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Winter Garden Single Family Homes For Sale - 729 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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  • 5024 PALMETTO PARK DR, WINTER GARDEN, FL 34787

    $805,00044 Days on yellowkey   MLS ID: O6414749

    REDUCED by $14,000 (1.7%) on 07/20/2026

    For Sale O6414749 - 5024 PALMETTO PARK DR, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3061
       Built: 2017
    Monthly Fee: $187
       Tax: $10,816 (2025)
    Community: Orchard Hills Ph 3
    Single Family


    Estimated Monthly Payment: $5,499 (change assumption)
    Mortgage ($4,411) + Fees ($187) + Taxes in 2025 ($901)


    Taxes:$10,816

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 18344 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $660,000212 Days on yellowkey   MLS ID: S5140531

    2 Days Off yellowkey (back on 7/20/2026)

    REDUCED by $65,000 (9.0%) on 07/14/2026

    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: $4,059 (change assumption)
    Mortgage ($3,616) + Fees ($300) + Taxes in 2024 ($142)


    Taxes:$1,706

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 8114 SAYINGS DR, WINTER GARDEN, FL 34787

    $699,99090 Days on yellowkey   MLS ID: O6401941

    REDUCED by $29,010 (4.0%) on 07/20/2026

    For Sale O6401941 - 8114 SAYINGS DR, WINTER GARDEN, FL 34787 56 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3284
       Built: 2023
    Monthly Fee: $221
       Tax: $9,107 (2025)
    Community: Storey Grove Ph 4
    Single Family


    Estimated Monthly Payment: $4,815 (change assumption)
    Mortgage ($3,835) + Fees ($221) + Taxes in 2025 ($759)


    Taxes:$9,107

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15665 CITRUS HARVEST RD, WINTER GARDEN, FL 34787

    $699,90081 Days on yellowkey   MLS ID: O6400896

    REDUCED by $20,000 (2.8%) on 07/11/2026

    For Sale O6400896 - 15665 CITRUS HARVEST RD, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2931
       Built: 2016
    Monthly Fee: $235
       Tax: $5,441 (2025)
    Community: Hickory Hammock Ph 2A
    Single Family


    Estimated Monthly Payment: $4,523 (change assumption)
    Mortgage ($3,835) + Fees ($235) + Taxes in 2025 ($453)


    Taxes:$5,441

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 925 EASLEY AVE, WINTER GARDEN, FL 34787

    $1,165,00037 Days on yellowkey   MLS ID: O6412977

    REDUCED by $10,000 (0.9%) on 07/20/2026

    For Sale O6412977 - 925 EASLEY AVE, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2667
       Built: 2016
    Monthly Fee: $208
       Tax: $12,692 (2025)
    Community: Oakland Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,649 (change assumption)
    Mortgage ($6,383) + Fees ($208) + Taxes in 2025 ($1,058)


    Taxes:$12,692

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14779 MCCLANE RD, WINTER GARDEN, FL 34787

    $899,0004 Days on yellowkey   MLS ID: O6426346

    For Sale O6426346 - 14779 MCCLANE RD, WINTER GARDEN, FL 34787 39 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3118
       Built: 2018
    Monthly Fee: $212
       Tax: $10,367 (2025)
    Community: Oxford Chase
    Single Family


    Estimated Monthly Payment: $6,002 (change assumption)
    Mortgage ($4,926) + Fees ($212) + Taxes in 2025 ($864)


    Taxes:$10,367

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 14301 WHITE MOSS WAY, WINTER GARDEN, FL 34787

    $949,99923 Days on yellowkey   MLS ID: G5114391

    For Sale G5114391 - 14301 WHITE MOSS WAY, WINTER GARDEN, FL 34787 66 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4053
       Built: 2015
    Monthly Fee: $190
       Tax: $9,701 (2026)
    Community: Orchard Hills
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,204 (change assumption)
    Mortgage ($5,205) + Fees ($190) + Taxes in 2026 ($808)


    Taxes:$9,701

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2026

    Middle School: Bridgewater Middle


  • 15037 LAKE BESSIE LOOP, WINTER GARDEN, FL 34787

    $1,045,00033 Days on yellowkey   MLS ID: O6418541

    0 Days Off yellowkey (back on 7/20/2026)

    REDUCED by $55,000 (5.0%) on 07/06/2026

    For Sale O6418541 - 15037 LAKE BESSIE LOOP, WINTER GARDEN, FL 34787 39 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: $6,858 (change assumption)
    Mortgage ($5,726) + 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


  • 14802 SPEER LAKE DR, WINTER GARDEN, FL 34787

    $1,690,0006 Days on yellowkey   MLS ID: O6425462

    1 Days Off yellowkey (back on 7/20/2026)

    For Sale O6425462 - 14802 SPEER LAKE DR, WINTER GARDEN, FL 34787 76 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3742
       Built: 2014
    Monthly Fee: $195
       Tax: $20,904 (2025)
    Community: Independence
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,197 (change assumption)
    Mortgage ($9,260) + Fees ($195) + Taxes in 2025 ($1,742)


    Taxes:$20,904

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 7840 WINTER WREN ST, WINTER GARDEN, FL 34787

