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Waterleigh Single Family Homes For Sale in Winter Garden - 71 homes

Waterleigh single family homes for sale are located in Orange County, Florida. Find Waterleigh single family homes in Winter Garden for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Waterleigh, Winter Garden single family houses.

Location: Waterleigh, Winter Garden

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  • 15878 MOONLIGHT BAY ST, WINTER GARDEN, FL 34787

    $565,00053 Days on yellowkey   MLS ID: O6384745

    REDUCED by $10,000 (1.7%) on 04/06/2026

    For Sale O6384745 - 15878 MOONLIGHT BAY ST, WINTER GARDEN, FL 34787 63 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2472
       Built: 2021
    Monthly Fee: $257
       Tax: $7,417 (2025)
    Community: Waterleigh Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $3,971 (change assumption)
    Mortgage ($3,096) + Fees ($257) + Taxes in 2025 ($618)


    Taxes:$7,417

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17865 ADRIFT RD, WINTER GARDEN, FL 34787

    $599,000268 Days on yellowkey   MLS ID: O6329586

    For Sale O6329586 - 17865 ADRIFT RD, WINTER GARDEN, FL 34787 26 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2484
       Built: 2023
    Monthly Fee: $277
       Tax: $9,155 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,322 (change assumption)
    Mortgage ($3,282) + Fees ($277) + Taxes in 2024 ($763)


    Taxes:$9,155

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 10007 LITTLE ALCOVE LOOP, WINTER GARDEN, FL 34787

    $999,990249 Days on yellowkey   MLS ID: S5132434

    1 Days Off yellowkey (back on 4/3/2026)

    For Sale S5132434 - 10007 LITTLE ALCOVE LOOP, WINTER GARDEN, FL 34787 56 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2921
       Built: 2018
    Monthly Fee: $250
       Tax: $6,381 (2024)
    Community: Waterleigh Ph 2B
    Single Family


    Estimated Monthly Payment: $6,261 (change assumption)
    Mortgage ($5,479) + Fees ($250) + Taxes in 2024 ($532)


    Taxes:$6,381

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 11045 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $749,90020 Days on yellowkey   MLS ID: O6394192

    For Sale O6394192 - 11045 HOLLOW BAY DR, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2025
    Monthly Fee: $295
       Tax: $3,196 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,670 (change assumption)
    Mortgage ($4,109) + Fees ($295) + Taxes in 2025 ($266)


    Taxes:$3,196

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 8197 LAKEVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $434,900116 Days on yellowkey   MLS ID: TB8458488

    0 Days Off yellowkey (back on 4/2/2026)

    For Sale TB8458488 - 8197 LAKEVIEW CROSSING DR, WINTER GARDEN, FL 34787 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1685
       Built: 2016
    Monthly Fee: $265
       Tax: $6,511 (2024)
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $3,191 (change assumption)
    Mortgage ($2,383) + Fees ($265) + Taxes in 2024 ($543)


    Taxes:$6,511

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 18386 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $724,90040 Days on yellowkey   MLS ID: O6388830

    For Sale O6388830 - 18386 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2924
       Built: 2024
    Monthly Fee: $280
       Tax: $10,366 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $5,116 (change assumption)
    Mortgage ($3,972) + Fees ($280) + Taxes in 2024 ($864)


    Taxes:$10,366

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: None


  • 10291 ATWATER BAY DR, WINTER GARDEN, FL 34787

    $1,274,500277 Days on yellowkey   MLS ID: O6326819

    REDUCED by $25,000 (1.9%) on 04/01/2026

    For Sale O6326819 - 10291 ATWATER BAY DR, WINTER GARDEN, FL 34787 63 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3910
       Built: 2019
    Monthly Fee: $250
       Tax: $15,141 (2024)
    Community: Waterleigh Ph 2B
    Single Family


    Estimated Monthly Payment: $8,495 (change assumption)
    Mortgage ($6,983) + Fees ($250) + Taxes in 2024 ($1,262)


    Taxes:$15,141

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 11205 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $969,09125 Days on yellowkey   MLS ID: O6392839

    For Sale O6392839 - 11205 HOLLOW BAY DR, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3327
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $5,726 (change assumption)
    Mortgage ($5,310) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9459 JAYWOOD RD, WINTER GARDEN, FL 34787

    $760,00046 Days on yellowkey   MLS ID: O6386488

    0 Days Off yellowkey (back on 3/31/2026)

    For Sale O6386488 - 9459 JAYWOOD RD, WINTER GARDEN, FL 34787 55 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2020
    Monthly Fee: $261
       Tax: $6,669 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $4,981 (change assumption)
    Mortgage ($4,164) + Fees ($261) + Taxes in 2025 ($556)


