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Winter Garden Homes For Sale & Real Estate - 932 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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  • 642 MEDORA WAY, WINTER GARDEN, FL 34787

    $1,137,1504 Days on yellowkey   MLS ID: O6413483

    For Sale O6413483 - 642 MEDORA WAY, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2995
       Built: 2026
    Monthly Fee: $155
       Tax: $993 (2025)
    Community: Lakeview Village Estates
    Single Family


    Estimated Monthly Payment: $6,469 (change assumption)
    Mortgage ($6,231) + Fees ($155) + Taxes in 2025 ($83)


    Taxes:$993

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 1706 HOLCOMB CREEK ST, WINTER GARDEN, FL 34787

    $1,070,0001 Day on yellowkey   MLS ID: O6416109

    For Sale O6416109 - 1706 HOLCOMB CREEK ST, WINTER GARDEN, FL 34787 56 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4305
       Built: 2018
    Monthly Fee: $184
       Tax: $13,571 (2025)
    Community: Twinwaters
    Single Family


    Estimated Monthly Payment: $7,178 (change assumption)
    Mortgage ($5,863) + Fees ($184) + Taxes in 2025 ($1,131)


    Taxes:$13,571

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787

    $750,00060 Days on yellowkey   MLS ID: O6398720

    For Sale O6398720 - 2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3747
       Built: 2000
    Monthly Fee: $90
       Tax: $10,152 (2025)
    Community: Wintermere Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,045 (change assumption)
    Mortgage ($4,109) + Fees ($90) + Taxes in 2025 ($846)


    Taxes:$10,152

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15357 OAK APPLE CT #4C, WINTER GARDEN, FL 34787

    $350,00051 Days on yellowkey   MLS ID: O6401625

    REDUCED by $5,000 (1.4%) on 06/04/2026

    For Sale O6401625 - 15357 OAK APPLE CT #4C, WINTER GARDEN, FL 34787 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1699
       Built: 2008
    Monthly Fee: $285
       Tax: $4,779 (2025)
    Community: Tucker Oaks
    Condo


    Estimated Monthly Payment: $2,601 (change assumption)
    Mortgage ($1,918) + Fees ($285) + Taxes in 2025 ($398)


    Taxes:$4,779

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1979 STANDING ROCK CIR, WINTER GARDEN, FL 34787

    $520,00017 Days on yellowkey   MLS ID: S5150723

    For Sale S5150723 - 1979 STANDING ROCK CIR, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2082
       Built: 2019
    Monthly Fee: $105
       Tax: $8,301 (2025)
    Community: Oakland Trails Ph 2
    Single Family


    Estimated Monthly Payment: $3,646 (change assumption)
    Mortgage ($2,849) + Fees ($105) + Taxes in 2025 ($692)


    Taxes:$8,301

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 10043 SEQUEL ALY, WINTER GARDEN, FL 34787

    $535,000110 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


  • 636 SIGLER DR, WINTER GARDEN, FL 34787

    $611,6104 Days on yellowkey   MLS ID: O6413662

    For Sale O6413662 - 636 SIGLER DR, WINTER GARDEN, FL 34787 13 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1634
       Built: 2026
    Monthly Fee: $275
       Tax: $993 (2025)
    Community: Lakeview Village Estates
    Townhouse


    Estimated Monthly Payment: $3,709 (change assumption)
    Mortgage ($3,351) + Fees ($275) + Taxes in 2025 ($83)


    Taxes:$993

    Elementary School: Dillard Street Elem

    High School: None

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14542 BLACK CHERRY TRL, WINTER GARDEN, FL 34787

    $600,00018 Days on yellowkey   MLS ID: O6410574

    For Sale O6410574 - 14542 BLACK CHERRY TRL, WINTER GARDEN, FL 34787 36 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2234
       Built: 2008
    Monthly Fee: $184
       Tax: $5,498 (2025)
    Community: Signature Lks-Pcl 01D Ph 01
    Single Family


    Estimated Monthly Payment: $3,930 (change assumption)
    Mortgage ($3,288) + Fees ($184) + Taxes in 2025 ($458)


    Taxes:$5,498

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6131 ELFIN HERB WAY, WINTER GARDEN, FL 34787

    $450,0008 Days on yellowkey   MLS ID: O6414015

    For Sale O6414015 - 6131 ELFIN HERB WAY, WINTER GARDEN, FL 34787 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1714
       Built: 2020
    Monthly Fee: $28,900
       Tax: $5,990 (2025)
    Community: Hamilton Gardens
    Townhouse


    Estimated Monthly Payment: $31,865 (change assumption)
    Mortgage ($2,466) + Fees ($28,900) + Taxes in 2025 ($499)


    Taxes:$5,990

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: None


  • 14501 GROVE RESORT AVE #2101, WINTER GARDEN, FL 34787

    $460,000233 Days on yellowkey   MLS ID: O6353080

    For Sale O6353080 - 14501 GROVE RESORT AVE #2101, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1544
       Built: 2018
    Monthly Fee: $826
       Tax: $8,802 (2024)
    Community: Grove Resort And Spa Hotel Condo 1
    Condo


    Estimated Monthly Payment: $4,080 (change assumption)
    Mortgage ($2,520) + Fees ($826) + Taxes in 2024 ($734)


