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Winter Garden Homes For Sale & Real Estate - 869 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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  • 14282 CREEKBED CIR, WINTER GARDEN, FL 34787

    $899,900160 Days on yellowkey   MLS ID: O6365928

    REDUCED by $24,600 (2.7%) on 05/20/2026

    For Sale O6365928 - 14282 CREEKBED CIR, WINTER GARDEN, FL 34787 25 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3479
       Built: 2015
    Monthly Fee: $180
       Tax: $7,163 (2025)
    Community: Bradford Creek
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,708 (change assumption)
    Mortgage ($4,931) + Fees ($180) + Taxes in 2025 ($597)


    Taxes:$7,163

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15058 SAWGRASS BLUFF DR, WINTER GARDEN, FL 34787

    $579,90037 Days on yellowkey   MLS ID: O6396640

    1 Days Off yellowkey (back on 5/5/2026)

    For Sale O6396640 - 15058 SAWGRASS BLUFF DR, WINTER GARDEN, FL 34787 26 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2626
       Built: 2013
    Monthly Fee: $128
       Tax: $6,746 (2025)
    Community: Johns Lake Pointe A & S
    Single Family


    Estimated Monthly Payment: $3,868 (change assumption)
    Mortgage ($3,177) + Fees ($128) + Taxes in 2025 ($562)


    Taxes:$6,746

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15075 TEA TREE DR, WINTER GARDEN, FL 34787

    $829,347248 Days on yellowkey   MLS ID: G5102184

    8 Days Off yellowkey (back on 5/19/2026)

    For Sale G5102184 - 15075 TEA TREE DR, WINTER GARDEN, FL 34787 44 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3038
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,694 (change assumption)
    Mortgage ($4,544) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


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

    $355,00029 Days on yellowkey   MLS ID: O6401625

    REDUCED by $5,000 (1.4%) on 05/19/2026

    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: $2,628 (change assumption)
    Mortgage ($1,945) + Fees ($285) + Taxes in 2025 ($398)


    Taxes:$4,779

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3208 SAILING PIER AVE, WINTER GARDEN, FL 34787

    $1,049,90027 Days on yellowkey   MLS ID: O6402332

    1 Days Off yellowkey (back on 5/19/2026)

    For Sale O6402332 - 3208 SAILING PIER AVE, WINTER GARDEN, FL 34787 50 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3998
       Built: 2023
    Monthly Fee: $208
       Tax: $12,135 (2024)
    Community: Ests/Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $6,972 (change assumption)
    Mortgage ($5,753) + Fees ($208) + Taxes in 2024 ($1,011)


    Taxes:$12,135

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 17406 HONEYBELL TANGELO CT, WINTER GARDEN, FL 34787

    $845,00027 Days on yellowkey   MLS ID: O6402286

    REDUCED by $2,000 (0.2%) on 05/09/2026

    For Sale O6402286 - 17406 HONEYBELL TANGELO CT, WINTER GARDEN, FL 34787 54 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3427
       Built: 2026
    Monthly Fee: $83

    Community: Northlake At Ovation
    Single Family


    Estimated Monthly Payment: $4,713 (change assumption)
    Mortgage ($4,630) + Fees ($83) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 5526 TINY RD, WINTER GARDEN, FL 34787

    $1,675,000288 Days on yellowkey   MLS ID: O6334009

    0 Days Off yellowkey (back on 4/3/2026)

    For Sale O6334009 - 5526 TINY RD, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2474
       Built: 2007   Tax: $10,165 (2024)
    Community: None
    Single Family


    Estimated Monthly Payment: $10,025 (change assumption)
    Mortgage ($9,178) + Taxes in 2024 ($847)


    Taxes:$10,165

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14525 WHITTRIDGE DR, WINTER GARDEN, FL 34787

    $629,0006 Days on yellowkey   MLS ID: O6407375

    0 Days Off yellowkey (back on 5/19/2026)

    For Sale O6407375 - 14525 WHITTRIDGE DR, WINTER GARDEN, FL 34787 45 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3487
       Built: 2006
    Monthly Fee: $195
       Tax: $10,373 (2025)
    Community: Signature Lks-Pcl 01B
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,506 (change assumption)
    Mortgage ($3,446) + Fees ($195) + Taxes in 2025 ($864)


    Taxes:$10,373

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 408 S BOYD ST, WINTER GARDEN, FL 34787

    $795,00052 Days on yellowkey   MLS ID: O6394810

    0 Days Off yellowkey (back on 5/19/2026)

    REDUCED by $20,000 (2.5%) on 05/11/2026

    For Sale O6394810 - 408 S BOYD ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2295
       Built: 1939   Tax: $2,572 (2025)
    Community: G T Smith Sub 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,570 (change assumption)
    Mortgage ($4,356) + Taxes in 2025 ($214)


    Taxes:$2,572

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14736 FIELD DAISY DR, WINTER GARDEN, FL 34787

    $550,00066 Days on yellowkey   MLS ID: O6391435

    1 Days Off yellowkey (back on 5/19/2026)

    For Sale O6391435 - 14736 FIELD DAISY DR, WINTER GARDEN, FL 34787 43 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2149
       Built: 2026
    Monthly Fee: $229

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $3,243 (change assumption)
    Mortgage ($3,014) + Fees ($229) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 170 WINDTREE LN, WINTER GARDEN, FL 34787

