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Winter Garden Single Family Homes For Sale - 528 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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  • 14168 LARKSPUR LAKE DR, WINTER GARDEN, FL 34787

    $2,999,990206 Days on yellowkey   MLS ID: O6346469

    REDUCED by $333,389 (10.0%) on 04/14/2026

    For Sale O6346469 - 14168 LARKSPUR LAKE DR, WINTER GARDEN, FL 34787 19 photos

    Bed: 6   Bath: 7.0   Gar: 4
    Liv Area Sq Ft: 6442
       Built: 2025
    Monthly Fee: $112
       Tax: $6,673 (2024)
    Community: Shorefront Cove
    Single Family


    Estimated Monthly Payment: $17,106 (change assumption)
    Mortgage ($16,438) + Fees ($112) + Taxes in 2024 ($556)


    Taxes:$6,673

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4642 PRAIRIE CREEK ST, WINTER GARDEN, FL 34787

    $585,00047 Days on yellowkey   MLS ID: S5144794

    REDUCED by $6,000 (1.0%) on 04/14/2026

    For Sale S5144794 - 4642 PRAIRIE CREEK ST, WINTER GARDEN, FL 34787 50 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2149
       Built: 2021
    Monthly Fee: $281
       Tax: $6,500 (2024)
    Community: Enclave At Hamlin
    Single Family


    Estimated Monthly Payment: $4,028 (change assumption)
    Mortgage ($3,205) + Fees ($281) + Taxes in 2024 ($542)


    Taxes:$6,500

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 931 KYLEE ALY, WINTER GARDEN, FL 34787

    $849,00044 Days on yellowkey   MLS ID: O6387922

    REDUCED by $26,000 (3.0%) on 04/14/2026

    For Sale O6387922 - 931 KYLEE ALY, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2831
       Built: 2022
    Monthly Fee: $401
       Tax: $9,637 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $5,856 (change assumption)
    Mortgage ($4,652) + Fees ($401) + Taxes in 2025 ($803)


    Taxes:$9,637

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 12112 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787

    $540,000128 Days on yellowkey   MLS ID: O6366467

    REDUCED by $10,000 (1.8%) on 04/14/2026

    For Sale O6366467 - 12112 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2801
       Built: 2021
    Monthly Fee: $192
       Tax: $9,460 (2025)
    Community: Encore At Ovation
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,939 (change assumption)
    Mortgage ($2,959) + Fees ($192) + Taxes in 2025 ($788)


    Taxes:$9,460

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15312 GILLIGAN CT, WINTER GARDEN, FL 34787

    $1,150,00086 Days on yellowkey   MLS ID: O6372954

    0 Days Off yellowkey (back on 4/14/2026)

    For Sale O6372954 - 15312 GILLIGAN CT, WINTER GARDEN, FL 34787 69 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3652
       Built: 2020
    Monthly Fee: $102
       Tax: $9,787 (2024)
    Community: Winding Bay Ii Llc
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,219 (change assumption)
    Mortgage ($6,301) + Fees ($102) + Taxes in 2024 ($816)


    Taxes:$9,787

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 17156 INGRAM BLUFF DR, WINTER GARDEN, FL 34787

    $606,44031 Days on yellowkey   MLS ID: G5109791

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

    For Sale G5109791 - 17156 INGRAM BLUFF DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 2026
    Monthly Fee: $140

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,463 (change assumption)
    Mortgage ($3,323) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14241 COLONIAL POINTE DR, WINTER GARDEN, FL 34787

    $1,390,00072 Days on yellowkey   MLS ID: O6379808

    3 Days Off yellowkey (back on 4/14/2026)

    For Sale O6379808 - 14241 COLONIAL POINTE DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 7   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5001
       Built: 2017
    Monthly Fee: $215
       Tax: $9,308 (2024)
    Community: Overlook 2 At Hamlin
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,607 (change assumption)
    Mortgage ($7,616) + Fees ($215) + Taxes in 2024 ($776)


    Taxes:$9,308

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 14788 FIELD DAISY DR, WINTER GARDEN, FL 34787

    $617,5005 Days on yellowkey   MLS ID: O6398754

    For Sale O6398754 - 14788 FIELD DAISY DR, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1992
       Built: 2026
    Monthly Fee: $229

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $3,612 (change assumption)
    Mortgage ($3,383) + Fees ($229) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14006 FRASIER STREET, WINTER GARDEN, FL 34787

    $659,0005 Days on yellowkey   MLS ID: O6398760

    For Sale O6398760 - 14006 FRASIER STREET, WINTER GARDEN, FL 34787 79 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2098
       Built: 2023
    Monthly Fee: $100
       Tax: $8,274 (2025)
    Community: Highland Ridge
    Single Family


    Estimated Monthly Payment: $4,400 (change assumption)
    Mortgage ($3,611) + Fees ($100) + Taxes in 2025 ($689)


    Taxes:$8,274

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 883 TILDEN OAKS TRL, WINTER GARDEN, FL 34787

    $1,075,0005 Days on yellowkey   MLS ID: O6393635

    0 Days Off yellowkey (back on 4/13/2026)

    For Sale O6393635 - 883 TILDEN OAKS TRL, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2811
       Built: 2025
    Monthly Fee: $625
       Tax: $3,649 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $6,819 (change assumption)
    Mortgage ($5,890) + Fees ($625) + Taxes in 2025 ($304)


    Taxes:$3,649

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15524 AVIATION ALY, WINTER GARDEN, FL 34787

