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Winter Garden Single Family Homes For Sale - 609 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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  • 11864 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $649,680176 Days on yellowkey   MLS ID: O6361583

    INCREASED by $29,690 (4.8%) on 05/11/2026

    For Sale O6361583 - 11864 SHINE VIEW LN, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2489
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,916 (change assumption)
    Mortgage ($3,560) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 107 TRADITIONS DR, WINTER GARDEN, FL 34787

    $474,97557 Days on yellowkey   MLS ID: S5145650

    REDUCED by $25,020 (5.0%) on 04/20/2026

    For Sale S5145650 - 107 TRADITIONS DR, WINTER GARDEN, FL 34787 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1582
       Built: 1999
    Monthly Fee: $45
       Tax: $1,458 (2024)
    Community: Traditions Sub
    Single Family


    Estimated Monthly Payment: $2,769 (change assumption)
    Mortgage ($2,603) + Fees ($45) + Taxes in 2024 ($121)


    Taxes:$1,458

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 17372 GLOSSY POMELO WAY, WINTER GARDEN, FL 34787

    $1,860,0003 Days on yellowkey   MLS ID: O6406639

    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: $10,278 (change assumption)
    Mortgage ($10,192) + 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


  • 375 REGAL DOWNS CIR, WINTER GARDEN, FL 34787

    $334,90077 Days on yellowkey   MLS ID: O6377205

    0 Days Off yellowkey (back on 3/20/2026)

    For Sale O6377205 - 375 REGAL DOWNS CIR, WINTER GARDEN, FL 34787 16 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1464
       Built: 2001   Tax: $4,413 (2024)
    Community: Regal Pointe Ph 01 43/129
    Single Family


    Estimated Monthly Payment: $2,203 (change assumption)
    Mortgage ($1,835) + Taxes in 2024 ($368)


    Taxes:$4,413

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 2478 PRAIRIE VIEW DR, WINTER GARDEN, FL 34787

    $499,90022 Days on yellowkey   MLS ID: O6400594

    2 Days Off yellowkey (back on 5/10/2026)

    For Sale O6400594 - 2478 PRAIRIE VIEW DR, WINTER GARDEN, FL 34787 21 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2766
       Built: 2002
    Monthly Fee: $90
       Tax: $8,172 (2025)
    Community: Wintermere Pointe Ph 02 46/141
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,510 (change assumption)
    Mortgage ($2,739) + Fees ($90) + Taxes in 2025 ($681)


    Taxes:$8,172

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 12390 CLEAR SAPPHIRE #260, WINTER GARDEN, FL 34787

    $819,99044 Days on yellowkey   MLS ID: O6394850

    REDUCED by $30,000 (3.5%) on 04/30/2026

    For Sale O6394850 - 12390 CLEAR SAPPHIRE #260, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2552
       Built: 2026
    Monthly Fee: $96

    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $4,589 (change assumption)
    Mortgage ($4,493) + Fees ($96) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 1040 MAXEY DR, WINTER GARDEN, FL 34787

    $225,00053 Days on yellowkey   MLS ID: O6391395

    REDUCED by $25,000 (10.0%) on 05/10/2026

    For Sale O6391395 - 1040 MAXEY DR, WINTER GARDEN, FL 34787 22 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1184
       Built: 1968   Tax: $1,671 (2025)
    Community: Bay St Park
    Single Family


    Estimated Monthly Payment: $1,372 (change assumption)
    Mortgage ($1,233) + Taxes in 2025 ($139)


    Taxes:$1,671

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 1005 CHASE DR, WINTER GARDEN, FL 34787

    $629,000159 Days on yellowkey   MLS ID: A4674195

    REDUCED by $10,000 (1.6%) on 05/07/2026

    For Sale A4674195 - 1005 CHASE DR, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2319
       Built: 2005
    Monthly Fee: $68
       Tax: $7,086 (2024)
    Community: Island Pointe Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,105 (change assumption)
    Mortgage ($3,446) + Fees ($68) + Taxes in 2024 ($591)


    Taxes:$7,086

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 921 BENDING OAK TRL, WINTER GARDEN, FL 34787

    $575,0005 Days on yellowkey   MLS ID: O6405328

    For Sale O6405328 - 921 BENDING OAK TRL, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2481
       Built: 2012
    Monthly Fee: $125
       Tax: $3,791 (2025)
    Community: Oaks/Brandy Lake 01 Rep A & B
    Single Family


    Estimated Monthly Payment: $3,591 (change assumption)
    Mortgage ($3,151) + Fees ($125) + Taxes in 2025 ($316)


    Taxes:$3,791

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 13332 SUBURBAN TER, WINTER GARDEN, FL 34787

    $714,90012 Days on yellowkey   MLS ID: O6402778

    For Sale O6402778 - 13332 SUBURBAN TER, WINTER GARDEN, FL 34787 52 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2706
       Built: 1994   Tax: $2,841 (2024)
    Community: Citrus Cove Unit 01
    Single Family


    Estimated Monthly Payment: $4,154 (change assumption)
    Mortgage ($3,917) + Taxes in 2024 ($237)


    Taxes:$2,841

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16461 OLIVE HILL DR, WINTER GARDEN, FL 34787

    $588,900100 Days on yellowkey   MLS ID: O6379181

    For Sale O6379181 - 16461 OLIVE HILL DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2008
       Built: 2019
    Monthly Fee: $127
       Tax: $7,241 (2024)
    Community: Hawksmoor
    Single Family


