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    Winchester, VA Bed & Breakfasts for Sale

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    Stephenson, VA Stephens City, VA Clear Brook, 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 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.

    Opportunities in Nearby Cities

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

    Leesburg Land with Event Barn
    $1,295,000
    3,800 SF
    Leesburg Land with Event Barn

    18-acre Leesburg property with barn, dwelling, and development potential.

    14558 CHAPEL Lane, Leesburg, VA 20176

    View details
    Unique Loudoun Property in Wine Country
    $1,295,000
    3,800 SF
    Unique Loudoun Property in Wine Country

    Scenic property ideal for home, event venue, or agritourism.

    14558 Chapel Ln, Leesburg, VA 20176

    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

    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.

    Land on Route 3
    $45,000
    2.00 Acres
    Land on Route 3

    Two-acre lot with road frontage, potential for B&B.

    Mary Ball Road, White Stone, VA 22578

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    Land with Rental Income Potential
    $1,299,900
    Land with Rental Income Potential

    Large parcel zoned for business with existing rental income.

    1021-1025-1029 S 47 Route lot: 37,38,36, Rio Grande, NJ 08242

    View details
    Pocono Lake Acreage Opportunity
    Contact for pricing
    1.06 Acres
    Pocono Lake Acreage Opportunity

    1+ acre lot near Poconos attractions, short-term rental potential.

    Oak Leaf Ln 25, Pocono Lake, PA 18347

    View details
    Waterfront Multifamily with Marina Potential
    $1,200,000
    Waterfront Multifamily with Marina Potential

    Unique waterfront multifamily with marina potential near casinos and beaches.

    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 7,650 square feet of properties for sale, with an estimated market value of $649,000.

    Sale prices for inns 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

    Bed & breakfasts 3

    Property Size Breakdown

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

    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 median 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 sq ft
    Average Loan-to-Value 65.0%

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