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Chester, VT 1-Story Homes for Sale

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  • /42

    $429,000

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

    1979 N Hill Rd, Chester, VT 05143

    Welcome to this attractive Andover Contemporary home, perfectly suited for year-round living or as a Vermont vacation retreat. Built in 2005, this 3 bedroom, 2 bath residence offers modern comfort in a peaceful country setting on 2.1 acres while being just minutes from Okemo Mountain Resort and close to scenic snowmobile trails—ideal for outdoor enthusiasts in every season. The inviting

    Geralyn Donohue Engel & Völkers Okemo

    1979 N Hill 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
  • /20

    $169,000

    • 1 Bed
    • 1 Bath
    • 200 Sq Ft

    3019 Popple Dungeon Rd, Chester, VT 05143

    Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation. This property offers numerous options, allowing you to live in the cozy tiny

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3019 Popple Dungeon Rd, Chester, VT 05143
  • /48

    $899,000

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

    1269 Howard Hill Rd, Chester, VT 05143

    Discover a truly one-of-a-kind Vermont retreat set on 10 acres of peaceful woodland and open meadow. Originally built as a family-run maple sugar shack, this architect-designed home has been thoughtfully reimagined and newly completed, seamlessly blending rustic charm with contemporary comfort to create a warm and inviting hideaway unlike anything else on the market. Post-and-beam construction,

    Cheyanne Pugliese

    1269 Howard Hill Rd, Chester, VT 05143
  • /20

    $149,900

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

    4351 Vermont 11, Chester, VT 05143

    Almost there! This owner has taken this property to a new level...had the septic discovered and has a report, upgraded the electric entrance and added an EV station, laid flooring, opened up a wall for a much nicer open concept, cleaned and made into a little cottage for skiing, nature loving or just plain home. There are rain barrels for water, let nature fill them up or hire the local water

    Christine Lewis Brattleboro Area Realty

    4351 Vermont 11, Chester, VT 05143
  • /12

    $229,000

    • 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
  • /40

    $280,000

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    818 Davidson Hill Rd, Chester, VT 05143

    Located on the Chester, N. Springfield town line, this cute house sited on just under 3 acres is move in ready. It offers It offers 3 bedrooms two full baths and a designated laundry room. The renovated kitchen featuring stone countertops and nicely styled cabinets. In addition, there is beautiful post and beam back porch that is perfect for morning coffee and late afternoon quiet. With a small

    John Tolosky Barrett and Valley Associates Inc.

    818 Davidson Hill Rd, 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

Home Trends in Chester, VT

Housing Trends

Median Sale Price
$400,000
Median Single Family Sale Price
$373,000
Median Townhouse Sale Price
$560,000
Average Price Per Sq Ft
$273
Number of Homes for Sale
14
Last 12 months Home Sales
57
Months of Supply
2.90
Median List Price
$425,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
2%
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