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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 DRIVE, 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: Dec 26, 2025
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    Winter Park Duplex-Style Office Building
    $875,000
    2,456 SF

    Winter Park Duplex-Style Office Building

    2445 LEE ROAD, 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.
    Updated: Mar 12
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    Based on your search, we've compiled 10 Potential Opportunities for your consideration. Besides 2 Active listings in Winter Park, FL, we suggest exploring several alternatives: 4 properties in Nearby Cities, 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.

    Renovated Duplex in College Park
    $810,000
    1,742 SF

    Renovated Duplex in College Park

    Turn-key duplex investment opportunity in Orlando's College Park District.

    101 E WINTER PARK STREET, Orlando, FL 32804
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    Orlando Duplex: Income Potential
    $600,000
    1,390 SF

    Orlando Duplex: Income Potential

    Two homes on one property in College Park, Florida.

    235/237 EMORY PLACE, Orlando, FL 32804
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    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 AVENUE, Orlando, FL 32804
    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 STREET, Maitland, FL 32751
    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.

    Winter Park Commercial Land Available
    $1,795,000

    Winter Park Commercial Land Available

    Land with frontage on Formosa and Kentucky Avenues.

    700 Formosa Ave, Winter Park, FL 32789
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    Orlando Mixed-Use Development Opportunity
    $4,900,000

    Orlando Mixed-Use Development Opportunity

    6.9-acre Orlando portfolio with mixed-use zoning and income potential.

    4421 Edgewater Dr, Orlando, FL 32804
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    Commercial Land in Winter Park
    $190,000
    0.05 Acres

    Commercial Land in Winter Park

    Commercial land available in Winter Park, Florida.

    669 W COMSTOCK AVENUE, Winter Park, FL 32789
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    Winter Park Land Opportunity
    Contact for pricing
    0.44 Acres

    Winter Park Land Opportunity

    Land for sale in the heart of Winter Park.

    2161 N Park Ave, Winter Park, FL
    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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