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    Winchester, VA Hospitality Properties for Sale

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    Richmond, VA Roanoke, VA Fredericksburg, VA
    Historic Winchester Inn/Office Opportunity
    $1,200,000
    0.30 Acres

    Historic Winchester Inn/Office Opportunity

    217 W BOSCAWEN Street, Winchester, VA 22601

    Historic property suitable for B&B, office, or residence.

    • Prime location in Winchester's Historic District, two blocks from Old Town Walking Mall.
    • Zoned B1, allowing for use as a single‑family residence, bed and breakfast, or professional office.
    • Six large bedrooms and five full baths.
    • Historically significant property with unique architectural features, including wrap‑around stairs and floor‑to‑ceiling windows.
    • Private parking in the rear, a downtown rarity.
    Updated: Mar 16
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    Historic Inn or Office Opportunity
    $1,200,000
    0.30 Acres

    Historic Inn or Office Opportunity

    217 W Boscawen St, Winchester, VA 22601

    Historic property in Winchester's Historic District, ideal for various uses.

    • Prime location in Winchester's Historic District, two blocks from Old Town Walking Mall.
    • Zoned B1, suitable for single‑family residence, bed and breakfast, or professional offices.
    • Six large bedrooms and five full baths.
    • Historically significant property with unique architectural features (wrap‑around stairs, floor‑to‑ceiling windows).
    • Private garden spaces, romantic terraces, and sunlight‑filled porches.
    Updated: Mar 16
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    Historical Winchester Property with Courtyard
    $649,000
    7,650 SF

    Historical Winchester Property with Courtyard

    Redevelopment opportunity in Old Town Winchester with courtyard.

    230 W Boscawen Street, Winchester, VA 22601
    View details
    Based on your search, we've compiled 12 Potential Opportunities for your consideration. Besides 3 Active listings in Winchester, VA, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 1 Off-Market properties to explore as potential leads, plus 4 Land Listings that present a potential for development.

    Explore Opportunities in Nearby Cities

    Here are 4 Similar properties we found in Nearby Locations for your consideration.

    Historic Charles Town Bed & Breakfast
    $975,000
    1.06 Acres

    Historic Charles Town Bed & Breakfast

    Elegant property in Charles Town, operating as a bed and breakfast.

    417 E Washington St, Charles Town, WV 25414
    View details
    Historic Wayside Inn For Sale
    $1,300,000
    3.88 Acres

    Historic Wayside Inn For Sale

    Historic inn with 22 suites, bars, and expansion potential.

    7783 MAIN STREET, Middletown, VA 22645
    View details
    Motel with Apartments on 2.58 Acres
    $340,000
    3,873 SF

    Motel with Apartments on 2.58 Acres

    8-room motel with two apartments on 2.58 acres.

    6825 Valley Pike, Middletown, VA 22645
    View details
    2.03 Acres on Route 340
    $795,000

    2.03 Acres on Route 340

    2.03 acres with high visibility and commercial zoning.

    847 Berryville Pike, Charles Town, WV 25414
    View details

    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 Land For Sale
    $2,286,000
    5.08 Acres

    Winchester Land For Sale

    5.08 acres of commercial land in Rutherford Crossing.

    MARKET Street, Winchester, VA 22603
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    Lake Holiday Membership Lot
    Contact for pricing
    0.27 Acres

    Lake Holiday Membership Lot

    Membership lot with access to Lake Holiday amenities.

    FOREST DRIVE lot: 25, Cross Junction, VA 22625
    View details
    Commercial Land Near I-81
    $325,000
    1.15 Acres

    Commercial Land Near I-81

    1.15-acre commercial parcel with B-1 zoning near I-81.

    BRANDY CT., Strasburg, VA 22657
    View details
    Prime Commercial Site on Highway
    $3,400,000
    13.13 Acres

    Prime Commercial Site on Highway

    13.13-acre commercial site with highway frontage and excellent visibility.

    OLD VALLEY Pike, Strasburg, VA 22657
    View details

    Explore Off-Market Properties in Winchester, VA

    Consider similar Off-Market properties in Winchester, VA. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

    2645 Vly Ave

    2645 Vly Ave

    MOTEL • 5,796 SF
    Value Estimation
    $930,000
    2645 Vly Ave, Winchester, VA 22601-2625
    View details

    Winchester, VA Hospitality Properties Investment Opportunities Market Analysis

    Explore 4 hospitality properties for sale in Winchester, VA, showcased through 3 active listings on our real estate platform. These investment opportunities span a total of 7,650 square feet of properties for sale, with an estimated market value of $649,000.

    Sale prices for hospitality properties in Winchester, VA start at $649,000, averaging $649,000, and reaching up to $649,000 — 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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