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Winter Garden Homes For Sale & Real Estate - 945 homes

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

Location: Winter Garden

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  • 16596 POINT ROCK DR, WINTER GARDEN, FL 34787

    $539,90013 Days on yellowkey   MLS ID: O6412721

    REDUCED by $20,100 (3.6%) on 06/10/2026

    For Sale O6412721 - 16596 POINT ROCK DR, WINTER GARDEN, FL 34787 54 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2023
    Monthly Fee: $254
       Tax: $8,961 (2025)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $3,959 (change assumption)
    Mortgage ($2,958) + Fees ($254) + Taxes in 2025 ($747)


    Taxes:$8,961

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15182 SUNRISE GROVE CT, WINTER GARDEN, FL 34787

    $384,990103 Days on yellowkey   MLS ID: O6382211

    1 Days Off yellowkey (back on 6/10/2026)

    REDUCED by $4,910 (1.3%) on 05/30/2026

    For Sale O6382211 - 15182 SUNRISE GROVE CT, WINTER GARDEN, FL 34787 27 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1844
       Built: 2018
    Monthly Fee: $346
       Tax: $3,222 (2024)
    Community: Hickory Hammock Ph 2B
    Townhouse


    Estimated Monthly Payment: $2,724 (change assumption)
    Mortgage ($2,109) + Fees ($346) + Taxes in 2024 ($268)


    Taxes:$3,222

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 1681 E SPRING RIDGE CIR, WINTER GARDEN, FL 34787

    $469,00037 Days on yellowkey   MLS ID: B4902258

    REDUCED by $10,000 (2.1%) on 06/10/2026

    For Sale B4902258 - 1681 E SPRING RIDGE CIR, WINTER GARDEN, FL 34787 70 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1858
       Built: 1990
    Monthly Fee: $25
       Tax: $2,403 (2025)
    Community: Crown Point Spgs
    Single Family


    Estimated Monthly Payment: $2,795 (change assumption)
    Mortgage ($2,570) + Fees ($25) + Taxes in 2025 ($200)


    Taxes:$2,403

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5374 LAKE VIRGINIA ST, WINTER GARDEN, FL 34787

    $571,900111 Days on yellowkey   MLS ID: O6385721

    REDUCED by $8,100 (1.4%) on 04/06/2026

    For Sale O6385721 - 5374 LAKE VIRGINIA ST, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2038
       Built: 2023
    Monthly Fee: $160
       Tax: $7,532 (2024)
    Community: Lakeside/Hamlin
    Single Family


    Estimated Monthly Payment: $3,921 (change assumption)
    Mortgage ($3,134) + Fees ($160) + Taxes in 2024 ($628)


    Taxes:$7,532

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 7832 FREESTYLE LN, WINTER GARDEN, FL 34787

    $1,075,000134 Days on yellowkey   MLS ID: G5107680

    0 Days Off yellowkey (back on 6/10/2026)

    REDUCED by $25,000 (2.3%) on 05/06/2026

    For Sale G5107680 - 7832 FREESTYLE LN, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2650
       Built: 2018
    Monthly Fee: $300
       Tax: $16,616 (2025)
    Community: Isles Of Lake Hancock
    Single Family


    Estimated Monthly Payment: $7,575 (change assumption)
    Mortgage ($5,890) + Fees ($300) + Taxes in 2025 ($1,385)


    Taxes:$16,616

    Elementary School: Independence Elementary

    High School: None

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1300 EASTERN PECAN PL #102, WINTER GARDEN, FL 34787

    $275,0008 Days on yellowkey   MLS ID: S5151632

    For Sale S5151632 - 1300 EASTERN PECAN PL #102, WINTER GARDEN, FL 34787 26 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1152
       Built: 2005   Tax: $3,619 (2025)
    Community: Southern Pines Condo
    Condo


    Estimated Monthly Payment: $1,808 (change assumption)
    Mortgage ($1,507) + Taxes in 2025 ($302)


    Taxes:$3,619

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 13861 EASDALE ALY, WINTER GARDEN, FL 34787

