71

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 $393,500

    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 $477,365

    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 $270,457

    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 $592,640

    Last Listing Agent Betty McEnaney Diamond Realty

    2510 E Hill Rd, Chester, VT 05143
  • /14

    $289,000

    Sold Aug 14, 2026

    106 Contro Rd, Chester, VT 05143

    • 2 Beds
    • 2.5 Baths
    • 1,475 Sq Ft
    • Built 1985

    Last Sold Summary

    • $196/SF
    • 240 Days On Market

    Current Estimated Value $257,292

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    106 Contro 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 $1,315,401

    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 $598,571

    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 $235,321

    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 $231,313

    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 $296,455

    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 $274,567

    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
  • /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 $925,827

    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
  • /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 $351,875

    Last Listing Agent Katherine Burns William Raveis Real Estate Vermont Properties

    531 Main 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 $196,769

    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 $363,687

    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 $801,853

    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 $58,560

    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 $200,839

    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 $680,089

    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 $548,269

    Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

    1937 Green Mountain Turnpike, 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 $129,946

    Last Listing Agent Chelsea Richardson Barrett and Valley Associates Inc.

    469 Williams Rd, Chester, VT 05143
  • /20

    $250,000

    Sold Jun 30, 2026

    202 Mountain View, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 1,140 Sq Ft
    • Built 1945

    Last Sold Summary

    • $219/SF
    • 5 Days On Market

    Current Estimated Value $252,046

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    202 Mountain View, 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 $213,925

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1876 Popple Dungeon Rd, Chester, VT 05143
  • /60

    $460,000

    Sold Jul 09, 2026

    547 Williams Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft
    • Built 1989

    Last Sold Summary

    • 8% Below List Price
    • $348/SF
    • 45 Days On Market

    Current Estimated Value $471,416

    Last Listing Agent Terri Edgerley Edge Realty Vermont

    547 Williams 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 $460,909

    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 $825,660

    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 $1,324,810

    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 $569,316

    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
  • /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 $822,515

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    810 Quarry Rd, Chester, VT 05143
  • /22

    $190,000

    Sold Aug 10, 2026

    1372 Potash Brook Rd, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 732 Sq Ft
    • Built 1960

    Last Sold Summary

    • 5% Below List Price
    • $260/SF
    • 6 Days On Market

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    1372 Potash Brook 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 $364,957

    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 $238,429

    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 $324,707

    Last Listing Agent Julie Buffum Buffum Realty

    870 Cummings Rd, Chester, VT 05143
  • /41

    $327,500

    Sold Aug 21, 2025

    769 Davidson Hill Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2002

    Last Sold Summary

    • 2% Below List Price
    • $234/SF
    • 7 Days On Market

    Current Estimated Value $350,691

    Last Listing Agent Frank Provance Diamond Realty

    769 Davidson Hill 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 $558,223.
What is the average time to sell a house in Chester, VT?
The houses for sale in Chester, VT spend an average of 54 days on the market.
What is the number of active homes for sale in Chester, VT?
There are 19 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
$369,500
Median Single Family Sale Price
$338,750
Median Townhouse Sale Price
$598,000
Median 2 Bedroom Sale Price
$330,000
Median 1 Bedroom Sale Price
$210,000
Average Price Per Sq Ft
$259
Number of Homes for Sale
19
Last 12 months Home Sales
56
Months of Supply
4.10
Median List Price
$425,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
-13%
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