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Apartments and Houses for Rent in Winter Park, FL | Realty.com
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100 listings
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3 bedsHousesWith a pool

Apartments and Houses for Rent in Winter Park, FL

Apartments and Houses for Rent in Winter Park, FL

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24 of 100 Listings
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Apartments and Houses for Rent in Winter Park, FL

24 of 100 Listings

  1. 500 N Pennsylvania Ave #G — photo23Active

    $2,300/mo

    2 bd · 1 ba · 709 sqft

    500 N Pennsylvania Ave #G, Winter Park, FL

    Sylvia Young · FLORIDA RENTAL TEAM

  2. listing photo18Active

    $2,200/mo

    3 bd · 2 ba · 1,266 sqft

    Address withheld · Winter Park, FL

    Kirsten Cantello · TRUSTHOME PROPERTIES INC

  3. 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

  4. 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

  5. 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

  6. 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

  7. 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

  8. 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

  9. 737 Minnesota Ave — photo11Active

    $3,995/mo

    3 bd · 4 ba · 1,760 sqft

    737 Minnesota Ave, Winter Park, FL

    Marilyn Kuczynski · FLORIDA HOMES SALES & MANAGEMENT LLC

  10. 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

  11. 2181 Linden Rd — photo1Active

    $2,800/mo

    5 bd · 4 ba · 1,442 sqft

    2181 Linden Rd, Winter Park, FL

    Paula Chavez · KELLER WILLIAMS ADVANTAGE III

  12. 541 W Canton Ave — photo50Active

    $12,000/mo

    4 bd · 4 ba · 3,553 sqft

    541 W Canton Ave, Winter Park, FL

    Bianca Khoury · PREMIER SOTHEBY'S INTL. REALTY

  13. 1750 Carollee Lane — photo45Active

    $7,500/mo

    4 bd · 4 ba · 3,249 sqft

    1750 Carollee Lane, Winter Park, FL

    Michelle Hochfelder · PREMIER SOTHEBY'S INTL. REALTY

  14. 2056 Wood Thrush Ln — photo37Active

    $5,500/mo

    4 bd · 3 ba · 3,050 sqft

    2056 Wood Thrush Ln, Winter Park, FL

    Kimberley Gernert LLC · BALDWIN PARK REALTY LLC

  15. 163 Scottsdale Sq #163 — photo13Active

    $1,600/mo

    2 bd · 2 ba · 1,020 sqft

    163 Scottsdale Sq #163, Winter Park, FL

    Simone Pinto de Almeida Santos · NOVA REAL ESTATE SERVICES INC

  16. 7101 Swallow Run — photo33Active

    $2,000/mo

    3 bd · 3 ba · 1,565 sqft

    7101 Swallow Run, Winter Park, FL

    Jackie O'Leary · FANNIE HILLMAN & ASSOCIATES

  17. 2918 Antique Oaks Cir #30 — photo21Active

    $1,550/mo

    2 bd · 2 ba · 1,018 sqft

    2918 Antique Oaks Cir #30, Winter Park, FL

    Kyle Petteway · EXIT REAL ESTATE RESULTS

  18. 2352 Kestrel Perch Pl — photo39Active

    $4,140/mo

    4 bd · 4 ba · 3,094 sqft

    2352 Kestrel Perch Pl, Winter Park, FL

    Angela Fettig · KELLER WILLIAMS REALTY AT THE PARKS

  19. 155 Stefanik Rd — photo17Active

    $2,000/mo

    2 bd · 2 ba · 1,040 sqft

    155 Stefanik Rd, Winter Park, FL

    Paul Jimenez · URBANISTA BROKERS

  20. 1667 Mizell Ave — photo20Active

    $3,500/mo

    3 bd · 3 ba · 1,715 sqft

    1667 Mizell Ave, Winter Park, FL

    Justin LaManna · HOMEVEST REALTY

  21. 2809 W Fairbanks Ave — photo16Active

    $2,400/mo

    3 bd · 2 ba · 1,570 sqft

    2809 W Fairbanks Ave, Winter Park, FL

    Anne Coburn · H. & H. REALTY, INC.

  22. 3217 Royal St — photo18Active

    $2,100/mo

    3 bd · 2 ba · 1,174 sqft

    3217 Royal St, Winter Park, FL

    Stephen Murphy · DALTON WADE INC

  23. listing photo18Active

    $2,200/mo

    3 bd · 2 ba · 1,467 sqft

    Address withheld · Winter Park, FL

    Kirsten Cantello · TRUSTHOME PROPERTIES INC

  24. 4870 Seminole Ave — photo33Active

    $2,500/mo

    3 bd · 2 ba · 1,277 sqft

    4870 Seminole Ave, Winter Park, FL

    Tamara Mazo Ferro · COLDWELL BANKER REALTY

12…5

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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