76

Recently Sold Chester, VT Homes

Section Image
  • /42

    $415,000

    Sold Mar 30, 2026

    1979 N Hill Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft
    • Built 2005

    Last Sold Summary

    • 10% Below List Price
    • $222/SF
    • 113 Days On Market

    Current Estimated Value $433,185

    Last Listing Agent Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    1979 N Hill Rd, Chester, VT 05143
  • /60

    $475,000

    Sold Aug 27, 2025

    472 Main St, Chester, VT 05143

    • 5 Beds
    • 7 Baths
    • 5,546 Sq Ft
    • Built 1850

    Last Sold Summary

    • 5% Below List Price
    • $86/SF
    • 36 Days On Market

    Current Estimated Value $473,496

    Last Listing Agent Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    472 Main St, Chester, VT 05143
  • /34

    $269,000

    Sold Jun 15, 2026

    45 Dalrymple St, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 1,168 Sq Ft
    • Built 1986

    Last Sold Summary

    • $230/SF
    • 6 Days On Market

    Current Estimated Value $265,992

    Last Listing Agent Julie Buffum Buffum Realty

    45 Dalrymple St, Chester, VT 05143
  • /52

    $598,000

    Sold Oct 10, 2025

    2510 E Hill Rd, Chester, VT 05143

    • 3 Beds
    • 2.5 Baths
    • 2,264 Sq Ft
    • Built 1978

    Last Sold Summary

    • 5% Below List Price
    • $264/SF
    • 94 Days On Market

    Current Estimated Value $591,115

    Last Listing Agent Betty McEnaney Diamond Realty

    2510 E Hill Rd, Chester, VT 05143
  • /36

    $1,400,000

    Sold Aug 27, 2025

    938 Stigers Rd, Chester, VT 05143

    • 3 Beds
    • 3.5 Baths
    • 2,614 Sq Ft
    • Built 2011

    Last Sold Summary

    • 15% Below List Price
    • $536/SF
    • 42 Days On Market

    Current Estimated Value $1,246,867

    Last Listing Agent Liz Moore Real Broker LLC

    938 Stigers Rd, Chester, VT 05143
  • /55

    $605,000

    Sold Oct 02, 2025

    656 Main St, Chester, VT 05143

    • 3 Beds
    • 2.5 Baths
    • 3,040 Sq Ft
    • Built 1904

    Last Sold Summary

    • 7% Below List Price
    • $199/SF
    • 47 Days On Market

    Current Estimated Value $596,275

    Last Listing Agent Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    656 Main St, Chester, VT 05143
  • /60

    $220,000

    Sold Nov 07, 2025

    442 Vermont 103, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 1,024 Sq Ft
    • Built 1941

    Last Sold Summary

    • 8% Below List Price
    • $215/SF
    • 70 Days On Market

    Current Estimated Value $228,101

    Last Listing Agent Rachael Lange Lange & Lange

    442 Vermont 103, Chester, VT 05143
  • /21

    $227,000

    Sold Jan 30, 2026

    1374 Vt Route 103 N, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 1,222 Sq Ft
    • Built 1949

    Last Sold Summary

    • 5% Below List Price
    • $186/SF
    • 20 Days On Market

    Current Estimated Value $232,848

    Last Listing Agent Lisa Kelley Cummings & Co

    1374 Vt Route 103 N, Chester, VT 05143
  • /58

    $475,000

    Sold Oct 10, 2025

    1923 N Hill Rd, Chester, VT 05143

    • 5 Beds
    • 3 Baths
    • 2,316 Sq Ft
    • Built 1981

    Last Sold Summary

    • 2% Below List Price
    • $205/SF
    • 6 Days On Market

    Last Listing Agent Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    1923 N Hill Rd, Chester, VT 05143
  • /2

    $345,000

    Sold Oct 07, 2025

    154 Reed Rd, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Above List Price
    • $308/SF
    • 10 Days On Market

    Current Estimated Value $248,331

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    154 Reed Rd, Chester, VT 05143
  • /13

    $275,000

    Sold Sep 10, 2025

    230 Kevadus Cir, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 894 Sq Ft
    • Built 1970

    Last Sold Summary

    • $308/SF
    • 7 Days On Market

    Current Estimated Value $278,909

    Last Listing Agent Jim Bialowski BHG Masiello Keene

    230 Kevadus Cir, Chester, VT 05143
  • /2

    $230,000

    Sold Nov 07, 2025

    2739 Route 11, Chester, VT 05143

    • 1 Bed
    • 1 Bath
    • 1,424 Sq Ft
    • Built 1987

    Last Sold Summary

    • 23% Below List Price
    • $162/SF
    • 13 Days On Market

    Last Listing Agent Glenn Olney Barrett and Valley Associates Inc.

