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Rentals Under $4,000/mo in Winter Park, FL
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Start here

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80 listings
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3 bedsHouses

Rentals Under $4,000/mo for Rent in Winter Park, FL

Rentals Under $4,000/mo for Rent in Winter Park, FL

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24 of 80 Listings
Map

Rentals Under $4,000/mo for Rent in Winter Park, FL

24 of 80 Listings

  1. 307 Sandlewood Trl — photoNew15Active

    $1,895/mo

    2 bd · 3 ba · 960 sqft

    307 Sandlewood Trl, Winter Park, FL

    Matthew Kirsch · REAL PROPERTY MANAGEMENT AND REALTY

  2. 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

  3. 2941 Antique Oaks Cir #80 — photoNew12Active

    $1,525/mo

    2 bd · 2 ba · 1,018 sqft

    2941 Antique Oaks Cir #80, Winter Park, FL

    Summer Hornburg · BELMONT REALTY

  4. listing photo18Active

    $2,200/mo

    3 bd · 2 ba · 1,266 sqft

    Address withheld · Winter Park, FL

    Kirsten Cantello · TRUSTHOME PROPERTIES INC

  5. 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

  6. 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

  7. 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

  8. 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

  9. 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

  10. 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

  11. 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. 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

  13. 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

  14. 7101 Swallow Run — photoPrice Reduced33Active

    $1,895/mo

    3 bd · 3 ba · 1,565 sqft

    7101 Swallow Run, Winter Park, FL

    Jackie O'Leary · FANNIE HILLMAN & ASSOCIATES

  15. 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

  16. 155 Stefanik Rd — photo17Active

    $2,000/mo

    2 bd · 2 ba · 1,040 sqft

    155 Stefanik Rd, Winter Park, FL

    Paul Jimenez · URBANISTA BROKERS

  17. 1667 Mizell Ave — photo20Active

    $3,500/mo

    3 bd · 3 ba · 1,715 sqft

    1667 Mizell Ave, Winter Park, FL

    Justin LaManna · HOMEVEST REALTY

  18. 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.

  19. 3217 Royal St — photoPrice Reduced19Active

    $1,995/mo

    3 bd · 2 ba · 1,174 sqft

    3217 Royal St, Winter Park, FL

    Stephen Murphy · DALTON WADE INC

  20. listing photo18Active

    $2,200/mo

    3 bd · 2 ba · 1,467 sqft

    Address withheld · Winter Park, FL

    Kirsten Cantello · TRUSTHOME PROPERTIES INC

  21. 4870 Seminole Ave — photoPrice ReducedOpen house Sat, Oct 3 · 11:00 AM33Active

    $2,400/mo

    3 bd · 2 ba · 1,277 sqft

    4870 Seminole Ave, Winter Park, FL

    Tamara Mazo Ferro · COLDWELL BANKER REALTY

  22. 3651 N Goldenrod Rd #C201 — photo12Active

    $1,395/mo

    2 bd · 2 ba · 840 sqft

    3651 N Goldenrod Rd #C201, Winter Park, FL

    Matthew Kirsch · REAL PROPERTY MANAGEMENT AND REALTY

  23. 5354 Lanyard Ct — photoPrice Reduced38Active

    $2,798/mo

    5 bd · 3 ba · 2,300 sqft

    5354 Lanyard Ct, Winter Park, FL

    Johanna Chandler · LPT REALTY, LLC

  24. 2452 Firstlight Way — photo26Active

    $2,800/mo

    3 bd · 3 ba · 2,308 sqft

    2452 Firstlight Way, Winter Park, FL

    Yan Zuo · EAST PEARL REALTY

12…4

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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