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    Windsor County, VT Bed & Breakfasts for Sale

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    Victorian Multi-Family Home
    $599,000
    3,850 SF

    Victorian Multi-Family Home

    534 Elm St, Chester, VT 05143

    Impressive Victorian home with carriage house in Chester, Vermont.

    • Main house features 4 bedrooms and a 3‑bedroom carriage house, offering flexibility.
    • Turnkey sale for immediate occupancy.
    • Located in Chester, Vermont, one of the top 10 most beautiful towns in Vermont.
    • Proximity to multiple Vermont ski resorts: Okemo, Killington, Stratton, Bromley, and Magic Mountains.
    • Historic Victorian home (built in 1868) with original character.
    Updated: Dec 2, 2025
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    Woodstock Village Inn Opportunity
    $2,599,000
    0.46 Acres

    Woodstock Village Inn Opportunity

    41 Pleasant St, Wood Stock, VT 05091

    Charming 8-room Inn with owner's quarters in Woodstock, Vermont.

    • Established 8‑room Inn with a strong reputation and impressive revenue growth.
    • Includes a separate 1‑bedroom owner's quarters for convenient on‑site living.
    • Located in Woodstock, VT, recognized as one of America's most charming small towns and a popular tourist destination.
    • Features a cozy tavern and well‑regarded restaurant, enhancing guest experience and revenue potential.
    • Combines historic charm (built in 1899) with modern amenities.
    Updated: Nov 26, 2025
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    Based on your search, we've compiled 2 Potential Opportunities for your consideration. Besides 2 Active listings in Windsor County, VT, we suggest exploring several alternatives:

    Windsor County, VT Bed & Breakfasts Investment Opportunities Market Analysis

    Explore 2 bed & breakfasts for sale in Windsor County, VT on our real estate platform. These investment opportunities span a total of 52,708 square feet of properties for sale, with an estimated market value of $3,198,000.

    Prices for inns in Windsor County, VT start at $599,000, averaging $1,599,000, and reaching up to $2,599,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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