    2739 Route 11, Chester, VT 05143
  • /2

    $50,000

    Sold Oct 10, 2025

    Lot 1 Old Stage Rd, Chester, VT 05143

    • Land
    • 3.5 Acres
    • $14,286 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 9 Days On Market

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    Lot 1 Old Stage Rd, Chester, VT 05143
  • /2

    $259,000

    Sold Jul 31, 2025

    442 Elm St, Chester, VT 05143

    • 1,488 Sq Ft
    • Built 1950

    Last Sold Summary

    • $174/SF
    • 43 Days On Market

    Current Estimated Value $254,915

    Last Listing Agent Lisa Kelley Cummings & Co

    442 Elm St, Chester, VT 05143
  • /59

    $910,000

    Sold Aug 28, 2025

    1502 Popple Dungeon Rd, Chester, VT 05143

    • 3 Beds
    • 4 Baths
    • 3,739 Sq Ft
    • Built 1989

    Last Sold Summary

    • 24% Below List Price
    • $243/SF
    • 105 Days On Market

    Current Estimated Value $924,538

    Last Listing Agent Betty McEnaney Diamond Realty

    1502 Popple Dungeon Rd, Chester, VT 05143
  • /14

    $140,000

    Sold Oct 23, 2025

    515 Main St, Chester, VT 05143

    • 3,024 Sq Ft
    • Built 1850

    Last Sold Summary

    • 17% Below List Price
    • $46/SF
    • 422 Days On Market

    Last Listing Agent John Tolosky Barrett and Valley Associates Inc.

    515 Main St, Chester, VT 05143
  • /42

    $315,000

    Sold Aug 06, 2025

    4150 Trebo Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,566 Sq Ft
    • Built 1995

    Last Sold Summary

    • $201/SF
    • 5 Days On Market

    Last Listing Agent Alexandra Eatmon Kelley Real Estate, Inc.

    4150 Trebo Rd, Chester, VT 05143
  • /53

    $359,000

    Sold May 15, 2026

    531 Main St, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 1,608 Sq Ft
    • Built 1880

    Last Sold Summary

    • 16% Below List Price
    • $223/SF
    • 115 Days On Market

    Current Estimated Value $352,893

    Last Listing Agent Katherine Burns William Raveis Real Estate Vermont Properties

    531 Main St, Chester, VT 05143
  • /58

    $373,000

    Sold Jul 10, 2025

    270 North St, Chester, VT 05143

    • 4 Beds
    • 1.5 Baths
    • 2,919 Sq Ft
    • Built 1810

    Last Sold Summary

    • 7% Below List Price
    • $128/SF
    • 61 Days On Market

    Current Estimated Value $401,420

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    270 North St, Chester, VT 05143
  • /23

    $195,000

    Sold Dec 10, 2025

    1833 Mattson Rd, Chester, VT 05143

    • 2 Beds
    • 2.5 Baths
    • 1,640 Sq Ft
    • Built 2015

    Last Sold Summary

    • 2% Below List Price
    • $119/SF
    • 3 Days On Market

    Current Estimated Value $207,859

    Last Listing Agent Mike Masters Four Seasons Sotheby's Int'l Realty

    1833 Mattson Rd, Chester, VT 05143
  • /42

    $359,000

    Sold Nov 05, 2025

    1470 Flamstead Rd, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 803 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Above List Price
    • $447/SF
    • 12 Days On Market

    Current Estimated Value $354,036

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1470 Flamstead Rd, Chester, VT 05143
  • /56

