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    Chester, VT
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    45 Properties Available

    45 Properties Available

    The average price in the selected areas has remained stable. Learn more
    • Default
    • Price-High To Low
    • Price-Low To High
    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    314 Chester Knoll DR, Bennington, VT 05201
    1/32
    Active

    $315,000

    3 Beds2 Baths1,365 SqFt

    314 Chester Knoll DR, Bennington, VT 05201

    Listed by Faith Rhodes of Maple Leaf Real Estate

    PrimeMLS
    3537 Popple Dungeon RD, Chester, VT 05143
    1/22
    Active

    $249,900

    2 Beds1 Bath930 SqFt

    3537 Popple Dungeon RD, Chester, VT 05143

    Listed by Thaddeus J Abare of Barrett and Valley Associates Inc.

    PrimeMLS
    1260 Grafton RD, Chester, VT 05143
    1/50
    Under Contract

    $700,000

    2 Beds3 Baths1,556 SqFt

    1260 Grafton RD, Chester, VT 05143

    Listed by Geralyn Donohue of Four Seasons Sotheby's Int'l Realty geralyn.donohue@fourseasonssir.com

    PrimeMLS
    548 Crow Hill RD, Chester, VT 05143
    1/47
    Price Dropped by $11K

    $599,000

    4 Beds2 Baths1,908 SqFt

    548 Crow Hill RD, Chester, VT 05143

    Listed by Jay Farrar of Four Seasons Sotheby's Int'l Realty

    PrimeMLS
    3713 Trebo RD, Chester, VT 05143
    1/28
    Under Contract

    $289,900

    3 Beds3 Baths1,508 SqFt

    3713 Trebo RD, Chester, VT 05143

    Listed by Thaddeus J Abare of Barrett and Valley Associates Inc.

    PrimeMLS
    159 Lower Bartonsville RD, Chester, VT 05013
    1/23
    Under Contract

    $255,000

    3 Beds2 Baths1,683 SqFt

    159 Lower Bartonsville RD, Chester, VT 05013

    Listed by Abby Gerbick of Century 21 Highview Realty Off: 603-542-7766

    PrimeMLS
    302 Davidson Hill RD, Chester, VT 05143
    1/43
    Price Dropped by $24K

    $330,000

    2 Beds1 Bath900 SqFt

    302 Davidson Hill RD, Chester, VT 05143

    Listed by Tyler Buswell of Vermont Real Estate Company

    PrimeMLS
    1470 Popple Dungeon RD, Chester, VT 05143
    1/58
    Under Contract

    $879,900

    5 Beds3 Baths2,800 SqFt

    1470 Popple Dungeon RD, Chester, VT 05143

    Listed by Joseph Karl of William Raveis Real Estate Vermont Properties Off: 802-228-8877

    PrimeMLS
    223 Coach RD, Chester, VT 05143
    1/44
    Under Contract

    $789,000

    5 Beds3 Baths4,388 SqFt

    223 Coach RD, Chester, VT 05143

    Listed by Daire Gibney of Barrett and Valley Associates Inc.

    PrimeMLS
    168 Chandler RD, Chester, VT 05143
    1/60
    Active

    $649,000

    3 Beds2 Baths2,204 SqFt

    168 Chandler RD, Chester, VT 05143

    Listed by Diane Rousseau of Four Seasons Sotheby's Int'l Realty Diane.Rousseau@FourSeasonsSIR.com

    PrimeMLS
    3668 VT Route 103 North, Chester, VT 05143
    1/38
    Active

    $249,500

    4 Beds3 Baths1,922 SqFt

    3668 VT Route 103 North, Chester, VT 05143

    Listed by Dan Vigeant of Mary W. Davis Realtor & Assoc., Inc. Off: 802-228-8811

    PrimeMLS
    3668 VT Route 103 North, Chester, VT 05143
    1/38
    Price Dropped by $20K

    $229,500

    4 Beds3 Baths1,922 SqFt

    3668 VT Route 103 North, Chester, VT 05143

    Listed by Dan Vigeant of Mary W. Davis Realtor & Assoc., Inc. Off: 802-228-8811

    PrimeMLS
    3208 Green Mountain TPKE, Chester, VT 05143
    1/33
    Price Dropped by $30K

