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Winter Garden Single Family Homes For Sale - 691 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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  • 17090 HARBOR OAK PKWY, WINTER GARDEN, FL 34787

    $534,90045 Days on yellowkey   MLS ID: G5111718

    REDUCED by $5,000 (0.9%) on 06/02/2026

    For Sale G5111718 - 17090 HARBOR OAK PKWY, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2148
       Built: 2019
    Monthly Fee: $215
       Tax: $7,499 (2025)
    Community: Waterside/Johns Lk-Ph 2A
    Single Family


    Estimated Monthly Payment: $3,771 (change assumption)
    Mortgage ($2,931) + Fees ($215) + Taxes in 2025 ($625)


    Taxes:$7,499

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1701 E BAY ST, WINTER GARDEN, FL 34787

    $295,0007 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


  • 2241 WHITE FEATHER LOOP, WINTER GARDEN, FL 34787

    $525,00013 Days on yellowkey   MLS ID: O6411576

    For Sale O6411576 - 2241 WHITE FEATHER LOOP, WINTER GARDEN, FL 34787 55 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2152
       Built: 2018
    Monthly Fee: $105
       Tax: $4,991 (2025)
    Community: Oakland Trls Ph 1
    Single Family


    Estimated Monthly Payment: $3,398 (change assumption)
    Mortgage ($2,877) + Fees ($105) + Taxes in 2025 ($416)


    Taxes:$4,991

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15149 CANOE PL, WINTER GARDEN, FL 34787

    $799,00011 Days on yellowkey   MLS ID: O6412776

    For Sale O6412776 - 15149 CANOE PL, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3081
       Built: 2019
    Monthly Fee: $385
       Tax: $9,388 (2025)
    Community: Lakeshore Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $5,545 (change assumption)
    Mortgage ($4,378) + Fees ($385) + Taxes in 2025 ($782)


    Taxes:$9,388

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787

    $1,495,0005 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


  • 13526 FOX GLOVE ST, WINTER GARDEN, FL 34787

    $845,00081 Days on yellowkey   MLS ID: O6388630

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

    For Sale O6388630 - 13526 FOX GLOVE ST, WINTER GARDEN, FL 34787 54 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3866
       Built: 2005
    Monthly Fee: $243
       Tax: $11,960 (2025)
    Community: Stoneybrook West
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,870 (change assumption)
    Mortgage ($4,630) + Fees ($243) + Taxes in 2025 ($997)


    Taxes:$11,960

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 17126 ARROWHEAD BLVD, WINTER GARDEN, FL 34787

    $565,00024 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

    $525,00022 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


  • 720 LAKE BRIM DR, WINTER GARDEN, FL 34787

    $1,725,00099 Days on yellowkey   MLS ID: O6387519

    REDUCED by $45,000 (2.5%) on 06/01/2026

    For Sale O6387519 - 720 LAKE BRIM DR, WINTER GARDEN, FL 34787 88 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3781
       Built: 2020
    Monthly Fee: $208
       Tax: $14,831 (2025)
    Community: Oakland Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,896 (change assumption)
    Mortgage ($9,452) + Fees ($208) + Taxes in 2025 ($1,236)


    Taxes:$14,831

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 7687 BOWERY DR, WINTER GARDEN, FL 34787

    $830,0005 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

    $4,900,0007 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

    $435,000251 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

    $679,000194 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

    $1,790,00034 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


  • 617 MARSH REED DR, WINTER GARDEN, FL 34787

    $750,00045 Days on yellowkey   MLS ID: O6402724

    REDUCED by $9,000 (1.2%) on 06/05/2026

    For Sale O6402724 - 617 MARSH REED DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2828
       Built: 2016
    Monthly Fee: $128
       Tax: $5,746 (2025)
    Community: Johns Lake Pointe
    Single Family


    Estimated Monthly Payment: $4,716 (change assumption)
    Mortgage ($4,109) + Fees ($128) + Taxes in 2025 ($479)


    Taxes:$5,746

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 650 MEDORA WAY, WINTER GARDEN, FL 34787

    $1,157,1904 Days on yellowkey   MLS ID: O6413464

    For Sale O6413464 - 650 MEDORA WAY, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2902
       Built: 2026
    Monthly Fee: $155
       Tax: $993 (2025)
    Community: Lakeview Village Estates
    Single Family


    Estimated Monthly Payment: $6,578 (change assumption)
    Mortgage ($6,341) + 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


  • 6460 MAKRUT LIME DR, WINTER GARDEN, FL 34787

    $869,0005 Days on yellowkey   MLS ID: O6414802

    For Sale O6414802 - 6460 MAKRUT LIME DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3103
       Built: 2018
    Monthly Fee: $142
       Tax: $10,250 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $5,758 (change assumption)
    Mortgage ($4,762) + Fees ($142) + Taxes in 2025 ($854)


    Taxes:$10,250

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 611 SIGLER DR, WINTER GARDEN, FL 34787

    $899,7604 Days on yellowkey   MLS ID: O6415005

    For Sale O6415005 - 611 SIGLER DR, WINTER GARDEN, FL 34787 13 photos

    Bed: 4   Bath: 3.5   Gar: 22
    Liv Area Sq Ft: 2432
       Built: 2026
    Monthly Fee: $155
       Tax: $993 (2025)
    Community: Lakeview Village Estates
    Single Family


    Estimated Monthly Payment: $5,168 (change assumption)
    Mortgage ($4,930) + Fees ($155) + Taxes in 2025 ($83)


    Taxes:$993

    Elementary School: Dillard Street Elem

    High School: None

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 403 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787

    $999,96139 Days on yellowkey   MLS ID: O6405130

    For Sale O6405130 - 403 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787 39 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2681
       Built: 2024
    Monthly Fee: $240
       Tax: $9,118 (2025)
    Community: Winter Grove
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,479 (change assumption)
    Mortgage ($5,479) + Fees ($240) + Taxes in 2025 ($760)


    Taxes:$9,118

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16826 BROADWATER AVE, WINTER GARDEN, FL 34787

    $1,449,000101 Days on yellowkey   MLS ID: O6387379

    0 Days Off yellowkey (back on 6/9/2026)

    REDUCED by $50,000 (3.3%) on 05/29/2026

    For Sale O6387379 - 16826 BROADWATER AVE, WINTER GARDEN, FL 34787 58 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4451
       Built: 2019
    Monthly Fee: $218
       Tax: $9,892 (2025)
    Community: Waterside/Johns Lk-Ph 1
    Single Family


    Estimated Monthly Payment: $8,982 (change assumption)
    Mortgage ($7,940) + Fees ($218) + Taxes in 2025 ($824)


    Taxes:$9,892

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle




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.