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Waterleigh Single Family Homes For Sale in Winter Garden - 83 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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  • 16840 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $539,990191 Days on yellowkey   MLS ID: O6374947

    REDUCED by $30,000 (5.3%) on 07/29/2026

    For Sale O6374947 - 16840 HOBE SOUND CT, WINTER GARDEN, FL 34787 13 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,324 (change assumption)
    Mortgage ($2,959) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17070 WATER SPRING BLVD, WINTER GARDEN, FL 34787

    $575,00016 Days on yellowkey   MLS ID: O6424329

    For Sale O6424329 - 17070 WATER SPRING BLVD, WINTER GARDEN, FL 34787 31 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2215
       Built: 2022
    Monthly Fee: $291
       Tax: $7,640 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,078 (change assumption)
    Mortgage ($3,151) + Fees ($291) + Taxes in 2025 ($637)


    Taxes:$7,640

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 11265 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $859,99084 Days on yellowkey   MLS ID: O6405351

    REDUCED by $11,841 (1.4%) on 07/29/2026

    For Sale O6405351 - 11265 HOLLOW BAY DR, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3225
       Built: 2025
    Monthly Fee: $200
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,078 (change assumption)
    Mortgage ($4,712) + Fees ($200) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11259 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $884,99034 Days on yellowkey   MLS ID: O6419946

    REDUCED by $5,000 (0.6%) on 07/29/2026

    For Sale O6419946 - 11259 HOLLOW BAY DR, WINTER GARDEN, FL 34787 68 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3327
       Built: 2025
    Monthly Fee: $208
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,223 (change assumption)
    Mortgage ($4,849) + Fees ($208) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12026 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $569,99085 Days on yellowkey   MLS ID: O6405058

    REDUCED by $27,805 (4.7%) on 07/29/2026

    For Sale O6405058 - 12026 SHINE VIEW LN, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,479 (change assumption)
    Mortgage ($3,123) + Fees ($190) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 10007 LITTLE ALCOVE LOOP, WINTER GARDEN, FL 34787

    $989,900352 Days on yellowkey   MLS ID: S5132434

    REDUCED by $10,090 (1.0%) on 07/29/2026

    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
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,206 (change assumption)
    Mortgage ($5,424) + 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


  • 16845 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $529,990250 Days on yellowkey   MLS ID: O6362478

    REDUCED by $10,000 (1.9%) on 07/29/2026

    For Sale O6362478 - 16845 HOBE SOUND CT, 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: $3,260 (change assumption)
    Mortgage ($2,904) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 12014 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $549,99020 Days on yellowkey   MLS ID: O6423746

    REDUCED by $5,000 (0.9%) on 07/29/2026

    For Sale O6423746 - 12014 SHINE VIEW LN, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,429 (change assumption)
    Mortgage ($3,014) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16816 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $534,99020 Days on yellowkey   MLS ID: O6423763

    REDUCED by $15,000 (2.7%) on 07/29/2026

    For Sale O6423763 - 16816 HOBE SOUND CT, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,347 (change assumption)
    Mortgage ($2,931) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16821 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $529,990229 Days on yellowkey   MLS ID: O6367156

    REDUCED by $10,000 (1.9%) on 07/29/2026

    For Sale O6367156 - 16821 HOBE SOUND CT, WINTER GARDEN, FL 34787 7 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: $3,260 (change assumption)
    Mortgage ($2,904) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 10198 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787

    $1,200,00027 Days on yellowkey   MLS ID: O6421817

    For Sale O6421817 - 10198 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787 42 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3911
       Built: 2020
    Monthly Fee: $260
       Tax: $11,419 (2025)
    Community: Waterleigh Ph 2C-1
    Single Family


    Estimated Monthly Payment: $7,787 (change assumption)
    Mortgage ($6,575) + Fees ($260) + Taxes in 2025 ($952)


    Taxes:$11,419

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 11043 JACKSON CV, WINTER GARDEN, FL 34787

