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    Winchester, VA Short Term Rental Properties for Sale

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    Stephenson, VA Stephens City, VA Clear Brook, VA
    Turnkey Winchester Triplex Investment Opportunity
    $605,000
    4,396 SF

    Turnkey Winchester Triplex Investment Opportunity

    540 MONTICELLO Street, Winchester, VA 22601

    Triplex in downtown Winchester with strong cash flow potential.

    • Turnkey triplex investment property with all units currently leased, providing immediate and reliable income.
    • Prime downtown Winchester location, offering convenience and commuter access to I‑81, I‑66, and Northern Virginia.
    • Diverse unit mix: two 2‑bedroom units with updated kitchens, laundry rooms, and a large 5‑bedroom unit with a unique two‑level layout, private patio, and deck.
    • Recent renovations including LVP flooring, fresh paint, updated kitchens and baths, and newer appliances in each unit.
    • Newer roof (less than 3 years old) and new HVAC system (installed in 2025).
    Updated: Feb 17
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    Based on your search, we've compiled 5 Potential Opportunities for your consideration. Besides 1 Active listings in Winchester, VA, we suggest exploring several alternatives: 4 properties in Nearby Cities

    Opportunities in Nearby Cities

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

    Mountain View Cabins - Luray
    $1,349,900
    6,730 SF

    Mountain View Cabins - Luray

    Two furnished cabins on 9.5 acres, ideal short-term rentals.

    2225 & 2319 VALLEY BURG RD, Luray, VA 22835
    View details
    Unrestricted Land with Mountain Views
    $269,900
    5.20 Acres

    Unrestricted Land with Mountain Views

    5.2 acres with potential for Airbnb, business, or dream home.

    187 SUNNY MEADOW Place, Berkeley Springs, WV 25411
    View details
    Berkeley Springs Mixed-Use Investment
    $1,500,000
    0.27 Acres

    Berkeley Springs Mixed-Use Investment

    Premier mixed-use property in downtown Berkeley Springs, fully renovated.

    33 Washington St N, Berkeley Springs, WV 25411
    View details
    Boutique Hotel Investment Opportunity
    $1,999,000
    11,000 SF

    Boutique Hotel Investment Opportunity

    Hospitality property with 12 boutique rooms in Luray, Virginia.

    2 S Court St, Luray, VA 22835
    View details

    Winchester, VA Short Term Rental Properties Investment Opportunities Market Analysis

    Explore 1 short term rental properties for sale in Winchester, VA on our real estate platform. These investment opportunities span a total of 4,396 square feet of properties for sale, with an estimated market value of $605,000.

    Sale prices for short term rental properties in Winchester, VA start at $605,000, averaging $605,000, and reaching up to $605,000 — 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

    Apartment buildings 9
    Triplexes 5
    Duplexes 3
    Quadplexes 2
    Short term rental properties 1

    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 $605K

    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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