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Winter Garden Single Family Homes For Sale - 643 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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  • 18339 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $748,000415 Days on yellowkey   MLS ID: O6280496

    For Sale O6280496 - 18339 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2931
       Built: 2023
    Monthly Fee: $250
       Tax: $9,777 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $5,163 (change assumption)
    Mortgage ($4,099) + Fees ($250) + Taxes in 2024 ($815)


    Taxes:$9,777

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 115 ZACHARY WADE ST, WINTER GARDEN, FL 34787

    $496,000196 Days on yellowkey   MLS ID: O6356997

    For Sale O6356997 - 115 ZACHARY WADE ST, WINTER GARDEN, FL 34787 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1780
       Built: 2001
    Monthly Fee: $58
       Tax: $5,467 (2024)
    Community: Lakeview Reserve 46/149
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,231 (change assumption)
    Mortgage ($2,718) + Fees ($58) + Taxes in 2024 ($456)


    Taxes:$5,467

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 16038 JOHNS LAKE OVERLOOK DR, WINTER GARDEN, FL 34787

    $2,175,000120 Days on yellowkey   MLS ID: G5107162

    For Sale G5107162 - 16038 JOHNS LAKE OVERLOOK DR, WINTER GARDEN, FL 34787 77 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4139
       Built: 2015
    Monthly Fee: $235
       Tax: $23,164 (2025)
    Community: Hickory Hammock
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,083 (change assumption)
    Mortgage ($11,918) + Fees ($235) + Taxes in 2025 ($1,930)


    Taxes:$23,164

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 204 SUNSET GARDEN LN, WINTER GARDEN, FL 34787

    $693,27035 Days on yellowkey   MLS ID: O6400441

    INCREASED by $3,000 (0.4%) on 04/30/2026

    For Sale O6400441 - 204 SUNSET GARDEN LN, WINTER GARDEN, FL 34787 3 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2686
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $4,069 (change assumption)
    Mortgage ($3,799) + Fees ($77) + Taxes in 2025 ($194)


    Taxes:$2,326

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 198 SUNSET GARDEN LN, WINTER GARDEN, FL 34787

    $547,16036 Days on yellowkey   MLS ID: O6400188

    INCREASED by $3,000 (0.6%) on 04/30/2026

    For Sale O6400188 - 198 SUNSET GARDEN LN, WINTER GARDEN, FL 34787 3 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1908
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $3,269 (change assumption)
    Mortgage ($2,998) + Fees ($77) + Taxes in 2025 ($194)


    Taxes:$2,326

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15783 TANGERINE DREAM CT, WINTER GARDEN, FL 34787

    $2,150,000190 Days on yellowkey   MLS ID: O6360410

    112 Days Off yellowkey (back on 4/30/2026)

    For Sale O6360410 - 15783 TANGERINE DREAM CT, WINTER GARDEN, FL 34787 83 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4478
       Built: 2018
    Monthly Fee: $743
       Tax: $28,879 (2025)
    Community: Emerald Pointe
    Single Family


    Estimated Monthly Payment: $14,930 (change assumption)
    Mortgage ($11,781) + Fees ($743) + Taxes in 2025 ($2,407)


    Taxes:$28,879

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 7935 WINTER WREN ST, WINTER GARDEN, FL 34787

    $535,000100 Days on yellowkey   MLS ID: O6379423

    2 Days Off yellowkey (back on 4/30/2026)

    For Sale O6379423 - 7935 WINTER WREN ST, WINTER GARDEN, FL 34787 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1850
       Built: 2013
    Monthly Fee: $252
       Tax: $7,834 (2025)
    Community: Summerlake Pd Ph 1B-A Rep
    Single Family


    Estimated Monthly Payment: $3,836 (change assumption)
    Mortgage ($2,931) + Fees ($252) + Taxes in 2025 ($653)


    Taxes:$7,834

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 236 DONALD DR, WINTER GARDEN, FL 34787

    $465,00029 Days on yellowkey   MLS ID: O6401940

    2 Days Off yellowkey (back on 4/30/2026)

    For Sale O6401940 - 236 DONALD DR, WINTER GARDEN, FL 34787 12 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1080
       Built: 1930   Tax: $410 (2025)
    Community: Showalter Park
    Single Family


    Estimated Monthly Payment: $2,582 (change assumption)
    Mortgage ($2,548) + Taxes in 2025 ($34)


    Taxes:$410

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 521 COPPERDALE AVE, WINTER GARDEN, FL 34787

    $525,00025 Days on yellowkey   MLS ID: O6402408

    1 Days Off yellowkey (back on 4/30/2026)

    For Sale O6402408 - 521 COPPERDALE AVE, WINTER GARDEN, FL 34787 67 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2328
       Built: 2013
    Monthly Fee: $72
       Tax: $4,040 (2025)
    Community: Covington Chase
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,285 (change assumption)
    Mortgage ($2,877) + Fees ($72) + Taxes in 2025 ($337)


    Taxes:$4,040

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 17085 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $939,88024 Days on yellowkey   MLS ID: G5111738

    0 Days Off yellowkey (back on 4/29/2026)

    For Sale G5111738 - 17085 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3409
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $5,272 (change assumption)
    Mortgage ($5,150) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 10361 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787

    $550,00024 Days on yellowkey   MLS ID: S5148904

    For Sale S5148904 - 10361 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2204
       Built: 2020
    Monthly Fee: $162
       Tax: $5,953 (2024)
    Community: Watermark Ph 4
    Single Family


