76

Recently Sold Chester, VT Homes

Section Image
  • 206 Cummings Rd, Chester, VT 05143
    206 Cummings Rd, Chester, VT 05143
    /2

    $30,000 Sold Jun 04, 2025

    206 Cummings Rd, Chester, VT 05143

    • Land
    • 0.5 Acre
    • $60,000 per Acre

    Last Sold Summary

    • 43% Below List Price
    • 208 Days On Market

    Current Estimated Value $35,275

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    206 Cummings Rd, Chester, VT 05143
  • 472 Main St, Chester, VT 05143
    472 Main St, Chester, VT 05143
    472 Main St, 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 $476,187

    Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    472 Main St, Chester, VT 05143
  • 198 Coach Rd, Chester, VT 05143
    198 Coach Rd, Chester, VT 05143
    /2

    $350,000 Sold Jun 25, 2025

    198 Coach Rd, Chester, VT 05143

    • 4 Beds
    • 2.5 Baths
    • 2,904 Sq Ft
    • Built 1987

    Last Sold Summary

    • 6% Above List Price
    • $121/SF
    • 82 Days On Market

    Current Estimated Value $354,346

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    198 Coach Rd, Chester, VT 05143
  • 656 Main St, Chester, VT 05143
    656 Main St, Chester, VT 05143
    656 Main St, Chester, VT 05143
    /56

    $575,000 Sold Jan 10, 2025

    656 Main St, Chester, VT 05143

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

    Last Sold Summary

    • 11% Below List Price
    • $189/SF
    • 145 Days On Market

    Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    656 Main St, Chester, VT 05143
  • 3057 Vt Route 11 E, Chester, VT 05143
    3057 Vt Route 11 E, Chester, VT 05143
    3057 Vt Route 11 E, Chester, VT 05143
    /43

    $400,000 Sold Apr 25, 2025

    3057 Vt Route 11 E, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 1,800 Sq Ft
    • Built 1984

    Last Sold Summary

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

    Current Estimated Value $397,856

    Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    3057 Vt Route 11 E, Chester, VT 05143
  • 203 Marcs Dr, Chester, VT 05143
    203 Marcs Dr, Chester, VT 05143
    203 Marcs Dr, Chester, VT 05143
    /26

    $270,000 Sold Feb 05, 2025

    203 Marcs Dr, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 871 Sq Ft
    • Built 1988

    Last Sold Summary

    • 5% Below List Price
    • $310/SF
    • 0 Days On Market

    Current Estimated Value $299,569

    Last Listing Agent Sarah Sheehan William Raveis Real Estate Vermont Properties

    203 Marcs Dr, Chester, VT 05143
  • 2510 E Hill Rd, Chester, VT 05143
    2510 E Hill Rd, Chester, VT 05143
    2510 E Hill Rd, 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

    Last Listing Agent Betty McEnaney Diamond Realty

    2510 E Hill Rd, Chester, VT 05143
  • 196 North St, Chester, VT 05143
    196 North St, Chester, VT 05143
    196 North St, Chester, VT 05143
    /60

    $400,000 Sold May 19, 2025

    196 North St, Chester, VT 05143

    • 3 Beds
    • 3 Baths
    • 2,960 Sq Ft
    • Built 1844

    Last Sold Summary

    • 6% Below List Price
    • $135/SF
    • 166 Days On Market

    Current Estimated Value $403,060

    Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    196 North St, Chester, VT 05143
  • 938 Stigers Rd, Chester, VT 05143
    938 Stigers Rd, Chester, VT 05143
    938 Stigers 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 $1,522,114

    Last Listing Agent Liz Moore Four Seasons Sotheby's Int'l Realty

    938 Stigers Rd, Chester, VT 05143
  • 656 Main St, Chester, VT 05143
    656 Main St, Chester, VT 05143
    656 Main St, 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

    Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    656 Main St, Chester, VT 05143
  • 442 Vermont 103, Chester, VT 05143
    442 Vermont 103, Chester, VT 05143
    442 Vermont 103, 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