    Taxes:$6,669

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 11229 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $806,80188 Days on yellowkey   MLS ID: O6375011

    2 Days Off yellowkey (back on 3/31/2026)

    For Sale O6375011 - 11229 HOLLOW BAY DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 5   Bath: 4.5
    Liv Area Sq Ft: 3225
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,785 (change assumption)
    Mortgage ($4,421) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11187 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $814,56699 Days on yellowkey   MLS ID: O6372260

    2 Days Off yellowkey (back on 3/31/2026)

    For Sale O6372260 - 11187 HOLLOW BAY DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 5   Bath: 4.0
    Liv Area Sq Ft: 2866
       Built: 2025
    Monthly Fee: $249
       Tax: $1,989 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,878 (change assumption)
    Mortgage ($4,463) + Fees ($249) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16136 WIND VIEW LN, WINTER GARDEN, FL 34787

    $609,00099 Days on yellowkey   MLS ID: O6372050

    For Sale O6372050 - 16136 WIND VIEW LN, WINTER GARDEN, FL 34787 71 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2291
       Built: 2016
    Monthly Fee: $341
       Tax: $92,223 (2025)
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $11,363 (change assumption)
    Mortgage ($3,337) + Fees ($341) + Taxes in 2025 ($7,685)


    Taxes:$92,223

    Elementary School: Water Spring Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 8256 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $675,000201 Days on yellowkey   MLS ID: O6346538

    For Sale O6346538 - 8256 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 64 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 2557
       Built: 2016
    Monthly Fee: $290
       Tax: $10,027 (2024)
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $4,824 (change assumption)
    Mortgage ($3,699) + Fees ($290) + Taxes in 2024 ($836)


    Taxes:$10,027

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16845 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $572,555147 Days on yellowkey   MLS ID: O6362478

    For Sale O6362478 - 16845 HOBE SOUND CT, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,493 (change assumption)
    Mortgage ($3,137) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 10241 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787

    $795,00044 Days on yellowkey   MLS ID: O6387182

    0 Days Off yellowkey (back on 3/23/2026)

    For Sale O6387182 - 10241 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787 62 photos

    Bed: 5   Bath: 4.0
    Liv Area Sq Ft: 2840
       Built: 2019
    Monthly Fee: $256
       Tax: $9,877 (2024)
    Community: Waterleigh Ph 2C-1
    Single Family


    Estimated Monthly Payment: $5,435 (change assumption)
    Mortgage ($4,356) + Fees ($256) + Taxes in 2024 ($823)


    Taxes:$9,877

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 8807 EDEN COVE DR, WINTER GARDEN, FL 34787

    $734,50074 Days on yellowkey   MLS ID: G5107610

    For Sale G5107610 - 8807 EDEN COVE DR, WINTER GARDEN, FL 34787 37 photos

    Bed: 5   Bath: 4.5
    Liv Area Sq Ft: 3278
       Built: 2015
    Community: Waterleigh Ph 1A
    Single Family


    Estimated Monthly Payment: $4,025 (change assumption)
    Mortgage ($4,025)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 11112 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $799,990239 Days on yellowkey   MLS ID: O6337905

    1 Days Off yellowkey (back on 3/26/2026)

    For Sale O6337905 - 11112 HOLLOW BAY DR, WINTER GARDEN, FL 34787 10 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2113
       Built: 2025
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,383 (change assumption)
    Mortgage ($4,383)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 17936 ADRIFT RD, WINTER GARDEN, FL 34787

    $725,00038 Days on yellowkey   MLS ID: TB8483039

    For Sale TB8483039 - 17936 ADRIFT RD, WINTER GARDEN, FL 34787 44 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2113
       Built: 2023
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $3,973 (change assumption)
    Mortgage ($3,973)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 16632 POINT ROCK DR, WINTER GARDEN, FL 34787

    $550,000109 Days on yellowkey   MLS ID: OM715702

    For Sale OM715702 - 16632 POINT ROCK DR, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 2292
       Built: 2023
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $3,014 (change assumption)
    Mortgage ($3,014)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 16857 HOBE SOUBND CT, WINTER GARDEN, FL 34787

    $564,990155 Days on yellowkey   MLS ID: O6360518

    2 Days Off yellowkey (back on 3/24/2026)

    For Sale O6360518 - 16857 HOBE SOUBND CT, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2216
       Built: 2025
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,096 (change assumption)
    Mortgage ($3,096)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None




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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.