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Waterleigh Single Family Homes For Sale in Winter Garden - 71 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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  • 11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $899,990124 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


  • 16137 WIND VIEW LN, WINTER GARDEN, FL 34787

    $575,000238 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


  • 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787

    $568,00082 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


  • 8768 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $1,025,00075 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


  • 16140 HARBOR MIST ALY, WINTER GARDEN, FL 34787

    $565,000135 Days on yellowkey   MLS ID: O6365057

    For Sale O6365057 - 16140 HARBOR MIST ALY, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2018
    Monthly Fee: $245
       Tax: $8,615 (2025)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $4,059 (change assumption)
    Mortgage ($3,096) + Fees ($245) + Taxes in 2025 ($718)


    Taxes:$8,615

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16632 POINT ROCK DR, WINTER GARDEN, FL 34787

    $550,000110 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


  • 9354 MCLAREN ALY, WINTER GARDEN, FL 34787

    $529,50037 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


  • 16242 OUTLOOK SHORE ALY, WINTER GARDEN, FL 34787

    $515,00044 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


  • 16330 BRISK BREEZE ALY, WINTER GARDEN, FL 34787

    $550,000107 Days on yellowkey   MLS ID: G5106012

    For Sale G5106012 - 16330 BRISK BREEZE ALY, WINTER GARDEN, FL 34787 54 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2170
       Built: 2018
    Monthly Fee: $245
       Tax: $7,556 (2024)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $3,888 (change assumption)
    Mortgage ($3,014) + Fees ($245) + Taxes in 2024 ($630)


    Taxes:$7,556

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 8978 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $1,299,50023 Days on yellowkey   MLS ID: O6393744

    For Sale O6393744 - 8978 SONOMA COAST DR, WINTER GARDEN, FL 34787 76 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3911
       Built: 2022
    Monthly Fee: $277
       Tax: $13,033 (2025)
    Community: Waterleigh
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,483 (change assumption)
    Mortgage ($7,120) + Fees ($277) + Taxes in 2025 ($1,086)


    Taxes:$13,033

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16856 HYPATIA ALY, WINTER GARDEN, FL 34787

    $459,99944 Days on yellowkey   MLS ID: O6387941

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

    For Sale O6387941 - 16856 HYPATIA ALY, WINTER GARDEN, FL 34787 74 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1705
       Built: 2019
    Monthly Fee: $250
       Tax: $6,769 (2024)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $3,335 (change assumption)
    Mortgage ($2,520) + Fees ($250) + Taxes in 2024 ($564)


    Taxes:$6,769

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11181 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $852,49065 Days on yellowkey   MLS ID: O6382203

    REDUCED by $8,286 (1.0%) on 04/16/2026

    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
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,087 (change assumption)
    Mortgage ($4,671) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11241 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $799,99079 Days on yellowkey   MLS ID: O6378044

    REDUCED by $7,956 (1.0%) on 04/16/2026

    For Sale O6378044 - 11241 HOLLOW BAY DR, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2025
    Monthly Fee: $248
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,797 (change assumption)
    Mortgage ($4,383) + Fees ($248) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16809 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $579,990100 Days on yellowkey   MLS ID: O6372242

    REDUCED by $7,805 (1.3%) on 04/16/2026

    For Sale O6372242 - 16809 HOBE SOUND CT, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2025
    Monthly Fee: $248
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,592 (change assumption)
    Mortgage ($3,178) + Fees ($248) + 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

    $839,99038 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


  • 16827 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $639,99082 Days on yellowkey   MLS ID: O6376919

    REDUCED by $8,085 (1.2%) on 04/16/2026

    For Sale O6376919 - 16827 HOBE SOUND CT, WINTER GARDEN, FL 34787 18 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: $3,920 (change assumption)
    Mortgage ($3,507) + Fees ($248) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16833 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $574,990127 Days on yellowkey   MLS ID: O6367151

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

    REDUCED by $6,200 (1.1%) on 04/08/2026

    For Sale O6367151 - 16833 HOBE SOUND CT, 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 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,506 (change assumption)
    Mortgage ($3,151) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16149 WIND VIEW LN, WINTER GARDEN, FL 34787

    $498,00036 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


  • 11858 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $539,990197 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


  • 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $590,000233 Days on yellowkey   MLS ID: O6337436

    For Sale O6337436 - 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787 89 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2292
       Built: 2023
    Monthly Fee: $245
       Tax: $9,031 (2024)
    Community: Waterleigh Ph 4A
    Single Family


    Estimated Monthly Payment: $4,230 (change assumption)
    Mortgage ($3,233) + Fees ($245) + Taxes in 2024 ($753)


    Taxes:$9,031

    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.