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    Bennington, VT
    Map
    406 Properties Available

    406 Properties Available

    The average price in the selected areas has remained stable. Learn more
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    • Price-High To Low
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    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    848 Mad Tom RD, Dorset, VT 05253
    1/59
    Team Listing
    Under Contract

    $689,000

    3 Beds3 Baths2,400 SqFt

    848 Mad Tom RD, Dorset, VT 05253

    Listed by Erin McCormick of KW Vermont Cell: 802-989-2390

    PrimeMLS
    142 Schenkar RD, Pownal, VT 05261
    1/60
    Team Listing
    Active

    $625,000

    3 Beds3 Baths3,295 SqFt

    142 Schenkar RD, Pownal, VT 05261

    Listed by Erin McCormick of KW Vermont Cell: 802-989-2390

    PrimeMLS
    1059 Bailey Hill RD, Readsboro, VT 05350
    1/38
    Team Listing
    Under Contract

    $502,900

    3 Beds1 Bath2,400 SqFt

    1059 Bailey Hill RD, Readsboro, VT 05350

    Listed by The Hammond Team of KW Vermont Phone: 802-654-8500

    PrimeMLS
    3373 Main ST, Manchester, VT 05254
    1/55
    Open 5/28 11AM-1PM

    $995,000

    4 Beds6 Baths4,502 SqFt

    3373 Main ST, Manchester, VT 05254

    Listed by David A Halligan of Four Seasons Sotheby's Int'l Realty

    PrimeMLS
    140 Route 30, Winhall, VT 05340
    1/39
    New

    $495,000

    4 Beds2 Baths1,824 SqFt

    140 Route 30, Winhall, VT 05340

    Listed by Carrie Mathews of Winhall Real Estate

    PrimeMLS
    45 Benson Fuller DR, Winhall, VT 05340
    1/35
    New

    $7,250

    4 Beds3 Baths2,000 SqFt

    45 Benson Fuller DR, Winhall, VT 05340

    Listed by David Powers of 42 North LP

    PrimeMLS
    233 Squires RD, Manchester, VT 05255
    1/27
    New

    $1,200,000

    2 Beds1 Bath1,056 SqFt

    233 Squires RD, Manchester, VT 05255

    Listed by Mark E Triller of Real Broker LLC

    PrimeMLS
    1310 Dorset Hill RD, Dorset, VT 05253
    1/38
    New

    $1,875,000

    4 Beds3 Baths3,370 SqFt

    1310 Dorset Hill RD, Dorset, VT 05253

    Listed by Annette Gallo of Real Broker LLC

    PrimeMLS
    39 Eagle RDG, Dorset, VT 05251
    1/49
    New

    $1,450,000

    5 Beds5 Baths4,376 SqFt

    39 Eagle RDG, Dorset, VT 05251

    Listed by Laura Beckwith of Josiah Allen Real Estate, Inc.

