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    Winchester, VA Hospitality Properties for Sale

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    Stephenson, VA Clear Brook, VA Berryville, VA
    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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    Commercial
    $1,200,000
    Commercial

    217 W BOSCAWEN St, Winchester, VA 22601

    Bed & breakfasts
    • Great Location on Major Hwy
    • Rustic and Ready
    • Various types of businesses will fit
    • Over 2 Acres
    • Fully furnished with equipment, tables, chairs etc.
    Updated: Apr 24
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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

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    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.

    Opportunities in Nearby Cities

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

    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
    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

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    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

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    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

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    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

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    10.36 Acres Commercial Land
    $595,000
    10.36 Acres
    10.36 Acres Commercial Land

    10.36 acres of land zoned agricultural, prime for development.

    171 HOSPITALITY, Front Royal, VA 22630

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    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

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    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
    MOTEL
    5,796 SF Lot: 2.77 Acres
    Estimated value
    $930,000

    2645 Vly Ave, Winchester, VA 22601-2625

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    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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    Top Commercial Asset Segments

    Commercial property segments ranked by active listings on the market

    Bed & breakfasts 3

    Demographics Overview

    Population 79K
    Population Growth (5Y) +7.1%
    Median Household Income $82,773
    College Educated 32.0%

    High-Yield Neighborhoods for Investment

    Identify Winchester submarkets with the highest inventory density on the market and evaluate the average listing prices of real estate assets

    Neighborhood Average Price
    22601 $1M

    Taxes & Financing

    Tax Rate (average for all types) 0.50%
    Property Tax per SF $5.70 per SF
    Average Loan-to-Value 65.0%

    Property Size Breakdown

    The majority of commercial real estate listings in Winchester fall within the 100,000+ square foot range.

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