    $539,00014 Days on yellowkey   MLS ID: O6413534

    REDUCED by $20,000 (3.6%) on 06/10/2026

    For Sale O6413534 - 13861 EASDALE ALY, WINTER GARDEN, FL 34787 15 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2031
       Built: 2026
    Monthly Fee: $150
       Tax: $400 (2025)
    Community: Westhaven At Ovation
    Townhouse


    Estimated Monthly Payment: $3,137 (change assumption)
    Mortgage ($2,953) + Fees ($150) + Taxes in 2025 ($33)


    Taxes:$400

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 12308 BRACCO ST, WINTER GARDEN, FL 34787

    $514,90037 Days on yellowkey   MLS ID: O6406923

    REDUCED by $10,100 (1.9%) on 06/10/2026

    For Sale O6406923 - 12308 BRACCO ST, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2094
       Built: 2024
    Monthly Fee: $105
       Tax: $8,152 (2025)
    Community: Highland Rdg Ph 2
    Single Family


    Estimated Monthly Payment: $3,606 (change assumption)
    Mortgage ($2,821) + Fees ($105) + Taxes in 2025 ($679)


    Taxes:$8,152

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 13728 FOX GLOVE ST, WINTER GARDEN, FL 34787

    $699,90042 Days on yellowkey   MLS ID: O6405142

    REDUCED by $20,000 (2.8%) on 06/10/2026

    For Sale O6405142 - 13728 FOX GLOVE ST, WINTER GARDEN, FL 34787 37 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3391
       Built: 2004
    Monthly Fee: $247
       Tax: $11,230 (2025)
    Community: Stoneybrook West Ut 04 48 48
    Single Family


    Estimated Monthly Payment: $5,018 (change assumption)
    Mortgage ($3,835) + Fees ($247) + Taxes in 2025 ($936)


    Taxes:$11,230

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 1701 E BAY ST, WINTER GARDEN, FL 34787

    $295,00011 Days on yellowkey   MLS ID: O6413973

    For Sale O6413973 - 1701 E BAY ST, WINTER GARDEN, FL 34787 32 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 825
       Built: 1950   Tax: $2,560 (2025)
    Community: Joe Louis Park First Add
    Single Family


    Estimated Monthly Payment: $1,830 (change assumption)
    Mortgage ($1,616) + Taxes in 2025 ($213)


    Taxes:$2,560

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787

    $1,495,0009 Days on yellowkey   MLS ID: O6414639

    For Sale O6414639 - 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787 69 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4882
       Built: 2016
    Monthly Fee: $168
       Tax: $11,216 (2025)
    Community: Waterside/Johns Lake Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,294 (change assumption)
    Mortgage ($8,192) + Fees ($168) + Taxes in 2025 ($935)


    Taxes:$11,216

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17126 ARROWHEAD BLVD, WINTER GARDEN, FL 34787

    $565,00028 Days on yellowkey   MLS ID: O6409499

    4 Days Off yellowkey (back on 5/27/2026)

    For Sale O6409499 - 17126 ARROWHEAD BLVD, WINTER GARDEN, FL 34787 6 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2114
       Built: 1984   Tax: $2,608 (2025)
    Community: Arrowhead Lakes
    Single Family


    Estimated Monthly Payment: $3,313 (change assumption)
    Mortgage ($3,096) + Taxes in 2025 ($217)


    Taxes:$2,608

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9606 WOODCRANE DR, WINTER GARDEN, FL 34787

    $525,00026 Days on yellowkey   MLS ID: O6410113

    2 Days Off yellowkey (back on 6/10/2026)

    For Sale O6410113 - 9606 WOODCRANE DR, WINTER GARDEN, FL 34787 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2101
       Built: 2017
    Monthly Fee: $164
       Tax: $5,079 (2025)
    Community: Watermark Ph 2B
    Single Family


    Estimated Monthly Payment: $3,464 (change assumption)
    Mortgage ($2,877) + Fees ($164) + Taxes in 2025 ($423)


    Taxes:$5,079

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14501 GROVE RESORT AVE #3215, WINTER GARDEN, FL 34787

    $239,000222 Days on yellowkey   MLS ID: S5138120

    For Sale S5138120 - 14501 GROVE RESORT AVE #3215, WINTER GARDEN, FL 34787 49 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1265
       Built: 2018
    Monthly Fee: $904
       Tax: $6,136 (2024)
    Community: Grove Resort
    Condo


