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    Windsor County, VT Bed & Breakfasts for Sale

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    6 properties
    Historic Mansion Wedding Venue
    Updated: Jul 31
    Historic Mansion Wedding Venue

    1589 Main Street, Cavendish, VT 05142

    $1,400,000
    2.40 AC lot
    10‑bedroom mansion built in 1860
    Five bedrooms have ensuite bathrooms; a private owner’s apartment is also included
    2.4‑acre property listed on the National Register of Historic Places
    Renovated 3,000‑square‑foot barn accommodates events for up to 125 guests
    English‑style pub includes a full bar and pool table
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    8-Room Bed & Breakfast Inn
    Updated: Aug 12, 2025
    8-Room Bed & Breakfast Inn

    Wood Stock, VT 05091

    $2,599,000
    0.46 AC lot
    Eight‑room inn with an additional one‑bedroom owner’s quarters
    Built in 1899 on 0.46 acres
    Post‑and‑beam and wood‑frame construction
    Non‑residential zoning with public water and propane utility service
    Metal roof and basement space
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    Historic Lakeside Hotel
    Historic Lakeside Hotel

    2 Dublin Road, Plymouth, VT 05149

    $2,400,000

    Full-service Vermont inn along Route 100 near Okemo Mountain Resort and Killington Resort.

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    Historic Bed And Breakfast Estate
    Historic Bed And Breakfast Estate

    1589 Main St, Cavendish, VT 05142

    $1,400,000
    5,500 sqft 2.40 AC lot

    Historic hospitality property with an event barn, chef’s kitchen, and multiple spaces for guest gatherings and celebrations.

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    Historic Bed And Breakfast
    Historic Bed And Breakfast

    505 Deweys Mills Road, Hartford, VT 05047

    $1,275,000
    0.90 AC lot

    Antique lodging property with updated interiors, water views, and access to nearby trails.

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    Charming Inn in Woodstock, VT
    Charming Inn in Woodstock, VT

    Wood Stock, VT 05091

    $2,599,000
    5,993 sqft

    8-room Inn with owner's quarters in vibrant Woodstock, VT.

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    6 active listings match your search: Bed & Breakfast for sale in Windsor County, VT.

    Windsor County, VT Bed & Breakfasts Market Trends and Statistics

    Explore 6 bed & breakfasts for sale in Windsor County, VT, showcased through 6 active listings on our real estate platform. These investment opportunities span a total of 11,493 square feet of properties for sale, with an estimated market value of $11,673,000.

    Sale prices for inns in Windsor County, VT start at $1,275,000, averaging $1,945,500, and reaching up to $2,599,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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    Featured Windsor County Real Estate Agencies

    Realmo connects you with licensed Windsor County CRE brokers providing property specifications, local market pricing, and commercial transaction underwriting support.

    Bassette Real Estate Group
    611 Route 12 Hartland, VT 05048
    Phone: (802) 457-2244
    www.vermontcountryrealestate.com
    Snyder Donegan Real Estate Group
    PO Box 161, 5 The Green West Woodstock, VT 05091
    Phone: (802) 457-2600
    www.snyderdonegan.com
    Mary Mitchell Miller Real Estate
    PO Box 8, 620 Main Street Weston, VT 05161
    Phone: (802) 824-3176
    www.mmmrealestate.com
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