    Estimated Monthly Payment: $3,957 (change assumption)
    Mortgage ($3,227) + Fees ($127) + Taxes in 2024 ($603)


    Taxes:$7,241

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 15200 LAKE CLAIRE OVERLOOK DR, WINTER GARDEN, FL 34787

    $1,325,00021 Days on yellowkey   MLS ID: O6401205

    1 Days Off yellowkey (back on 5/10/2026)

    For Sale O6401205 - 15200 LAKE CLAIRE OVERLOOK DR, WINTER GARDEN, FL 34787 70 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3904
       Built: 2016
    Monthly Fee: $235
       Tax: $8,218 (2025)
    Community: Hickory Hammock
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,180 (change assumption)
    Mortgage ($7,260) + Fees ($235) + Taxes in 2025 ($685)


    Taxes:$8,218

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1032 BURLAND CIR, WINTER GARDEN, FL 34787

    $529,99015 Days on yellowkey   MLS ID: O6401764

    1 Days Off yellowkey (back on 5/10/2026)

    INCREASED by $10,000 (1.9%) on 05/10/2026

    For Sale O6401764 - 1032 BURLAND CIR, WINTER GARDEN, FL 34787 58 photos

    Bed: 5   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2487
       Built: 2005
    Monthly Fee: $64
       Tax: $6,728 (2025)
    Community: Fullers Xing Ph 03 A-G
    Single Family


    Estimated Monthly Payment: $3,529 (change assumption)
    Mortgage ($2,904) + Fees ($64) + Taxes in 2025 ($561)


    Taxes:$6,728

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13536 SUNSET LAKES CIR, WINTER GARDEN, FL 34787

    $1,150,00027 Days on yellowkey   MLS ID: O6399227

    REDUCED by $50,000 (4.2%) on 05/04/2026

    For Sale O6399227 - 13536 SUNSET LAKES CIR, WINTER GARDEN, FL 34787 68 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3389
       Built: 1998
    Monthly Fee: $69
       Tax: $10,940 (2025)
    Community: Sunset Lakes
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,282 (change assumption)
    Mortgage ($6,301) + Fees ($69) + Taxes in 2025 ($912)


    Taxes:$10,940

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 13603 SUNSET LAKES CIR, WINTER GARDEN, FL 34787

    $787,00014 Days on yellowkey   MLS ID: G5111474

    0 Days Off yellowkey (back on 5/9/2026)

    For Sale G5111474 - 13603 SUNSET LAKES CIR, WINTER GARDEN, FL 34787 29 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2425
       Built: 1995
    Monthly Fee: $69
       Tax: $5,322 (2025)
    Community: Sunset Lakes
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,825 (change assumption)
    Mortgage ($4,312) + Fees ($69) + Taxes in 2025 ($444)


    Taxes:$5,322

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $1,287,00044 Days on yellowkey   MLS ID: O6394059

    REDUCED by $30,000 (2.3%) on 05/09/2026

    For Sale O6394059 - 706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 4019
       Built: 2018
    Monthly Fee: $188
       Tax: $17,895 (2025)
    Community: Canopy Oaks Ph 1
    Single Family


    Estimated Monthly Payment: $8,731 (change assumption)
    Mortgage ($7,052) + Fees ($188) + Taxes in 2025 ($1,491)


    Taxes:$17,895

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 12983 HARVEST RAIN AVE, WINTER GARDEN, FL 34787

    $750,00035 Days on yellowkey   MLS ID: O6397592

    For Sale O6397592 - 12983 HARVEST RAIN AVE, WINTER GARDEN, FL 34787 53 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2858
       Built: 2026
    Monthly Fee: $140

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,249 (change assumption)
    Mortgage ($4,109) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16137 WIND VIEW LN, WINTER GARDEN, FL 34787

    $565,000263 Days on yellowkey   MLS ID: O6335769

    REDUCED by $10,000 (1.7%) on 05/09/2026

    For Sale O6335769 - 16137 WIND VIEW LN, WINTER GARDEN, FL 34787 29 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2016
    Monthly Fee: $283
       Tax: $6,800 (2024)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,946 (change assumption)
    Mortgage ($3,096) + Fees ($283) + Taxes in 2024 ($567)


    Taxes:$6,800

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 7190 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787

    $545,0006 Days on yellowkey   MLS ID: O6402423

    For Sale O6402423 - 7190 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787 24 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2016
    Monthly Fee: $253
       Tax: $5,148 (2025)
    Community: Lakeview Pointe/Horizon West P
    Single Family


    Estimated Monthly Payment: $3,668 (change assumption)
    Mortgage ($2,986) + Fees ($253) + Taxes in 2025 ($429)


    Taxes:$5,148

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 402 EGRET PLACE DR, WINTER GARDEN, FL 34787

    $689,00015 Days on yellowkey   MLS ID: O6402689

    For Sale O6402689 - 402 EGRET PLACE DR, WINTER GARDEN, FL 34787 59 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2711
       Built: 2013
    Monthly Fee: $128
       Tax: $4,659 (2025)
    Community: Johns Lake Pointe
    Single Family


    Estimated Monthly Payment: $4,291 (change assumption)
    Mortgage ($3,775) + Fees ($128) + Taxes in 2025 ($388)


    Taxes:$4,659

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge 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.