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Apartments and Houses for Rent in Winter Park, FL | Realty.com
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200 listings
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3 bedsHouses

Apartments and Houses for Rent in Winter Park, FL

Apartments and Houses for Rent in Winter Park, FL

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24 of 200 Listings
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Apartments and Houses for Rent in Winter Park, FL

24 of 200 Listings

  1. 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.

  2. 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

  3. 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

  4. 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

  5. 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

  6. 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

  7. 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

  8. 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

  9. 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

  10. 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.

  11. 1603 Winter Green Blvd — photo17Active

    $1,999/mo

    3 bd · 2 ba · 1,096 sqft

    1603 Winter Green Blvd, Winter Park, FL

    Nancy Guadagnino · SPECIALIZED PROPERTY MANAGEMENT

  12. 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

  13. 440 Clarendon Avenue — photo47Active

    $8,500/mo

    4 bd · 4 ba · 3,184 sqft

    440 Clarendon Avenue, Winter Park, FL

    Meg Dolan · FANNIE HILLMAN & ASSOCIATES

  14. listing photo18Active

    $2,200/mo

    3 bd · 2 ba · 1,266 sqft

    Address withheld · Winter Park, FL

    Kirsten Cantello · TRUSTHOME PROPERTIES INC

  15. 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

  16. 2300 Barbados Drive — photo45Active

    $2,149/mo

    2 bd · 3 ba · 1,250 sqft

    2300 Barbados Drive, Winter Park, FL

    Cristian Cen Chen · SIMPSON REALTY LLC

  17. listing photo18Active

    $2,200/mo

    3 bd · 2 ba · 1,266 sqft

    Address withheld · Winter Park, FL

    Kirsten Cantello · TRUSTHOME PROPERTIES INC

  18. 2503 Tahoe Circle 2503 — photo24Active

    $1,900/mo

    2 bd · 2 ba · 1,173 sqft

    2503 Tahoe Circle 2503, Winter Park, FL

    Carissa Lawhun · FLORIDA REALTY INVESTMENTS

  19. 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

  20. 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

  21. 800 W Canton Avenue — photo30Active

    $2,500/mo

    2 bd · 1 ba · 924 sqft

    800 W Canton Avenue, Winter Park, FL

    Kelly Price · KELLY PRICE & COMPANY LLC

  22. 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

  23. 7487 Canford Court 5 — photo20Active

    $2,300/mo

    4 bd · 3 ba · 1,611 sqft

    7487 Canford Court 5, Winter Park, FL

    Jiny Lee · THE FLORIDA LOUNGE REALTY LLC

  24. 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

12…9

Explore Winter Park rentals

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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