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Winter Garden Single Family Homes For Sale - 644 homes

Winter Garden Single Family Homes for Sale are located in Orange County, Florida. Find single family homes for sale in Winter Garden with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Garden single family houses.

Location: Winter Garden

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  • 16385 ADMIRALS COVE LN, WINTER GARDEN, FL 34787

    $469,90058 Days on yellowkey   MLS ID: O6393056

    0 Days Off yellowkey (back on 5/18/2026)

    REDUCED by $100 (0.0%) on 04/27/2026

    For Sale O6393056 - 16385 ADMIRALS COVE LN, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1705
       Built: 2020
    Monthly Fee: $257
       Tax: $4,805 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,232 (change assumption)
    Mortgage ($2,575) + Fees ($257) + Taxes in 2025 ($400)


    Taxes:$4,805

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1335 DANIELS COVE DR, WINTER GARDEN, FL 34787

    $325,0007 Days on yellowkey   MLS ID: O6402285

    0 Days Off yellowkey (back on 5/18/2026)

    For Sale O6402285 - 1335 DANIELS COVE DR, WINTER GARDEN, FL 34787 22 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1371
       Built: 1998
    Monthly Fee: $54
       Tax: $1,024 (2025)
    Community: Daniels Crossing Rep
    Single Family


    Estimated Monthly Payment: $1,920 (change assumption)
    Mortgage ($1,781) + Fees ($54) + Taxes in 2025 ($85)


    Taxes:$1,024

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 8124 RED CROSSBILL ST, WINTER GARDEN, FL 34787

    $840,000246 Days on yellowkey   MLS ID: O6345400

    REDUCED by $10,000 (1.2%) on 04/21/2026

    For Sale O6345400 - 8124 RED CROSSBILL ST, WINTER GARDEN, FL 34787 67 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3708
       Built: 2013
    Monthly Fee: $246
       Tax: $7,515 (2024)
    Community: Summerlake Pd Ph 1A
    Single Family


    Estimated Monthly Payment: $5,475 (change assumption)
    Mortgage ($4,603) + Fees ($246) + Taxes in 2024 ($626)


    Taxes:$7,515

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6102 WHISPERING GLEN, WINTER GARDEN, FL 34787

    $576,8909 Days on yellowkey   MLS ID: O6407803

    3 Days Off yellowkey (back on 5/18/2026)

    For Sale O6407803 - 6102 WHISPERING GLEN, WINTER GARDEN, FL 34787 28 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1913
       Built: 2024
    Monthly Fee: $152
       Tax: $1,372 (2024)
    Community: Silverleaf Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,427 (change assumption)
    Mortgage ($3,161) + Fees ($152) + Taxes in 2024 ($114)


    Taxes:$1,372

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 2640 GROVE VIEW DR, WINTER GARDEN, FL 34787

    $789,90028 Days on yellowkey   MLS ID: O6401215

    REDUCED by $5,100 (0.6%) on 05/18/2026

    For Sale O6401215 - 2640 GROVE VIEW DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3738
       Built: 2001
    Monthly Fee: $90
       Tax: $10,261 (2025)
    Community: Wintermere Pointe Ph 02 46/141
    Single Family


    Estimated Monthly Payment: $5,273 (change assumption)
    Mortgage ($4,328) + Fees ($90) + Taxes in 2025 ($855)


    Taxes:$10,261

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15197 BLUE PEACOCK LN, WINTER GARDEN, FL 34787

    $704,90070 Days on yellowkey   MLS ID: O6390611

    REDUCED by $5,100 (0.7%) on 05/18/2026

    For Sale O6390611 - 15197 BLUE PEACOCK LN, WINTER GARDEN, FL 34787 67 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2440
       Built: 2024
    Monthly Fee: $100
       Tax: $8,695 (2025)
    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $4,687 (change assumption)
    Mortgage ($3,862) + Fees ($100) + Taxes in 2025 ($725)


    Taxes:$8,695

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15026 SUMMER HARVEST ST, WINTER GARDEN, FL 34787

    $689,990114 Days on yellowkey   MLS ID: S5142710

    For Sale S5142710 - 15026 SUMMER HARVEST ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2908
       Built: 2024
    Monthly Fee: $202
       Tax: $9,669 (2025)
    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,788 (change assumption)
    Mortgage ($3,781) + Fees ($202) + Taxes in 2025 ($806)


    Taxes:$9,669

    Elementary School: Whispering Oak Elem

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 15025 PIGEON PLUM LN, WINTER GARDEN, FL 34787

    $599,99010 Days on yellowkey   MLS ID: O6404948

    1 Days Off yellowkey (back on 5/16/2026)

    For Sale O6404948 - 15025 PIGEON PLUM LN, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2605
       Built: 2016
    Monthly Fee: $252
       Tax: $6,086 (2025)
    Community: Summerlake Pd Ph 2C
    Single Family


    Estimated Monthly Payment: $4,047 (change assumption)
    Mortgage ($3,288) + Fees ($252) + Taxes in 2025 ($507)


    Taxes:$6,086

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9231 GRAND ISLAND WAY, WINTER GARDEN, FL 34787

    $495,00015 Days on yellowkey   MLS ID: O6405710

    For Sale O6405710 - 9231 GRAND ISLAND WAY, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2060
       Built: 2017
    Monthly Fee: $154
       Tax: $6,732 (2025)
    Community: Lakeside
    Single Family


    Estimated Monthly Payment: $3,427 (change assumption)
    Mortgage ($2,712) + Fees ($154) + Taxes in 2025 ($561)


