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Chester, VT Homes for Sale under $400,000

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  • 447 Elm St, Chester, VT 05143
    447 Elm St, Chester, VT 05143
    447 Elm St, Chester, VT 05143
    /29

    $349,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    447 Elm St, Chester, VT 05143

    Welcome to your dream home – This meticulously maintained and efficient New England-style gem is bursting with charm and modern convenience. Extra insulation, new windows and new hot water heater make this home as energy-efficient as it is beautiful. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by

    Agent Photo

    Lisa Kelley

    Cummings & Co

    (802) 200-2452

    447 Elm St, Chester, VT 05143
  • 1397 Popple Dungeon Rd, Chester, VT 05143
    1397 Popple Dungeon Rd, Chester, VT 05143
    1397 Popple Dungeon Rd, Chester, VT 05143
    /31

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft

    1397 Popple Dungeon Rd, Chester, VT 05143

    Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for—flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved

    Daire Gibney Barrett and Valley Associates Inc.

    1397 Popple Dungeon Rd, Chester, VT 05143
  • 40 Fenton Rd, Chester, VT 05143
    40 Fenton Rd, Chester, VT 05143
    40 Fenton Rd, Chester, VT 05143
    /37

    $399,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,148 Sq Ft

    40 Fenton Rd, Chester, VT 05143

    This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of

    John Napier TPW Real Estate

    40 Fenton Rd, Chester, VT 05143
Vermont Windsor County Chester

Real Estate & Homes in Chester, VT under $400,000

Home Trends in Chester, VT

On average, homes in Chester, VT sell after 59 days on the market compared to the national average of 55 days. The median sale price for homes in Chester, VT over the last 12 months is $401,119, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$401,119
Median Single Family Sale Price
$394,000
Median Townhouse Sale Price
$598,000
Average Price Per Sq Ft
$276
Number of Homes for Sale
12
Last 12 months Home Sales
56
Months of Supply
2.60
Median List Price
$449,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
4%
How to Buy a Home How to Finance a Home How to Sell a Home

Explore the array of homes and houses for sale under $400,000 in Chester, where you'll find 3 options tailored for those seeking affordable real estate opportunities. Whether you're interested in spacious family homes, modern townhouses, or cozy bungalows, Chester offers a diverse range of choices to match your needs and financial considerations. Take advantage of these affordably-priced properties to make your move into the real estate market in Chester, VT.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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.

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