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Waterleigh Homes for Sale in Winter Garden - 101 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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  • 16802 OAKBORO ST, WINTER GARDEN, FL 34787

    $500,000Listed 07/21/2026 3:26PM   MLS ID: O6425489

    For Sale O6425489 - 16802 OAKBORO ST, WINTER GARDEN, FL 34787 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1705
       Built: 2020
    Monthly Fee: $21
       Tax: $7,269 (2025)
    Community: Waterleigh Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,366 (change assumption)
    Mortgage ($2,740) + Fees ($21) + Taxes in 2025 ($606)


    Taxes:$7,269

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9561 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787

    $729,0005 Days on yellowkey   MLS ID: O6426027

    For Sale O6426027 - 9561 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787 71 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3267
       Built: 2018
    Monthly Fee: $255
       Tax: $6,570 (2025)
    Community: Waterleigh Ph 2B
    Single Family


    Estimated Monthly Payment: $4,797 (change assumption)
    Mortgage ($3,994) + Fees ($255) + Taxes in 2025 ($548)


    Taxes:$6,570

    Elementary School: Atwater Bay Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16082 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787

    $739,90019 Days on yellowkey   MLS ID: O6420606

    For Sale O6420606 - 16082 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787 60 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2240
       Built: 2017
    Monthly Fee: $342
       Tax: $5,019 (2025)
    Community: Waterleigh Phase 1C
    Single Family


    Estimated Monthly Payment: $4,814 (change assumption)
    Mortgage ($4,054) + Fees ($342) + Taxes in 2025 ($418)


    Taxes:$5,019

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16098 MANGROVE RD, WINTER GARDEN, FL 34787

    $559,000188 Days on yellowkey   MLS ID: O6373125

    1 Days Off yellowkey (back on 7/6/2026)

    REDUCED by $9,000 (1.6%) on 07/02/2026

    For Sale O6373125 - 16098 MANGROVE RD, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2472
       Built: 2021
    Monthly Fee: $257
       Tax: $5,612 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,788 (change assumption)
    Mortgage ($3,063) + Fees ($257) + Taxes in 2025 ($468)


    Taxes:$5,612

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8721 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $679,00080 Days on yellowkey   MLS ID: G5111855

    REDUCED by $16,000 (2.3%) on 06/08/2026

    For Sale G5111855 - 8721 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2842
       Built: 2015
    Monthly Fee: $342
       Tax: $8,082 (2025)
    Community: Waterleigh Ph 1A
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,736 (change assumption)
    Mortgage ($3,720) + Fees ($342) + Taxes in 2025 ($673)


    Taxes:$8,082

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16161 MANGROVE RD, WINTER GARDEN, FL 34787

    $499,90015 Days on yellowkey   MLS ID: O6420311

    REDUCED by $15,100 (2.9%) on 07/21/2026

    For Sale O6420311 - 16161 MANGROVE RD, WINTER GARDEN, FL 34787 48 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2200
       Built: 2021
    Monthly Fee: $257
       Tax: $6,775 (2025)
    Community: Waterleigh Ph 3B 3C &3D
    Single Family


    Estimated Monthly Payment: $3,561 (change assumption)
    Mortgage ($2,739) + Fees ($257) + Taxes in 2025 ($565)


    Taxes:$6,775

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 18344 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $660,000212 Days on yellowkey   MLS ID: S5140531

    2 Days Off yellowkey (back on 7/20/2026)

    REDUCED by $65,000 (9.0%) on 07/14/2026

    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: $4,059 (change assumption)
    Mortgage ($3,616) + Fees ($300) + Taxes in 2024 ($142)


    Taxes:$1,706

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16131 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787

    $649,90034 Days on yellowkey   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


  • 8530 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $1,375,00047 Days on yellowkey   MLS ID: O6413249

    REDUCED by $124,000 (8.3%) on 07/20/2026

    For Sale O6413249 - 8530 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4130
       Built: 2018
    Monthly Fee: $266
       Tax: $2,479 (2025)
    Community: Waterleigh Ph 1A
    Single Family


    Estimated Monthly Payment: $8,007 (change assumption)
    Mortgage ($7,534) + Fees ($266) + Taxes in 2025 ($207)


    Taxes:$2,479

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11031 JACKSON CV, WINTER GARDEN, FL 34787

    $715,0006 Days on yellowkey   MLS ID: O6425544

    For Sale O6425544 - 11031 JACKSON CV, WINTER GARDEN, FL 34787 70 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2931
       Built: 2023
    Monthly Fee: $300
       Tax: $10,935 (2025)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $5,129 (change assumption)
    Mortgage ($3,918) + Fees ($300) + Taxes in 2025 ($911)


    Taxes:$10,935

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9611 LOST CREEK DR, WINTER GARDEN, FL 34787

