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    Winchester, VA Short Term Rental Properties for Sale

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    Stephenson, VA Berryville, VA Boyce, VA Clear Brook, VA Stephens City, VA White Post, VA Gore, VA Summit Point, WV
    Boutique Vineyard & Winery Estate
    Updated: Jul 24
    Boutique Vineyard & Winery Estate

    450 GREEN SPRING Rd, Winchester, VA 22603

    $3,500,000
    Briede Family Vineyards boutique vineyard and winery estate with established vineyard and winery operations
    Tasting room plus adjoining great room for tastings, private gatherings, and special events
    Covered pavilion overlooking the vineyard for outdoor events and live entertainment
    Country residence (built in 2000) currently operating as a licensed short‑term rental
    Property acreage includes 3 additional building lots with approved well and septic (subject to applicable approvals)
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    Turn Any Listing Into an Investment Snapshot Owner equity, real caprate, demand score for every listing. Go To Analytics Center
    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.

    Triplex with Detached Rental Units
    Triplex with Detached Rental Units

    64-86-108 BEAMER Lane, Harpers Ferry, WV 25425

    $724,995
    3,623 sqft 1.74 AC lot

    Three detached units on one parcel, including two operating short-term rentals with 3 bed/1 bath layouts and one vacant unit.

    View details
    Mixed-Use Restaurant Building
    Mixed-Use Restaurant Building

    200 East Main Street, Hancock, MD 21750

    $325,000
    5,490 sqft

    Restaurant building with three apartments above, offered for sale as real estate only.

    View details
    Three-Unit Income Property
    Three-Unit Income Property

    64-86-108 BEAMER Ln, Harpers Ferry, WV 25425

    $724,995

    Three detached rental units on one parcel, including two short-term rentals and one long-term leased unit.

    View details
    Mixed-Use Income Building
    Mixed-Use Income Building

    134 W Main St, Hancock, MD 21750

    Contact for pricing

    Large building on W Main St with a wide open interior layout and multiple residential use options.

    View details

    Winchester, VA Short Term Rental Properties Market Trends and Statistics

    Explore 1 short term rental properties for sale in Winchester, VA on our real estate platform.

    Sale prices for short term rental properties in Winchester, VA average $3,500,000 — 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

    Apartment buildings 6
    Duplexes 4
    Quadplexes 2
    Short term rental properties 1
    Triplexes 1

    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 $605K

    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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