    $805,000

    Sold Jan 13, 2026

    1342 Old Stage Rd, Chester, VT 05143

    • 2 Beds
    • 2 Baths
    • 1,576 Sq Ft
    • Built 1971

    Last Sold Summary

    • 10% Below List Price
    • $511/SF
    • 97 Days On Market

    Current Estimated Value $803,047

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    1342 Old Stage Rd, Chester, VT 05143
  • /23

    $59,000

    Sold Oct 08, 2025

    58 Remington Rd, Chester, VT 05143

    • Land
    • 2.86 Acres
    • $20,629 per Acre

    Last Sold Summary

    • 25% Below List Price
    • 169 Days On Market

    Current Estimated Value $57,998

    Last Listing Agent John Napier TPW Real Estate

    58 Remington Rd, Chester, VT 05143
  • /27

    $178,000

    Sold Nov 05, 2025

    284 Flamstead Rd, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 960 Sq Ft
    • Built 1969

    Last Sold Summary

    • 6% Below List Price
    • $185/SF
    • 9 Days On Market

    Current Estimated Value $221,989

    Last Listing Agent Linda Benoit Highland Realty

    284 Flamstead Rd, Chester, VT 05143
  • /49

    $950,000

    Sold Dec 05, 2025

    1847 Trebo Rd, Chester, VT 05143

    • 4 Beds
    • 4 Baths
    • 3,920 Sq Ft
    • Built 1849

    Last Sold Summary

    • 19% Below List Price
    • $242/SF
    • 127 Days On Market

    Current Estimated Value $817,175

    Last Listing Agent Gary Coger Four Seasons Sotheby's Int'l Realty

    1847 Trebo Rd, Chester, VT 05143
  • /53

    $550,000

    Sold Oct 06, 2025

    1937 Green Mountain Turnpike, Chester, VT 05143

    • 2 Beds
    • 2 Baths
    • 1,812 Sq Ft
    • Built 1864

    Last Sold Summary

    • 3% Below List Price
    • $304/SF
    • 6 Days On Market

    Current Estimated Value $557,790

    Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

    1937 Green Mountain Turnpike, Chester, VT 05143
  • /2

    $421,833

    Sold Jul 10, 2025

    332 Hidden Heights Rd, Chester, VT 05143

    • 4 Beds
    • 2.5 Baths
    • 2,868 Sq Ft
    • Built 1988

    Last Sold Summary

    • 6% Below List Price
    • $147/SF
    • 50 Days On Market

    Current Estimated Value $503,985

    Last Listing Agent John Tolosky Barrett and Valley Associates Inc.

    332 Hidden Heights Rd, Chester, VT 05143
  • /10

    $129,000

    Sold Feb 24, 2026

    469 Williams Rd, Chester, VT 05143

    • Land
    • 10.88 Acres
    • $11,857 per Acre

    Last Sold Summary

    • 7 Days On Market

    Current Estimated Value $129,687

    Last Listing Agent Chelsea Richardson Barrett and Valley Associates Inc.

    469 Williams Rd, Chester, VT 05143
  • /16

    $205,000

    Sold Apr 10, 2026

    1876 Popple Dungeon Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1984

    Last Sold Summary

    • $166/SF
    • 6 Days On Market

    Current Estimated Value $206,898

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1876 Popple Dungeon Rd, Chester, VT 05143
  • /56

