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Winter Garden Single Family Homes For Sale - 707 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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  • 14280 BRAEMAR ST, WINTER GARDEN, FL 34787

    $499,00064 Days on yellowkey   MLS ID: TB8500322

    REDUCED by $40,000 (7.4%) on 06/12/2026

    For Sale TB8500322 - 14280 BRAEMAR ST, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1964
       Built: 2023
    Monthly Fee: $100
       Tax: $7,928 (2025)
    Community: Highland Rdg
    Single Family


    Estimated Monthly Payment: $3,495 (change assumption)
    Mortgage ($2,734) + Fees ($100) + Taxes in 2025 ($661)


    Taxes:$7,928

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15037 LAKE BESSIE LOOP, WINTER GARDEN, FL 34787

    $1,100,0006 Days on yellowkey   MLS ID: O6418541

    For Sale O6418541 - 15037 LAKE BESSIE LOOP, WINTER GARDEN, FL 34787 35 photos

    Bed: 7   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3938
       Built: 2022
    Monthly Fee: $160
       Tax: $11,662 (2025)
    Community: Lakeside/Hamlin 60
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,159 (change assumption)
    Mortgage ($6,027) + Fees ($160) + Taxes in 2025 ($972)


    Taxes:$11,662

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 13086 SUNRISE HARVEST DR, WINTER GARDEN, FL 34787

    $849,0009 Days on yellowkey   MLS ID: O6415942

    For Sale O6415942 - 13086 SUNRISE HARVEST DR, WINTER GARDEN, FL 34787 57 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2835
       Built: 2025
    Monthly Fee: $140
       Tax: $2,829 (2025)
    Community: Harvest/Ovation
    Single Family


    Estimated Monthly Payment: $5,028 (change assumption)
    Mortgage ($4,652) + Fees ($140) + Taxes in 2025 ($236)


    Taxes:$2,829

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 2241 WHITE FEATHER LOOP, WINTER GARDEN, FL 34787

    $525,00025 Days on yellowkey   MLS ID: O6411576

    For Sale O6411576 - 2241 WHITE FEATHER LOOP, WINTER GARDEN, FL 34787 55 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2152
       Built: 2018
    Monthly Fee: $105
       Tax: $4,991 (2025)
    Community: Oakland Trls Ph 1
    Single Family


    Estimated Monthly Payment: $3,398 (change assumption)
    Mortgage ($2,877) + Fees ($105) + Taxes in 2025 ($416)


    Taxes:$4,991

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 16186 HONEY HARVEST ST, WINTER GARDEN, FL 34787

    $610,00028 Days on yellowkey   MLS ID: O6411495

    REDUCED by $20,000 (3.2%) on 06/12/2026

    For Sale O6411495 - 16186 HONEY HARVEST ST, WINTER GARDEN, FL 34787 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2445
       Built: 2025
    Monthly Fee: $229
       Tax: $1,614 (2025)
    Community: Harvest/Ovation Ph 2
    Single Family


    Estimated Monthly Payment: $3,706 (change assumption)
    Mortgage ($3,342) + Fees ($229) + Taxes in 2025 ($134)


    Taxes:$1,614

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 729 MEADOW GLADE DR, WINTER GARDEN, FL 34787

    $515,00042 Days on yellowkey   MLS ID: O6407943

    REDUCED by $14,000 (2.6%) on 06/16/2026

    For Sale O6407943 - 729 MEADOW GLADE DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2070
       Built: 2011
    Monthly Fee: $72
       Tax: $3,138 (2025)
    Community: Covington Park A B D E F G & J
    Single Family


    Estimated Monthly Payment: $3,155 (change assumption)
    Mortgage ($2,822) + Fees ($72) + Taxes in 2025 ($262)


    Taxes:$3,138

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14511 ISLEVIEW DR, WINTER GARDEN, FL 34787

    $3,330,00057 Days on yellowkey   MLS ID: O6403188

    For Sale O6403188 - 14511 ISLEVIEW DR, WINTER GARDEN, FL 34787 65 photos

    Bed: 6   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 5290
       Built: 2001
    Monthly Fee: $300
       Tax: $32,571 (2025)
    Community: Isles Lake Hancock
    Single Family


    Estimated Monthly Payment: $21,260 (change assumption)
    Mortgage ($18,246) + Fees ($300) + Taxes in 2025 ($2,714)


    Taxes:$32,571

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14790 TULLAMORE LOOP, WINTER GARDEN, FL 34787

    $675,00085 Days on yellowkey   MLS ID: O6395287

    REDUCED by $14,999 (2.2%) on 06/13/2026

    For Sale O6395287 - 14790 TULLAMORE LOOP, WINTER GARDEN, FL 34787 42 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3410
       Built: 2005
    Monthly Fee: $100
       Tax: $3,503 (2025)
    Community: Emerald Ridge
    Single Family


    Estimated Monthly Payment: $4,090 (change assumption)
    Mortgage ($3,699) + Fees ($100) + Taxes in 2025 ($292)


    Taxes:$3,503

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 617 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $1,139,000105 Days on yellowkey   MLS ID: O6389100

    REDUCED by $11,000 (1.0%) on 06/01/2026

    For Sale O6389100 - 617 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3624
       Built: 2019
    Monthly Fee: $255
       Tax: $16,181 (2025)
    Community: Canopy Oaks Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,844 (change assumption)
    Mortgage ($6,241) + Fees ($255) + Taxes in 2025 ($1,348)


    Taxes:$16,181

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 10043 SEQUEL ALY, WINTER GARDEN, FL 34787

    $535,000122 Days on yellowkey   MLS ID: O6384246

    REDUCED by $25,000 (4.5%) on 06/10/2026

    For Sale O6384246 - 10043 SEQUEL ALY, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2502
       Built: 2018
    Monthly Fee: $100
       Tax: $8,237 (2024)
    Community: Storey Grove Ph 1B-2
    Single Family