    Last Listing Agent Rachael Rogala Lange & Lange

    442 Vermont 103, Chester, VT 05143
  • 0 Gould Rd Unit 5023598, Chester, VT 05143
    0 Gould Rd Unit 5023598, Chester, VT 05143
    0 Gould Rd Unit 5023598, Chester, VT 05143
    /10

    $35,500 Sold Jan 17, 2025

    0 Gould Rd Unit 5023598, Chester, VT 05143

    • Land
    • 8.75 Acres
    • $4,057 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 17 Days On Market

    Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    0 Gould Rd Unit 5023598, Chester, VT 05143
  • 1923 N Hill Rd, Chester, VT 05143
    1923 N Hill Rd, Chester, VT 05143
    1923 N Hill Rd, 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
  • 154 Reed Rd, Chester, VT 05143
    154 Reed 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

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    154 Reed Rd, Chester, VT 05143
  • 230 Kevadus Cir, Chester, VT 05143
    230 Kevadus Cir, Chester, VT 05143
    230 Kevadus Cir, 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 $275,406

    Last Listing Agent Jim Bialowski BHG Masiello Keene

    230 Kevadus Cir, Chester, VT 05143
  • 2739 Route 11, Chester, VT 05143
    2739 Route 11, 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
  • Lot 1 Old Stage Rd, Chester, VT 05143
    Lot 1 Old Stage Rd, 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
  • 442 Elm St, Chester, VT 05143
    442 Elm St, 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 $259,647

    Last Listing Agent Lisa Kelley Cummings & Co

    442 Elm St, Chester, VT 05143
  • 1502 Popple Dungeon Rd, Chester, VT 05143
    1502 Popple Dungeon Rd, Chester, VT 05143
    1502 Popple Dungeon 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 $893,132

    Last Listing Agent Betty McEnaney Diamond Realty

    1502 Popple Dungeon Rd, Chester, VT 05143
  • 515 Main St, Chester, VT 05143
    515 Main St, Chester, VT 05143
    515 Main St, 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
  • 4150 Trebo Rd, Chester, VT 05143
    4150 Trebo Rd, Chester, VT 05143
    4150 Trebo Rd, 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
  • 270 North St, Chester, VT 05143
    270 North St, Chester, VT 05143
    270 North 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 $369,455

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    270 North St, Chester, VT 05143
  • 1470 Flamstead Rd, Chester, VT 05143
    1470 Flamstead Rd, Chester, VT 05143
    1470 Flamstead 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

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1470 Flamstead Rd, Chester, VT 05143
  • 58 Remington Rd, Chester, VT 05143
    58 Remington Rd, Chester, VT 05143
    58 Remington 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

    Last Listing Agent John Napier TPW Real Estate

    58 Remington Rd, Chester, VT 05143
  • 17 Grafton St, Chester, VT 05143
    17 Grafton St, Chester, VT 05143
    /2

    $285,000 Sold Mar 26, 2025

    17 Grafton St, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,824 Sq Ft
    • Built 1852

    Last Sold Summary

    • 2% Below List Price
    • $156/SF
    • 87 Days On Market

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

    17 Grafton St, Chester, VT 05143
  • 284 Flamstead Rd, Chester, VT 05143
    284 Flamstead Rd, Chester, VT 05143
    284 Flamstead 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

    Last Listing Agent Linda Benoit Highland Realty

    284 Flamstead Rd, Chester, VT 05143
  • 0 Remington Rd Unit 8 4996410, Chester, VT 05143
    0 Remington Rd Unit 8 4996410, Chester, VT 05143
    0 Remington Rd Unit 8 4996410, Chester, VT 05143
    /6

    $23,000 Sold Jan 31, 2025

    0 Remington Rd Unit 8 4996410, Chester, VT 05143

    • Land
    • 1.64 Acres
    • $14,024 per Acre

    Last Sold Summary

    • 34% Below List Price
    • 215 Days On Market

    Last Listing Agent Frank Provance Diamond Realty

    0 Remington Rd Unit 8 4996410, Chester, VT 05143
  • 1847 Trebo Rd, Chester, VT 05143
    1847 Trebo Rd, Chester, VT 05143
    1847 Trebo 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

