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3 bedsHouses
Rentals Under $2,000/mo in Winter Park, FL
23 listings

Rentals Under $2,000/mo for Rent in Winter Park, FL

Rentals Under $2,000/mo for Rent in Winter Park, FL

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23 Listings
Map

Rentals Under $2,000/mo for Rent in Winter Park, FL

23 Listings

  1. 3027 Aaron Burr Ave #L1 — photo25Active

$1,795/mo

2 bd · 3 ba · 1,090 sqft

3027 Aaron Burr Ave #L1, Winter Park, FL

Jocelyne Yanez · HOMESMART

  • 1695 Lee Rd #E213 — photo8Active

    $1,600/mo

    2 bd · 1 ba · 881 sqft

    1695 Lee Rd #E213, Winter Park, FL

    Mirna Perez · LOKATION

  • 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

  • 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

  • 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

  • 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

  • 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

  • 7453 Daniel Webster Dr #a5 — photoPrice Reduced18Active

    $1,500/mo

    2 bd · 2 ba · 1,063 sqft

    7453 Daniel Webster Dr #a5, Winter Park, FL

    Laila Dkhissi · LA ROSA REALTY PREMIER LLC

  • 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

  • listing photoPrice Reduced18Active

    $2,000/mo

    3 bd · 2 ba · 1,467 sqft

    Address withheld · Winter Park, FL

    Kirsten Cantello · TRUSTHOME PROPERTIES INC

  • 3651 N Goldenrod Rd #C201 — photoPrice Reduced12Active

    $1,350/mo

    2 bd · 2 ba · 840 sqft

    3651 N Goldenrod Rd #C201, Winter Park, FL

    Matthew Kirsch · REAL PROPERTY MANAGEMENT AND REALTY

  • 3367 River View Way #450 — photo12Active

    $1,800/mo

    3 bd · 3 ba · 1,151 sqft

    3367 River View Way #450, Winter Park, FL

    Hao Jun Chang · CINO INTERNATIONAL INC

  • 1695 Lee Rd #a113 — photo13Active

    $1,600/mo

    2 bd · 1 ba · 881 sqft

    1695 Lee Rd #a113, Winter Park, FL

    Yigit Orer · EMPIRE NETWORK REALTY

  • 3651 N Goldenrod Rd #a103 — photoPrice Reduced18Active

    $1,575/mo

    2 bd · 2 ba · 840 sqft

    3651 N Goldenrod Rd #a103, Winter Park, FL

    Youree Lundy · KELLER WILLIAMS ADVANTAGE III

  • 7336 Forest Hill Ct #240 — photoPrice Reduced10Active

    $1,680/mo

    2 bd · 2 ba · 990 sqft

    7336 Forest Hill Ct #240, Winter Park, FL

    Mara Brasil · REALIZE INTERNATIONAL REALTY L

  • 2481 Tahoe Cir #2481 — photoPrice Reduced19Active

    $1,799/mo

    2 bd · 3 ba · 1,495 sqft

    2481 Tahoe Cir #2481, Winter Park, FL

    Sebastian Lozano · COLDWELL BANKER REALTY

  • 1000 S Semoran Blvd #305 — photoPrice Reduced19Active

    $1,050/mo

    1 bd · 1 ba · 735 sqft

    1000 S Semoran Blvd #305, Winter Park, FL

    Melissa Vance · MAINFRAME REAL ESTATE

  • 1695 Lee Rd #E215 — photo40Active

    $1,850/mo

    3 bd · 2 ba · 1,149 sqft

    1695 Lee Rd #E215, Winter Park, FL

    Jenaia Fowlkes · FOWLKES REALTY CO

  • 1695 Lee Rd #C103 — photo14Active

    $1,600/mo

    2 bd · 1 ba · 881 sqft

    1695 Lee Rd #C103, Winter Park, FL

    Yigit Orer · EMPIRE NETWORK REALTY

  • 1000 S Semoran Blvd #715 — photoPrice Reduced11Active

    $1,150/mo

    1 bd · 1 ba · 735 sqft

    1000 S Semoran Blvd #715, Winter Park, FL

    Leticia Morales · LPT REALTY, LLC

  • 1695 Lee Rd #a103 — photoPrice Reduced15Active

    $1,350/mo

    2 bd · 1 ba · 881 sqft

    1695 Lee Rd #a103, Winter Park, FL

    Kirsten Cantello · TRUSTHOME PROPERTIES INC

  • 151 N Orlando Ave #118 — photoPrice Reduced20Active

    $1,900/mo

    2 bd · 1 ba · 710 sqft

    151 N Orlando Ave #118, Winter Park, FL

    Adriana Montes · FLORIDA DREAMS REALTY GRP INC

  • 3651 N Goldenrod Rd #110 — photo19Active

    $1,450/mo

    2 bd · 2 ba · 840 sqft

    3651 N Goldenrod Rd #110, Winter Park, FL

    Praveen Setty · RIGHTHOUSE REALTY LLC

  • Explore Winter Park rentals

    By price

    • Rentals Under $2,000/mo
    • Rentals Under $3,000/mo
    • Rentals Under $4,000/mo
    • Rentals Under $5,000/mo

    By bedrooms

    • 2 Bedroom Rentals
    • 3 Bedroom Rentals

    By type

    • Single-Family Rentals
    • Condo Rentals
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    Listing data & MLS disclosures

    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