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    Chester, VT
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    44 Properties Available

    44 Properties Available

    The average price in the selected areas has remained stable. Learn more
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    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    1302 Popple Dungeon RD, Chester, VT 05143
    1/53
    Open Sun 11AM-2PM

    $1,490,000

    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
    223 Coach RD, Chester, VT 05143
    1/44
    New

    $849,000

    5 Beds3 Baths4,388 SqFt

    223 Coach RD, Chester, VT 05143

    Listed by Daire Gibney of Barrett and Valley Associates Inc.

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

    $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
    New

    $249,000

    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
    1/34
    Active

    $489,000

    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
    Active
    3D

    $475,000

    5 Beds4 Baths3,865 SqFt

    81 Main ST, Chester, VT 05143

    Listed by Betsy Adamovich of Real Broker LLC

    PrimeMLS
    3078 VT Route 10, Chester, VT 05143
    1/60
    Under Contract

    $495,000

    3 Beds2 Baths1,800 SqFt

    3078 VT Route 10, Chester, VT 05143

    Listed by Tyleen Murray of Kelley Real Estate, Inc.

    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
    735 Main ST, Chester, VT 05143
    1/11
    Active

    $3,300

    4 Beds3 Baths2,200 SqFt

    735 Main ST, Chester, VT 05143

    Listed by Team BVA Rentals of Barrett and Valley Associates Inc.

    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
    397 River ST, Chester, VT 05143
    1/41
    Under Contract

    $325,000

    4 Beds3 Baths3,332 SqFt

    397 River ST, Chester, VT 05143

    Listed by Lisa Kelley of Cummings & Co

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

    $479,000

    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
    Active

    $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
    Under Contract

    $549,000

    4 Beds3 Baths2,464 SqFt

    3341 Trebo RD, Chester, VT 05143

    Listed by Daire Gibney of Barrett and Valley Associates Inc.

    PrimeMLS
    547 Williams RD, Chester, VT 05143
    1/60
    Under Contract

    $474,900

    3 Beds2 Baths1,320 SqFt

    547 Williams RD, Chester, VT 05143

    Listed by Terri Edgerley of Edge Realty Vermont

    PrimeMLS
    335 North ST, Chester, VT 05143
    1/55
    Under Contract

    $340,000

    3 Beds1 Bath2,096 SqFt

    335 North ST, Chester, VT 05143

    Listed by Brendan McNamara of William Raveis Real Estate Vermont Properties Off: 802-228-8877

    PrimeMLS
    32 S. Main ST ##7, Chester, VT 05143
    1/8
    Active

    $1,400

    2 Beds1 Bath750 SqFt

    32 S. Main ST ##7, Chester, VT 05143

    Listed by Team BVA Rentals of Barrett and Valley Associates Inc.

    PrimeMLS
    688 Hidden Heights RD, Chester, VT 05143
    1/60
    Active

    $649,000

    3 Beds2 Baths2,205 SqFt

    688 Hidden Heights RD, Chester, VT 05143

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

    PrimeMLS
    1397 Popple Dungeon RD, Chester, VT 05143
    1/31
    Price Dropped by $50K

    $349,000

    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
    106 Contro RD, Chester, VT 05143
    1/14
    Active

    $289,000

    2 Beds3 Baths1,475 SqFt

    106 Contro RD, Chester, VT 05143

    Listed by Christine M Lewis of Brattleboro Area Realty

    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
    447 Elm ST, Chester, VT 05143
    1/30
    Under Contract

    $299,000

    3 Beds2 Baths1,488 SqFt

    447 Elm ST, Chester, VT 05143

    Listed by Lisa Kelley of Cummings & Co

    PrimeMLS
    3630 Vt Route 103 N, Chester, VT 05143
    1/30
    Active

    $650,000

    3 Beds3 Baths4,324 SqFt

    3630 Vt Route 103 N, Chester, VT 05143

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

    PrimeMLS
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    Kara & Company Realty
    Kyle Cavanaugh | # #075088
    900 Hanover Street, Manchester, New Hampshire, 03103, USA

    +1(603) 203-8187

    kyle@karacorealty.com

    Get My App

    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.

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

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

    site logo
    Kara & Company Realty
    Kyle Cavanaugh | # #075088
    900 Hanover Street, Manchester, New Hampshire, 03103, USA

    +1(603) 203-8187

    kyle@karacorealty.com

    Get My App

    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.

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

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