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3 bedsHouses
95 listings

Apartments and Houses for Rent in Winter Park, FL

Apartments and Houses for Rent in Winter Park, FL

Show Map
24 of 95 Listings
Map

Apartments and Houses for Rent in Winter Park, FL

24 of 95 Listings

  1. 1824 Howell Branch Rd — photoNew16
Active

$2,000/mo

2 bd · 1 ba · 1,100 sqft

1824 Howell Branch Rd, Winter Park, FL

Asher Chen · AAA GLOBAL VENTURES PA

  • 1695 Lee Rd #E103 — photoNew15Active

    $1,600/mo

    2 bd · 1 ba · 881 sqft

    1695 Lee Rd #E103, Winter Park, FL

    Jason Price · RE/MAX SELECT GROUP

  • 1415 Harmon Ave — photo34Active

    $3,600/mo

    3 bd · 3 ba · 1,753 sqft

    1415 Harmon Ave, Winter Park, FL

    Lukasz Sokolowski · HOST MANAGEMENT GROUP LLC

  • 2500 Lee Rd #145 — photo12Active

    $1,099/mo

    1 bd · 1 ba · 645 sqft

    2500 Lee Rd #145, Winter Park, FL

    Jason Hamilton · THE REALTY MEDICS

  • 300 N Knowles Ave 214 — photo8Active

    $1,750/mo

    2 bd · 1 ba · 1,100 sqft

    300 N Knowles Ave 214, Winter Park, FL

    Robert Bush · Property Professionals, Inc.

  • 7444 Woodburn Ct #29 — photo8Active

    $1,585/mo

    2 bd · 3 ba · 1,031 sqft

    7444 Woodburn Ct #29, Winter Park, FL

    Abranette Lopez · LPT REALTY, LLC

  • 1954 Spring St — photo30Active

    $1,900/mo

    3 bd · 2 ba · 1,230 sqft

    1954 Spring St, Winter Park, FL

    Irina Paul, LLC · FUTURE HOME REALTY INC

  • 735 Minnesota Ave — photo10Active

    $3,995/mo

    3 bd · 4 ba · 1,810 sqft

    735 Minnesota Ave, Winter Park, FL

    Marilyn Kuczynski · FLORIDA HOMES SALES & MANAGEMENT LLC

  • 7262 Swallow Run #7262 — photo18Active

    $1,600/mo

    2 bd · 2 ba · 756 sqft

    7262 Swallow Run #7262, Winter Park, FL

    Karla Pacheco · LUMINA PROPERTY MANAGEMENT LLC

  • listing photo54Active

    $6,495/mo

    5 bd · 2 ba · 2,750 sqft

    Address withheld · Winter Park, FL

    Monica Vega Stiskin, LLC · PREFERRED REAL ESTATE BROKERS

  • 690 Osceola Ave #407 — photo30Active

    $2,200/mo

    1 bd · 2 ba · 915 sqft

    690 Osceola Ave #407, Winter Park, FL

    Delaney Heidenescher · CREEGAN GROUP

  • 737 Minnesota Ave — photo10Active

    $3,995/mo

    3 bd · 4 ba · 1,810 sqft

    737 Minnesota Ave, Winter Park, FL

    Marilyn Kuczynski · FLORIDA HOMES SALES & MANAGEMENT LLC

  • 300 N Knowles Ave 205 — photo5Active

    $1,330/mo

    0 bd · 1 ba · 475 sqft

    300 N Knowles Ave 205, Winter Park, FL

    Robert Bush · Property Professionals, Inc.

  • 1603 Winter Green Blvd — photoPrice Reduced17Active

    $1,950/mo

    3 bd · 2 ba · 1,096 sqft

    1603 Winter Green Blvd, Winter Park, FL

    Nancy Guadagnino · SPECIALIZED PROPERTY MANAGEMENT

  • 307 Sandlewood Trl — photo15Active

    $1,895/mo

    2 bd · 3 ba · 960 sqft

    307 Sandlewood Trl, Winter Park, FL

    Matthew Kirsch · REAL PROPERTY MANAGEMENT AND REALTY

  • 2941 Antique Oaks Cir #80 — photo12Active

    $1,525/mo

    2 bd · 2 ba · 1,018 sqft

    2941 Antique Oaks Cir #80, Winter Park, FL

    Summer Hornburg · BELMONT REALTY

  • listing photo18Active

    $2,200/mo

    3 bd · 2 ba · 1,266 sqft

    Address withheld · Winter Park, FL

    Kirsten Cantello · TRUSTHOME PROPERTIES INC

  • 2503 Tahoe Cir #2503 — photo24Active

    $1,900/mo

    2 bd · 2 ba · 1,173 sqft

    2503 Tahoe Cir #2503, Winter Park, FL

    Carissa Lawhun · FLORIDA REALTY INVESTMENTS

  • 2300 Barbados Dr — photo45Active

    $2,149/mo

    2 bd · 3 ba · 1,250 sqft

    2300 Barbados Dr, Winter Park, FL

    Cristian Cen Chen · SIMPSON REALTY LLC

  • 440 Clarendon Ave — photo47Active

    $8,500/mo

    4 bd · 4 ba · 3,184 sqft

    440 Clarendon Ave, Winter Park, FL

    Meg Dolan · FANNIE HILLMAN & ASSOCIATES

  • 7487 Canford Ct #5 — photo20Active

    $2,300/mo

    4 bd · 3 ba · 1,611 sqft

    7487 Canford Ct #5, Winter Park, FL

    Jiny Lee · THE FLORIDA LOUNGE REALTY LLC

  • 2305 Shadowland Loop — photo26Active

    $2,800/mo

    3 bd · 3 ba · 2,378 sqft

    2305 Shadowland Loop, Winter Park, FL

    Laura Lerma · 2 GOOD REALTY

  • 800 W Canton Ave — photo30Active

    $2,500/mo

    2 bd · 1 ba · 924 sqft

    800 W Canton Ave, Winter Park, FL

    Kelly Price · KELLY PRICE & COMPANY LLC

  • 7453 Daniel Webster Dr #a5 — photo18Active

    $1,600/mo

    2 bd · 2 ba · 1,063 sqft

    7453 Daniel Webster Dr #a5, Winter Park, FL

    Laila Dkhissi · LA ROSA REALTY PREMIER LLC

  • 12…4

    Explore Winter Park rentals

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    • Rentals Under $2,000/mo
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    Equal Housing OpportunityEqual Housing Lender

    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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    Listing data & MLS disclosures

    MIAMI REALTORS MLS
    The multiple listing information is provided by MIAMI Association of Realtors® from a copyrighted compilation of listings. The compilation of listings and each individual listingare ©2026 MIAMI Association of Realtors®. All Rights Reserved.
    The information provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Last Updated: 2026-10-06 04:01:36 UTC
    Stellar MLS
    Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

    Winter Park, FL community profile

    Population
    31,855
    Median income
    $98,252
    Housing units
    15,404
    People per sq. mi.
    1,409.5
    Area
    22.6 sq. mi.

    Source: HJN community data

    Apartments and Houses for Rent in Winter Park, FL | Realty.com