    Taxes:$6,732

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 12362 BRACCO ST, WINTER GARDEN, FL 34787

    $515,00021 Days on yellowkey   MLS ID: O6404125

    For Sale O6404125 - 12362 BRACCO ST, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2094
       Built: 2023
    Monthly Fee: $105
       Tax: $8,231 (2025)
    Community: Highland Rdg Ph 2
    Single Family


    Estimated Monthly Payment: $3,613 (change assumption)
    Mortgage ($2,822) + Fees ($105) + Taxes in 2025 ($686)


    Taxes:$8,231

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9459 JAYWOOD RD, WINTER GARDEN, FL 34787

    $755,00081 Days on yellowkey   MLS ID: O6386488

    REDUCED by $5,000 (0.7%) on 04/20/2026

    For Sale O6386488 - 9459 JAYWOOD RD, WINTER GARDEN, FL 34787 55 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2020
    Monthly Fee: $261
       Tax: $6,669 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $4,954 (change assumption)
    Mortgage ($4,137) + Fees ($261) + Taxes in 2025 ($556)


    Taxes:$6,669

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 156 STANTON ESTATES CIR, WINTER GARDEN, FL 34787

    $1,200,00078 Days on yellowkey   MLS ID: O6384801

    For Sale O6384801 - 156 STANTON ESTATES CIR, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3170
       Built: 2018
    Monthly Fee: $188
       Tax: $7,979 (2024)
    Community: Stanton Estates
    Single Family


    Estimated Monthly Payment: $7,428 (change assumption)
    Mortgage ($6,575) + Fees ($188) + Taxes in 2024 ($665)


    Taxes:$7,979

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 2202 ROMANUM DR, WINTER GARDEN, FL 34787

    $579,90036 Days on yellowkey   MLS ID: O6398743

    REDUCED by $5,100 (0.9%) on 05/18/2026

    For Sale O6398743 - 2202 ROMANUM DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1889
       Built: 2015
    Monthly Fee: $211
       Tax: $3,839 (2025)
    Community: Alexander Ridge
    Single Family


    Estimated Monthly Payment: $3,708 (change assumption)
    Mortgage ($3,177) + Fees ($211) + Taxes in 2025 ($320)


    Taxes:$3,839

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15111 DRIFTWOOD BEND ST, WINTER GARDEN, FL 34787

    $628,0005 Days on yellowkey   MLS ID: O6408574

    For Sale O6408574 - 15111 DRIFTWOOD BEND ST, WINTER GARDEN, FL 34787 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2573
       Built: 2017
    Monthly Fee: $195
       Tax: $9,620 (2025)
    Community: Signature Lakes Ph 3B-4, 3B-5
    Single Family


    Estimated Monthly Payment: $4,438 (change assumption)
    Mortgage ($3,441) + Fees ($195) + Taxes in 2025 ($802)


    Taxes:$9,620

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12597 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787

    $520,0005 Days on yellowkey   MLS ID: O6407413

    For Sale O6407413 - 12597 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2322
       Built: 2021
    Monthly Fee: $225
       Tax: $8,365 (2025)
    Community: Encore At Ovation
    Single Family


    Estimated Monthly Payment: $3,771 (change assumption)
    Mortgage ($2,849) + Fees ($225) + Taxes in 2025 ($697)


    Taxes:$8,365

    Elementary School: Water Spring Elementary

    High School: Lake Nona High

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16185 TALIESIN ST, WINTER GARDEN, FL 34787

    $660,0008 Days on yellowkey   MLS ID: O6407177

    For Sale O6407177 - 16185 TALIESIN ST, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2372
       Built: 2020
    Monthly Fee: $127
       Tax: $6,048 (2025)
    Community: Hawksmoor
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,247 (change assumption)
    Mortgage ($3,616) + Fees ($127) + Taxes in 2025 ($504)


    Taxes:$6,048

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1157 VINSETTA CIR, WINTER GARDEN, FL 34787

    $800,0007 Days on yellowkey   MLS ID: O6403597

    For Sale O6403597 - 1157 VINSETTA CIR, WINTER GARDEN, FL 34787 64 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3598
       Built: 2014
    Monthly Fee: $112
       Tax: $6,599 (2025)
    Community: Avalon Reserve Village 1
    Single Family


    Estimated Monthly Payment: $5,045 (change assumption)
    Mortgage ($4,383) + Fees ($112) + Taxes in 2025 ($550)


    Taxes:$6,599

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $590,000267 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


  • 15456 GILLIGAN CT, WINTER GARDEN, FL 34787

    $575,000295 Days on yellowkey   MLS ID: A4660262

    REDUCED by $25,000 (4.2%) on 05/08/2026

    For Sale A4660262 - 15456 GILLIGAN CT, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2571
       Built: 2020
    Monthly Fee: $102
       Tax: $8,702 (2024)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $3,978 (change assumption)
    Mortgage ($3,151) + Fees ($102) + Taxes in 2024 ($725)


    Taxes:$8,702

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16197 WIND VIEW LN, WINTER GARDEN, FL 34787

    $520,00043 Days on yellowkey   MLS ID: O6397229

    REDUCED by $7,000 (1.3%) on 05/18/2026

    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: $3,821 (change assumption)
    Mortgage ($2,849) + 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




Why Bother Searching Elsewhere for Winter Garden Single Family Homes for Sale?

Winter Garden home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Garden. You can use our website to view Multiple Listing Service (MLS) data on Winter Garden single family homes. 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 Winter Garden single family home 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.