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Displaying: For Rent

Location: Winter Garden

Property Type(s): Single Family

Price: $3,500 to $4,999

Winter Garden - 32 properties found

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  • 720 PARKMONT PL, WINTER GARDEN, FL 34787

    $3,965Listed 06/23/2026 2:54PM   MLS ID: O6419049

    For RENT O6419049 - 720 PARKMONT PL, WINTER GARDEN, FL 34787 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2210
       Built: 2016
    Community: Covington Park A B D E F G & J
    Single Family


    Estimated Monthly Payment: $22 (change assumption)
    Mortgage ($22)


    Taxes:

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year:

    Middle School: Lakeview Middle


  • 10224 ATWATER BAY DR, WINTER GARDEN, FL 34787

    $4,0001 Day on yellowkey   MLS ID: S5152340

    For RENT S5152340 - 10224 ATWATER BAY DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3227
       Built: 2018
    Community: Waterleigh Ph 2B
    Single Family


    Estimated Monthly Payment: $22 (change assumption)
    Mortgage ($22)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 14768 FIELD DAISY DR, WINTER GARDEN, FL 34787

    $4,0001 Day on yellowkey   MLS ID: O6416610

    For RENT O6416610 - 14768 FIELD DAISY DR, WINTER GARDEN, FL 34787 45 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3619
       Built: 2026
    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $22 (change assumption)
    Mortgage ($22)


    Taxes:

    Elementary School: None

    High School: Horizon High School

    Tax Year:

    Middle School: Water Spring Middle


  • 10194 ATWATER BAY DR, WINTER GARDEN, FL 34787

    $3,99919 Days on yellowkey   MLS ID: O6413400

    0 Days Off yellowkey (back on 6/22/2026)

    For RENT O6413400 - 10194 ATWATER BAY DR, WINTER GARDEN, FL 34787 22 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2541
       Built: 2019
    Community: Waterleigh Ph 2C-1
    Single Family


    Estimated Monthly Payment: $22 (change assumption)
    Mortgage ($22)


    Taxes:

    Elementary School: None

    High School: Horizon High School

    Tax Year:

    Middle School: Water Spring Middle


  • 2158 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787

    $3,6008 Days on yellowkey   MLS ID: O6417265

    For RENT O6417265 - 2158 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2966
       Built: 1999
    Community: Wintermere Pointe
    Single Family


    Estimated Monthly Payment: $20 (change assumption)
    Mortgage ($20)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 806 LOST GROVE CIR, WINTER GARDEN, FL 34787

    $3,9955 Days on yellowkey   MLS ID: S5152166

    INCREASED by $395 (11.0%) on 06/19/2026

    For RENT S5152166 - 806 LOST GROVE CIR, WINTER GARDEN, FL 34787 17 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3462
       Built: 2006
    Community: Grove Park At Stone Crest
    Spa: No

    Single Family


    Estimated Monthly Payment: $22 (change assumption)
    Mortgage ($22)


    Taxes:

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year:

    Middle School: SunRidge Middle


  • 7853 ICELAND GULL ST, WINTER GARDEN, FL 34787

    $3,60014 Days on yellowkey   MLS ID: O6415406

    REDUCED by $200 (5.3%) on 06/19/2026

    For RENT O6415406 - 7853 ICELAND GULL ST, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2612
       Built: 2013
    Community: Summerlake Pd Ph 1B-A Rep
    Single Family


    Estimated Monthly Payment: $20 (change assumption)
    Mortgage ($20)


    Taxes:

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Hamlin Middle


  • 17876 ADRIFT RD, WINTER GARDEN, FL 34787

    $3,99910 Days on yellowkey   MLS ID: O6415044

    0 Days Off yellowkey (back on 6/18/2026)

    For RENT O6415044 - 17876 ADRIFT RD, WINTER GARDEN, FL 34787 53 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2866
       Built: 2023
    Community: Waterleigh Ph 4B & 4C
    Spa: No

    Single Family


    Estimated Monthly Payment: $22 (change assumption)
    Mortgage ($22)


    Taxes:

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Water Spring Middle


  • 16137 WIND VIEW LN, WINTER GARDEN, FL 34787

    $3,50011 Days on yellowkey   MLS ID: O6416733

    0 Days Off yellowkey (back on 6/18/2026)

    For RENT O6416733 - 16137 WIND VIEW LN, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2016
    Community: Waterleigh Ph 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $19 (change assumption)
    Mortgage ($19)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 14787 OLD THICKET TRCE, WINTER GARDEN, FL 34787

