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Winter Garden Single Family Homes For Sale - 734 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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  • 12547 GOLD HONEYSUCKLE ST, WINTER GARDEN, FL 34787

    $819,99050 Days on yellowkey   MLS ID: O6413409

    0 Days Off yellowkey (back on 7/19/2026)

    REDUCED by $50,000 (5.7%) on 07/08/2026

    For Sale O6413409 - 12547 GOLD HONEYSUCKLE ST, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3291
       Built: 2026
    Monthly Fee: $96
       Tax: $13,460 (2026)
    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $5,711 (change assumption)
    Mortgage ($4,493) + Fees ($96) + Taxes in 2026 ($1,122)


    Taxes:$13,460

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2026

    Middle School: Water Spring Middle


  • 641 S BOYD ST, WINTER GARDEN, FL 34787

    $165,0007 Days on yellowkey   MLS ID: O6425850

    0 Days Off yellowkey (back on 7/19/2026)

    For Sale O6425850 - 641 S BOYD ST, WINTER GARDEN, FL 34787 17 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 912
       Built: 1924   Tax: $373 (2025)
    Community: Jewel Heights
    Single Family


    Estimated Monthly Payment: $935 (change assumption)
    Mortgage ($904) + Taxes in 2025 ($31)


    Taxes:$373

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 5960 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $597,99673 Days on yellowkey   MLS ID: G5112227

    INCREASED by $40,873 (7.3%) on 06/10/2026

    For Sale G5112227 - 5960 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 5 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1772
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $3,427 (change assumption)
    Mortgage ($3,277) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14280 BRAEMAR ST, WINTER GARDEN, FL 34787

    $499,00092 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


  • 15518 FOUNTAIN COVE CT, WINTER GARDEN, FL 34787

    $550,00070 Days on yellowkey   MLS ID: O6407942

    REDUCED by $24,990 (4.3%) on 07/17/2026

    For Sale O6407942 - 15518 FOUNTAIN COVE CT, WINTER GARDEN, FL 34787 64 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2040
       Built: 2018
    Monthly Fee: $342
       Tax: $8,434 (2025)
    Community: Waterleigh Ph 1A
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,058 (change assumption)
    Mortgage ($3,014) + Fees ($342) + Taxes in 2025 ($703)


    Taxes:$8,434

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 4642 PRAIRIE CREEK ST, WINTER GARDEN, FL 34787

    $565,000143 Days on yellowkey   MLS ID: S5144794

    REDUCED by $10,000 (1.7%) on 07/15/2026

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

    Bed: 3   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: $3,918 (change assumption)
    Mortgage ($3,096) + Fees ($281) + Taxes in 2024 ($542)


    Taxes:$6,500

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 443 WRANGLER RD, WINTER GARDEN, FL 34787

    $795,0008 Days on yellowkey   MLS ID: O6423892

    For Sale O6423892 - 443 WRANGLER RD, WINTER GARDEN, FL 34787 57 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2877
       Built: 2019
    Monthly Fee: $142
       Tax: $9,968 (2025)
    Community: Roper Reserve
    Single Family


    Estimated Monthly Payment: $5,329 (change assumption)
    Mortgage ($4,356) + Fees ($142) + Taxes in 2025 ($831)


    Taxes:$9,968

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13086 SUNRISE HARVEST DR, WINTER GARDEN, FL 34787

    $849,00037 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


  • 3286 MAINSAIL CT, WINTER GARDEN, FL 34787

    $889,00058 Days on yellowkey   MLS ID: O6411073

    For Sale O6411073 - 3286 MAINSAIL CT, WINTER GARDEN, FL 34787 65 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4293
       Built: 2023
    Monthly Fee: $208
       Tax: $12,028 (2024)
    Community: Ests/Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $6,081 (change assumption)
    Mortgage ($4,871) + Fees ($208) + Taxes in 2024 ($1,002)


    Taxes:$12,028

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2024

    Middle School: Windy Hill Middle


  • 16754 OAKBORO ST, WINTER GARDEN, FL 34787

    $520,00077 Days on yellowkey   MLS ID: O6404652

    REDUCED by $9,000 (1.7%) on 07/19/2026

    For Sale O6404652 - 16754 OAKBORO ST, WINTER GARDEN, FL 34787 85 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2020
    Monthly Fee: $254
       Tax: $8,808 (2025)
    Community: Waterleigh Ph 3B 3C 3D
    Single Family


    Estimated Monthly Payment: $3,837 (change assumption)
    Mortgage ($2,849) + Fees ($254) + Taxes in 2025 ($734)


    Taxes:$8,808

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15078 CANOPY COVER DR, WINTER GARDEN, FL 34787

    $969,00082 Days on yellowkey   MLS ID: O6404208

    0 Days Off yellowkey (back on 7/19/2026)

    REDUCED by $5,000 (0.5%) on 06/24/2026

    For Sale O6404208 - 15078 CANOPY COVER DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2270
       Built: 2024
    Monthly Fee: $545
       Tax: $10,412 (2025)
    Community: Del Webb Oasis
    Single Family