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

    1847 Trebo Rd, Chester, VT 05143
  • 1937 Green Mountain Turnpike, Chester, VT 05143
    1937 Green Mountain Turnpike, Chester, VT 05143
    1937 Green Mountain Turnpike, 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

    Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

    1937 Green Mountain Turnpike, Chester, VT 05143
  • 0 Remington Rd Unit 9 4997325, Chester, VT 05143
    0 Remington Rd Unit 9 4997325, Chester, VT 05143
    0 Remington Rd Unit 9 4997325, Chester, VT 05143
    /5

    $22,000 Sold Jan 31, 2025

    0 Remington Rd Unit 9 4997325, Chester, VT 05143

    • Land
    • 3.28 Acres
    • $6,707 per Acre

    Last Sold Summary

    • 32% Below List Price
    • 211 Days On Market

    Last Listing Agent Frank Provance Diamond Realty

    0 Remington Rd Unit 9 4997325, Chester, VT 05143
  • 332 Hidden Heights Rd, Chester, VT 05143
    332 Hidden Heights Rd, 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 $437,928

    Last Listing Agent John Tolosky Barrett and Valley Associates Inc.

    332 Hidden Heights Rd, Chester, VT 05143
  • 4877 Vt Route 103 N, Chester, VT 05143
    4877 Vt Route 103 N, Chester, VT 05143
    4877 Vt Route 103 N, 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

    Last Listing Agent Erin Kendall EXP Realty

    4877 Vt Route 103 N, Chester, VT 05143
  • 465 Pennell Rd, Chester, VT 05143
    465 Pennell Rd, Chester, VT 05143
    465 Pennell 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

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

    465 Pennell Rd, Chester, VT 05143
  • Lot 2 Old Stage Rd, Chester, VT 05143
    Lot 2 Old Stage 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
  • 1436 Route 103, Chester, VT 05143
    1436 Route 103, 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
  • 115 Orcutt Dr, Chester, VT 05143
    115 Orcutt Dr, Chester, VT 05143
    115 Orcutt Dr, 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 $412,471

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    115 Orcutt Dr, Chester, VT 05143
  • 491 Farrar Rd, Chester, VT 05143
    491 Farrar 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

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    491 Farrar Rd, Chester, VT 05143
  • 87 Kevadus Cir, Chester, VT 05143
    87 Kevadus Cir, 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 $225,172

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    87 Kevadus Cir, Chester, VT 05143
  • 1328 Chandler Rd, Chester, VT 05143
    1328 Chandler Rd, Chester, VT 05143
    1328 Chandler Rd, Chester, VT 05143
    /52

    $1,850,000 Sold Apr 30, 2025

    1328 Chandler Rd, Chester, VT 05143

    • 4 Beds
    • 3.5 Baths
    • 3,779 Sq Ft
    • Built 1972

    Last Sold Summary

    • 21% Below List Price
    • $490/SF
    • 220 Days On Market

    Current Estimated Value $1,435,412

    Last Listing Agent Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

    1328 Chandler Rd, Chester, VT 05143
  • 870 Cummings Rd, Chester, VT 05143
    870 Cummings Rd, Chester, VT 05143
    870 Cummings Rd, 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

    Last Listing Agent Julie Buffum Buffum Realty

    870 Cummings Rd, Chester, VT 05143

Showing Results 1 - 40, Page 1 of 2

Vermont Windsor County Chester

Recently Sold Real Estate & Homes in Chester, VT

Frequently Asked Questions

What is the average home price in Chester, VT?
Homes for sale in Chester, VT have an average home price of $574,831.
What is the average time to sell a house in Chester, VT?
The houses for sale in Chester, VT spend an average of 66 days on the market.
What is the number of active homes for sale in Chester, VT?
There are 14 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 Trends in Chester, VT

On average, homes in Chester, VT sell after 66 days on the market compared to the national average of 53 days. The median sale price for homes in Chester, VT over the last 12 months is $400,000, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$400,000
Median Single Family Sale Price
$381,000
Median Townhouse Sale Price
$598,000
Average Price Per Sq Ft
$278
Number of Homes for Sale
14
Last 12 months Home Sales
56
Months of Supply
3.00
Median List Price
$446,444
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
3%
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