    $449,000

    3 Beds2 Baths1,626 SqFt

    3208 Green Mountain TPKE, Chester, VT 05143

    Listed by Geralyn Donohue of Four Seasons Sotheby's Int'l Realty geralyn.donohue@fourseasonssir.com

    PrimeMLS
    81 Main ST, Chester, VT 05143
    1/58
    Price Dropped by $5K
    3D

    $445,000

    5 Beds4 Baths3,865 SqFt

    81 Main ST, Chester, VT 05143

    Listed by Betsy Adamovich of Real Broker LLC

    PrimeMLS
    1144 Potash Brook RD, Chester, VT 05143
    1/17
    Active

    $75,000

    2 Beds1 Bath620 SqFt

    1144 Potash Brook RD, Chester, VT 05143

    Listed by Julie Buffum of Buffum Realty

    PrimeMLS
    76 Goldthwaite RD, Chester, VT 05143
    1/39
    Active

    $1,200,000

    4 Beds3 Baths3,308 SqFt

    76 Goldthwaite RD, Chester, VT 05143

    Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty gary.coger@fourseasonssir.com

    PrimeMLS
    1302 Popple Dungeon RD, Chester, VT 05143
    1/53
    Price Dropped by $141K

    $1,349,000

    5 Beds5 Baths5,400 SqFt

    1302 Popple Dungeon RD, Chester, VT 05143

    Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty gary.coger@fourseasonssir.com

    PrimeMLS
    64 Maple ST, Chester, VT 05143
    1/60
    Under Contract
    3D

    $469,000

    3 Beds3 Baths2,676 SqFt

    64 Maple ST, Chester, VT 05143

    Listed by Betsy Adamovich of Real Broker LLC

    PrimeMLS
    663 Depot ST, Chester, VT 05143
    1/51
    Under Contract

    $390,000

    3 Beds2 Baths1,304 SqFt

    663 Depot ST, Chester, VT 05143

    Listed by Betsy Adamovich of Real Broker LLC

    PrimeMLS
    3341 Trebo RD, Chester, VT 05143
    1/47
    Active

    $549,000

    4 Beds3 Baths2,464 SqFt

    3341 Trebo RD, Chester, VT 05143

    Listed by Daire Gibney of Barrett and Valley Associates Inc.

    PrimeMLS
    176 Meadow RD, Chester, VT 05143
    1/43
    Under Contract

    $419,900

    5 Beds2 Baths1,982 SqFt

    176 Meadow RD, Chester, VT 05143

    Listed by Lauren Behm of Berkshire Hathaway HomeServices Stratton Home

    PrimeMLS
    1397 Popple Dungeon RD, Chester, VT 05143
    1/31
    Under Contract

    $299,000

    3 Beds2 Baths1,788 SqFt

    1397 Popple Dungeon RD, Chester, VT 05143

    Listed by Daire Gibney of Barrett and Valley Associates Inc.

    PrimeMLS
    40 Fenton RD, Chester, VT 05143
    1/37
    Active

    $399,000

    4 Beds3 Baths2,148 SqFt

    40 Fenton RD, Chester, VT 05143

    Listed by John M Napier of TPW Real Estate

    PrimeMLS
    3019 Popple Dungeon RD, Chester, VT 05143
    1/20
    Active

    $169,000

    1 Bed1 Bath200 SqFt

    3019 Popple Dungeon RD, Chester, VT 05143

    Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty gary.coger@fourseasonssir.com

    PrimeMLS
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        Market Snapshot
    Real Broker NH, LLC

    Allison Driscoll License ID: 070756

    +1(603) 553-9932 allison@fernandfrondhomes.com

    170 Commercial Way, Portsmouth, NH

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    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

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        Home
        Buy
        1. All Listings
        2. Featured Listings
        3. Sold Listings
        Sell
        1. Sell My Home
        2. Home Valuation
        About
        1. About Us
        2. Contact Us
        3. Reviews
        Market Snapshot
    Real Broker NH, LLC

    Allison Driscoll License ID: 070756

    +1(603) 553-9932 allison@fernandfrondhomes.com

    170 Commercial Way, Portsmouth, NH

    Get My App

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.