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Winter Garden Homes For Sale & Real Estate - 940 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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  • 15456 GILLIGAN CT, WINTER GARDEN, FL 34787

    $550,000341 Days on yellowkey   MLS ID: A4660262

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

    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


  • 1105 LINCOLN TER, WINTER GARDEN, FL 34787

    $255,00021 Days on yellowkey   MLS ID: O6416937

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

    For Sale O6416937 - 1105 LINCOLN TER, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 814
       Built: 1961   Tax: $1,586 (2025)
    Community: Bay St Park
    Single Family


    Estimated Monthly Payment: $1,529 (change assumption)
    Mortgage ($1,397) + Taxes in 2025 ($132)


    Taxes:$1,586

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 17126 ARROWHEAD BLVD, WINTER GARDEN, FL 34787

    $565,00048 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


  • 8170 BLUEJACK OAK DR, WINTER GARDEN, FL 34787

    $445,00082 Days on yellowkey   MLS ID: O6399484

    REDUCED by $15,000 (3.3%) on 07/02/2026

    For Sale O6399484 - 8170 BLUEJACK OAK DR, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1853
       Built: 2016
    Monthly Fee: $315
       Tax: $4,738 (2025)
    Community: Summerlake Pd Ph 2C 2D 2E
    Townhouse


    Estimated Monthly Payment: $3,148 (change assumption)
    Mortgage ($2,438) + Fees ($315) + Taxes in 2025 ($395)


    Taxes:$4,738

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 22 WINDTREE LN #203, WINTER GARDEN, FL 34787

    $169,900210 Days on yellowkey   MLS ID: S5139914

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

    REDUCED by $10,000 (5.6%) on 06/18/2026

    For Sale S5139914 - 22 WINDTREE LN #203, WINTER GARDEN, FL 34787 30 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 918
       Built: 1983
    Monthly Fee: $300
       Tax: $875 (2025)
    Community: Windtree Gardens Condo Ph 01
    Condo


    Estimated Monthly Payment: $1,304 (change assumption)
    Mortgage ($931) + Fees ($300) + Taxes in 2025 ($73)


    Taxes:$875

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787

    $1,495,00029 Days on yellowkey   MLS ID: O6414639

    0 Days Off yellowkey (back on 6/29/2026)

    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


  • 15039 GROVESIDE RD, WINTER GARDEN, FL 34787

    $497,38087 Days on yellowkey   MLS ID: O6398354

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

    INCREASED by $5,000 (1.0%) on 06/17/2026

    For Sale O6398354 - 15039 GROVESIDE RD, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2026
    Monthly Fee: $247
       Tax: $1,375 (2025)
    Community: Parkview At Hamlin
    Townhouse


    Estimated Monthly Payment: $3,087 (change assumption)
    Mortgage ($2,725) + Fees ($247) + Taxes in 2025 ($115)


    Taxes:$1,375

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 2022 BOSS HEWETT ST, WINTER GARDEN, FL 34787

    $679,00019 Days on yellowkey   MLS ID: O6417697

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

    For Sale O6417697 - 2022 BOSS HEWETT ST, WINTER GARDEN, FL 34787 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2281
       Built: 2022
    Monthly Fee: $171
       Tax: $7,948 (2025)
    Community: Hull Island/Oakland Ph 2
    Single Family


    Estimated Monthly Payment: $4,554 (change assumption)
    Mortgage ($3,720) + Fees ($171) + Taxes in 2025 ($662)


    Taxes:$7,948

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 168 WINDTREE LN #203, WINTER GARDEN, FL 34787

    $202,900267 Days on yellowkey   MLS ID: O6351954

    4 Days Off yellowkey (back on 6/26/2026)

    REDUCED by $6,500 (3.1%) on 06/04/2026

    For Sale O6351954 - 168 WINDTREE LN #203, WINTER GARDEN, FL 34787 27 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 918
       Built: 1985
    Monthly Fee: $260
       Tax: $2,004 (2024)
    Community: Windtree Gardens Ph 6
    Condo


    Estimated Monthly Payment: $1,539 (change assumption)
    Mortgage ($1,112) + Fees ($260) + Taxes in 2024 ($167)


    Taxes:$2,004

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1711 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787

    $1,046,0006 Days on yellowkey   MLS ID: G5114517

    For Sale G5114517 - 1711 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787 72 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3863
       Built: 2017
    Monthly Fee: $187
       Tax: $10,792 (2024)
    Community: Twinwaters
    Single Family


    Estimated Monthly Payment: $6,818 (change assumption)
    Mortgage ($5,731) + Fees ($187) + Taxes in 2024 ($899)