    Estimated Monthly Payment: $6,722 (change assumption)
    Mortgage ($5,309) + Fees ($545) + Taxes in 2025 ($868)


    Taxes:$10,412

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1808 WESTERN TRAILWAY DR, WINTER GARDEN, FL 34787

    $599,00016 Days on yellowkey   MLS ID: S5152973

    For Sale S5152973 - 1808 WESTERN TRAILWAY DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1860
       Built: 2019
    Monthly Fee: $165
       Tax: $8,389 (2025)
    Community: Hull Island/Oakland
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,146 (change assumption)
    Mortgage ($3,282) + Fees ($165) + Taxes in 2025 ($699)


    Taxes:$8,389

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14102 LOCHEND WAY, WINTER GARDEN, FL 34787

    $935,00050 Days on yellowkey   MLS ID: O6411646

    REDUCED by $43,800 (4.5%) on 06/19/2026

    For Sale O6411646 - 14102 LOCHEND WAY, WINTER GARDEN, FL 34787 62 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3606
       Built: 2024
    Monthly Fee: $77
       Tax: $11,605 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $6,167 (change assumption)
    Mortgage ($5,123) + Fees ($77) + Taxes in 2025 ($967)


    Taxes:$11,605

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9240 BRADLEIGH DR, WINTER GARDEN, FL 34787

    $1,050,00017 Days on yellowkey   MLS ID: O6421967

    For Sale O6421967 - 9240 BRADLEIGH DR, WINTER GARDEN, FL 34787 66 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4124
       Built: 2018
    Monthly Fee: $116
       Tax: $13,272 (2025)
    Community: Latham Park South
    Single Family


    Estimated Monthly Payment: $6,975 (change assumption)
    Mortgage ($5,753) + Fees ($116) + Taxes in 2025 ($1,106)


    Taxes:$13,272

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 10043 SEQUEL ALY, WINTER GARDEN, FL 34787

    $530,000150 Days on yellowkey   MLS ID: O6384246

    REDUCED by $5,000 (0.9%) on 07/02/2026

    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: $3,690 (change assumption)
    Mortgage ($2,904) + Fees ($100) + Taxes in 2024 ($686)


    Taxes:$8,237

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13624 LARSEN LN, WINTER GARDEN, FL 34787

    $900,0007 Days on yellowkey   MLS ID: O6425287

    For Sale O6425287 - 13624 LARSEN LN, WINTER GARDEN, FL 34787 42 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3779
       Built: 2005
    Monthly Fee: $189
       Tax: $5,781 (2025)
    Community: Lake Forest Sec 10A
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,602 (change assumption)
    Mortgage ($4,931) + Fees ($189) + Taxes in 2025 ($482)


    Taxes:$5,781

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 7460 JOHN HANCOCK DR, WINTER GARDEN, FL 34787

    $2,295,00093 Days on yellowkey   MLS ID: O6400891

    0 Days Off yellowkey (back on 7/19/2026)

    REDUCED by $150,000 (6.1%) on 07/14/2026

    For Sale O6400891 - 7460 JOHN HANCOCK DR, WINTER GARDEN, FL 34787 89 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4817
       Built: 2020
    Monthly Fee: $210
       Tax: $17,060 (2025)
    Community: Overlook At Hamlin
    Single Family


    Estimated Monthly Payment: $14,207 (change assumption)
    Mortgage ($12,575) + Fees ($210) + Taxes in 2025 ($1,422)


    Taxes:$17,060

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 15101 PURPLE MARTIN ST, WINTER GARDEN, FL 34787

    $519,9005 Days on yellowkey   MLS ID: O6425221

    For Sale O6425221 - 15101 PURPLE MARTIN ST, WINTER GARDEN, FL 34787 43 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1998
       Built: 2017
    Monthly Fee: $248
       Tax: $7,661 (2025)
    Community: Summerlake Pd Ph 3B
    Single Family


    Estimated Monthly Payment: $3,735 (change assumption)
    Mortgage ($2,849) + Fees ($248) + Taxes in 2025 ($638)


    Taxes:$7,661

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13856 GLYNSHEL DR, WINTER GARDEN, FL 34787

    $850,00038 Days on yellowkey   MLS ID: O6416757

    For Sale O6416757 - 13856 GLYNSHEL DR, WINTER GARDEN, FL 34787 31 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3538
       Built: 2003
    Monthly Fee: $167
       Tax: $11,261 (2025)
    Community: Glynwood
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,763 (change assumption)
    Mortgage ($4,657) + Fees ($167) + Taxes in 2025 ($938)


    Taxes:$11,261

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 6051 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $737,11040 Days on yellowkey   MLS ID: G5113741

    For Sale G5113741 - 6051 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2235
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,189 (change assumption)
    Mortgage ($4,039) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin 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.