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3 bedsHouses
Rentals Under $2,000/mo in Winter Garden, FL
26 listings

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

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

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24 of 26 Listings
Map

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

24 of 26 Listings

  1. 15337 Southern Martin St — photo14Active

$2,000/mo

1 bd · 1 ba · 700 sqft

15337 Southern Martin St, Winter Garden, FL

Judson Osbon · RE/MAX PRIME PROPERTIES

  • 433 Sand Lime Rd — photoNew1Active

    $1,800/mo

    3 bd · 2 ba · 1,322 sqft

    433 Sand Lime Rd, Winter Garden, FL

    Rick Sein · REALSOURCE PROPERTY MANGNT LLC

  • listing photo31Active

    $1,850/mo

    3 bd · 2 ba · 1,156 sqft

    Address withheld · Winter Garden, FL

    Benjamin Larbus · THE EXPERTS TEAM REALTY INC

  • 5972 Flowering Cherry Bnd Unit B — photo9Active

    $1,500/mo

    1 bd · 1 ba · 600 sqft

    5972 Flowering Cherry Bnd Unit B, Winter Garden, FL

    Drielen Ferreira · MANAGER PROP

  • 6393 Wild Persimmon Way Unit B — photo9Active

    $1,500/mo

    1 bd · 2 ba · 600 sqft

    6393 Wild Persimmon Way Unit B, Winter Garden, FL

    Drielen Ferreira · MANAGER PROP

  • 214 2nd St — photoPrice Reduced4Active

    $1,200/mo

    1 bd · 1 ba · 300 sqft

    214 2nd St, Winter Garden, FL

    Luis Bello · ACTION PLUS REALTY SERVICES

  • 1418 Daniels Cove Dr — photoPrice Reduced6Active

    $1,200/mo

    2 bd · 1 ba · 300 sqft

    1418 Daniels Cove Dr, Winter Garden, FL

    Luis Bello · ACTION PLUS REALTY SERVICES

  • 170 Windtree Ln #U — photo20Active

    $1,750/mo

    2 bd · 2 ba · 918 sqft

    170 Windtree Ln #U, Winter Garden, FL

    Romina Cabanas · LA ROSA REALTY LLC

  • 417 Southern Pecan Cir #208 — photo40Active

    $1,825/mo

    2 bd · 2 ba · 1,264 sqft

    417 Southern Pecan Cir #208, Winter Garden, FL

    Vicky Ramos · ALL COUNTY CFL PROPERTY MGMT

  • 405 Southern Pecan Cir #108 — photo21Active

    $1,950/mo

    2 bd · 2 ba · 1,152 sqft

    405 Southern Pecan Cir #108, Winter Garden, FL

    Francisco Orchilles · LAKESIDE REALTY WINDERMERE INC

  • 955 Butterfly Blvd — photo11Active

    $1,850/mo

    3 bd · 2 ba · 1,216 sqft

    955 Butterfly Blvd, Winter Garden, FL

    Suzanne Seenandan · PREFERRED RE BROKERS III

  • 509 Varsity St — photo10Active

    $1,750/mo

    2 bd · 1 ba · 780 sqft

    509 Varsity St, Winter Garden, FL

    Angela Chapman · CAPITAL REALTY GROUP FLORIDA

  • 502 Dunbar Ave — photoPrice Reduced13Active

    $1,399/mo

    2 bd · 1 ba · 816 sqft

    502 Dunbar Ave, Winter Garden, FL

    Nancy Guadagnino · SPECIALIZED PROPERTY MANAGEMENT

  • 430 Southern Pecan Cir #106 — photo29Active

    $1,695/mo

    1 bd · 1 ba · 838 sqft

    430 Southern Pecan Cir #106, Winter Garden, FL

    Seyed Azimi · AFT PROPERTY LLC

  • 200 Southern Pecan Cir #206 — photoPrice Reduced53Active

    $1,795/mo

    2 bd · 2 ba · 1,276 sqft

    200 Southern Pecan Cir #206, Winter Garden, FL

    Nicole Howell · FANNIE HILLMAN & ASSOCIATES

  • 15347 Gilligan Ct — photo9Active

    $1,650/mo

    1 bd · 1 ba · 620 sqft

    15347 Gilligan Ct, Winter Garden, FL

    Andrea Munoz · MOSAIC PARTNERS GROUP

  • 502 Varsity St — photoPrice Reduced5Active

    $1,675/mo

    2 bd · 1 ba · 780 sqft

    502 Varsity St, Winter Garden, FL

    Angela Chapman · CAPITAL REALTY GROUP FLORIDA

  • 508 Varsity St — photoPrice Reduced10Active

    $1,675/mo

    2 bd · 1 ba · 780 sqft

    508 Varsity St, Winter Garden, FL

    Angela Chapman · CAPITAL REALTY GROUP FLORIDA

  • 1105 Lincoln Ter — photoPrice Reduced22Active

    $1,850/mo

    3 bd · 1 ba · 814 sqft

    1105 Lincoln Ter, Winter Garden, FL

    Simone Pinto de Almeida Santos · NOVA REAL ESTATE SERVICES INC

  • 407 Douglas Way #66 — photoPrice Reduced15Active

    $1,695/mo

    2 bd · 2 ba · 930 sqft

    407 Douglas Way #66, Winter Garden, FL

    Justin LaManna · HOMEVEST REALTY

  • 1301 Eastern Pecan Pl #208 — photoPrice Reduced33Active

    $1,900/mo

    2 bd · 2 ba · 1,264 sqft

    1301 Eastern Pecan Pl #208, Winter Garden, FL

    Neyla Alvarez · EXP REALTY LLC

  • 417 Southern Pecan Cir #204 — photo14Active

    $1,950/mo

    2 bd · 2 ba · 1,264 sqft

    417 Southern Pecan Cir #204, Winter Garden, FL

    Alejandro Hernandez · HP PROPERTY SOLUTIONS, LLC

  • 1432 Broken Oak Dr #31a — photo20Active

    $1,900/mo

    2 bd · 2 ba · 1,216 sqft

    1432 Broken Oak Dr #31a, Winter Garden, FL

    Dan Thompson · OPTIMA ONE REALTY, INC.

  • 200 Southern Pecan Cir #203 — photoPrice Reduced30Active

    $1,800/mo

    2 bd · 2 ba · 1,276 sqft

    200 Southern Pecan Cir #203, Winter Garden, FL

    Hans Tank · FLORIDA SCANDI REALTY LLC

  • 12

    Explore Winter Garden rentals

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

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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 Garden, FL community profile

    Population
    50,261
    Median income
    $102,195
    Housing units
    18,962
    People per sq. mi.
    562.2
    Area
    89.4 sq. mi.

    Source: HJN community data