 3 Beds
  • 3 Baths
  • 2 Acres
  • 2,676 SqFt
  • 42 Days on Market
Listed by Betsy Adamovich of Real Broker LLC
MLS#: 5087175

$390,000

Chester, VT

663 Depot Street

  • 3 Beds
  • 2 Baths
  • 1 Acre
  • 1,304 SqFt
  • 48 Days on Market
Listed by Betsy Adamovich of Real Broker LLC
MLS#: 5086202
Active Under Contract

$549,000

Chester, VT

3341 Trebo Road

  • 4 Beds
  • 3 Baths
  • 2.13 Acres
  • 2,464 SqFt
  • 48 Days on Market
Listed by Daire Gibney of Barrett and Valley Associates Inc.
MLS#: 5086105
Sold

Sale Price: $239,000

Chester, VT

15 Breezy Lane

  • 2 Beds
  • 1 Bath
  • 0.32 Acres
  • 1,026 SqFt
  • 33 Days on Market
Listed by Julie Buffum of Buffum Realty
Listing Sold by Kelley Real Estate,Inc.
MLS#: 5086079
Active Under Contract

$474,900

Chester, VT

547 Williams Road

  • 3 Beds
  • 2 Baths
  • 10.86 Acres
  • 1,320 SqFt
  • 54 Days on Market
Listed by Terri Edgerley of Edge Realty Vermont
MLS#: 5085214
Pending

$569,000

Chester, VT

147 Pleasant View Lane

  • 3 Beds
  • 2 Baths
  • 3.08 Acres
  • 2,966 SqFt
  • 58 Days on Market
Listed by Jay Farrar of Four Seasons Sotheby's Int'l Realty
MLS#: 5084462
Sold

Sale Price: $269,000

Chester, VT

45 Dalrymple Street

  • 3 Beds
  • 1 Bath
  • 0.5 Acres
  • 1,168 SqFt
  • 70 Days on Market
Listed by Julie Buffum of Buffum Realty
Listing Sold by Kelley Real Estate,Inc.
MLS#: 5082324

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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 17, 2026 6:53 AM EDT