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Waterleigh Single Family Homes For Sale in Winter Garden - 73 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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  • 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787

    $568,00085 Days on yellowkey   MLS ID: NS1087076

    REDUCED by $5,000 (0.9%) on 04/17/2026

    For Sale NS1087076 - 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787 23 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: $3,593 (change assumption)
    Mortgage ($3,112) + Fees ($291) + Taxes in 2024 ($189)


    Taxes:$2,273

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16149 WIND VIEW LN, WINTER GARDEN, FL 34787

    $498,00039 Days on yellowkey   MLS ID: O6389892

    REDUCED by $7,000 (1.4%) on 04/15/2026

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

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2036
       Built: 2016
    Monthly Fee: $332
       Tax: $4,472 (2025)
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $3,433 (change assumption)
    Mortgage ($2,729) + 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


  • 9459 JAYWOOD RD, WINTER GARDEN, FL 34787

    $755,00050 Days on yellowkey   MLS ID: O6386488

    REDUCED by $5,000 (0.7%) on 04/20/2026

    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: $4,954 (change assumption)
    Mortgage ($4,137) + 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


  • 16749 HARPER COVE DR, WINTER GARDEN, FL 34787

    $515,0001 Day on yellowkey   MLS ID: O6400511

    For Sale O6400511 - 16749 HARPER COVE DR, WINTER GARDEN, FL 34787 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2014
       Built: 2019
    Monthly Fee: $257
       Tax: $7,287 (2024)
    Community: Waterleigh Ph 2C-1
    Single Family


    Estimated Monthly Payment: $3,686 (change assumption)
    Mortgage ($2,822) + Fees ($257) + Taxes in 2024 ($607)


    Taxes:$7,287

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 8220 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $599,99949 Days on yellowkey   MLS ID: TB8482364

    INCREASED by $42,000 (7.5%) on 03/31/2026

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

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2016
    Monthly Fee: $335
       Tax: $7,983 (2025)
    Community: Waterleigh Ph 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,288 (change assumption)
    Mortgage ($3,288) + 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


  • 15878 MOONLIGHT BAY ST, WINTER GARDEN, FL 34787

    $559,00057 Days on yellowkey   MLS ID: O6384745

    REDUCED by $6,000 (1.1%) on 04/20/2026

    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
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,938 (change assumption)
    Mortgage ($3,063) + 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


  • 11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $899,990127 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
    Spa: No

    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


  • 11193 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $839,99041 Days on yellowkey   MLS ID: O6389839

    REDUCED by $5,661 (0.7%) on 04/16/2026

    For Sale O6389839 - 11193 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
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,018 (change assumption)
    Mortgage ($4,603) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16242 OUTLOOK SHORE ALY, WINTER GARDEN, FL 34787

    $515,00047 Days on yellowkey   MLS ID: O6388026

    For Sale O6388026 - 16242 OUTLOOK SHORE ALY, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2014
       Built: 2018
    Monthly Fee: $257
       Tax: $7,296 (2024)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $3,687 (change assumption)
    Mortgage ($2,822) + Fees ($257) + Taxes in 2024 ($608)


    Taxes:$7,296

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 11858 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $539,990200 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
    Spa: No

    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

    $990,000516 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
    Spa: No

    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


  • 16137 WIND VIEW LN, WINTER GARDEN, FL 34787

    $575,000241 Days on yellowkey   MLS ID: O6335769

    REDUCED by $14,000 (2.4%) on 04/13/2026

    For Sale O6335769 - 16137 WIND VIEW LN, WINTER GARDEN, FL 34787 29 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2016
    Monthly Fee: $283
       Tax: $6,800 (2024)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,000 (change assumption)
    Mortgage ($3,151) + Fees ($283) + Taxes in 2024 ($567)


    Taxes:$6,800

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16385 ADMIRALS COVE LN, WINTER GARDEN, FL 34787

    $470,00027 Days on yellowkey   MLS ID: O6393056

    REDUCED by $4,900 (1.0%) on 04/15/2026

    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: $3,233 (change assumption)
    Mortgage ($2,575) + 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


  • 9354 MCLAREN ALY, WINTER GARDEN, FL 34787

    $529,50040 Days on yellowkey   MLS ID: O6390060

    REDUCED by $15,500 (2.8%) on 04/17/2026

    For Sale O6390060 - 9354 MCLAREN ALY, WINTER GARDEN, FL 34787 59 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2014
       Built: 2020
    Monthly Fee: $257
       Tax: $614 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $3,209 (change assumption)
    Mortgage ($2,901) + Fees ($257) + Taxes in 2025 ($51)


    Taxes:$614

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 13617 SALAMANDER ST, WINTER GARDEN, FL 34787

    $549,90033 Days on yellowkey   MLS ID: O6391534

    For Sale O6391534 - 13617 SALAMANDER ST, WINTER GARDEN, FL 34787 59 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2022
    Monthly Fee: $291
       Tax: $7,653 (2025)
    Community: Waterleigh Ph 4A
    Single Family


    Estimated Monthly Payment: $3,942 (change assumption)
    Mortgage ($3,013) + Fees ($291) + Taxes in 2025 ($638)


    Taxes:$7,653

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16933 OAKBORO ST, WINTER GARDEN, FL 34787

    $560,00030 Days on yellowkey   MLS ID: R4910916

    For Sale R4910916 - 16933 OAKBORO ST, WINTER GARDEN, FL 34787 32 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2020
    Monthly Fee: $257
       Tax: $3,651 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $3,630 (change assumption)
    Mortgage ($3,068) + Fees ($257) + Taxes in 2025 ($304)


    Taxes:$3,651

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16736 OAKBORO ST, WINTER GARDEN, FL 34787

    $575,00033 Days on yellowkey   MLS ID: O6388784

    REDUCED by $10,000 (1.7%) on 04/15/2026

    For Sale O6388784 - 16736 OAKBORO ST, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2020
    Monthly Fee: $257
       Tax: $6,967 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,988 (change assumption)
    Mortgage ($3,151) + Fees ($257) + Taxes in 2024 ($581)


    Taxes:$6,967

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 18309 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $725,00054 Days on yellowkey   MLS ID: O6386008

    For Sale O6386008 - 18309 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 37 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2832
       Built: 2023
    Monthly Fee: $281
       Tax: $497 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,295 (change assumption)
    Mortgage ($3,973) + Fees ($281) + Taxes in 2024 ($41)


    Taxes:$497

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16232 ROCK COAST DR, WINTER GARDEN, FL 34787

    $925,00048 Days on yellowkey   MLS ID: O6385935

    1 Days Off yellowkey (back on 4/18/2026)

    REDUCED by $15,000 (1.6%) on 04/12/2026

    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
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,974 (change assumption)
    Mortgage ($5,068) + 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


  • 8768 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $1,025,00078 Days on yellowkey   MLS ID: O6378658

    For Sale O6378658 - 8768 SONOMA COAST DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 3416
       Built: 2022
    Monthly Fee: $271
       Tax: $11,513 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,847 (change assumption)
    Mortgage ($5,616) + Fees ($271) + Taxes in 2024 ($959)


    Taxes:$11,513

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    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.