    $745,000189 Days on yellowkey   MLS ID: O6373845

    REDUCED by $20,000 (2.6%) on 07/20/2026

    For Sale O6373845 - 9611 LOST CREEK DR, WINTER GARDEN, FL 34787 57 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2909
       Built: 2021
    Monthly Fee: $260
       Tax: $11,300 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $5,284 (change assumption)
    Mortgage ($4,082) + Fees ($260) + Taxes in 2025 ($942)


    Taxes:$11,300

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16149 WIND VIEW LN, WINTER GARDEN, FL 34787

    $495,000131 Days on yellowkey   MLS ID: O6389892

    REDUCED by $3,000 (0.6%) on 05/30/2026

    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: $3,417 (change assumption)
    Mortgage ($2,712) + 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


  • 15518 FOUNTAIN COVE CT, WINTER GARDEN, FL 34787

    $550,00069 Days on yellowkey   MLS ID: O6407942

    REDUCED by $24,990 (4.3%) on 07/17/2026

    For Sale O6407942 - 15518 FOUNTAIN COVE CT, WINTER GARDEN, FL 34787 64 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2040
       Built: 2018
    Monthly Fee: $342
       Tax: $8,434 (2025)
    Community: Waterleigh Ph 1A
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,058 (change assumption)
    Mortgage ($3,014) + Fees ($342) + Taxes in 2025 ($703)


    Taxes:$8,434

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16754 OAKBORO ST, WINTER GARDEN, FL 34787

    $520,00076 Days on yellowkey   MLS ID: O6404652

    REDUCED by $9,000 (1.7%) on 07/19/2026

    For Sale O6404652 - 16754 OAKBORO ST, WINTER GARDEN, FL 34787 85 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2020
    Monthly Fee: $254
       Tax: $8,808 (2025)
    Community: Waterleigh Ph 3B 3C 3D
    Single Family


    Estimated Monthly Payment: $3,837 (change assumption)
    Mortgage ($2,849) + Fees ($254) + Taxes in 2025 ($734)


    Taxes:$8,808

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 13158 BOUNTY AVE, WINTER GARDEN, FL 34787

    $395,00021 Days on yellowkey   MLS ID: O6421321

    For Sale O6421321 - 13158 BOUNTY AVE, WINTER GARDEN, FL 34787 46 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1567
       Built: 2023
    Monthly Fee: $257
       Tax: $5,577 (2025)
    Community: Waterleigh Ph 4A
    Townhouse


    Estimated Monthly Payment: $2,886 (change assumption)
    Mortgage ($2,164) + Fees ($257) + Taxes in 2025 ($465)


    Taxes:$5,577

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 8807 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $780,00027 Days on yellowkey   MLS ID: O6419920

    For Sale O6419920 - 8807 SONOMA COAST DR, WINTER GARDEN, FL 34787 25 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2022
    Monthly Fee: $261
       Tax: $9,520 (2025)
    Community: Waterleigh Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,328 (change assumption)
    Mortgage ($4,274) + Fees ($261) + Taxes in 2025 ($793)


    Taxes:$9,520

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 8768 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $890,00046 Days on yellowkey   MLS ID: O6414519

    For Sale O6414519 - 8768 SONOMA COAST DR, WINTER GARDEN, FL 34787 38 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 3416
       Built: 2022
    Monthly Fee: $275
       Tax: $11,513 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,111 (change assumption)
    Mortgage ($4,877) + Fees ($275) + 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


  • 16596 POINT ROCK DR, WINTER GARDEN, FL 34787

    $539,90048 Days on yellowkey   MLS ID: O6412721

    REDUCED by $20,100 (3.6%) on 06/10/2026

    For Sale O6412721 - 16596 POINT ROCK DR, WINTER GARDEN, FL 34787 54 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2023
    Monthly Fee: $254
       Tax: $8,961 (2025)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $3,959 (change assumption)
    Mortgage ($2,958) + Fees ($254) + Taxes in 2025 ($747)


    Taxes:$8,961

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 18422 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $815,00050 Days on yellowkey   MLS ID: O6412770

    1 Days Off yellowkey (back on 6/21/2026)

    For Sale O6412770 - 18422 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 66 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3231
       Built: 2024
    Monthly Fee: $300
       Tax: $10,531 (2025)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $5,643 (change assumption)
    Mortgage ($4,466) + Fees ($300) + Taxes in 2025 ($878)


    Taxes:$10,531

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15537 MANGO ISLE ST, WINTER GARDEN, FL 34787

    $690,00056 Days on yellowkey   MLS ID: S5150619

    REDUCED by $21,000 (3.0%) on 07/09/2026

    For Sale S5150619 - 15537 MANGO ISLE ST, WINTER GARDEN, FL 34787 60 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: $4,917 (change assumption)
    Mortgage ($3,781) + 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




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.