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    Winter Park, FL Multifamily Properties for Sale

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    Orlando, FL Maitland, FL Casselberry, FL
    Winter Park Income-Producing Duplex
    $675,000
    1,604 SF

    Winter Park Income-Producing Duplex

    1618 INDIANA AVENUE, Winter Park, FL 32789

    Well-maintained duplex in Winter Park, great investment opportunity.

    • Prime Winter Park location, minutes from Park Avenue, shopping, and dining.
    • Income‑producing duplex, ideal for investors or owner‑occupants.
    • Two well‑maintained units, each with 2 bedrooms and 1 bathroom.
    • Each unit has a dedicated utility room.
    • Functional layouts with comfortable living spaces in both units.
    Updated: Apr 13
    View details
    Winter Park Duplex Near Park Avenue
    $1,185,999
    2,282 SF

    Winter Park Duplex Near Park Avenue

    726/720 N PENNSYLVANIA AVENUE, Winter Park, FL 32789

    Duplex near Park Avenue with strong rental income potential.

    • Prime location: Walk to Park Avenue, minutes from Rollins College in a high‑demand rental area.
    • Income potential: Two 3‑bedroom, 2‑bathroom units are ideal for rental income or owner‑occupancy with rental offset.
    • Modern amenities: Enjoy open‑concept layouts, stone countertops, stainless steel appliances, and in‑unit laundry.
    • Durable & appealing design: Features wood and tile flooring, custom cabinetry, and private fenced patios.
    • Winter Park Country Club membership: Included membership enhances appeal.
    Updated: Apr 27
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    Charming Income-Producing Multifamily Property
    $650,000

    Charming Income-Producing Multifamily Property

    Income-producing property with main house, studio office, and apartment.

    352 CAMBRIDGE Blvd, Winter Park, FL 32789
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    Winter Park Duplex-Style Office Building
    $875,000
    2,456 SF

    Winter Park Duplex-Style Office Building

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

    2445 LEE ROAD, Winter Park, FL 32789
    View details
    Based on your search, we've compiled 14 Potential Opportunities for your consideration. Besides 4 Active listings in Winter Park, FL, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 2 Off-Market properties to explore as potential leads, plus 4 Land Listings that present a potential for development.

    Opportunities in Nearby Cities

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

    Updated Duplex in College Park
    $600,000
    1,316 SF

    Updated Duplex in College Park

    Well-maintained duplex with updated units and private backyard.

    2513 MUSSELWHITE AVENUE, Orlando, FL 32804
    View details
    Turn-Key Duplex Investment Opportunity
    $725,000
    1,742 SF

    Turn-Key Duplex Investment Opportunity

    Renovated duplex in College Park District, ideal for income.

    101 E WINTER PARK STREET, Orlando, FL 32804
    View details
    Maitland Mixed-Use Development Opportunity
    $3,500,000
    15,777 SF

    Maitland Mixed-Use Development Opportunity

    29-unit multifamily with commercial building and lot for development.

    421 E KENNEDY BOULEVARD, Maitland, FL 32751
    View details
    College Park Income Property
    $575,000
    1,756 SF

    College Park Income Property

    Full duplex with attached efficiency unit in College Park.

    2515 FORMOSA AVENUE, Orlando, FL 32804
    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.

    Casselberry Land For Sale
    $144,999

    Casselberry Land For Sale

    Land available in Casselberry, Florida.

    1329 LAKE DRIVE, Casselberry, FL 32707
    View details
    Waterfront Development Property in Orlando
    Contact for pricing

    Waterfront Development Property in Orlando

    Largest waterfront development property in Central Florida with extensive frontage.

    19543 E Colonial Dr, Orlando, FL 32820
    View details
    Premium Water View RV Lot
    $135,000
    0.06 Acres

    Premium Water View RV Lot

    40x60 RV lot in 55+ gated community.

    21-20285 Us Highway 27, Clermont, FL 34714
    View details
    EUSTIS, FL Corner Lot
    Contact for pricing
    0.15 Acres

    EUSTIS, FL Corner Lot

    Corner lot suitable for a home, mobile, or manufactured home.

    40850 PINE TREE LANE, Eustis, FL 32736
    View details

    Off-Market Properties in Winter Park, FL

    Consider similar Off-Market properties in Winter Park, FL. 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.

    1099 Clay St
    HIGH-RISE APARTMENTS
    131,680 SF Lot: 0.16 Acres
    Estimated value
    $3,600,000

    1099 Clay St, Winter Park, FL 32789-5474

    View details
    500 Knowles Ave
    BOARDING/ROOMING HOUSE
    4,518 SF Lot: 0.27 Acres
    Estimated value
    $600,000

    500 Knowles Ave, Winter Park, FL 32789-3231

    View details

    Winter Park, FL Multifamily Properties Investment Opportunities Market Analysis

    Explore 6 multifamily properties for sale in Winter Park, FL, showcased through 4 active listings on our real estate platform. These investment opportunities span a total of 6,342 square feet of properties for sale, with an estimated market value of $2,735,999.

    Sale prices for multifamily properties in Winter Park, FL start at $675,000, averaging $911,999, and reaching up to $1,185,999 — 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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    Top Commercial Asset Segments

    Duplexes 3

    Property Size Breakdown

    The majority of commercial real estate listings in Winter Park fall within the 100,000+ square foot range.

    Demographics Overview

    Population 80K
    Population Growth (5Y) +2.4%
    Median Household Income $77,660
    College Educated 37.4%

    High-Yield Neighborhoods for Investment

    Identify Winter Park submarkets with the highest inventory density on the market and evaluate the median listing prices of real estate assets

    Neighborhood Average Price
    32789 $846.5K

    Taxes & Financing

    Tax Rate (average for all types) 1.38%
    Property Tax per SF $12.70 per sq ft
    Tax Rate vs County Average 0.18 pp below county avg
    Average Loan-to-Value 65.0%

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