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Waterleigh Single Family Homes For Sale in Winter Garden - 88 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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  • 18339 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $650,000475 Days on yellowkey   MLS ID: O6280496

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

    REDUCED by $98,000 (13.1%) on 06/10/2026

    SHORT SALE O6280496 - 18339 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2931
       Built: 2023
    Monthly Fee: $250
       Tax: $9,777 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,626 (change assumption)
    Mortgage ($3,562) + Fees ($250) + Taxes in 2024 ($815)


    Taxes:$9,777

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 11277 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $899,99027 Days on yellowkey   MLS ID: O6419923

    REDUCED by $15,000 (1.6%) on 07/02/2026

    For Sale O6419923 - 11277 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: $208
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,305 (change assumption)
    Mortgage ($4,931) + Fees ($208) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16845 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $539,990243 Days on yellowkey   MLS ID: O6362478

    REDUCED by $7,000 (1.3%) on 07/02/2026

    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: $3,315 (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


  • 16827 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $594,990177 Days on yellowkey   MLS ID: O6376919

    REDUCED by $5,000 (0.8%) on 07/02/2026

    For Sale O6376919 - 16827 HOBE SOUND CT, WINTER GARDEN, FL 34787 21 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2489
       Built: 2025
    Monthly Fee: $248
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,674 (change assumption)
    Mortgage ($3,260) + Fees ($248) + 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

    $539,990222 Days on yellowkey   MLS ID: O6367156

    REDUCED by $7,000 (1.3%) on 07/02/2026

    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: $3,315 (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


  • 16031 SCARPETTA ST, WINTER GARDEN, FL 34787

    $595,000190 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


  • 13617 SALAMANDER ST, WINTER GARDEN, FL 34787

    $530,000125 Days on yellowkey   MLS ID: O6391534

    REDUCED by $19,900 (3.6%) on 05/03/2026

    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: $3,833 (change assumption)
    Mortgage ($2,904) + 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


  • 9827 BEACH PORT DR, WINTER GARDEN, FL 34787

    $1,374,99076 Days on yellowkey   MLS ID: O6405480

    REDUCED by $25,000 (1.8%) on 06/30/2026

    For Sale O6405480 - 9827 BEACH PORT DR, WINTER GARDEN, FL 34787 68 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3910
       Built: 2020
    Monthly Fee: $259
       Tax: $11,122 (2025)
    Community: Waterleigh Ph 2C-2 & 2C-3
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,720 (change assumption)
    Mortgage ($7,534) + Fees ($259) + Taxes in 2025 ($927)


    Taxes:$11,122

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 11821 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $852,63627 Days on yellowkey   MLS ID: O6420002

    For Sale O6420002 - 11821 SHINE VIEW LN, WINTER GARDEN, FL 34787 77 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2866
       Built: 2025
    Monthly Fee: $208
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,046 (change assumption)
    Mortgage ($4,672) + Fees ($208) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11827 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $879,83127 Days on yellowkey   MLS ID: O6419995

    For Sale O6419995 - 11827 SHINE VIEW LN, WINTER GARDEN, FL 34787 63 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3225
       Built: 2025
    Monthly Fee: $208
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,195 (change assumption)
    Mortgage ($4,821) + Fees ($208) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11857 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $780,14127 Days on yellowkey   MLS ID: O6419967

    For Sale O6419967 - 11857 SHINE VIEW LN, WINTER GARDEN, FL 34787 76 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2025
    Monthly Fee: $208
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,648 (change assumption)
    Mortgage ($4,275) + Fees ($208) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 18309 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $725,000146 Days on yellowkey   MLS ID: O6386008

    0 Days Off yellowkey (back on 5/27/2026)

    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


  • 9318 MCLAREN ALLEY, WINTER GARDEN, FL 34787

    $489,00067 Days on yellowkey   MLS ID: S5150019

    4 Days Off yellowkey (back on 6/22/2026)

    For Sale S5150019 - 9318 MCLAREN ALLEY, WINTER GARDEN, FL 34787 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1685
       Built: 2020
    Monthly Fee: $257
       Tax: $7,221 (2025)
    Community: Waterleigh Phase 3A
    Single Family


    Estimated Monthly Payment: $3,538 (change assumption)
    Mortgage ($2,679) + Fees ($257) + Taxes in 2025 ($602)


    Taxes:$7,221

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9849 LOST CREEK DR, WINTER GARDEN, FL 34787

    $990,000608 Days on yellowkey   MLS ID: O6258009

    1 Days Off yellowkey (back on 6/18/2026)

    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


  • 12026 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $597,79578 Days on yellowkey   MLS ID: O6405058

    INCREASED by $1,605 (0.3%) on 06/18/2026

    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: $3,631 (change assumption)
    Mortgage ($3,276) + Fees ($190) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11117 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $507,00069 Days on yellowkey   MLS ID: O6407552

    REDUCED by $13,000 (2.5%) on 06/17/2026

    For Sale O6407552 - 11117 BOSTWICK ALY, WINTER GARDEN, FL 34787 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1685
       Built: 2022
    Monthly Fee: $291
       Tax: $6,722 (2025)
    Community: Waterleigh Ph 4A
    Single Family


    Estimated Monthly Payment: $3,629 (change assumption)
    Mortgage ($2,778) + Fees ($291) + Taxes in 2025 ($560)


    Taxes:$6,722

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 8275 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $555,000103 Days on yellowkey   MLS ID: TB8496196

    REDUCED by $10,000 (1.8%) on 06/09/2026

    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: $3,779 (change assumption)
    Mortgage ($3,041) + 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


  • 17865 ADRIFT RD, WINTER GARDEN, FL 34787

    $599,000364 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


  • 16840 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $569,990184 Days on yellowkey   MLS ID: O6374947

    REDUCED by $5,000 (0.9%) on 06/04/2026

    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: $3,488 (change assumption)
    Mortgage ($3,123) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16834 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $599,99091 Days on yellowkey   MLS ID: O6401373

    REDUCED by $25,000 (4.0%) on 06/04/2026

    For Sale O6401373 - 16834 HOBE SOUND CT, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2494
       Built: 2026
    Monthly Fee: $190
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,643 (change assumption)
    Mortgage ($3,288) + Fees ($190) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    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.