Add Listing
    For Sale
    • For Sale
    • For Lease
    • Recently Sold
    • Property Lookup
    • Brokers
    Specialty
    1
    • Retail
    • Office
    • Residential Income
    • Restaurants
    • Industrial
    • Mixed-Use
    • Hospitality
    • Health Care
    • Sports & Entertainment
    • Land
    • Agricultural
    • Specialty
    Price
    Price range
    $
    $
    Size
    Property size / sq.ft.
    AI Search

    Winchester, VA Specialty Properties for Sale

    Notify Me
    List
    Map
    Downtown Winchester Triplex Investment Opportunity
    $605,000
    4,396 SF

    Downtown Winchester Triplex Investment Opportunity

    540 MONTICELLO Street, Winchester, VA 22601

    Turnkey triplex in downtown Winchester with strong cash flow.

    • Turnkey triplex investment property with all units currently leased, providing immediate and reliable income.
    • Prime downtown Winchester location, commuter‑friendly with easy access to I‑81 and I‑66, and proximity to Northern Virginia.
    • Diverse unit mix: two 2‑bedroom units with updated finishes and laundry, plus a large 5‑bedroom unit with a unique two‑level layout and private outdoor space.
    • 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 2025), minimizing immediate maintenance concerns.
    Updated: Feb 17
    View details
    Medical Condo Suite For Sale
    $1,385,000
    6,200 SF

    Medical Condo Suite For Sale

    142 LINDEN DRIVE 106-107, Winchester, VA 22601

    Fully-leased medical condo suite near Winchester Medical Center.

    • Fully‑Leased Medical Condo Suite
    • Located Adjacent to Winchester Medical Center
    • Multi‑Year Leases in Place with Established Practitioners
    • Excellent Condition, Fully Updated, Easy to Maintain
    • Prominent, Highly Visible Location with Ample Parking
    Updated: Mar 11
    View details
    Land For Sale Winchester, VA
    Contact for pricing

    Land For Sale Winchester, VA

    Land available for purchase in Winchester, Virginia.

    Winchester, VA 22602
    View details
    Established Garden Center For Sale
    $899,000
    33,000 SF

    Established Garden Center For Sale

    Operating garden center with over 33,000 sq ft under roof.

    2731 Front Royal Pike, Winchester, VA 22602
    View details
    Premium Hangars at Winchester Airport
    $665,000

    Premium Hangars at Winchester Airport

    Premium customizable hangars for sale near Washington, D.C.

    741 Airport Rd #2, Winchester, VA 22602
    View details
    Based on your search, we've compiled 25 Potential Opportunities for your consideration. Besides 5 Active listings in Winchester, VA, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 12 Off-Market properties to explore as potential leads, 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.

    Martinsburg Commercial Land Near Airport
    $200,000
    1.19 Acres

    Martinsburg Commercial Land Near Airport

    1.19 acre commercial lot near Interstate 81 and airport.

    NOVAK Drive lot: B2, Martinsburg, WV 25405
    View details
    Martinsburg Commercial Land Near Airport
    $150,000
    1.12 Acres

    Martinsburg Commercial Land Near Airport

    1.12 acre commercial lot near Interstate 81 and airport.

    NOVAK Drive lot: B1, Martinsburg, WV 25405
    View details
    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
    7.79-Acre Commercial Land Investment
    $879,000

    7.79-Acre Commercial Land Investment

    Prime land near future I-81 interchange with rental income.

    349 Town Run Ln, Stephens City, VA 22655
    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.

    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
    View details
    Martinsburg Development Land For Sale
    $469,900
    6.64 Acres

    Martinsburg Development Land For Sale

    Development-ready land in Martinsburg with approved site plan.

    BALTIMORE & BOSTON ST, Martinsburg, WV 25401
    View details
    Gainesville, VA Raw Land
    $1,060,800
    6.24 Acres

    Gainesville, VA Raw Land

    6.24 acres of raw land on James Madison Highway.

    7503 JAMES MADISON Highway, Gainesville, VA 20155
    View details
    Redevelopment Opportunity in Western Maryland
    $550,000
    14.58 Acres

    Redevelopment Opportunity in Western Maryland

    14-acre commercial property with redevelopment potential near Cumberland, Maryland.

    10105 COTTAGE INN Lane NE, Cumberland, MD 21502
    View details

    Explore 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.

    1400 Millwood Pike

    1400 Millwood Pike

    COMMERCIAL MISC • 5,984 SF
    Value Estimation
    $7,690,000
    1400 Millwood Pike, Winchester, VA 22602-4320
    View details
    3257 Vly Pike

    3257 Vly Pike

    COMMERCIAL MISC • 1,200 SF
    Value Estimation by Request
    3257 Vly Pike, Winchester, VA 22602
    View details
    1186 Millwood Pike

    1186 Millwood Pike

    COMMERCIAL MISC • 1,660 SF
    Value Estimation by Request
    1186 Millwood Pike, Winchester, VA 22602-4314
    View details
    230 Airport Rd

    230 Airport Rd

    COMMERCIAL MISC • 6,100 SF
    Value Estimation
    $690,000
    230 Airport Rd, Winchester, VA 22602-4569
    View details
    116 Piccadilly St

    116 Piccadilly St

    Land
    Value Estimation by Request
    116 Piccadilly St, Winchester, VA 22601
    View details
    141 Security Dr

    141 Security Dr

    COMMERCIAL MISC • 110,584 SF
    Value Estimation
    $17,960,000
    141 Security Dr, Winchester, VA 22602-4672
    View details
    1025 Martinsburg Pike

    1025 Martinsburg Pike

    COMMERCIAL MISC • 1,536 SF
    Value Estimation by Request
    1025 Martinsburg Pike, Winchester, VA 22601-4978
    View details
    133 Lincoln St

    133 Lincoln St

    DAY CARE, PRE-SCHOOL • 3,411 SF
    Value Estimation by Request
    133 Lincoln St, Winchester, VA 22601-5207
    View details
    414 Kent St

    414 Kent St

    PROFESSIONAL CLUBS/ASSOCIATIONS • 5,258 SF
    Value Estimation by Request
    414 Kent St, Winchester, VA 22601-5046
    View details
    533 Fremont St

    533 Fremont St

    DAY CARE, PRE-SCHOOL • 4,760 SF
    Value Estimation by Request
    533 Fremont St, Winchester, VA 22601-5341
    View details
    115 Featherbed Ln

    115 Featherbed Ln

    VETERINARY, ANIMAL HOSPITAL • 2,794 SF
    Value Estimation by Request
    115 Featherbed Ln, Winchester, VA 22601-4486
    View details
    509 Airport Rd

    509 Airport Rd

    COMMERCIAL MISC • 33,800 SF
    Value Estimation
    $5,490,000
    509 Airport Rd, Winchester, VA 22602-7340
    View details

    Winchester, VA Specialty Properties Investment Opportunities Market Analysis

    Explore 17 specialty properties for sale in Winchester, VA, showcased through 5 active listings on our real estate platform. These investment opportunities span a total of 5,406,998 square feet of properties for sale, with an estimated market value of $14,680,000.

    Sale prices for properties in Winchester, VA start at $245,000, averaging $1,835,000, and reaching up to $9,180,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

    List
    Map

    Browse Specialty properties for Sale Near Winchester, VA

    Popular Searches in Winchester, VA

    Popular Categories

    Most Searched ZIP Codes in Winchester, VA

    • 22602
    • 22601

    Select Neighborhood

    Google sign-in failed. Please try again or use another login method.
    Sign Up Successful!
    You now have access to more from Realmo!