8

Chester, VT Homes for Sale under $300,000

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  • 106 Contro Rd, Chester, VT 05143
    106 Contro Rd, Chester, VT 05143
    106 Contro Rd, Chester, VT 05143
    /14

    $289,000

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

    106 Contro Rd, Chester, VT 05143

    Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and electric. The basement has been partially finished with the fixtures of a 3/4 bath but no wall coverings, so the square footage is not counted here. The tenant does not have internet so it is best to check on phone/tv and internet from the providers. The property is being divided

    Christine Lewis Brattleboro Area Realty

    106 Contro Rd, Chester, VT 05143
  • 160 Depot St, Chester, VT 05143
    160 Depot St, Chester, VT 05143
    160 Depot St, Chester, VT 05143
    /26

    $225,000

    • 3 Beds
    • 1 Bath
    • 1,327 Sq Ft

    160 Depot St, Chester, VT 05143

    Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer,

    Joshua Lemieux Remax Summit

    160 Depot St, Chester, VT 05143
  • 00 Vermont 103, Andover, VT 05143
    00 Vermont 103, Andover, VT 05143
    00 Vermont 103, Andover, VT 05143
    /60

    $200,000

    • Land
    • 6.63 Acres
    • $30,166 per Acre

    00 Vermont 103, Andover, VT 05143

    Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With aproposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offersample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

    Rachael Rogala Lange & Lange

    00 Vermont 103, Andover, VT 05143
  • 00 Quarry Rd, Chester, VT 05143
    00 Quarry Rd, Chester, VT 05143
    00 Quarry Rd, Chester, VT 05143
    /25

    $229,000

    • Land
    • 27.8 Acres
    • $8,237 per Acre

    00 Quarry Rd, Chester, VT 05143

    Discover your perfect Vermont getaway on this exceptional 27.8± acre hillside parcel in picturesque Chester, Vermont. Offering sweeping mountain views, privacy, and endless possibilities, this property is ready for your vision. With an approved Vermont state wastewater permit for a 4-bedroom home, you can begin designing your dream family retreat or vacation home right away. A cleared preliminary

    Geralyn Donohue Engel & Völkers Okemo

    00 Quarry Rd, Chester, VT 05143
  • 000 Green Mountain Turnpike, Andover, VT 05143
    000 Green Mountain Turnpike, Andover, VT 05143
    000 Green Mountain Turnpike, Andover, VT 05143
    /22

    $275,000

    • Land
    • 91 Acres
    • $3,022 per Acre

    000 Green Mountain Turnpike, Andover, VT 05143

    91± Acres with Stunning Mountain Views in Chester, VermontDiscover a breathtaking 91± acre property just minutes from the charming village of Chester, Vermont. This expansive parcel features stunning alpine views of Fox Chair Mountain, over 3,000 feet of road frontage, and power and internet access along more than half the frontage. Located on the historic Green Mountain Turnpike, this

    Daire Gibney Barrett and Valley Associates Inc.

    000 Green Mountain Turnpike, Andover, VT 05143
  • 419 Coach Rd, Chester, VT 05143
    419 Coach Rd, Chester, VT 05143
    419 Coach Rd, Chester, VT 05143
    /12

    $219,000

    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft

    419 Coach Rd, Chester, VT 05143

    Price Reduction! Come see this private 2-acre lot, off a side street close to the picturesque Chester village. This well maintained 1968 mobile home has a bright open concept addition. Close to ski mountains and other snowmobile trails. Make this a Vermont getaway or a permanent home joining a wonderful community.

    Amy Carson Lowe's Real Estate, LLC

    419 Coach Rd, Chester, VT 05143
  • 1175 Quarry Rd, Chester, VT 05143
    1175 Quarry Rd, Chester, VT 05143
    1175 Quarry Rd, Chester, VT 05143
    /22

    $290,000

    • Land
    • 75 Acres
    • $3,867 per Acre

    1175 Quarry Rd, Chester, VT 05143

    An extraordinary potential homesite set in the hills of southern Vermont. This expansive 75-acre parcel offers the perfect blend of privacy, natural beauty, and endless potential. Whether you dream of building a secluded hilltop retreat or preserving land for recreation and conservation, this property invites endless possibilties. Improvements include a septic system, dug well, electricity and a

    Jessica Samples BHG Masiello Keene

    1175 Quarry Rd, Chester, VT 05143
  • 41 Vt Route 103 S, Chester, VT 05143
    41 Vt Route 103 S, Chester, VT 05143
    41 Vt Route 103 S, Chester, VT 05143
    /33

    $299,000

    • 2,702 Sq Ft

    41 Vt Route 103 S, Chester, VT 05143

    Here's a great opportunity to own a property on Chester's busy Main Street, Route 103 and Route 11. Situated between the Jiffy Mart and the General Dollar Store, there are many possibilities here for a commercial enterprise. Or you can use one unit for a nice business office and continue to rent the other two existing apartments. Presently, all three units are vacant. Easy to show! There is good

    Glenn Olney Barrett and Valley Associates Inc.

    41 Vt Route 103 S, Chester, VT 05143
Vermont Windsor County Chester

Real Estate & Homes in Chester, VT under $300,000

Home Trends in Chester, VT

On average, homes in Chester, VT sell after 62 days on the market compared to the national average of 54 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
$390,000
Median Townhouse Sale Price
$598,000
Average Price Per Sq Ft
$271
Number of Homes for Sale
14
Last 12 months Home Sales
56
Months of Supply
3.00
Median List Price
$448,944
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
3%
How to Buy a Home How to Finance a Home How to Sell a Home

Browse a range of homes for sale under $300,000 in Chester, offering accessible options for prospective buyers. With 8 listings available, there's a variety of affordable properties to explore, from charming starter homes to spacious family residences. These homes present an excellent opportunity to enter the housing market and secure a property that fits both your preferences and your budget in Chester, VT.

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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.

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