    Estimated Monthly Payment: $3,672 (change assumption)
    Mortgage ($3,014) + Fees ($162) + Taxes in 2024 ($496)


    Taxes:$5,953

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 11271 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $869,99624 Days on yellowkey   MLS ID: O6403252

    For Sale O6403252 - 11271 HOLLOW BAY DR, 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: $5,132 (change assumption)
    Mortgage ($4,767) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14372 SUNBRIDGE CIR, WINTER GARDEN, FL 34787

    $745,000203 Days on yellowkey   MLS ID: O6356579

    REDUCED by $30,000 (3.9%) on 04/29/2026

    For Sale O6356579 - 14372 SUNBRIDGE CIR, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3468
       Built: 2016
    Monthly Fee: $166
       Tax: $5,745 (2023)
    Community: Bradford Crk Ph Ii
    Single Family


    Estimated Monthly Payment: $4,727 (change assumption)
    Mortgage ($4,082) + Fees ($166) + Taxes in 2023 ($479)


    Taxes:$5,745

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2023

    Middle School: SunRidge Middle


  • 723 SUNBURST COVE LN, WINTER GARDEN, FL 34787

    $555,00047 Days on yellowkey   MLS ID: S5145002

    0 Days Off yellowkey (back on 4/28/2026)

    For Sale S5145002 - 723 SUNBURST COVE LN, WINTER GARDEN, FL 34787 77 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2189
       Built: 2000
    Monthly Fee: $44
       Tax: $4,217 (2025)
    Community: Orange Cove
    Single Family


    Estimated Monthly Payment: $3,436 (change assumption)
    Mortgage ($3,041) + Fees ($44) + Taxes in 2025 ($351)


    Taxes:$4,217

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16331 TALIESIN ST, WINTER GARDEN, FL 34787

    $815,00083 Days on yellowkey   MLS ID: O6385168

    0 Days Off yellowkey (back on 4/29/2026)

    REDUCED by $14,000 (1.7%) on 04/16/2026

    For Sale O6385168 - 16331 TALIESIN ST, WINTER GARDEN, FL 34787 75 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3104
       Built: 2020
    Monthly Fee: $115
       Tax: $7,882 (2025)
    Community: Hawksmoor Ph 4
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,237 (change assumption)
    Mortgage ($4,466) + Fees ($115) + Taxes in 2025 ($657)


    Taxes:$7,882

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15878 MOONLIGHT BAY ST, WINTER GARDEN, FL 34787

    $540,00089 Days on yellowkey   MLS ID: O6384745

    0 Days Off yellowkey (back on 4/29/2026)

    REDUCED by $19,000 (3.4%) on 04/27/2026

    For Sale O6384745 - 15878 MOONLIGHT BAY ST, WINTER GARDEN, FL 34787 63 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2472
       Built: 2021
    Monthly Fee: $257
       Tax: $7,417 (2025)
    Community: Waterleigh Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,834 (change assumption)
    Mortgage ($2,959) + Fees ($257) + Taxes in 2025 ($618)


    Taxes:$7,417

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 10007 LITTLE ALCOVE LOOP, WINTER GARDEN, FL 34787

    $999,990285 Days on yellowkey   MLS ID: S5132434

    For Sale S5132434 - 10007 LITTLE ALCOVE LOOP, WINTER GARDEN, FL 34787 56 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2921
       Built: 2018
    Monthly Fee: $250
       Tax: $6,381 (2024)
    Community: Waterleigh Ph 2B
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,261 (change assumption)
    Mortgage ($5,479) + Fees ($250) + Taxes in 2024 ($532)


    Taxes:$6,381

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 17335 BEACHGRASS ALY, WINTER GARDEN, FL 34787

    $559,990282 Days on yellowkey   MLS ID: O6335800

    0 Days Off yellowkey (back on 4/28/2026)

    For Sale O6335800 - 17335 BEACHGRASS ALY, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2341
       Built: 2025
    Monthly Fee: $172
       Tax: $7,430 (2024)
    Community: Lake Star At Ovation
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,860 (change assumption)
    Mortgage ($3,068) + Fees ($172) + Taxes in 2024 ($619)


    Taxes:$7,430

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 15196 NEWTONIA ST, WINTER GARDEN, FL 34787

    $615,00080 Days on yellowkey   MLS ID: O6387201

    1 Days Off yellowkey (back on 4/29/2026)

    For Sale O6387201 - 15196 NEWTONIA ST, WINTER GARDEN, FL 34787 47 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2326
       Built: 2018
    Monthly Fee: $328
       Tax: $8,216 (2024)
    Community: Overlook 2/Hamlin Ph 2 & 5
    Single Family


    Estimated Monthly Payment: $4,382 (change assumption)
    Mortgage ($3,370) + Fees ($328) + Taxes in 2024 ($685)


    Taxes:$8,216

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 615 SIGLER DR, WINTER GARDEN, FL 34787

    $899,84081 Days on yellowkey   MLS ID: O6387120

    For Sale O6387120 - 615 SIGLER DR, WINTER GARDEN, FL 34787 13 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2432
       Built: 2026
    Monthly Fee: $155
       Tax: $99,279 (2025)
    Community: Lakeview Village Estates
    Single Family


    Estimated Monthly Payment: $13,359 (change assumption)
    Mortgage ($4,931) + Fees ($155) + Taxes in 2025 ($8,273)


    Taxes:$99,279

    Elementary School: Dillard Street Elem

    High School: None

    Tax Year: 2025

    Middle School: Lakeview 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.