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    Winter Park, FL Duplexes for Sale

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    Income-Producing Duplex with In-Law Apartment
    $489,900
    1,197 SF

    Income-Producing Duplex with In-Law Apartment

    1518 Pinewood Dr, Winter Park, FL 32789

    Income-producing duplex with detached in-law apartment in central Orlando.

    • 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: Jan 6
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    Updated Duplex in Winter Park
    Pending
    $485,000
    2,000 SF

    Updated Duplex in Winter Park

    2608 Dora Ct, Winter Park, FL 32792

    Updated duplex with rental income potential in a prime location.

    • Updated Duplex: Two units, each with 2 bedrooms and 1.5 bathrooms.
    • Income Potential: Tenant in place through 9/30/2025, providing immediate rental income.
    • Renovated Unit: Vacant unit features fresh paint, luxury vinyl plank flooring, granite countertops, stainless steel appliances, and updated bathrooms.
    • Private Outdoor Space: Each unit has a private, fully fenced patio area.
    • No HOA: Enjoy the property without HOA fees or restrictions.
    Updated: Oct 3, 2025
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    Income-Producing Duplex in Winter Park
    Pending
    $485,000
    2,000 SF

    Income-Producing Duplex in Winter Park

    Winter Park duplex with renovated unit and tenant-occupied unit.

    131 Stefanik Rd, Winter Park, FL 32792
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    Winter Park Duplex with Suites
    $1,215,000
    2,284 SF

    Winter Park Duplex with Suites

    Duplex in Winter Park near Park Avenue and Winter Park Golf Course.

    726 N Pennsylvania Ave, Winter Park, FL 32789
    View details
    Based on your search, we've compiled 8 Potential Opportunities for your consideration. Besides 4 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
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    Maitland Duplex Near Sunrail Station
    $699,900

    Maitland Duplex Near Sunrail Station

    Duplex in Maitland near Sunrail, great investment opportunity.

    933 Robinhood Ct, Maitland, FL 32751
    View details
    Orlando Duplex with Updated Plumbing
    Pending
    $485,000
    1,772 SF

    Orlando Duplex with Updated Plumbing

    Spacious duplex in central Orlando with updated plumbing and new roof.

    5540 Charleston St, Orlando, FL 32807
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    Orlando Duplex: Investment Opportunity
    Pending
    $589,000
    1,626 SF

    Orlando Duplex: Investment Opportunity

    Well-maintained Orlando duplex near downtown with rental income potential.

    1104 Hardy Ave, Orlando, FL 32803
    View details

    Winter Park, FL Duplexes Investment Opportunities Market Analysis

    Explore 4 duplexes for sale in Winter Park, FL, showcased through 4 active listings on our real estate platform. These investment opportunities span a total of 31,799 square feet of properties for sale, with an estimated market value of $2,674,900.

    Prices for duplexes in Winter Park, FL start at $485,000, averaging $668,725, and reaching up to $1,215,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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    Most Searched ZIP Codes in Winter Park, FL

    • 32792
    • 32789

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