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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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  • 16098 MANGROVE RD, WINTER GARDEN, FL 34787

    $559,000173 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


  • 9605 LOST CREEK DR, WINTER GARDEN, FL 34787

    $699,000298 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


  • 11253 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $799,99063 Days on yellowkey   MLS ID: O6405126

    REDUCED by $19,116 (2.3%) on 07/02/2026

    For Sale O6405126 - 11253 HOLLOW BAY DR, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,748 (change assumption)
    Mortgage ($4,383) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16570 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787

    $414,99069 Days on yellowkey   MLS ID: O6403257

    REDUCED by $5,000 (1.2%) on 07/02/2026

    For Sale O6403257 - 16570 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787 15 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1567
       Built: 2025
    Monthly Fee: $204
       Tax: $1,424 (2025)
    Community: Waterleigh
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,597 (change assumption)
    Mortgage ($2,274) + Fees ($204) + Taxes in 2025 ($119)


    Taxes:$1,424

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11864 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $589,990231 Days on yellowkey   MLS ID: O6361583

    REDUCED by $10,000 (1.7%) on 07/03/2026

    For Sale O6361583 - 11864 SHINE VIEW LN, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2489
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,588 (change assumption)
    Mortgage ($3,233) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 9969 LOST CREEK DR, WINTER GARDEN, FL 34787

    $1,299,00012 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


  • 8220 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $539,90033 Days on yellowkey   MLS ID: O6412974

    REDUCED by $10,100 (1.8%) on 07/03/2026

    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: $4,007 (change assumption)
    Mortgage ($2,958) + 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


  • 15537 MANGO ISLE ST, WINTER GARDEN, FL 34787

    $711,00041 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


  • 8530 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $1,499,00032 Days on yellowkey   MLS ID: O6413249

    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: $8,686 (change assumption)
    Mortgage ($8,213) + Fees ($266) + Taxes in 2025 ($207)


    Taxes:$2,479

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8768 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $890,00031 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


  • 9296 BOLERO RD, WINTER GARDEN, FL 34787

    $799,0004 Days on yellowkey   MLS ID: O6422122

    For Sale O6422122 - 9296 BOLERO RD, WINTER GARDEN, FL 34787 42 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2117
       Built: 2020
    Monthly Fee: $193
       Tax: $9,402 (2025)
    Community: Waterleigh Phs 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $5,354 (change assumption)
    Mortgage ($4,378) + Fees ($193) + Taxes in 2025 ($784)


    Taxes:$9,402

    Elementary School: Water Spring Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 16031 PEBBLE BLUFF LOOP, WINTER GARDEN, FL 34787

    $560,00065 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


  • 10198 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787

    $1,200,0005 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


  • 16330 BRISK BREEZE ALY, WINTER GARDEN, FL 34787

    $525,000187 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


  • 16632 POINT ROCK DR, WINTER GARDEN, FL 34787

    $550,000190 Days on yellowkey   MLS ID: OM715702

    0 Days Off yellowkey (back on 5/29/2026)

    SHORT SALE OM715702 - 16632 POINT ROCK DR, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2292
       Built: 2023
    Monthly Fee: $281
       Tax: $8,546 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,007 (change assumption)
    Mortgage ($3,014) + Fees ($281) + Taxes in 2024 ($712)


    Taxes:$8,546

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16353 LAKELET ALY, WINTER GARDEN, FL 34787

    $444,990396 Days on yellowkey   MLS ID: O6316011

    For Sale O6316011 - 16353 LAKELET ALY, WINTER GARDEN, FL 34787 32 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1567
       Built: 2025
    Monthly Fee: $205
       Tax: $2,130 (2024)
    Community: Waterleigh
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,821 (change assumption)
    Mortgage ($2,438) + Fees ($205) + Taxes in 2024 ($178)


    Taxes:$2,130

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $575,000313 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


  • 18339 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $650,000460 Days on yellowkey   MLS ID: O6280496

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

    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


  • 18344 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $725,000197 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


  • 16503 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787

    $459,00012 Days on yellowkey   MLS ID: O6420071

    REDUCED by $20,000 (4.2%) on 07/02/2026

    For Sale O6420071 - 16503 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787 67 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1817
       Built: 2025
    Monthly Fee: $204
       Tax: $1,424 (2025)
    Community: Waterleigh
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,838 (change assumption)
    Mortgage ($2,515) + Fees ($204) + Taxes in 2025 ($119)


    Taxes:$1,424

    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.