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Waterleigh Homes for Sale in Winter Garden - 92 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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  • 16131 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787

    $649,900Listed 06/18/2026 6:09AM   MLS ID: O6417701

    For Sale O6417701 - 16131 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2117
       Built: 2017
    Monthly Fee: $342
       Tax: $6,366 (2025)
    Community: Waterleigh Ph 1C
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,433 (change assumption)
    Mortgage ($3,561) + Fees ($342) + Taxes in 2025 ($530)


    Taxes:$6,366

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 11170 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $535,00013 Days on yellowkey   MLS ID: O6414335

    REDUCED by $30,000 (5.3%) on 06/17/2026

    For Sale O6414335 - 11170 HOLLOW BAY DR, WINTER GARDEN, FL 34787 69 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2474
       Built: 2025
    Monthly Fee: $288
       Tax: $2,389 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,419 (change assumption)
    Mortgage ($2,931) + Fees ($288) + Taxes in 2025 ($199)


    Taxes:$2,389

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17798 ADRIFT RD, WINTER GARDEN, FL 34787

    $807,00021 Days on yellowkey   MLS ID: O6409173

    REDUCED by $28,000 (3.4%) on 06/17/2026

    For Sale O6409173 - 17798 ADRIFT RD, WINTER GARDEN, FL 34787 81 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3334
       Built: 2023
    Monthly Fee: $214
       Tax: $11,089 (2025)
    Community: Waterleigh Ph 4B & 4C
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,560 (change assumption)
    Mortgage ($4,422) + Fees ($214) + Taxes in 2025 ($924)


    Taxes:$11,089

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 11117 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $507,00035 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


  • 8807 EDEN COVE DR, WINTER GARDEN, FL 34787

    $699,500136 Days on yellowkey   MLS ID: G5107610

    REDUCED by $25,000 (3.5%) on 05/03/2026

    For Sale G5107610 - 8807 EDEN COVE DR, WINTER GARDEN, FL 34787 45 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3278
       Built: 2015
    Monthly Fee: $342
       Tax: $11,198 (2025)
    Community: Marina Bay At Waterl
    Single Family


    Estimated Monthly Payment: $5,108 (change assumption)
    Mortgage ($3,833) + Fees ($342) + Taxes in 2025 ($933)


    Taxes:$11,198

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 18339 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $650,000441 Days on yellowkey   MLS ID: O6280496

    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


  • 11205 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $939,99087 Days on yellowkey   MLS ID: O6392839

    1 Days Off yellowkey (back on 5/15/2026)

    REDUCED by $10,000 (1.1%) on 05/15/2026

    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: $5,566 (change assumption)
    Mortgage ($5,151) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8750 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $1,895,0002 Days on yellowkey   MLS ID: O6416046

    For Sale O6416046 - 8750 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 88 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4641
       Built: 2017
    Monthly Fee: $380
       Tax: $16,679 (2025)
    Community: Waterleigh Ph 1
    Single Family


    Estimated Monthly Payment: $12,153 (change assumption)
    Mortgage ($10,383) + Fees ($380) + Taxes in 2025 ($1,390)


    Taxes:$16,679

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16031 SCARPETTA ST, WINTER GARDEN, FL 34787

    $605,500156 Days on yellowkey   MLS ID: O6373345

    REDUCED by $4,500 (0.7%) on 05/06/2026

    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: $4,293 (change assumption)
    Mortgage ($3,318) + 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


  • 9463 KOMIKA LN, WINTER GARDEN, FL 34787

    $589,9008 Days on yellowkey   MLS ID: O6415771

    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: $4,230 (change assumption)
    Mortgage ($3,232) + 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


  • 9723 LOST CREEK DR, WINTER GARDEN, FL 34787

    $669,000220 Days on yellowkey   MLS ID: O6359309

    0 Days Off yellowkey (back on 5/4/2026)

    For Sale O6359309 - 9723 LOST CREEK DR, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2117
       Built: 2021
    Monthly Fee: $261
       Tax: $10,499 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,802 (change assumption)
    Mortgage ($3,666) + Fees ($261) + Taxes in 2025 ($875)


    Taxes:$10,499

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16736 OAKBORO ST, WINTER GARDEN, FL 34787

    $563,90091 Days on yellowkey   MLS ID: O6388784

    0 Days Off yellowkey (back on 5/30/2026)

    REDUCED by $11,100 (1.9%) on 05/12/2026

    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: $3,927 (change assumption)
    Mortgage ($3,090) + Fees ($257) + Taxes in 2024 ($581)


    Taxes:$6,967

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 18053 CIDER MILL LN, WINTER GARDEN, FL 34787

    $790,86170 Days on yellowkey   MLS ID: O6397726

    2 Days Off yellowkey (back on 6/16/2026)

    INCREASED by $3,020 (0.4%) on 06/12/2026

    For Sale O6397726 - 18053 CIDER MILL LN, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2866
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,698 (change assumption)
    Mortgage ($4,333) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15537 MANGO ISLE ST, WINTER GARDEN, FL 34787

    $711,00022 Days on yellowkey   MLS ID: S5150619

    REDUCED by $11,000 (1.5%) on 06/15/2026

    For Sale S5150619 - 15537 MANGO ISLE ST, WINTER GARDEN, FL 34787 58 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2909
       Built: 2021
    Monthly Fee: $267
       Tax: $10,430 (2025)
    Community: Waterleigh Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $5,032 (change assumption)
    Mortgage ($3,896) + Fees ($267) + Taxes in 2025 ($869)


    Taxes:$10,430

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $590,000294 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


  • 16140 HARBOR MIST ALY, WINTER GARDEN, FL 34787

    $560,000196 Days on yellowkey   MLS ID: O6365057

    0 Days Off yellowkey (back on 5/22/2026)

    REDUCED by $5,000 (0.9%) on 05/12/2026

    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: $4,031 (change assumption)
    Mortgage ($3,068) + 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


  • 10294 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787

    $459,90035 Days on yellowkey   MLS ID: O6407798

    REDUCED by $9,000 (1.9%) on 06/15/2026

    For Sale O6407798 - 10294 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787 58 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1689
       Built: 2019
    Monthly Fee: $245
       Tax: $7,600 (2025)
    Community: Waterleigh Ph 2C-1
    Single Family


    Estimated Monthly Payment: $3,398 (change assumption)
    Mortgage ($2,520) + Fees ($245) + Taxes in 2025 ($633)


    Taxes:$7,600

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9849 LOST CREEK DR, WINTER GARDEN, FL 34787

    $990,000574 Days on yellowkey   MLS ID: O6258009

    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


  • 8220 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $550,00014 Days on yellowkey   MLS ID: O6412974

    For Sale O6412974 - 8220 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2016
    Monthly Fee: $332
       Tax: $8,597 (2025)
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $4,062 (change assumption)
    Mortgage ($3,014) + Fees ($332) + Taxes in 2025 ($716)


    Taxes:$8,597

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 18344 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $725,000178 Days on yellowkey   MLS ID: S5140531

    REDUCED by $20,000 (2.7%) on 06/13/2026

    SHORT 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: $4,415 (change assumption)
    Mortgage ($3,973) + Fees ($300) + Taxes in 2024 ($142)


    Taxes:$1,706

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




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.