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Waterleigh Single Family Homes For Sale in Winter Garden - 80 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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  • 11170 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $535,00012 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: $295
       Tax: $2,389 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,426 (change assumption)
    Mortgage ($2,931) + Fees ($295) + 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


  • 8750 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $1,895,000Listed 06/16/2026 4:51PM   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

    $605,500155 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

    $589,9007 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

    $669,000219 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


  • 8807 EDEN COVE DR, WINTER GARDEN, FL 34787

    $699,500135 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


  • 16736 OAKBORO ST, WINTER GARDEN, FL 34787

    $563,90090 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

    $790,86169 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

    $711,00021 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

    $590,000293 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


  • 17798 ADRIFT RD, WINTER GARDEN, FL 34787

    $835,00020 Days on yellowkey   MLS ID: O6409173

    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: $5,713 (change assumption)
    Mortgage ($4,575) + 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


  • 16140 HARBOR MIST ALY, WINTER GARDEN, FL 34787

    $560,000195 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

    $459,90034 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

    $990,000573 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

    $550,00013 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

    $725,000177 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


  • 8768 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $890,00011 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


  • 8275 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $555,00068 Days on yellowkey   MLS ID: TB8496196

    REDUCED by $10,000 (1.8%) on 06/09/2026

    For Sale TB8496196 - 8275 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 96 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2019
       Built: 2017
    Monthly Fee: $312
       Tax: $5,109 (2025)
    Community: Waterleigh Ph 1B
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,779 (change assumption)
    Mortgage ($3,041) + Fees ($312) + Taxes in 2025 ($426)


    Taxes:$5,109

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16330 BRISK BREEZE ALY, WINTER GARDEN, FL 34787

    $540,000167 Days on yellowkey   MLS ID: G5106012

    REDUCED by $10,000 (1.8%) on 06/13/2026

    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: $3,833 (change assumption)
    Mortgage ($2,959) + 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


  • 18386 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $724,900101 Days on yellowkey   MLS ID: O6388830

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

    For Sale O6388830 - 18386 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2924
       Built: 2024
    Monthly Fee: $280
       Tax: $10,366 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $5,116 (change assumption)
    Mortgage ($3,972) + Fees ($280) + Taxes in 2024 ($864)


    Taxes:$10,366

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: None




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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.