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Waterleigh Homes for Sale in Winter Garden - 84 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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  • 8750 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $1,895,00021 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


  • 16140 HARBOR MIST ALY, WINTER GARDEN, FL 34787

    $560,000215 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

    $459,90054 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


  • 8275 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $555,00088 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


  • 17865 ADRIFT RD, WINTER GARDEN, FL 34787

    $599,000349 Days on yellowkey   MLS ID: O6329586

    For Sale O6329586 - 17865 ADRIFT RD, WINTER GARDEN, FL 34787 26 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2484
       Built: 2023
    Monthly Fee: $277
       Tax: $9,155 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,322 (change assumption)
    Mortgage ($3,282) + Fees ($277) + Taxes in 2024 ($763)


    Taxes:$9,155

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16840 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $569,990169 Days on yellowkey   MLS ID: O6374947

    REDUCED by $5,000 (0.9%) on 06/04/2026

    For Sale O6374947 - 16840 HOBE SOUND CT, WINTER GARDEN, FL 34787 13 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,488 (change assumption)
    Mortgage ($3,123) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16149 WIND VIEW LN, WINTER GARDEN, FL 34787

    $495,000116 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


  • 12003 HOLYSTONE ST, WINTER GARDEN, FL 34787

    $445,00064 Days on yellowkey   MLS ID: L4961121

    For Sale L4961121 - 12003 HOLYSTONE ST, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1814
       Built: 2023
    Monthly Fee: $269
       Tax: $5,292 (2025)
    Community: Waterleigh Ph 4A
    Townhouse


    Estimated Monthly Payment: $3,148 (change assumption)
    Mortgage ($2,438) + Fees ($269) + Taxes in 2025 ($441)


    Taxes:$5,292

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 10089 SALT POINT DR, WINTER GARDEN, FL 34787

    $465,00099 Days on yellowkey   MLS ID: O6392385

    REDUCED by $10,000 (2.1%) on 06/05/2026

    For Sale O6392385 - 10089 SALT POINT DR, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1654
       Built: 2022
    Monthly Fee: $260
       Tax: $6,886 (2025)
    Community: Waterleigh Ph 2E
    Townhouse


    Estimated Monthly Payment: $3,382 (change assumption)
    Mortgage ($2,548) + Fees ($260) + Taxes in 2025 ($574)


    Taxes:$6,886

    Elementary School: Avalon Elem

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16834 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $599,99076 Days on yellowkey   MLS ID: O6401373

    REDUCED by $25,000 (4.0%) on 06/04/2026

    For Sale O6401373 - 16834 HOBE SOUND CT, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2494
       Built: 2026
    Monthly Fee: $190
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,643 (change assumption)
    Mortgage ($3,288) + Fees ($190) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11283 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $909,46663 Days on yellowkey   MLS ID: O6405091

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

    For Sale O6405091 - 11283 HOLLOW BAY DR, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3225
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,348 (change assumption)
    Mortgage ($4,983) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11271 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $869,99669 Days on yellowkey   MLS ID: O6403252

    3 Days Off yellowkey (back on 5/27/2026)

    For Sale O6403252 - 11271 HOLLOW BAY DR, 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: $5,132 (change assumption)
    Mortgage ($4,767) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16197 WIND VIEW LN, WINTER GARDEN, FL 34787

    $517,00089 Days on yellowkey   MLS ID: O6397229

    REDUCED by $3,000 (0.6%) on 05/24/2026

    For Sale O6397229 - 16197 WIND VIEW LN, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2016
    Monthly Fee: $332
       Tax: $7,677 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,805 (change assumption)
    Mortgage ($2,833) + Fees ($332) + Taxes in 2025 ($640)


    Taxes:$7,677

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16533 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787

    $470,50047 Days on yellowkey   MLS ID: O6409798

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

    For Sale O6409798 - 16533 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787 18 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1817
       Built: 2025
    Monthly Fee: $205
       Tax: $1,424 (2025)
    Community: Waterleigh
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,902 (change assumption)
    Mortgage ($2,578) + Fees ($205) + Taxes in 2025 ($119)


    Taxes:$1,424

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17098 WATER SPRING BLVD, WINTER GARDEN, FL 34787

    $560,000239 Days on yellowkey   MLS ID: O6357599

    REDUCED by $20,000 (3.4%) on 05/21/2026

    For Sale O6357599 - 17098 WATER SPRING BLVD, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2484
       Built: 2023
    Monthly Fee: $271
       Tax: $9,199 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,106 (change assumption)
    Mortgage ($3,068) + Fees ($271) + Taxes in 2024 ($767)


    Taxes:$9,199

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787

    $529,999162 Days on yellowkey   MLS ID: NS1087076

    1 Days Off yellowkey (back on 5/21/2026)

    REDUCED by $38,001 (6.7%) on 05/02/2026

    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: $3,384 (change assumption)
    Mortgage ($2,904) + Fees ($291) + Taxes in 2024 ($189)


    Taxes:$2,273

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11803 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $781,18649 Days on yellowkey   MLS ID: O6407993

    0 Days Off yellowkey (back on 5/19/2026)

    For Sale O6407993 - 11803 SHINE VIEW LN, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,696 (change assumption)
    Mortgage ($4,280) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11265 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $870,33162 Days on yellowkey   MLS ID: O6405351

    2 Days Off yellowkey (back on 5/19/2026)

    For Sale O6405351 - 11265 HOLLOW BAY DR, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3225
       Built: 2025
    Monthly Fee: $200
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,135 (change assumption)
    Mortgage ($4,769) + Fees ($200) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9456 KOMIKA LN W #1, WINTER GARDEN, FL 34787

    $468,150157 Days on yellowkey   MLS ID: S5142815

    REDUCED by $1,850 (0.4%) on 05/14/2026

    For Sale S5142815 - 9456 KOMIKA LN W #1, WINTER GARDEN, FL 34787 56 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1705
       Built: 2020
    Monthly Fee: $262
       Tax: $5,902 (2025)
    Community: Waterleigh Phase 3A
    Single Family


    Estimated Monthly Payment: $3,319 (change assumption)
    Mortgage ($2,565) + Fees ($262) + Taxes in 2025 ($492)


    Taxes:$5,902

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 18041 CIDER MILL LN, WINTER GARDEN, FL 34787

    $833,191144 Days on yellowkey   MLS ID: O6382386

    1 Days Off yellowkey (back on 5/8/2026)

    For Sale O6382386 - 18041 CIDER MILL LN, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3225
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,981 (change assumption)
    Mortgage ($4,565) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    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.