    Estimated Monthly Payment: $3,718 (change assumption)
    Mortgage ($2,931) + Fees ($100) + Taxes in 2024 ($686)


    Taxes:$8,237

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 12731 GROVEHURST AVE, WINTER GARDEN, FL 34787

    $580,000141 Days on yellowkey   MLS ID: O6379203

    REDUCED by $19,900 (3.3%) on 06/18/2026

    For Sale O6379203 - 12731 GROVEHURST AVE, WINTER GARDEN, FL 34787 59 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3474
       Built: 2006
    Monthly Fee: $111
       Tax: $8,378 (2025)
    Community: Grovehurst A-D
    Single Family


    Estimated Monthly Payment: $3,987 (change assumption)
    Mortgage ($3,178) + Fees ($111) + Taxes in 2025 ($698)


    Taxes:$8,378

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 9459 JAYWOOD RD, WINTER GARDEN, FL 34787

    $749,500115 Days on yellowkey   MLS ID: O6386488

    0 Days Off yellowkey (back on 6/20/2026)

    REDUCED by $5,500 (0.7%) on 05/28/2026

    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: $4,923 (change assumption)
    Mortgage ($4,107) + 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


  • 16131 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787

    $649,9007 Days on yellowkey   MLS ID: O6417701

    For Sale O6417701 - 16131 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2117
       Built: 2017
    Monthly Fee: $342
       Tax: $6,366 (2025)
    Community: Waterleigh Ph 1C
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,433 (change assumption)
    Mortgage ($3,561) + Fees ($342) + Taxes in 2025 ($530)


    Taxes:$6,366

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17738 SEDONA ST, WINTER GARDEN, FL 34787

    $905,93942 Days on yellowkey   MLS ID: O6407986

    1 Days Off yellowkey (back on 6/20/2026)

    INCREASED by $3,275 (0.4%) on 06/06/2026

    For Sale O6407986 - 17738 SEDONA ST, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2573
       Built: 2026
    Monthly Fee: $142

    Community: Esplanade At Mckinnon Groves
    Single Family


    Estimated Monthly Payment: $5,106 (change assumption)
    Mortgage ($4,964) + Fees ($142) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 14312 SUNBRIDGE CIR, WINTER GARDEN, FL 34787

    $1,200,0006 Days on yellowkey   MLS ID: O6414430

    For Sale O6414430 - 14312 SUNBRIDGE CIR, WINTER GARDEN, FL 34787 51 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4225
       Built: 2019
    Monthly Fee: $166
       Tax: $13,616 (2024)
    Community: Bradford Creek Ii
    Single Family


    Estimated Monthly Payment: $7,876 (change assumption)
    Mortgage ($6,575) + Fees ($166) + Taxes in 2024 ($1,135)


    Taxes:$13,616

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 9738 TOWER PINE DR, WINTER GARDEN, FL 34787

    $950,0006 Days on yellowkey   MLS ID: O6417627

    For Sale O6417627 - 9738 TOWER PINE DR, WINTER GARDEN, FL 34787 55 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2526
       Built: 1993   Tax: $7,549 (2025)
    Community: Lake Avalon Rural Settlement
    Single Family


    Estimated Monthly Payment: $5,834 (change assumption)
    Mortgage ($5,205) + Taxes in 2025 ($629)


    Taxes:$7,549

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1085 CHASE DR, WINTER GARDEN, FL 34787

    $600,0006 Days on yellowkey   MLS ID: O6417827

    For Sale O6417827 - 1085 CHASE DR, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2967
       Built: 2002
    Monthly Fee: $41
       Tax: $3,262 (2025)
    Community: Island Pointe Sub
    Single Family


    Estimated Monthly Payment: $3,600 (change assumption)
    Mortgage ($3,288) + Fees ($41) + Taxes in 2025 ($272)


    Taxes:$3,262

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 11165 GREEN CITRON ALY, WINTER GARDEN, FL 34787

    $648,00022 Days on yellowkey   MLS ID: O6413226

    REDUCED by $1,000 (0.2%) on 06/20/2026

    For Sale O6413226 - 11165 GREEN CITRON ALY, WINTER GARDEN, FL 34787 61 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2043
       Built: 2024
    Monthly Fee: $89
       Tax: $8,682 (2025)
    Community: Northlake/Ovation Ph 1
    Single Family


    Estimated Monthly Payment: $4,363 (change assumption)
    Mortgage ($3,551) + Fees ($89) + Taxes in 2025 ($724)


    Taxes:$8,682

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 205 HORSTFIELD DR, WINTER GARDEN, FL 34787

    $310,00034 Days on yellowkey   MLS ID: O6410222

    3 Days Off yellowkey (back on 6/17/2026)

    REDUCED by $5,000 (1.6%) on 06/12/2026

    For Sale O6410222 - 205 HORSTFIELD DR, WINTER GARDEN, FL 34787 20 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1048
       Built: 1998
    Monthly Fee: $40
       Tax: $1,983 (2025)
    Community: Park Ave Estates
    Single Family


    Estimated Monthly Payment: $1,904 (change assumption)
    Mortgage ($1,699) + Fees ($40) + Taxes in 2025 ($165)


    Taxes:$1,983

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 9717 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787

    $669,50021 Days on yellowkey   MLS ID: O6413773

    For Sale O6413773 - 9717 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787 54 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2117
       Built: 2018
    Monthly Fee: $250
       Tax: $614 (2025)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $3,970 (change assumption)
    Mortgage ($3,668) + Fees ($250) + Taxes in 2025 ($51)


    Taxes:$614

    Elementary School: Water Spring 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.