REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search


Displaying: For Rent

Location: Winter Garden

Property Type(s): Single Family

Beds: 5 to 5

Winter Garden - 22 properties found

Sort:
  • 10224 ATWATER BAY DR, WINTER GARDEN, FL 34787

    $4,000Listed 06/22/2026 5:50PM   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

    $4,000Listed 06/22/2026 3:15PM   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


  • 706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $6,50011 Days on yellowkey   MLS ID: O6416527

    INCREASED by $500 (8.3%) on 06/20/2026

    For RENT O6416527 - 706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 27 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 4019
       Built: 2018
    Community: Canopy Oaks Ph 1
    Single Family


    Estimated Monthly Payment: $36 (change assumption)
    Mortgage ($36)


    Taxes:

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year:

    Middle School: SunRidge Middle


  • 806 LOST GROVE CIR, WINTER GARDEN, FL 34787

    $3,9954 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


  • 17876 ADRIFT RD, WINTER GARDEN, FL 34787

    $3,9999 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


  • 16628 SILVER BROOK WAY, WINTER GARDEN, FL 34787

    $5,9006 Days on yellowkey   MLS ID: O6417547

    For RENT O6417547 - 16628 SILVER BROOK WAY, WINTER GARDEN, FL 34787 44 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3643
       Built: 2026
    Community: Silverleaf Oaks At Hamlin
    Single Family


    Estimated Monthly Payment: $32 (change assumption)
    Mortgage ($32)


    Taxes:

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Hamlin Middle


  • 15168 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787

    $3,60016 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


  • 16031 SILVER BROOK WAY, WINTER GARDEN, FL 34787

    $6,50035 Days on yellowkey   MLS ID: O6409094

    0 Days Off yellowkey (back on 6/14/2026)

    For RENT O6409094 - 16031 SILVER BROOK WAY, WINTER GARDEN, FL 34787 37 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3979
       Built: 2023
    Community: Silverleaf Reserve/Haml Ph 2A
    Single Family


    Estimated Monthly Payment: $36 (change assumption)
    Mortgage ($36)


    Taxes:

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Hamlin Middle


  • 8222 TOPSAIL PL, WINTER GARDEN, FL 34787

    $6,25010 Days on yellowkey   MLS ID: O6416728

    For RENT O6416728 - 8222 TOPSAIL PL, WINTER GARDEN, FL 34787 57 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4199
       Built: 2021
    Community: Lakeshore Preserve Ph 5
    Single Family


    Estimated Monthly Payment: $34 (change assumption)
    Mortgage ($34)


    Taxes:

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Water Spring Middle


  • 15030 SUMMER HARVEST ST, WINTER GARDEN, FL 34787

    $3,80062 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

    $3,90036 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


  • 14612 GLADE HILL PARK WAY, WINTER GARDEN, FL 34787

    $5,90018 Days on yellowkey   MLS ID: S5151295

    For RENT S5151295 - 14612 GLADE HILL PARK WAY, WINTER GARDEN, FL 34787 79 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3892
       Built: 2015
    Community: Watermark Ph 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $32 (change assumption)
    Mortgage ($32)


    Taxes:

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Hamlin Middle


  • 15143 KIRSTY ALY, WINTER GARDEN, FL 34787

    $4,00025 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

    $4,79978 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


  • 14582 OLD THICKET TRCE, WINTER GARDEN, FL 34787

    $4,50019 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


  • 12927 CANOPY WOODS WAY, WINTER GARDEN, FL 34787

    $9,250258 Days on yellowkey   MLS ID: S5136184

    0 Days Off yellowkey (back on 6/4/2026)

    For RENT S5136184 - 12927 CANOPY WOODS WAY, WINTER GARDEN, FL 34787 41 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4671
       Built: 2019
    Community: Canopy Oaks Phase 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $51 (change assumption)
    Mortgage ($51)


    Taxes:

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year:

    Middle School: SunRidge Middle


  • 16324 SILVER GROVE BLVD, WINTER GARDEN, FL 34787

    $4,700228 Days on yellowkey   MLS ID: O6358862

    For RENT O6358862 - 16324 SILVER GROVE BLVD, WINTER GARDEN, FL 34787 51 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3743
       Built: 2023
    Community: Silverleaf Reserve/Hamlin Ph 2
    Single Family


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


    Taxes:

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Hamlin Middle


  • 6148 WATERSIDE ISLAND LN, WINTER GARDEN, FL 34787

    $3,50072 Days on yellowkey   MLS ID: O6398414

    0 Days Off yellowkey (back on 5/20/2026)

    For RENT O6398414 - 6148 WATERSIDE ISLAND LN, WINTER GARDEN, FL 34787 20 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3468
       Built: 2014
    Community: Signature Lakes Ph 3B-1
    Single Family


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


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 16870 SANCTUARY DR, WINTER GARDEN, FL 34787

    $12,95082 Days on yellowkey   MLS ID: O6394261

    For RENT O6394261 - 16870 SANCTUARY DR, WINTER GARDEN, FL 34787 100 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4038
       Built: 2022

    Single Family


    Estimated Monthly Payment: $71 (change assumption)
    Mortgage ($71)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 455 WINTER GROVE BLVD, WINTER GARDEN, FL 34787

    $5,00077 Days on yellowkey   MLS ID: O6397196

    REDUCED by $90 (1.8%) on 05/08/2026

    For RENT O6397196 - 455 WINTER GROVE BLVD, WINTER GARDEN, FL 34787 47 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2631
       Built: 2026

    Single Family


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


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


12




Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.