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    Winter Park, FL Duplexes for Sale

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    Income-Producing Duplex in Central Orlando
    $415,000
    1,197 SF

    Income-Producing Duplex in Central Orlando

    1518 Pinewood Dr, Winter Park, FL 32789

    Duplex with detached in-law apartment, ideal for rental.

    • Income‑producing property with detached in‑law apartment, ideal for house hacking or rental income.
    • Prime central Orlando location near Winter Park, College Park, Downtown Orlando, and major amenities.
    • Detached in‑law apartment currently rented for $1,350/month, providing immediate income.
    • Main house previously rented for $1,850/month, demonstrating strong rental history.
    • Separate entrances and mailboxes for both units ensure privacy and flexibility.
    Updated: Mar 3
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    Winter Park Duplex-Style Office Building
    $875,000
    2,456 SF

    Winter Park Duplex-Style Office Building

    2445 Lee Rd, Winter Park, FL 32789

    Renovated duplex-style office building in Winter Park with flexible layout.

    • Prime commercial location in the heart of Winter Park, close to I‑4.
    • Fully renovated, duplex‑style building with two separate office suites.
    • Each suite includes three private offices, a meeting room, bathrooms, and a kitchenette.
    • Low maintenance with 11 dedicated parking spaces and no HOA.
    • Flexible use: occupy one suite and rent the other, or convert to a full investment property.
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    Based on your search, we've compiled 6 Potential Opportunities for your consideration. Besides 2 Active listings in Winter Park, FL, we suggest exploring several alternatives: 4 properties in Nearby Cities

    Explore Opportunities in Nearby Cities

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

    Eatonville Duplex: Investment Opportunity
    $419,900

    Eatonville Duplex: Investment Opportunity

    Duplex in historic Eatonville with recent upgrades and strong rental income.

    385 Lime St, Maitland, FL 32751
    View details
    Updated Duplex in Eatonville
    $419,900
    1,680 SF

    Updated Duplex in Eatonville

    Updated duplex with new roof, HVAC, and updated interiors.

    385 Lime St, Maitland, FL 32751
    View details
    Remodeled Orlando Duplex For Sale
    $475,000
    2,393 SF

    Remodeled Orlando Duplex For Sale

    Fully leased duplex in Orlando with updated features and fenced yards.

    4711 Eggleston Ave, Orlando, FL 32804
    View details
    Renovated Duplex in College Park
    $625,000
    1,853 SF

    Renovated Duplex in College Park

    Income-generating duplex in Orlando's desirable College Park neighborhood.

    731 Guernsey St, Orlando, FL 32804
    View details

    Winter Park, FL Duplexes Investment Opportunities Market Analysis

    Explore 2 duplexes for sale in Winter Park, FL on our real estate platform. These investment opportunities span a total of 8,276 square feet of properties for sale, with an estimated market value of $415,000.

    Sale prices for duplexes in Winter Park, FL start at $415,000, averaging $415,000, and reaching up to $415,000 — 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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