    PrimeMLS
    2572 Morse Hill RD, Dorset, VT 05251
    1/57
    New

    $899,000

    4 Beds3 Baths4,112 SqFt

    2572 Morse Hill RD, Dorset, VT 05251

    Listed by Hayleyanne Van Der Kar of Four Seasons Sotheby's Int'l Realty

    PrimeMLS
    52 High Meadow RD #11, Winhall, VT 05155
    1/39
    New

    $798,000

    3 Beds5 Baths3,100 SqFt

    52 High Meadow RD #11, Winhall, VT 05155

    Listed by Betsy Wadsworth of Four Seasons Sotheby's Int'l Realty

    PrimeMLS
    764 Myers RD, Shaftsbury, VT 05262
    1/32
    New

    $534,900

    3 Beds2 Baths1,820 SqFt

    764 Myers RD, Shaftsbury, VT 05262

    Listed by Matt Waddington of Hoffman Real Estate Matt@HoffmanVTRealEstate.com

    PrimeMLS
    3589 Morse Hill RD, Dorset, VT 05251
    1/37
    Under Contract

    $359,000

    2 Beds1 Bath1,171 SqFt

    3589 Morse Hill RD, Dorset, VT 05251

    Listed by Hayleyanne Van Der Kar of Four Seasons Sotheby's Int'l Realty

    PrimeMLS
    6 Old Ridge RD, Winhall, VT 05340
    1/40
    New
    3D

    $1,100,000

    5 Beds5 Baths4,453 SqFt

    6 Old Ridge RD, Winhall, VT 05340

    Listed by Trent K Stephens of Wohler Realty Group

    PrimeMLS
    63 Raspberry Hill RD, Winhall, VT 05340
    1/35
    New

    $799,000

    4 Beds4 Baths3,078 SqFt

    63 Raspberry Hill RD, Winhall, VT 05340

    Listed by Carrie Mathews of Winhall Real Estate

    PrimeMLS
    2677 Route 30, Dorset, VT 05251
    1/60
    New

    $765,000

    5 Beds5 Baths5,083 SqFt

    2677 Route 30, Dorset, VT 05251

    Listed by Laura Beckwith of Josiah Allen Real Estate, Inc.

    PrimeMLS
    85 Sylvan Ridge RD, Winhall, VT 05340
    1/60
    Price Dropped by $26K
    3D

    $649,000

    4 Beds5 Baths3,350 SqFt

    85 Sylvan Ridge RD, Winhall, VT 05340

    Listed by KC Gandee of Real Broker LLC

    PrimeMLS
    185 Kelleher RD #10-00-99, Dorset, VT 05251
    1/35
    New

    $645,000

    3 Beds2 Baths1,809 SqFt

    185 Kelleher RD #10-00-99, Dorset, VT 05251

    Listed by Laura Beckwith of Josiah Allen Real Estate, Inc.

    PrimeMLS
    36 Birch Hill RD #8 Red Maple, Winhall, VT 05340
    1/26
    New

    $450,000

    3 Beds2 Baths1,215 SqFt

    36 Birch Hill RD #8 Red Maple, Winhall, VT 05340

    Listed by Helen Nault of The Haven Group

    PrimeMLS
    524 Jennings Brook DR, Bennington, VT 05201
    1/4
    Under Contract

    $350,000

    2 Beds2 Baths1,190 SqFt

    524 Jennings Brook DR, Bennington, VT 05201

    Listed by Lillian West of Maple Leaf Real Estate

    PrimeMLS
    32 Albe DR, Bennington, VT 05201
    1/41
    New

    $279,000

    2 Beds1 Bath2,142 SqFt

    32 Albe DR, Bennington, VT 05201

    Listed by Beatrice O'Connell of Maple Leaf Real Estate

    PrimeMLS
    3039 Route 30, Dorset, VT 05251
    1/44
    New

    $2,495,000

    4 Beds6 Baths4,506 SqFt

    3039 Route 30, Dorset, VT 05251

    Listed by Carrie Mathews of Winhall Real Estate

    PrimeMLS
    543 Lower Hollow RD, Dorset, VT 05251
    1/52
    New

    $2,285,000

    5 Beds5 Baths4,647 SqFt

    543 Lower Hollow RD, Dorset, VT 05251

    Listed by Britt M Wohler of WOHLER REALTY GROUP

    PrimeMLS
    3746-3738 Main ST #1, Manchester, VT 05254
    1/47
    New

    $1,375,000

    3 Beds5 Baths3,415 SqFt

    3746-3738 Main ST #1, Manchester, VT 05254

    Listed by Britt M Wohler of WOHLER REALTY GROUP

    PrimeMLS
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    12000x900
    Keller Williams Realty
    Isaiah Donaldson | License ID: 082.0134518
    68 Randall Street, Burlington, VT, 05403, USA

    +1(802) 999-8410

    isaiah@identityrealestate.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.

    12000x900
    Keller Williams Realty
    Isaiah Donaldson | License ID: 082.0134518
    68 Randall Street, Burlington, VT, 05403, USA

    +1(802) 999-8410

    isaiah@identityrealestate.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.