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    Winchester, VA Residential Income Properties for Sale

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    Richmond, VA Fredericksburg, VA Roanoke, VA
    17 results
    Charming Duplex in Winchester, VA
    $599,900
    3,511 SF

    Charming Duplex in Winchester, VA

    1400 VALLEY Avenue, Winchester, VA 22601

    Versatile duplex with historic charm and income potential.

    • Income‑generating duplex with a reliable tenant already in place.
    • Front unit ideal for owner‑occupancy, boasting historic charm with wood floors, tall ceilings, fireplace, and a stunning staircase. Enjoy the sunroom.
    • Recent updates include a new roof and gutters (installed last year) and updated bathrooms with walk‑in tiled showers.
    • Separate utilities for each unit (except water/sewer).
    • Heating converted to natural gas with new boilers installed in 2011.
    Updated: Apr 13
    View details
    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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    Renovated Duplex Near Walking Mall
    $625,000
    1,948 SF

    Renovated Duplex Near Walking Mall

    Upgraded duplex near Winchester's historic Walking Mall, fully renovated in 2022.

    446 N LOUDOUN Street, Winchester, VA 22601
    View details
    Winchester Multi-Family Investment Opportunity
    $699,900
    0.17 Acres

    Winchester Multi-Family Investment Opportunity

    Three-unit property in Winchester, fully rented and well-maintained.

    434 FAIRMONT AVE, Winchester, VA 22601
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    Mixed-Use Property in Historic Downtown
    $1,500,000
    0.42 Acres

    Mixed-Use Property in Historic Downtown

    Versatile B1-zoned property with income and redevelopment potential.

    314 N BRADDOCK Street, Winchester, VA 22601
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    Rehabbed Duplex Near Old Town
    $299,000
    1,249 SF

    Rehabbed Duplex Near Old Town

    Low-maintenance duplex with strong rental income near historic Old Town.

    45 and 45 1/2 RACE Street, Winchester, VA 22601
    View details
    Turnkey Multifamily Investment Opportunity
    $699,900

    Turnkey Multifamily Investment Opportunity

    Three-unit property, fully rented, well-maintained, near downtown.

    434 FAIRMONT Ave, Winchester, VA 22601
    View details
    Downtown Mixed-Use Redevelopment Opportunity
    $1,500,000
    7,000 SF

    Downtown Mixed-Use Redevelopment Opportunity

    B1-zoned property with income, redevelopment potential, and downtown location.

    314 N Braddock St, Winchester, VA 22601
    View details
    Charming Duplex: Investor Opportunity
    $325,000
    1,478 SF

    Charming Duplex: Investor Opportunity

    Turnkey duplex with excellent cash flow and private yard.

    433-435 Bryarly Road, Winchester, VA 22603
    View details
    Approved Mixed-Use Development Opportunity
    $449,000
    0.09 Acres

    Approved Mixed-Use Development Opportunity

    Approved mixed-use development site in downtown Winchester, Virginia.

    1 N BRADDOCK Street, Winchester, VA 22601
    View details
    16-Unit Apartment Building Near Park
    $2,490,000
    0.50 Acres

    16-Unit Apartment Building Near Park

    Fully occupied apartment building with long-term tenants and off-street parking.

    600 -612 Smithfield Ave, Winchester, VA 22601
    View details
    Remodeled Multi-Unit Property For Sale
    $1,850,000
    7,190 SF

    Remodeled Multi-Unit Property For Sale

    Completely remodeled multi-unit property with garage and high rental income.

    908 Cedar Creek Grade, Winchester, VA 22601
    View details
    Renovated Winchester Home Near I-81
    $359,800

    Renovated Winchester Home Near I-81

    Renovated home with B2 zoning near Interstate 81.

    148 Amoco Lane, Winchester, VA 22603
    View details
    Mixed-Use Building Near Walking Mall
    $229,900
    0.08 Acres

    Mixed-Use Building Near Walking Mall

    Two-story mixed-use building near Winchester Downtown Walking Mall.

    109 S Kent St, Winchester, VA 22601
    View details
    Approved Mixed-Use Development Opportunity
    $449,000
    1,340 SF

    Approved Mixed-Use Development Opportunity

    Approved mixed-use site plan in downtown Winchester, Virginia.

    1 N Braddock St, Winchester, VA 22601
    View details
    4.20 Acres with Rental Income
    $1,200,000
    4.20 Acres

    4.20 Acres with Rental Income

    4.20 acres with income-producing dwellings near downtown Winchester.

    3266 Valley Pike, Winchester, VA 22602
    View details
    Mixed-Use Building Near Walking Mall
    $249,900
    1,779 SF

    Mixed-Use Building Near Walking Mall

    Two-story mixed-use building near Winchester Downtown Walking Mall.

    109 S Kent St, Winchester, VA 22601
    View details
    Based on your search, we've compiled Potential Opportunities for your consideration. Besides 17 Active Listings in Winchester, VA, we suggest to view alternatives - similar 494 Off-Market properties to explore as potential leads.

    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.

    308 Smithfield Ave

    308 Smithfield Ave

    APARTMENT HOUSE (UNDER 5 UNITS) • 1,307 SF
    Value Estimation by Request
    308 Smithfield Ave, Winchester, VA 22601-5248
    View details
    329 National Ave

    329 National Ave

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,288 SF
    Value Estimation by Request
    329 National Ave, Winchester, VA 22601-5208
    View details
    422 Braddock St

    422 Braddock St

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,416 SF
    Value Estimation
    $535,000
    422 Braddock St, Winchester, VA 22601-3922
    View details
    821 Pennsylvania Ave

    821 Pennsylvania Ave

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,072 SF
    Value Estimation by Request
    821 Pennsylvania Ave, Winchester, VA 22601-4957
    View details
    45 Race St

    45 Race St

    APARTMENT HOUSE (UNDER 5 UNITS) • 1,248 SF
    Value Estimation by Request
    45 Race St, Winchester, VA 22601-5320
    View details
    301 Braddock St

    301 Braddock St

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,040 SF
    Value Estimation by Request
    301 Braddock St, Winchester, VA 22601-4180
    View details
    680 Berryville Ave

    680 Berryville Ave

    APARTMENT HOUSE (UNDER 5 UNITS) • 1,672 SF
    Value Estimation by Request
    680 Berryville Ave, Winchester, VA 22601-5665
    View details

    Winchester, VA Residential Income Properties Investment Opportunities Market Analysis

    Explore 511 residential income properties for sale in Winchester, VA, showcased through 17 active listings on our real estate platform. These investment opportunities span a total of 2,594,491 square feet of properties for sale, with an estimated market value of $142,672,800.

    Sale prices for residential income properties in Winchester, VA start at $95,000, averaging $339,697, and reaching up to $19,195,000 — 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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