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Waterleigh Homes for Sale in Winter Garden - 100 homes

Waterleigh homes for sale are located in Orange County, Florida. Find Waterleigh 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 homes.

Location: Waterleigh, Winter Garden

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  • 16845 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $564,990169 Days on yellowkey   MLS ID: O6362478

    REDUCED by $7,565 (1.3%) on 04/22/2026

    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: $3,452 (change assumption)
    Mortgage ($3,096) + Fees ($190) + 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

    $534,990218 Days on yellowkey   MLS ID: O6349514

    REDUCED by $5,000 (0.9%) on 04/22/2026

    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: $3,287 (change assumption)
    Mortgage ($2,931) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 18179 CIDER MILL LN, WINTER GARDEN, FL 34787

    $419,99025 Days on yellowkey   MLS ID: O6399141

    REDUCED by $5,000 (1.2%) on 04/22/2026

    For Sale O6399141 - 18179 CIDER MILL LN, WINTER GARDEN, FL 34787 15 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1567
       Built: 2025
    Monthly Fee: $204
       Tax: $1,424 (2025)
    Community: Waterleigh
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,624 (change assumption)
    Mortgage ($2,301) + Fees ($204) + Taxes in 2025 ($119)


    Taxes:$1,424

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11223 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $819,99085 Days on yellowkey   MLS ID: O6382359

    REDUCED by $9,746 (1.2%) on 04/22/2026

    For Sale O6382359 - 11223 HOLLOW BAY DR, WINTER GARDEN, FL 34787 10 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2866
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,909 (change assumption)
    Mortgage ($4,493) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 18167 CIDER MILL LN, WINTER GARDEN, FL 34787

    $469,99071 Days on yellowkey   MLS ID: O6386278

    REDUCED by $5,000 (1.1%) on 04/22/2026

    For Sale O6386278 - 18167 CIDER MILL LN, WINTER GARDEN, FL 34787 15 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1817
       Built: 2025
    Monthly Fee: $205
       Tax: $1,424 (2025)
    Community: Waterleigh
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,899 (change assumption)
    Mortgage ($2,575) + Fees ($205) + Taxes in 2025 ($119)


    Taxes:$1,424

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11217 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $849,99025 Days on yellowkey   MLS ID: O6399115

    REDUCED by $16,821 (1.9%) on 04/22/2026

    For Sale O6399115 - 11217 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: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,022 (change assumption)
    Mortgage ($4,657) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16840 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $584,990110 Days on yellowkey   MLS ID: O6374947

    REDUCED by $5,710 (1.0%) on 04/22/2026

    For Sale O6374947 - 16840 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: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,570 (change assumption)
    Mortgage ($3,205) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11205 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $949,99047 Days on yellowkey   MLS ID: O6392839

    REDUCED by $19,101 (2.0%) on 04/22/2026

    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
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,621 (change assumption)
    Mortgage ($5,205) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11193 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $834,99059 Days on yellowkey   MLS ID: O6389839

    REDUCED by $5,000 (0.6%) on 04/22/2026

    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: $4,991 (change assumption)
    Mortgage ($4,575) + 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

    $559,990148 Days on yellowkey   MLS ID: O6367156

    REDUCED by $5,000 (0.9%) on 04/22/2026

    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: $3,424 (change assumption)
    Mortgage ($3,068) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $894,990145 Days on yellowkey   MLS ID: O6367437

    REDUCED by $5,000 (0.6%) on 04/22/2026

    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: $5,270 (change assumption)
    Mortgage ($4,904) + Fees ($200) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16632 POINT ROCK DR, WINTER GARDEN, FL 34787

    $550,000131 Days on yellowkey   MLS ID: OM715702

    SHORT SALE OM715702 - 16632 POINT ROCK DR, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2292
       Built: 2023
    Monthly Fee: $281
       Tax: $8,546 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,007 (change assumption)
    Mortgage ($3,014) + Fees ($281) + Taxes in 2024 ($712)


    Taxes:$8,546

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 9459 JAYWOOD RD, WINTER GARDEN, FL 34787

    $755,00068 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


  • 16137 WIND VIEW LN, WINTER GARDEN, FL 34787

    $575,000259 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


  • 16736 OAKBORO ST, WINTER GARDEN, FL 34787

    $575,00051 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

    $725,00072 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

    $925,00066 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


  • 18344 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $745,000138 Days on yellowkey   MLS ID: S5140531

    For Sale S5140531 - 18344 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2924
       Built: 2023
    Monthly Fee: $300
       Tax: $1,706 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,524 (change assumption)
    Mortgage ($4,082) + Fees ($300) + Taxes in 2024 ($142)


    Taxes:$1,706

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 12043 HOLYSTONE ST, WINTER GARDEN, FL 34787

    $385,000244 Days on yellowkey   MLS ID: O6339950

    1 Days Off yellowkey (back on 4/17/2026)

    REDUCED by $5,000 (1.3%) on 04/01/2026

    For Sale O6339950 - 12043 HOLYSTONE ST, WINTER GARDEN, FL 34787 38 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1568
       Built: 2023
    Monthly Fee: $259
       Tax: $6,198 (2024)
    Community: Waterleigh Ph 4A
    Townhouse


    Estimated Monthly Payment: $2,885 (change assumption)
    Mortgage ($2,110) + Fees ($259) + Taxes in 2024 ($516)


    Taxes:$6,198

    Elementary School: Waterbridge Elem

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 9936 GOLDEN LAGOON ALY, WINTER GARDEN, FL 34787

    $475,00059 Days on yellowkey   MLS ID: O6390052

    1 Days Off yellowkey (back on 4/16/2026)

    For Sale O6390052 - 9936 GOLDEN LAGOON ALY, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1816
       Built: 2018
    Monthly Fee: $292
       Tax: $3,994 (2025)
    Community: Waterleigh Phase 2B
    Townhouse


    Estimated Monthly Payment: $3,228 (change assumption)
    Mortgage ($2,603) + Fees ($292) + Taxes in 2025 ($333)


    Taxes:$3,994

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle




Why Bother Searching Elsewhere for Waterleigh Homes for Sale and Other Winter Garden Real Estate?

Waterleigh home, townhome, condo, villa, and other listing sales data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in Waterleigh. You can use our website to view Multiple Listing Service (MLS) data on Waterleigh Real Estate. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Waterleigh. Winter Garden listings.



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.