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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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  • 8506 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $1,299,00022 Days on yellowkey   MLS ID: O6421255

    For Sale O6421255 - 8506 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 51 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 3966
       Built: 2016
    Monthly Fee: $380
       Tax: $11,330 (2025)
    Community: Waterleigh Ph 1A
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,442 (change assumption)
    Mortgage ($7,118) + Fees ($380) + Taxes in 2025 ($944)


    Taxes:$11,330

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $575,000328 Days on yellowkey   MLS ID: O6337436

    REDUCED by $15,000 (2.5%) on 06/20/2026

    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: $4,148 (change assumption)
    Mortgage ($3,151) + 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


  • 10198 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787

    $1,200,00020 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


  • 11045 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $724,900116 Days on yellowkey   MLS ID: O6394192

    REDUCED by $5,000 (0.7%) on 07/11/2026

    For Sale O6394192 - 11045 HOLLOW BAY DR, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2025
    Monthly Fee: $295
       Tax: $3,196 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,533 (change assumption)
    Mortgage ($3,972) + Fees ($295) + Taxes in 2025 ($266)


    Taxes:$3,196

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15741 FOUNTAIN SPRINGS RD, WINTER GARDEN, FL 34787

    $565,00012 Days on yellowkey   MLS ID: O6423527

    For Sale O6423527 - 15741 FOUNTAIN SPRINGS RD, WINTER GARDEN, FL 34787 56 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2020
    Monthly Fee: $257
       Tax: $614 (2025)
    Community: Waterleigh Phase 3Bcd
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,404 (change assumption)
    Mortgage ($3,096) + Fees ($257) + Taxes in 2025 ($51)


    Taxes:$614

    Elementary School: Water Spring Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12014 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $554,99013 Days on yellowkey   MLS ID: O6423746

    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: $3,457 (change assumption)
    Mortgage ($3,041) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16625 POINT ROCK DR, WINTER GARDEN, FL 34787

    $569,90014 Days on yellowkey   MLS ID: O6423042

    For Sale O6423042 - 16625 POINT ROCK DR, WINTER GARDEN, FL 34787 53 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2022
    Monthly Fee: $291
       Tax: $7,740 (2025)
    Community: Waterleigh
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,059 (change assumption)
    Mortgage ($3,123) + Fees ($291) + Taxes in 2025 ($645)


    Taxes:$7,740

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 11863 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $850,62113 Days on yellowkey   MLS ID: O6423774

    For Sale O6423774 - 11863 SHINE VIEW LN, WINTER GARDEN, FL 34787 7 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: $5,077 (change assumption)
    Mortgage ($4,661) + 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

    $549,99013 Days on yellowkey   MLS ID: O6423763

    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: $3,429 (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


  • 16822 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $599,99013 Days on yellowkey   MLS ID: O6423720

    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


  • 11259 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $889,99027 Days on yellowkey   MLS ID: O6419946

    REDUCED by $6,301 (0.7%) on 07/09/2026

    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: $5,250 (change assumption)
    Mortgage ($4,877) + Fees ($208) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9463 KOMIKA LN, WINTER GARDEN, FL 34787

    $545,00042 Days on yellowkey   MLS ID: O6415771

    REDUCED by $11,000 (2.0%) on 07/08/2026

    For Sale O6415771 - 9463 KOMIKA LN, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2020
    Monthly Fee: $257
       Tax: $8,885 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $3,984 (change assumption)
    Mortgage ($2,986) + Fees ($257) + Taxes in 2025 ($740)


    Taxes:$8,885

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9506 BOLERO RD, WINTER GARDEN, FL 34787

    $749,00028 Days on yellowkey   MLS ID: O6419794

    0 Days Off yellowkey (back on 7/8/2026)

    For Sale O6419794 - 9506 BOLERO RD, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2117
       Built: 2020
    Monthly Fee: $267
       Tax: $6,938 (2025)
    Community: Waterleigh Ph 3A
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,949 (change assumption)
    Mortgage ($4,104) + Fees ($267) + Taxes in 2025 ($578)


    Taxes:$6,938

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16613 POINT ROCK DR, WINTER GARDEN, FL 34787

    $499,000158 Days on yellowkey   MLS ID: R4910718

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

    For Sale R4910718 - 16613 POINT ROCK DR, WINTER GARDEN, FL 34787 13 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1689
       Built: 2022
    Monthly Fee: $230
       Tax: $6,373 (2024)
    Community: Waterleigh Ph 4A
    Single Family


    Estimated Monthly Payment: $3,495 (change assumption)
    Mortgage ($2,734) + Fees ($230) + Taxes in 2024 ($531)


    Taxes:$6,373

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 9969 LOST CREEK DR, WINTER GARDEN, FL 34787

    $1,299,00027 Days on yellowkey   MLS ID: O6419414

    For Sale O6419414 - 9969 LOST CREEK DR, WINTER GARDEN, FL 34787 84 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3910
       Built: 2021
    Monthly Fee: $271
       Tax: $12,281 (2025)
    Community: Waterleigh Ph 3B 3C & 3D
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,412 (change assumption)
    Mortgage ($7,118) + Fees ($271) + Taxes in 2025 ($1,023)


    Taxes:$12,281

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9976 BEACH PORT DR, WINTER GARDEN, FL 34787

    $1,274,00023 Days on yellowkey   MLS ID: O6420960

    0 Days Off yellowkey (back on 6/29/2026)

    For Sale O6420960 - 9976 BEACH PORT DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3910
       Built: 2020
    Monthly Fee: $260
       Tax: $11,868 (2025)
    Community: Waterleigh Ph 2C-2 & 2C-3
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,230 (change assumption)
    Mortgage ($6,981) + Fees ($260) + Taxes in 2025 ($989)


    Taxes:$11,868

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9360 MCLAREN ALY, WINTER GARDEN, FL 34787

    $575,00061 Days on yellowkey   MLS ID: O6408913

    REDUCED by $20,000 (3.4%) on 07/07/2026

    For Sale O6408913 - 9360 MCLAREN ALY, WINTER GARDEN, FL 34787 23 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2020
    Monthly Fee: $257
       Tax: $7,373 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,022 (change assumption)
    Mortgage ($3,151) + Fees ($257) + Taxes in 2025 ($614)


    Taxes:$7,373

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9605 LOST CREEK DR, WINTER GARDEN, FL 34787

    $699,000313 Days on yellowkey   MLS ID: V4944858

    SHORT SALE V4944858 - 9605 LOST CREEK DR, WINTER GARDEN, FL 34787 83 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2117
       Built: 2021
    Monthly Fee: $261
       Tax: $614 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,142 (change assumption)
    Mortgage ($3,830) + Fees ($261) + Taxes in 2024 ($51)


    Taxes:$614

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16031 PEBBLE BLUFF LOOP, WINTER GARDEN, FL 34787

    $560,00080 Days on yellowkey   MLS ID: O6404448

    For Sale O6404448 - 16031 PEBBLE BLUFF LOOP, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2487
       Built: 2018
    Monthly Fee: $257
       Tax: $9,371 (2025)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $4,106 (change assumption)
    Mortgage ($3,068) + Fees ($257) + Taxes in 2025 ($781)


    Taxes:$9,371

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16330 BRISK BREEZE ALY, WINTER GARDEN, FL 34787

    $525,000202 Days on yellowkey   MLS ID: G5106012

    REDUCED by $15,000 (2.8%) on 06/19/2026

    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: $3,751 (change assumption)
    Mortgage ($2,877) + 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




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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.