    $402,239

    Sold Nov 12, 2025

    4877 Vt Route 103 N, Chester, VT 05143

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 1980

    Last Sold Summary

    • 10% Below List Price
    • $233/SF
    • 10 Days On Market

    Current Estimated Value $441,953

    Last Listing Agent Erin Kendall EXP Realty

    4877 Vt Route 103 N, Chester, VT 05143
  • /48

    $825,000

    Sold Apr 09, 2026

    1269 Howard Hill Rd, Chester, VT 05143

    • 3 Beds
    • 3 Baths
    • 2,172 Sq Ft
    • Built 2024

    Last Sold Summary

    • 8% Below List Price
    • $380/SF
    • 55 Days On Market

    Current Estimated Value $824,804

    Last Listing Agent Cheyanne Pugliese

    1269 Howard Hill Rd, Chester, VT 05143
  • /47

    $1,375,000

    Sold Sep 30, 2025

    465 Pennell Rd, Chester, VT 05143

    • 4 Beds
    • 4.5 Baths
    • 5,700 Sq Ft
    • Built 1967

    Last Sold Summary

    • 8% Below List Price
    • $241/SF
    • 20 Days On Market

    Current Estimated Value $1,335,715

    Last Listing Agent Gary Coger Four Seasons Sotheby's Int'l Realty

    465 Pennell Rd, Chester, VT 05143
  • /2

    $70,000

    Sold Oct 21, 2025

    Lot 2 Old Stage Rd, Chester, VT 05143

    • Land
    • 6.3 Acres
    • $11,111 per Acre

    Last Sold Summary

    • 7% Below List Price
    • 35 Days On Market

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    Lot 2 Old Stage Rd, Chester, VT 05143
  • /53

    $569,000

    Sold Jun 17, 2026

    147 Pleasantview Ln, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 2,966 Sq Ft
    • Built 1993

    Last Sold Summary

    • 4% Below List Price
    • $192/SF
    • 27 Days On Market

    Current Estimated Value $590,469

    Last Listing Agent Jay Farrar Four Seasons Sotheby's Int'l Realty

    147 Pleasantview Ln, Chester, VT 05143
  • /2

    $165,000

    Sold Oct 23, 2025

    1436 Route 103, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,544 Sq Ft
    • Built 1825

    Last Sold Summary

    • 4% Above List Price
    • $107/SF
    • 2 Days On Market

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1436 Route 103, Chester, VT 05143
  • /36

    $425,000

    Sold Jul 30, 2025

    115 Orcutt Dr, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 1,360 Sq Ft
    • Built 1955

    Last Sold Summary

    • $312/SF
    • 26 Days On Market

    Current Estimated Value $439,039

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    115 Orcutt Dr, Chester, VT 05143
  • /60

    $815,000

    Sold Feb 13, 2026

    810 Quarry Rd, Chester, VT 05143

    • 3 Beds
    • 2.5 Baths
    • 2,466 Sq Ft
    • Built 2006

    Last Sold Summary

    • $330/SF
    • 4 Days On Market

    Current Estimated Value $822,334

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    810 Quarry Rd, Chester, VT 05143
  • /2

    $350,000

    Sold Nov 09, 2025

    491 Farrar Rd, Chester, VT 05143

    • 4 Beds
    • 3.5 Baths
    • 2,710 Sq Ft
    • Built 1990

    Last Sold Summary

    • 12% Below List Price
    • $129/SF
    • 123 Days On Market

    Current Estimated Value $365,931

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    491 Farrar Rd, Chester, VT 05143
  • /2

    $229,000

    Sold Aug 29, 2025

    87 Kevadus Cir, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 840 Sq Ft
    • Built 1968

    Last Sold Summary

    • 7% Above List Price
    • $273/SF
    • 2 Days On Market

    Current Estimated Value $239,089

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    87 Kevadus Cir, Chester, VT 05143
  • /21

    $320,000

    Sold Dec 18, 2025

    870 Cummings Rd, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 1,525 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Below List Price
    • $210/SF
    • 30 Days On Market

    Current Estimated Value $322,358

    Last Listing Agent Julie Buffum Buffum Realty

    870 Cummings Rd, Chester, VT 05143

Showing Results 1 - 40, Page 1 of 2

Frequently Asked Questions

What is the average home price in Chester, VT?
Homes for sale in Chester, VT have an average home price of $556,849.
What is the average time to sell a house in Chester, VT?
The houses for sale in Chester, VT spend an average of 46 days on the market.
What is the number of active homes for sale in Chester, VT?
There are 17 active homes for sale in Chester, VT.
How many homes have sold over the last 12 months in Chester, VT?
56 homes have sold in Chester, VT over the last 12 months.

Home Price Trends

Median Sale Price
$394,000
Median Single Family Sale Price
$389,000
Median Townhouse Sale Price
$637,500
Median 2 Bedroom Sale Price
$309,500
Median 1 Bedroom Sale Price
$210,000
Average Price Per Sq Ft
$270
Number of Homes for Sale
17
Last 12 months Home Sales
56
Months of Supply
3.60
Median List Price
$449,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
-2%
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