    $569,9007 Days on yellowkey   MLS ID: O6398331

    For Sale O6398331 - 15524 AVIATION ALY, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2414
       Built: 2015
    Monthly Fee: $328
       Tax: $8,711 (2025)
    Community: Overlook 2/Hamlin Ph 1 & 6
    Single Family


    Estimated Monthly Payment: $4,177 (change assumption)
    Mortgage ($3,123) + Fees ($328) + Taxes in 2025 ($726)


    Taxes:$8,711

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 15442 ENCHANTED MELODY WAY, WINTER GARDEN, FL 34787

    $609,85028 Days on yellowkey   MLS ID: S5146095

    REDUCED by $3,050 (0.5%) on 04/13/2026

    For Sale S5146095 - 15442 ENCHANTED MELODY WAY, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2420
       Built: 2024
    Monthly Fee: $95
       Tax: $8,065 (2025)
    Community: Osprey Ranch Ph I
    Single Family


    Estimated Monthly Payment: $4,109 (change assumption)
    Mortgage ($3,342) + Fees ($95) + Taxes in 2025 ($672)


    Taxes:$8,065

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 7680 GREEN MOUNTAIN WAY, WINTER GARDEN, FL 34787

    $658,9009 Days on yellowkey   MLS ID: O6389013

    1 Days Off yellowkey (back on 4/13/2026)

    For Sale O6389013 - 7680 GREEN MOUNTAIN WAY, WINTER GARDEN, FL 34787 58 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2385
       Built: 2016
    Monthly Fee: $252
       Tax: $8,915 (2025)
    Community: Summerlake Pd Ph 3A
    Single Family


    Estimated Monthly Payment: $4,605 (change assumption)
    Mortgage ($3,610) + Fees ($252) + Taxes in 2025 ($743)


    Taxes:$8,915

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14058 FRASIER ST, WINTER GARDEN, FL 34787

    $459,00057 Days on yellowkey   MLS ID: V4947394

    For Sale V4947394 - 14058 FRASIER ST, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1996
       Built: 2023
    Monthly Fee: $110
       Tax: $7,893 (2024)
    Community: Highland Rdg
    Single Family


    Estimated Monthly Payment: $3,283 (change assumption)
    Mortgage ($2,515) + Fees ($110) + Taxes in 2024 ($658)


    Taxes:$7,893

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15324 GILLIGAN CT, WINTER GARDEN, FL 34787

    $950,00023 Days on yellowkey   MLS ID: O6393498

    0 Days Off yellowkey (back on 4/13/2026)

    For Sale O6393498 - 15324 GILLIGAN CT, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2794
       Built: 2020
    Monthly Fee: $102
       Tax: $641 (2025)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $5,361 (change assumption)
    Mortgage ($5,205) + Fees ($102) + Taxes in 2025 ($53)


    Taxes:$641

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15527 SWEET ORANGE AVE, WINTER GARDEN, FL 34787

    $700,00022 Days on yellowkey   MLS ID: O6394429

    For Sale O6394429 - 15527 SWEET ORANGE AVE, WINTER GARDEN, FL 34787 38 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2383
       Built: 2017
    Monthly Fee: $118
       Tax: $5,959 (2025)
    Community: Highlands/Summerlake Grvs Ph 1
    Single Family


    Estimated Monthly Payment: $4,450 (change assumption)
    Mortgage ($3,836) + Fees ($118) + Taxes in 2025 ($497)


    Taxes:$5,959

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 10224 ATWATER BAY DR, WINTER GARDEN, FL 34787

    $799,0006 Days on yellowkey   MLS ID: S5147252

    For Sale S5147252 - 10224 ATWATER BAY DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3227
       Built: 2018
    Monthly Fee: $230
       Tax: $7,456 (2025)
    Community: Waterleigh Ph 2B
    Single Family


    Estimated Monthly Payment: $5,229 (change assumption)
    Mortgage ($4,378) + Fees ($230) + Taxes in 2025 ($621)


    Taxes:$7,456

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15408 LEBEAU LOOP, WINTER GARDEN, FL 34787

    $580,00059 Days on yellowkey   MLS ID: O6383534

    For Sale O6383534 - 15408 LEBEAU LOOP, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2415
       Built: 2022
    Monthly Fee: $101
       Tax: $7,566 (2024)
    Community: Winding Bay Ph 3
    Single Family


    Estimated Monthly Payment: $3,909 (change assumption)
    Mortgage ($3,178) + Fees ($101) + Taxes in 2024 ($630)


    Taxes:$7,566

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15716 SWEET LEMON WAY, WINTER GARDEN, FL 34787

    $739,00088 Days on yellowkey   MLS ID: O6375190

    REDUCED by $26,000 (3.4%) on 04/13/2026

    For Sale O6375190 - 15716 SWEET LEMON WAY, WINTER GARDEN, FL 34787 63 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2945
       Built: 2021
    Monthly Fee: $118
       Tax: $9,510 (2025)
    Community: Highlands At Summerlake Groves
    Single Family


    Estimated Monthly Payment: $4,960 (change assumption)
    Mortgage ($4,049) + Fees ($118) + Taxes in 2025 ($793)


    Taxes:$9,510

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9256 GRAND ISLAND WAY, WINTER GARDEN, FL 34787

    $750,0008 Days on yellowkey   MLS ID: O6397917

    For Sale O6397917 - 9256 GRAND ISLAND WAY, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2507
       Built: 2017
    Monthly Fee: $164
       Tax: $6,475 (2025)
    Community: Watermark Ph 2C
    Single Family


    Estimated Monthly Payment: $4,813 (change assumption)
    Mortgage ($4,109) + Fees ($164) + Taxes in 2025 ($540)


    Taxes:$6,475

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin 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.