    Taxes:$10,792

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 120 BLUE STONE CIR, WINTER GARDEN, FL 34787

    $747,90047 Days on yellowkey   MLS ID: O6409811

    REDUCED by $2,000 (0.3%) on 06/05/2026

    For Sale O6409811 - 120 BLUE STONE CIR, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2529
       Built: 1998
    Monthly Fee: $68
       Tax: $4,291 (2025)
    Community: Westfield Lakes
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,524 (change assumption)
    Mortgage ($4,098) + Fees ($68) + Taxes in 2025 ($358)


    Taxes:$4,291

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1642 CHANDELLE LN, WINTER GARDEN, FL 34787

    $709,9006 Days on yellowkey   MLS ID: G5114093

    For Sale G5114093 - 1642 CHANDELLE LN, WINTER GARDEN, FL 34787 5 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: $4,763 (change assumption)
    Mortgage ($3,890) + 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


  • 13759 GOLDEN RUSSET DR, WINTER GARDEN, FL 34787

    $309,00047 Days on yellowkey   MLS ID: O6409757

    REDUCED by $19,500 (5.9%) on 07/02/2026

    For Sale O6409757 - 13759 GOLDEN RUSSET DR, WINTER GARDEN, FL 34787 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1647
       Built: 2007
    Monthly Fee: $206
       Tax: $855 (2025)
    Community: Orchard A1-A26 B1 B2 C D1-D4
    Townhouse


    Estimated Monthly Payment: $1,970 (change assumption)
    Mortgage ($1,693) + Fees ($206) + Taxes in 2025 ($71)


    Taxes:$855

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • WINTER GARDEN, FL 34787

    $217,5006 Days on yellowkey   MLS ID: O6420656

    For Sale O6420656 - WINTER GARDEN, FL 34787 16 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 942
       Built: 2005
    Monthly Fee: $378
       Tax: $2,727 (2025)
    Community: Southern Pines Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,797 (change assumption)
    Mortgage ($1,192) + Fees ($378) + Taxes in 2025 ($227)


    Taxes:$2,727

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16503 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787

    $459,00012 Days on yellowkey   MLS ID: O6420071

    REDUCED by $20,000 (4.2%) on 07/02/2026

    For Sale O6420071 - 16503 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787 67 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1817
       Built: 2025
    Monthly Fee: $204
       Tax: $1,424 (2025)
    Community: Waterleigh
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,838 (change assumption)
    Mortgage ($2,515) + Fees ($204) + Taxes in 2025 ($119)


    Taxes:$1,424

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16509 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787

    $414,99012 Days on yellowkey   MLS ID: O6420095

    REDUCED by $32,510 (7.3%) on 07/02/2026

    For Sale O6420095 - 16509 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787 63 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1567
       Built: 2025
    Monthly Fee: $208
       Tax: $1,424 (2025)
    Community: Waterleigh
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,601 (change assumption)
    Mortgage ($2,274) + Fees ($208) + Taxes in 2025 ($119)


    Taxes:$1,424

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16558 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787

    $464,99012 Days on yellowkey   MLS ID: O6420061

    REDUCED by $5,510 (1.2%) on 07/02/2026

    For Sale O6420061 - 16558 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787 67 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1817
       Built: 2025
    Monthly Fee: $204
       Tax: $1,424 (2025)
    Community: Waterleigh
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,870 (change assumption)
    Mortgage ($2,548) + Fees ($204) + Taxes in 2025 ($119)


    Taxes:$1,424

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2496 BARONSMEDE CT, WINTER GARDEN, FL 34787

    $875,00011 Days on yellowkey   MLS ID: G5114233

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

    For Sale G5114233 - 2496 BARONSMEDE CT, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4184
       Built: 2002
    Monthly Fee: $210
       Tax: $8,903 (2025)
    Community: Stoneybrook West 47/78
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,746 (change assumption)
    Mortgage ($4,794) + Fees ($210) + Taxes in 2025 ($742)


    Taxes:$8,903

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


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

    $344,90075 Days on yellowkey   MLS ID: O6401625

    REDUCED by $4,100 (1.2%) on 06/25/2026

    For Sale O6401625 - 15357 OAK APPLE CT #4C, WINTER GARDEN, FL 34787 35 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: $2,573 (change assumption)
    Mortgage ($1,890) + Fees ($285) + Taxes in 2025 ($398)


    Taxes:$4,779

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 729 MEADOW GLADE DR, WINTER GARDEN, FL 34787

    $515,00054 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




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.