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3 bedsHouses
Rentals Under $2,000/mo in Winter Park, FL
44 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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24 of 44 Listings
Map

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

24 of 44 Listings

  1. 2500 Lee Rd #145 — photoNew12
Active

$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

  • 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

  • 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

  • 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

  • 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

  • 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

  • 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

  • 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

  • 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

  • 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

  • 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

  • 155 Stefanik Rd — photo14Active

    $2,000/mo

    2 bd · 2 ba · 1,040 sqft

    155 Stefanik Rd, Winter Park, FL

    Paul Jimenez · URBANISTA BROKERS

  • 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

  • 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

  • 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

  • 759 Antonette Ave — photo17Active

    $1,800/mo

    1 bd · 1 ba · 705 sqft

    759 Antonette Ave, Winter Park, FL

    Meg Dolan · FANNIE HILLMAN & ASSOCIATES

  • 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

  • 7309 Daniel Webster Dr #O4 — photoPrice Reduced12Active

    $1,000/mo

    1 bd · 1 ba · 590 sqft

    7309 Daniel Webster Dr #O4, Winter Park, FL

    Nancy Guadagnino · SPECIALIZED PROPERTY MANAGEMENT

  • 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 — photo10Active

    $1,700/mo

    2 bd · 2 ba · 990 sqft

    7336 Forest Hill Ct #240, Winter Park, FL

    Mara Brasil · REALIZE INTERNATIONAL REALTY L

  • 652 Saint Johns Ct #652 — photoPrice Reduced19Active

    $1,695/mo

    2 bd · 2 ba · 1,037 sqft

    652 Saint Johns Ct #652, Winter Park, FL

    Marina Gamundi · KELLER WILLIAMS ADVANTAGE III

  • 12

    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