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    Windsor County, VT Bed & Breakfasts for Sale

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    Historic Bed & Breakfast Estate
    Updated: Jul 31
    Historic Bed & Breakfast Estate

    1589 Main Street, Cavendish, VT 05142

    $1,400,000
    2.40 AC lot
    2.4+/- landscaped acres in Cavendish, Vermont
    10‑bedroom mansion dating to 1860
    Five bedrooms with ensuite baths plus a private owner’s apartment
    Renovated 3,000‑square‑foot barn for events of up to 125 guests
    Listed on the National Historic Register
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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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    Turn a Listing Into an Investment Snapshot Cap Rate, Potential NOI, Demand score for every listing. Go To Analytics Center
    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
    0.46 AC lot

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

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    Barnard Inn: Event and Wedding Venue
    Barnard Inn: Event and Wedding Venue

    West Woodstock, VT 05091

    Contact for pricing
    10.00 AC lot

    Charming inn and event venue near Woodstock, Vermont.

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    Based on your search, we've compiled 7 Potential Opportunities for your consideration. Besides 7 Active listings in Windsor County, VT, we suggest exploring several alternatives:

    Windsor County, VT Bed & Breakfasts Market Trends and Statistics

    Explore 7 bed & breakfasts for sale in Windsor County, VT, showcased through 7 active listings on our real estate platform. These investment opportunities span a total of 5,500 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: 18024572244
    www.vermontcountryrealestate.com
    Dunrovin Real Estate
    PO Box 450 Royalton, VT 05068
    Phone: 18027637177
    dunrovincountryvermont.com
    Snyder Donegan Real Estate Group
    PO Box 161, 5 The Green West Woodstock, VT 05091
    Phone: 18024572600
    www.snyderdonegan.com

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