    Taxes:$8,802

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 18053 CIDER MILL LN, WINTER GARDEN, FL 34787

    $790,86165 Days on yellowkey   MLS ID: O6397726

    INCREASED by $3,020 (0.4%) on 06/12/2026

    For Sale O6397726 - 18053 CIDER MILL LN, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2866
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,698 (change assumption)
    Mortgage ($4,333) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16105 WATER SPRING BLVD, WINTER GARDEN, FL 34787

    $499,000250 Days on yellowkey   MLS ID: O6348822

    1 Days Off yellowkey (back on 6/11/2026)

    REDUCED by $20,000 (3.9%) on 04/16/2026

    For Sale O6348822 - 16105 WATER SPRING BLVD, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2042
       Built: 2020
    Monthly Fee: $103
       Tax: $4,770 (2024)
    Community: Storey Grove
    Single Family


    Estimated Monthly Payment: $3,235 (change assumption)
    Mortgage ($2,734) + Fees ($103) + Taxes in 2024 ($397)


    Taxes:$4,770

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 1019 PORTMOOR WAY, WINTER GARDEN, FL 34787

    $595,0002 Days on yellowkey   MLS ID: O6414940

    For Sale O6414940 - 1019 PORTMOOR WAY, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2401
       Built: 2001
    Monthly Fee: $243
       Tax: $646 (2025)
    Community: Stoneybrook West Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,557 (change assumption)
    Mortgage ($3,260) + Fees ($243) + Taxes in 2025 ($54)


    Taxes:$646

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15537 MANGO ISLE ST, WINTER GARDEN, FL 34787

    $722,00017 Days on yellowkey   MLS ID: S5150619

    For Sale S5150619 - 15537 MANGO ISLE ST, WINTER GARDEN, FL 34787 58 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2909
       Built: 2021
    Monthly Fee: $267
       Tax: $10,430 (2025)
    Community: Waterleigh Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $5,092 (change assumption)
    Mortgage ($3,956) + Fees ($267) + Taxes in 2025 ($869)


    Taxes:$10,430

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15456 GILLIGAN CT, WINTER GARDEN, FL 34787

    $550,000317 Days on yellowkey   MLS ID: A4660262

    REDUCED by $25,000 (4.3%) on 06/12/2026

    For Sale A4660262 - 15456 GILLIGAN CT, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2571
       Built: 2020
    Monthly Fee: $102
       Tax: $8,702 (2024)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $3,841 (change assumption)
    Mortgage ($3,014) + Fees ($102) + Taxes in 2024 ($725)


    Taxes:$8,702

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 181 ZACHARY WADE ST, WINTER GARDEN, FL 34787

    $600,00014 Days on yellowkey   MLS ID: O6412174

    For Sale O6412174 - 181 ZACHARY WADE ST, WINTER GARDEN, FL 34787 65 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2940
       Built: 2002
    Monthly Fee: $67
       Tax: $7,609 (2025)
    Community: Lakeview Reserve
    Single Family


    Estimated Monthly Payment: $3,989 (change assumption)
    Mortgage ($3,288) + Fees ($67) + Taxes in 2025 ($634)


    Taxes:$7,609

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17125 STILLNESS ALY, WINTER GARDEN, FL 34787

    $580,9331 Day on yellowkey   MLS ID: G5113666

    For Sale G5113666 - 17125 STILLNESS ALY, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2083
       Built: 2026
    Monthly Fee: $121

    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $3,304 (change assumption)
    Mortgage ($3,183) + Fees ($121) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 15121 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787

    $874,9002 Days on yellowkey   MLS ID: O6416065

    For Sale O6416065 - 15121 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787 43 photos

    Bed: 6   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4042
       Built: 2016
    Monthly Fee: $180
       Tax: $552 (2024)
    Community: Signature Lakes Ph 3B-4
    Single Family


    Estimated Monthly Payment: $5,020 (change assumption)
    Mortgage ($4,794) + Fees ($180) + Taxes in 2024 ($46)


    Taxes:$552

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 15073 VALVERSE ALY, WINTER GARDEN, FL 34787

    $515,0002 Days on yellowkey   MLS ID: O6416182

    For Sale O6416182 - 15073 VALVERSE ALY, WINTER GARDEN, FL 34787 38 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1892
       Built: 2017
    Monthly Fee: $339
       Tax: $4,172 (2025)
    Community: Overlook 2/Hamlin Ph 2 & 5
    Single Family


    Estimated Monthly Payment: $3,509 (change assumption)
    Mortgage ($2,822) + Fees ($339) + Taxes in 2025 ($348)


    Taxes:$4,172

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 16893 BROADWATER AVE, WINTER GARDEN, FL 34787

    $2,795,9002 Days on yellowkey   MLS ID: O6415972

    For Sale O6415972 - 16893 BROADWATER AVE, WINTER GARDEN, FL 34787 76 photos

    Bed: 7   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 6289
       Built: 2019
    Monthly Fee: $383
       Tax: $25,448 (2025)
    Community: Waterside 90'S
    Single Family


    Estimated Monthly Payment: $17,823 (change assumption)
    Mortgage ($15,320) + Fees ($383) + Taxes in 2025 ($2,121)


    Taxes:$25,448

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle




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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.