    Estimated Monthly Payment: $2,725 (change assumption)
    Mortgage ($1,310) + Fees ($904) + Taxes in 2024 ($511)


    Taxes:$6,136

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15663 KINNOW MANDARIN LN, WINTER GARDEN, FL 34787

    $399,900200 Days on yellowkey   MLS ID: O6363767

    1 Days Off yellowkey (back on 6/10/2026)

    REDUCED by $4,100 (1.0%) on 05/18/2026

    For Sale O6363767 - 15663 KINNOW MANDARIN LN, WINTER GARDEN, FL 34787 21 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1868
       Built: 2017
    Monthly Fee: $420
       Tax: $6,304 (2025)
    Community: Highlands/Summerlake
    Townhouse


    Estimated Monthly Payment: $3,137 (change assumption)
    Mortgage ($2,191) + Fees ($420) + Taxes in 2025 ($525)


    Taxes:$6,304

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 7687 BOWERY DR, WINTER GARDEN, FL 34787

    $830,0009 Days on yellowkey   MLS ID: O6415123

    For Sale O6415123 - 7687 BOWERY DR, WINTER GARDEN, FL 34787 40 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3179
       Built: 2020
    Monthly Fee: $134
       Tax: $9,576 (2025)
    Community: Ravenna Ph 1
    Single Family


    Estimated Monthly Payment: $5,480 (change assumption)
    Mortgage ($4,548) + Fees ($134) + Taxes in 2025 ($798)


    Taxes:$9,576

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 7827 SKIING WAY, WINTER GARDEN, FL 34787

    $4,900,00011 Days on yellowkey   MLS ID: O6414451

    For Sale O6414451 - 7827 SKIING WAY, WINTER GARDEN, FL 34787 82 photos

    Bed: 5   Bath: 6.0   Gar: 4
    Liv Area Sq Ft: 5564
       Built: 2018
    Monthly Fee: $300
       Tax: $46,587 (2025)
    Community: Isles Of Lake Hancock
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $31,031 (change assumption)
    Mortgage ($26,849) + Fees ($300) + Taxes in 2025 ($3,882)


    Taxes:$46,587

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9338 TYRELLA PINE TRL, WINTER GARDEN, FL 34787

    $435,000255 Days on yellowkey   MLS ID: O6349881

    REDUCED by $10,000 (2.2%) on 06/10/2026

    For Sale O6349881 - 9338 TYRELLA PINE TRL, WINTER GARDEN, FL 34787 21 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1696
       Built: 2018
    Monthly Fee: $142
       Tax: $7,556 (2024)
    Community: Watermark Ph 2B
    Single Family


    Estimated Monthly Payment: $3,155 (change assumption)
    Mortgage ($2,384) + Fees ($142) + Taxes in 2024 ($630)


    Taxes:$7,556

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14494 BREAKWATER WAY, WINTER GARDEN, FL 34787

    $679,000198 Days on yellowkey   MLS ID: S5139023

    1 Days Off yellowkey (back on 6/10/2026)

    INCREASED by $30,000 (4.6%) on 05/11/2026

    For Sale S5139023 - 14494 BREAKWATER WAY, WINTER GARDEN, FL 34787 52 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3638
       Built: 2016
    Monthly Fee: $140
       Tax: $9,261 (2024)
    Community: Black Lake Preserve
    Single Family


    Estimated Monthly Payment: $4,632 (change assumption)
    Mortgage ($3,720) + Fees ($140) + Taxes in 2024 ($772)


    Taxes:$9,261

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 17372 GLOSSY POMELO WAY, WINTER GARDEN, FL 34787

    $1,790,00038 Days on yellowkey   MLS ID: O6406639

    REDUCED by $35,000 (1.9%) on 06/10/2026

    For Sale O6406639 - 17372 GLOSSY POMELO WAY, WINTER GARDEN, FL 34787 78 photos

    Bed: 5   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 4977
       Built: 2025
    Monthly Fee: $86

    Community: Lake Star/Ovation Ph 1B
    Single Family


    Estimated Monthly Payment: $9,894 (change assumption)
    Mortgage ($9,808) + Fees ($86) + Taxes in 2025 ($0)


    Taxes:$0

    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 Homes for Sale and Other Real Estate?

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