    $674,99933 Days on yellowkey   MLS ID: O6420371

    REDUCED by $15,000 (2.2%) on 07/29/2026

    For Sale O6420371 - 11043 JACKSON CV, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2095
       Built: 2023
    Monthly Fee: $300
       Tax: $8,763 (2025)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,729 (change assumption)
    Mortgage ($3,699) + Fees ($300) + Taxes in 2025 ($730)


    Taxes:$8,763

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16031 SCARPETTA ST, WINTER GARDEN, FL 34787

    $595,000197 Days on yellowkey   MLS ID: O6373345

    REDUCED by $10,500 (1.7%) on 07/01/2026

    For Sale O6373345 - 16031 SCARPETTA ST, WINTER GARDEN, FL 34787 16 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2474
       Built: 2023
    Monthly Fee: $268
       Tax: $8,487 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,235 (change assumption)
    Mortgage ($3,260) + Fees ($268) + Taxes in 2024 ($707)


    Taxes:$8,487

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 11031 JACKSON CV, WINTER GARDEN, FL 34787

    $715,00013 Days on yellowkey   MLS ID: O6425544

    For Sale O6425544 - 11031 JACKSON CV, WINTER GARDEN, FL 34787 70 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2931
       Built: 2023
    Monthly Fee: $300
       Tax: $10,935 (2025)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $5,129 (change assumption)
    Mortgage ($3,918) + Fees ($300) + Taxes in 2025 ($911)


    Taxes:$10,935

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16822 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $599,99020 Days on yellowkey   MLS ID: O6423720

    2 Days Off yellowkey (back on 7/28/2026)

    For Sale O6423720 - 16822 HOBE SOUND CT, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2489
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,703 (change assumption)
    Mortgage ($3,288) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8807 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $765,00034 Days on yellowkey   MLS ID: O6419920

    REDUCED by $15,000 (1.9%) on 07/28/2026

    For Sale O6419920 - 8807 SONOMA COAST DR, WINTER GARDEN, FL 34787 25 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2022
    Monthly Fee: $261
       Tax: $9,520 (2025)
    Community: Waterleigh Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,246 (change assumption)
    Mortgage ($4,192) + Fees ($261) + Taxes in 2025 ($793)


    Taxes:$9,520

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9572 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787

    $859,9008 Days on yellowkey   MLS ID: O6426624

    For Sale O6426624 - 9572 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787 45 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2018
    Monthly Fee: $245
       Tax: $9,486 (2025)
    Community: Waterleigh Ph 2B
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,747 (change assumption)
    Mortgage ($4,712) + Fees ($245) + Taxes in 2025 ($790)


    Taxes:$9,486

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 8275 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $535,000110 Days on yellowkey   MLS ID: TB8496196

    REDUCED by $20,000 (3.6%) on 07/27/2026

    For Sale TB8496196 - 8275 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 96 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2019
       Built: 2017
    Monthly Fee: $312
       Tax: $5,109 (2025)
    Community: Waterleigh Ph 1B
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,669 (change assumption)
    Mortgage ($2,931) + Fees ($312) + Taxes in 2025 ($426)


    Taxes:$5,109

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 8721 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $679,00087 Days on yellowkey   MLS ID: G5111855

    REDUCED by $16,000 (2.3%) on 06/08/2026

    For Sale G5111855 - 8721 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2842
       Built: 2015
    Monthly Fee: $342
       Tax: $8,082 (2025)
    Community: Waterleigh Ph 1A
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,736 (change assumption)
    Mortgage ($3,720) + Fees ($342) + Taxes in 2025 ($673)


    Taxes:$8,082

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16754 OAKBORO ST, WINTER GARDEN, FL 34787

    $520,00083 Days on yellowkey   MLS ID: O6404652

    1 Days Off yellowkey (back on 7/27/2026)

    REDUCED by $9,000 (1.7%) on 07/19/2026

    For Sale O6404652 - 16754 OAKBORO ST, WINTER GARDEN, FL 34787 85 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2020
    Monthly Fee: $254
       Tax: $8,808 (2025)
    Community: Waterleigh Ph 3B 3C 3D
    Single Family


    Estimated Monthly Payment: $3,837 (change assumption)
    Mortgage ($2,849) + Fees ($254) + Taxes in 2025 ($734)


    Taxes:$8,808

    Elementary School: None

    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.