    $204,9006 Days on yellowkey   MLS ID: S5150050

    For Sale S5150050 - 170 WINDTREE LN, WINTER GARDEN, FL 34787 14 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 918
       Built: 1985   Tax: $2,782 (2025)
    Community: Windtree Gardens Condo Ph 06
    Condo


    Estimated Monthly Payment: $1,355 (change assumption)
    Mortgage ($1,123) + Taxes in 2025 ($232)


    Taxes:$2,782

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787

    $630,00024 Days on yellowkey   MLS ID: O6403063

    REDUCED by $5,500 (0.9%) on 05/19/2026

    For Sale O6403063 - 17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2692
       Built: 2017
    Monthly Fee: $215
       Tax: $8,922 (2025)
    Community: Waterside/Johns Lake Ph 2A
    Single Family


    Estimated Monthly Payment: $4,410 (change assumption)
    Mortgage ($3,452) + Fees ($215) + Taxes in 2025 ($744)


    Taxes:$8,922

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 503 FIRST CAPE CORAL DR, WINTER GARDEN, FL 34787

    $556,00066 Days on yellowkey   MLS ID: O6381166

    For Sale O6381166 - 503 FIRST CAPE CORAL DR, WINTER GARDEN, FL 34787 28 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2365
       Built: 2006
    Monthly Fee: $123
       Tax: $3,974 (2024)
    Community: Black Lake Park Ph 01
    Single Family


    Estimated Monthly Payment: $3,501 (change assumption)
    Mortgage ($3,046) + Fees ($123) + Taxes in 2024 ($331)


    Taxes:$3,974

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 11117 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $520,0008 Days on yellowkey   MLS ID: O6407552

    For Sale O6407552 - 11117 BOSTWICK ALY, WINTER GARDEN, FL 34787 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1685
       Built: 2022
    Monthly Fee: $291
       Tax: $6,722 (2025)
    Community: Waterleigh Ph 4A
    Single Family


    Estimated Monthly Payment: $3,700 (change assumption)
    Mortgage ($2,849) + Fees ($291) + Taxes in 2025 ($560)


    Taxes:$6,722

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14058 FRASIER ST, WINTER GARDEN, FL 34787

    $459,00091 Days on yellowkey   MLS ID: V4947394

    For Sale V4947394 - 14058 FRASIER ST, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1996
       Built: 2023
    Monthly Fee: $110
       Tax: $7,893 (2024)
    Community: Highland Rdg
    Single Family


    Estimated Monthly Payment: $3,283 (change assumption)
    Mortgage ($2,515) + Fees ($110) + Taxes in 2024 ($658)


    Taxes:$7,893

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3351 HANGING TIDE ST, WINTER GARDEN, FL 34787

    $635,0008 Days on yellowkey   MLS ID: O6407746

    For Sale O6407746 - 3351 HANGING TIDE ST, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2741
       Built: 2021
    Monthly Fee: $152
       Tax: $7,521 (2025)
    Community: Lakeview Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $4,258 (change assumption)
    Mortgage ($3,479) + Fees ($152) + Taxes in 2025 ($627)


    Taxes:$7,521

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 3518 TURNINGWIND LN, WINTER GARDEN, FL 34787

    $810,00037 Days on yellowkey   MLS ID: S5147067

    3 Days Off yellowkey (back on 5/19/2026)

    REDUCED by $15,000 (1.8%) on 04/30/2026

    For Sale S5147067 - 3518 TURNINGWIND LN, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2744
       Built: 2003
    Monthly Fee: $115
       Tax: $10,313 (2025)
    Community: Windward Cay 48 125
    Single Family


    Estimated Monthly Payment: $5,413 (change assumption)
    Mortgage ($4,438) + Fees ($115) + Taxes in 2025 ($859)


    Taxes:$10,313

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 14501 GROVE RESORT AVE #3611, WINTER GARDEN, FL 34787

    $220,00084 Days on yellowkey   MLS ID: TB8481342

    For Sale TB8481342 - 14501 GROVE RESORT AVE #3611, WINTER GARDEN, FL 34787 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1396
       Built: 2018
    Monthly Fee: $998
       Tax: $7,177 (2024)
    Community: Grove Residence & Spa Hotel Condo 3
    Condo


    Estimated Monthly Payment: $2,802 (change assumption)
    Mortgage ($1,205) + Fees ($998) + Taxes in 2024 ($598)


    Taxes:$7,177

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 419 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787

    $874,99050 Days on yellowkey   MLS ID: O6395693

    3 Days Off yellowkey (back on 5/19/2026)

    For Sale O6395693 - 419 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787 35 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2650
       Built: 2026
    Monthly Fee: $240
       Tax: $1,955 (2025)
    Community: Winter Grove
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,197 (change assumption)
    Mortgage ($4,794) + Fees ($240) + Taxes in 2025 ($163)


    Taxes:$1,955

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 1689 CRANLEIGH DR, WINTER GARDEN, FL 34787

    $875,00079 Days on yellowkey   MLS ID: O6387674

    0 Days Off yellowkey (back on 5/19/2026)

    REDUCED by $13,800 (1.6%) on 04/30/2026

    For Sale O6387674 - 1689 CRANLEIGH DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2937
       Built: 2020
    Monthly Fee: $165
       Tax: $7,225 (2025)
    Community: Sanctuary / Twin Waters
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,561 (change assumption)
    Mortgage ($4,794) + Fees ($165) + Taxes in 2025 ($602)


    Taxes:$7,225

    Elementary School: None

    High School: West Orange High

    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.