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3 bedsHouses
Rentals Under $5,000/mo in Winter Park, FL
80 listings

Rentals Under $5,000/mo for Rent in Winter Park, FL

Rentals Under $5,000/mo for Rent in Winter Park, FL

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24 of 80 Listings
Map

Rentals Under $5,000/mo for Rent in Winter Park, FL

24 of 80 Listings

  1. 1521 Heron Wood Pl — photo31Active

$2,500/mo

3 bd · 2 ba · 3,950 sqft

1521 Heron Wood Pl, Winter Park, FL

Ronald Trotter · RE/MAX INNOVATION

  • 7797 Broken Arrow Trl — photoNew54Active

    $3,900/mo

    4 bd · 2 ba · 2,548 sqft

    7797 Broken Arrow Trl, Winter Park, FL

    Claudia D'Aquino · CENTURY 21 CARIOTI

  • 3328 Hamlet Loop — photo24Active

    $2,500/mo

    3 bd · 3 ba · 1,397 sqft

    3328 Hamlet Loop, Winter Park, FL

    Marileen Nieves · LPT REALTY, LLC

  • 1695 Lee Rd #E213 — photo8Active

    $1,600/mo

    2 bd · 1 ba · 881 sqft

    1695 Lee Rd #E213, Winter Park, FL

    Mirna Perez · LOKATION

  • 5600 Revelwood Loop — photo37Active

    $2,650/mo

    4 bd · 2 ba · 1,598 sqft

    5600 Revelwood Loop, Winter Park, FL

    Max Leo Donzi · IRM INVEST., REAL EST.& MGMT.

  • 1462 Siciliano Pt — photo15Active

    $2,350/mo

    3 bd · 3 ba · 1,628 sqft

    1462 Siciliano Pt, Winter Park, FL

    Selena Rivera · NONA LEGACY POWERED BY LA ROSA

  • 1111 Washington Ave #3 — photo20Active

    $1,550/mo

    2 bd · 2 ba · 1,084 sqft

    1111 Washington Ave #3, Winter Park, FL

    Joe English, Jr · WILSON MANAGEMENT GROUP

  • 2712 Goldenrod Dr — photo24Active

    $4,500/mo

    3 bd · 2 ba · 1,948 sqft

    2712 Goldenrod Dr, Winter Park, FL

    Ryan Langley · FLORIDA REALTY INVESTMENTS

  • 1357 Indiana Ave — photo15Active

    $1,850/mo

    2 bd · 2 ba · 1,090 sqft

    1357 Indiana Ave, Winter Park, FL

    Brian LeMay · ROMAN REALTY GROUP, LLC

  • 1666 Tremont Ln — photo16Active

    $2,240/mo

    3 bd · 2 ba · 1,600 sqft

    1666 Tremont Ln, Winter Park, FL

    David Drawdy, Jr. · KELLER WILLIAMS REALTY AT THE PARKS

  • 2612 Roxbury Rd — photo10Active

    $2,500/mo

    5 bd · 3 ba · 2,472 sqft

    2612 Roxbury Rd, Winter Park, FL

    Susan Lattimore · HOMEPRIDE PROPERTY MANAGEMENT GROUP LLC

  • 1824 Howell Branch Rd — photo16Active

    $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 — photo15Active

    $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

  • 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

  • 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

  • 12…4

    Explore Winter Park rentals

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    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