    $4,03013 Days on yellowkey   MLS ID: O6410954

    0 Days Off yellowkey (back on 6/18/2026)

    REDUCED by $20 (0.5%) on 06/16/2026

    For RENT O6410954 - 14787 OLD THICKET TRCE, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3537
       Built: 2006
    Community: Signature Lakes Prcl 01C
    Single Family


    Estimated Monthly Payment: $22 (change assumption)
    Mortgage ($22)


    Taxes:

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Bridgewater Middle


  • 15168 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787

    $3,60017 Days on yellowkey   MLS ID: O6414641

    REDUCED by $100 (2.7%) on 06/18/2026

    For RENT O6414641 - 15168 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787 18 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3152
       Built: 2015
    Community: Signature Lakes Ph 3B
    Single Family


    Estimated Monthly Payment: $20 (change assumption)
    Mortgage ($20)


    Taxes:

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year:

    Middle School: Bridgewater Middle


  • 9648 LOST CREEK DR, WINTER GARDEN, FL 34787

    $3,80017 Days on yellowkey   MLS ID: O6414712

    0 Days Off yellowkey (back on 6/16/2026)

    For RENT O6414712 - 9648 LOST CREEK DR, WINTER GARDEN, FL 34787 22 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3267
       Built: 2021
    Community: Waterleigh Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $21 (change assumption)
    Mortgage ($21)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 15030 SUMMER HARVEST ST, WINTER GARDEN, FL 34787

    $3,80063 Days on yellowkey   MLS ID: O6400523

    For RENT O6400523 - 15030 SUMMER HARVEST ST, WINTER GARDEN, FL 34787 17 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2861
       Built: 2024
    Community: Harvest At Ovation 112/64 Lot 142
    Single Family


    Estimated Monthly Payment: $21 (change assumption)
    Mortgage ($21)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 15602 COMPASS ROSE ST, WINTER GARDEN, FL 34787

    $3,90037 Days on yellowkey   MLS ID: O6408929

    0 Days Off yellowkey (back on 6/9/2026)

    For RENT O6408929 - 15602 COMPASS ROSE ST, WINTER GARDEN, FL 34787 69 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3227
       Built: 2021
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $21 (change assumption)
    Mortgage ($21)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 17865 ADRIFT RD, WINTER GARDEN, FL 34787

    $3,700229 Days on yellowkey   MLS ID: O6359041

    INCREASED by $400 (12.1%) on 06/10/2026

    For RENT O6359041 - 17865 ADRIFT RD, WINTER GARDEN, FL 34787 26 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2484
       Built: 2023
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $20 (change assumption)
    Mortgage ($20)


    Taxes:

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Water Spring Middle


  • 15143 KIRSTY ALY, WINTER GARDEN, FL 34787

    $4,00026 Days on yellowkey   MLS ID: O6410585

    For RENT O6410585 - 15143 KIRSTY ALY, WINTER GARDEN, FL 34787 32 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2934
       Built: 2017

    Single Family


    Estimated Monthly Payment: $22 (change assumption)
    Mortgage ($22)


    Taxes:

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Bridgewater Middle


  • 9240 WOODCRANE DR, WINTER GARDEN, FL 34787

    $4,79979 Days on yellowkey   MLS ID: O6396748

    REDUCED by $700 (12.7%) on 06/09/2026

    For RENT O6396748 - 9240 WOODCRANE DR, WINTER GARDEN, FL 34787 31 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3760
       Built: 2015
    Community: Watermark Ph 1B
    Single Family


    Estimated Monthly Payment: $26 (change assumption)
    Mortgage ($26)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 16055 SILVER BROOK WAY, WINTER GARDEN, FL 34787

    $4,90019 Days on yellowkey   MLS ID: O6414023

    For RENT O6414023 - 16055 SILVER BROOK WAY, WINTER GARDEN, FL 34787 63 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2072
       Built: 2023
    Community: Silverleaf Reserve/Hamlin Ph 2
    Single Family


    Estimated Monthly Payment: $27 (change assumption)
    Mortgage ($27)


    Taxes:

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Hamlin Middle


  • 15617 MARINA BAY DR, WINTER GARDEN, FL 34787

    $4,30020 Days on yellowkey   MLS ID: O6407960

    For RENT O6407960 - 15617 MARINA BAY DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3127
       Built: 2016
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $24 (change assumption)
    Mortgage ($24)


    Taxes:

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Water Spring Middle


  • 14582 OLD THICKET TRCE, WINTER GARDEN, FL 34787

    $4,50020 Days on yellowkey   MLS ID: O6413688

    For RENT O6413688 - 14582 OLD THICKET TRCE, WINTER GARDEN, FL 34787 19 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3175
       Built: 2006
    Community: Signature Lakes Prcl 01C
    Single Family


    Estimated Monthly Payment: $25 (change assumption)
    Mortgage ($25)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


12




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