    $525,90022 Days on yellowkey   MLS ID: O6421167

    REDUCED by $4,000 (0.8%) on 07/20/2026

    For Sale O6421167 - 7840 WINTER WREN ST, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2004
       Built: 2015
    Monthly Fee: $251
       Tax: $7,385 (2025)
    Community: Summerlake Pd Ph 1B Rep
    Single Family


    Estimated Monthly Payment: $3,748 (change assumption)
    Mortgage ($2,882) + Fees ($251) + Taxes in 2025 ($615)


    Taxes:$7,385

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13155 SPRING GROVE WAY, WINTER GARDEN, FL 34787

    $600,00020 Days on yellowkey   MLS ID: O6421867

    For Sale O6421867 - 13155 SPRING GROVE WAY, WINTER GARDEN, FL 34787 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2818
       Built: 2021
    Monthly Fee: $225
       Tax: $7,057 (2025)
    Community: Encore/Ovation Ph 2
    Single Family


    Estimated Monthly Payment: $4,101 (change assumption)
    Mortgage ($3,288) + Fees ($225) + Taxes in 2025 ($588)


    Taxes:$7,057

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $609,611156 Days on yellowkey   MLS ID: G5108288

    0 Days Off yellowkey (back on 4/7/2026)

    For Sale G5108288 - 17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2520
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,462 (change assumption)
    Mortgage ($3,340) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16131 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787

    $649,90034 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


  • 944 KYLEE ALY, WINTER GARDEN, FL 34787

    $779,9004 Days on yellowkey   MLS ID: O6425976

    0 Days Off yellowkey (back on 7/20/2026)

    For Sale O6425976 - 944 KYLEE ALY, WINTER GARDEN, FL 34787 60 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2831
       Built: 2022
    Monthly Fee: $401
       Tax: $11,438 (2026)
    Community: Oakland Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,627 (change assumption)
    Mortgage ($4,273) + Fees ($401) + Taxes in 2026 ($953)


    Taxes:$11,438

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2026

    Middle School: Lakeview Middle


  • 8530 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $1,375,00047 Days on yellowkey   MLS ID: O6413249

    REDUCED by $124,000 (8.3%) on 07/20/2026

    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: $8,007 (change assumption)
    Mortgage ($7,534) + Fees ($266) + Taxes in 2025 ($207)


    Taxes:$2,479

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13019 SERENE GLADE RD, WINTER GARDEN, FL 34787

    $549,99040 Days on yellowkey   MLS ID: G5113698

    REDUCED by $20,000 (3.5%) on 06/17/2026

    For Sale G5113698 - 13019 SERENE GLADE RD, WINTER GARDEN, FL 34787 61 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2078
       Built: 2026
    Monthly Fee: $121

    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $3,135 (change assumption)
    Mortgage ($3,014) + Fees ($121) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 5320 LAKE VIRGINIA ST, WINTER GARDEN, FL 34787

    $695,9907 Days on yellowkey   MLS ID: O6424081

    For Sale O6424081 - 5320 LAKE VIRGINIA ST, WINTER GARDEN, FL 34787 67 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3366
       Built: 2024
    Monthly Fee: $176
       Tax: $10,233 (2025)
    Community: Lakeside/Hamlin
    Single Family


    Estimated Monthly Payment: $4,842 (change assumption)
    Mortgage ($3,814) + Fees ($176) + Taxes in 2025 ($853)


    Taxes:$10,233

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1642 CHANDELLE LN, WINTER GARDEN, FL 34787

    $689,90021 Days on yellowkey   MLS ID: G5114093

    REDUCED by $20,000 (2.8%) on 07/20/2026

    For Sale G5114093 - 1642 CHANDELLE LN, WINTER GARDEN, FL 34787 46 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2918
       Built: 2006
    Monthly Fee: $167
       Tax: $8,474 (2025)
    Community: Belle Meade-Ph I B D & G
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,653 (change assumption)
    Mortgage ($3,780) + Fees ($167) + Taxes in 2025 ($706)


    Taxes:$8,474

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 17167 WRITING ALY, WINTER GARDEN, FL 34787

    $535,00071 Days on yellowkey   MLS ID: O6406920

    For Sale O6406920 - 17167 WRITING ALY, WINTER GARDEN, FL 34787 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2486
       Built: 2020
    Monthly Fee: $110
       Tax: $7,916 (2025)
    Community: Storey Grove Ph 1B
    Single Family


    Estimated Monthly Payment: $3,701 (change assumption)
    Mortgage ($2,931) + Fees ($110) + Taxes in 2025 ($660)


    Taxes:$7,916

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14629 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787

    $484,90020 Days on yellowkey   MLS ID: O6421797

    REDUCED by $8,000 (1.6%) on 07/20/2026

    For Sale O6421797 - 14629 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2223
       Built: 2012
    Monthly Fee: $242
       Tax: $8,151 (2025)
    Community: Summerlake Pd Ph 01B
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,578 (change assumption)
    Mortgage ($2,657) + Fees ($242) + Taxes in 2025 ($679)


    Taxes:$8,151

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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.