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    Bennington County, VT Bed & Breakfasts for Sale

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    Burlington, VT Bennington, VT Brattleboro, VT
    Manchester Retreat: Income-Producing Potential
    $995,000
    3.20 Acres

    Manchester Retreat: Income-Producing Potential

    2001 Depot Street, Manchester, VT 05255

    Furnished 6-bedroom retreat near Bromley and Stratton with rental history.

    • Prime location: Just 8 minutes to Bromley, 20 minutes to Stratton, and close to Manchester's amenities.
    • Proven income potential: Strong history as a successful Airbnb/short‑term rental.
    • Spacious and well‑equipped: Features 6 bedrooms, 7 baths, and over 5,400 sq ft on 3.2 acres.
    • Fully furnished and move‑in‑ready: Impeccably maintained with freshly painted interiors.
    • Luxury amenities: Enjoy the chef’s kitchen, new outdoor hot tub, and gas fireplaces in upstairs bedrooms.
    Updated: May 23, 2025
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    Historic Victorian Inn For Sale
    $1,250,000
    0.47 Acres

    Historic Victorian Inn For Sale

    124 Elm Street, Bennington, VT 5201

    Meticulously restored inn with restaurant in prime tourist location.

    • Turnkey, established, and profitable boutique hotel business with a loyal client base.
    • Prime location in Bennington, VT, near Manchester, Williamstown, and the Berkshires, attracting tourists.
    • Meticulously restored historic Victorian property (South Shire Inn) built in 1890.
    • Restaurant leased to a thriving Thai restaurant, providing immediate income.
    • Newly zoned for expanded business opportunities, including restaurant, bar/lounge, and catering services.
    Updated: Mar 12
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    Historic Inn at Ormsby Hill
    $2,250,000

    Historic Inn at Ormsby Hill

    Premier New England bed and breakfast in Manchester, Vermont.

    1842 Main St, Manchester Center, VT 5255
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    Based on your search, we've compiled 7 Potential Opportunities for your consideration. Besides 3 Active listings in Bennington County, VT, we suggest exploring several alternatives: plus 4 Land Listings that present a potential for development.

    Potential Development Sites for Consideration

    Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

    Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

    Winchester Vacant Wooded Lot
    $33,750
    5.34 Acres

    Winchester Vacant Wooded Lot

    Vacant, wooded lot with high visibility in Winchester, NH.

    0 Ashuelot Main Street, Winchester, NH 03470
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    Level Lot Near Town Amenities
    $65,000
    1.90 Acres

    Level Lot Near Town Amenities

    1.9-acre lot near amenities, recreation, and ski resorts.

    TBD VT Route 15W, Johnson, VT 05656
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    Commercial Land in Woodridge, NY
    $69,000
    0.46 Acres

    Commercial Land in Woodridge, NY

    Prime commercial land with utilities available in Woodridge, NY.

    *** Mountaindale Road, Fallsburg, NY 12733
    View details
    Cochecton Land on Route 17B
    $68,500
    2.00 Acres

    Cochecton Land on Route 17B

    Two acres in Hamlet District, suitable for commercial or residential.

    2.-1-32.7 State Route 17B, Cochecton, NY 12726
    View details

    Bennington County, VT Bed & Breakfasts Investment Opportunities Market Analysis

    Explore 3 bed & breakfasts for sale in Bennington County, VT, showcased through 3 active listings on our real estate platform. These investment opportunities span a total of 139,392 square feet of properties for sale, with an estimated market value of $995,000.

    Sale prices for inns in Bennington County, VT start at $995,000, averaging $995,000, and reaching up to $995,000 — 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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