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Waterleigh Single Family Homes For Sale in Winter Garden - 65 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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  • 8685 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $555,000Listed 04/05/2026 4:46PM   MLS ID: O6394975

    For Sale O6394975 - 8685 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 38 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2489
       Built: 2015
    Monthly Fee: $332
       Tax: $8,849 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,110 (change assumption)
    Mortgage ($3,041) + Fees ($332) + Taxes in 2025 ($737)


    Taxes:$8,849

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787

    $573,00069 Days on yellowkey   MLS ID: NS1087076

    For Sale NS1087076 - 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787 27 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2474
       Built: 2024
    Monthly Fee: $291
       Tax: $2,273 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $3,620 (change assumption)
    Mortgage ($3,140) + Fees ($291) + Taxes in 2024 ($189)


    Taxes:$2,273

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $899,990111 Days on yellowkey   MLS ID: O6367437

    For Sale O6367437 - 11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3327
       Built: 2025
    Monthly Fee: $200
       Tax: $1,989 (2024)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $5,297 (change assumption)
    Mortgage ($4,931) + Fees ($200) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11858 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $539,990184 Days on yellowkey   MLS ID: O6349514

    For Sale O6349514 - 11858 SHINE VIEW LN, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,315 (change assumption)
    Mortgage ($2,959) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 9849 LOST CREEK DR, WINTER GARDEN, FL 34787

    $990,000500 Days on yellowkey   MLS ID: O6258009

    For Sale O6258009 - 9849 LOST CREEK DR, WINTER GARDEN, FL 34787 57 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3910
       Built: 2021
    Monthly Fee: $250
       Tax: $10,950 (2023)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $6,587 (change assumption)
    Mortgage ($5,425) + Fees ($250) + Taxes in 2023 ($913)


    Taxes:$10,950

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2023

    Middle School: Water Spring Middle


  • 16232 ROCK COAST DR, WINTER GARDEN, FL 34787

    $940,00032 Days on yellowkey   MLS ID: O6385935

    REDUCED by $9,000 (0.9%) on 04/04/2026

    For Sale O6385935 - 16232 ROCK COAST DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3491
       Built: 2017
    Monthly Fee: $270
       Tax: $7,627 (2024)
    Community: Waterleigh Ph 1C
    Single Family


    Estimated Monthly Payment: $6,056 (change assumption)
    Mortgage ($5,151) + Fees ($270) + Taxes in 2024 ($636)


    Taxes:$7,627

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 17865 ADRIFT RD, WINTER GARDEN, FL 34787

    $599,000256 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

    $999,990237 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


  • 16385 ADMIRALS COVE LN, WINTER GARDEN, FL 34787

    $475,00011 Days on yellowkey   MLS ID: O6393056

    For Sale O6393056 - 16385 ADMIRALS COVE LN, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1705
       Built: 2020
    Monthly Fee: $257
       Tax: $4,805 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,260 (change assumption)
    Mortgage ($2,603) + Fees ($257) + Taxes in 2025 ($400)


    Taxes:$4,805

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 11045 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $749,9008 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

    $434,900104 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

    $724,90028 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

    $1,274,500265 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

    $969,09113 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


  • 11181 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $860,77652 Days on yellowkey   MLS ID: O6382203

    For Sale O6382203 - 11181 HOLLOW BAY DR, WINTER GARDEN, FL 34787 32 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: $5,132 (change assumption)
    Mortgage ($4,716) + 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

    $760,00034 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


  • 16149 WIND VIEW LN, WINTER GARDEN, FL 34787

    $505,00023 Days on yellowkey   MLS ID: O6389892

    For Sale O6389892 - 16149 WIND VIEW LN, WINTER GARDEN, FL 34787 46 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2036
       Built: 2016
    Monthly Fee: $332
       Tax: $4,472 (2025)
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $3,472 (change assumption)
    Mortgage ($2,767) + Fees ($332) + Taxes in 2025 ($373)


    Taxes:$4,472

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 11229 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $806,80176 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

    $814,56687 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


  • 8220 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $539,95033 Days on yellowkey   MLS ID: TB8482364

    REDUCED by $18,049 (3.2%) on 03/31/2026

    For Sale TB8482364 - 8220 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 19 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 2477
       Built: 2016
    Monthly Fee: $335
       Tax: $7,983 (2025)
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $3,959 (change assumption)
    Mortgage ($2,959) + Fees ($335) + Taxes in 2025 ($665)


    Taxes:$7,983

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle




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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.