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    Winchester, VA Bed & Breakfasts for Sale

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    Richmond, VA Fredericksburg, VA Roanoke, 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 11 Potential Opportunities for your consideration. Besides 3 Active listings in Winchester, VA, we suggest exploring several alternatives: 4 properties in Nearby Cities, 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
    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
    Historic Estate with Development Potential
    $3,750,000
    13.49 Acres

    Historic Estate with Development Potential

    13.49 acre estate with multiple residences and development potential.

    5360 Winfield Rd, Fairfax, VA 22030
    View details
    Historic Estate on Winfield Road
    $3,750,000
    4,500 SF

    Historic Estate on Winfield Road

    13.49 acres with four residences and equestrian facilities.

    5300 Winfield Rd, Fairfax, VA 22030
    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.

    Residential Land in White Stone
    $45,000
    2.01 Acres

    Residential Land in White Stone

    Two-acre residential land parcel with road frontage.

    0 Mary Ball Road, White Stone, VA 22578
    View details
    Land with Rental Income Potential
    $1,299,900

    Land with Rental Income Potential

    Large parcel with three rental properties and business zoning.

    1021-1025-1029 S 47, Rio Grande, NJ 08242
    View details
    66 Acres Recreational Land For Sale
    $3,500,000
    9,120 SF

    66 Acres Recreational Land For Sale

    66-acre property with cabins, RV sites, and river access.

    213 Lazy K Drive, Elkview, WV 25071
    View details
    Waterfront Triplex with Marina Potential
    $1,200,000
    2,730 SF

    Waterfront Triplex with Marina Potential

    Waterfront triplex with marina rights and rental income potential.

    555 N Maryland Ave, Atlantic City, NJ 08401
    View details

    Winchester, VA Bed & Breakfasts Investment Opportunities Market Analysis

    Explore 3 bed & breakfasts for sale in Winchester, VA, showcased through 3 active listings on our real estate platform. These investment opportunities span a total of 12,946 square feet of properties for sale, with an estimated market value of $1,200,000.

    Sale prices for inns in Winchester, VA start at $1,200,000, averaging $1,200,000, and reaching up to $1,200,000 — 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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