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Winter Garden Single Family Homes For Sale - 695 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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  • 420 E CYPRESS ST, WINTER GARDEN, FL 34787

    $425,00013 Days on yellowkey   MLS ID: O6412414

    For Sale O6412414 - 420 E CYPRESS ST, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1616
       Built: 1950   Tax: $5,517 (2025)
    Community: Overstreet Crate
    Single Family


    Estimated Monthly Payment: $2,788 (change assumption)
    Mortgage ($2,329) + Taxes in 2025 ($460)


    Taxes:$5,517

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 13843 LANYARD WAY, WINTER GARDEN, FL 34787

    $648,00014 Days on yellowkey   MLS ID: O6412130

    For Sale O6412130 - 13843 LANYARD WAY, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2568
       Built: 2022
    Monthly Fee: $225
       Tax: $9,717 (2025)
    Community: Encore/Ovation Ph 3
    Single Family


    Estimated Monthly Payment: $4,585 (change assumption)
    Mortgage ($3,551) + Fees ($225) + Taxes in 2025 ($810)


    Taxes:$9,717

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787

    $339,90061 Days on yellowkey   MLS ID: O6398208

    For Sale O6398208 - 483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1008
       Built: 1988   Tax: $2,702 (2025)
    Community: East Garden Manor Add 03
    Single Family


    Estimated Monthly Payment: $2,088 (change assumption)
    Mortgage ($1,862) + Taxes in 2025 ($225)


    Taxes:$2,702

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 8289 TOPSAIL PL, WINTER GARDEN, FL 34787

    $920,00011 Days on yellowkey   MLS ID: S5151179

    REDUCED by $60,000 (6.1%) on 06/07/2026

    For Sale S5151179 - 8289 TOPSAIL PL, WINTER GARDEN, FL 34787 56 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2755
       Built: 2020
    Monthly Fee: $350
       Tax: $11,564 (2024)
    Community: Lakeshore Preserve Ph 5
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,355 (change assumption)
    Mortgage ($5,041) + Fees ($350) + Taxes in 2024 ($964)


    Taxes:$11,564

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 9354 MEADOW HUNT WAY, WINTER GARDEN, FL 34787

    $525,00050 Days on yellowkey   MLS ID: O6400695

    For Sale O6400695 - 9354 MEADOW HUNT WAY, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2079
       Built: 2017
    Monthly Fee: $164
       Tax: $4,974 (2025)
    Community: Watermark
    Single Family


    Estimated Monthly Payment: $3,455 (change assumption)
    Mortgage ($2,877) + Fees ($164) + Taxes in 2025 ($415)


    Taxes:$4,974

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 12410 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787

    $639,99023 Days on yellowkey   MLS ID: O6409937

    For Sale O6409937 - 12410 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1860
       Built: 2022
    Monthly Fee: $225
       Tax: $7,966 (2025)
    Community: Encore At Ovation
    Single Family


    Estimated Monthly Payment: $4,396 (change assumption)
    Mortgage ($3,507) + Fees ($225) + Taxes in 2025 ($664)


    Taxes:$7,966

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 205 SURPRISE DR, WINTER GARDEN, FL 34787

    $1,200,000192 Days on yellowkey   MLS ID: O6365188

    For Sale O6365188 - 205 SURPRISE DR, WINTER GARDEN, FL 34787 32 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2171
       Built: 1950   Tax: $3,406 (2024)
    Community: Winter Garden Shores Rep
    Single Family


    Estimated Monthly Payment: $6,859 (change assumption)
    Mortgage ($6,575) + Taxes in 2024 ($284)


    Taxes:$3,406

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 630 GRASSY STONE DR, WINTER GARDEN, FL 34787

    $545,0009 Days on yellowkey   MLS ID: O6414101

    1 Days Off yellowkey (back on 6/7/2026)

    For Sale O6414101 - 630 GRASSY STONE DR, WINTER GARDEN, FL 34787 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2210
       Built: 2013
    Monthly Fee: $72
       Tax: $4,479 (2025)
    Community: Covington Chase Ph 2B
    Single Family


    Estimated Monthly Payment: $3,431 (change assumption)
    Mortgage ($2,986) + Fees ($72) + Taxes in 2025 ($373)


    Taxes:$4,479

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 6279 SUNNY TIME AVENUE, WINTER GARDEN, FL 34787

    $546,49016 Days on yellowkey   MLS ID: O6412141

    REDUCED by $15,500 (2.8%) on 06/06/2026

    For Sale O6412141 - 6279 SUNNY TIME AVENUE, WINTER GARDEN, FL 34787 28 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1913
       Built: 2026
    Monthly Fee: $152
       Tax: $1,372 (2024)
    Community: Silverleaf Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,261 (change assumption)
    Mortgage ($2,994) + Fees ($152) + Taxes in 2024 ($114)


    Taxes:$1,372

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 6408 FLAT LEMON DR, WINTER GARDEN, FL 34787

    $550,00068 Days on yellowkey   MLS ID: O6396757

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

    REDUCED by $20,000 (3.5%) on 04/21/2026

    For Sale O6396757 - 6408 FLAT LEMON DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1979
       Built: 2019
    Monthly Fee: $142
       Tax: $8,155 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $3,835 (change assumption)
    Mortgage ($3,014) + Fees ($142) + Taxes in 2025 ($680)


    Taxes:$8,155

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 8530 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $1,499,0009 Days on yellowkey   MLS ID: O6413249

    For Sale O6413249 - 8530 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4130
       Built: 2018
    Monthly Fee: $266
       Tax: $2,479 (2025)
    Community: Waterleigh Ph 1A
    Single Family


    Estimated Monthly Payment: $8,686 (change assumption)
    Mortgage ($8,213) + Fees ($266) + Taxes in 2025 ($207)


    Taxes:$2,479

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13360 SUNNY RETREAT LN, WINTER GARDEN, FL 34787

    $585,000138 Days on yellowkey   MLS ID: S5142297

    For Sale S5142297 - 13360 SUNNY RETREAT LN, WINTER GARDEN, FL 34787 62 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2000
       Built: 2022
    Monthly Fee: $642
       Tax: $7,519 (2024)
    Community: Del Webb Oasis
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,474 (change assumption)
    Mortgage ($3,205) + Fees ($642) + Taxes in 2024 ($627)


    Taxes:$7,519

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 342 WINDFORD CT, WINTER GARDEN, FL 34787

    $339,90032 Days on yellowkey   MLS ID: O6407632

    REDUCED by $10,000 (2.9%) on 06/06/2026

    For Sale O6407632 - 342 WINDFORD CT, WINTER GARDEN, FL 34787 17 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1194
       Built: 1996
    Monthly Fee: $40
       Tax: $4,266 (2025)
    Community: Park Ave Estates
    Single Family


    Estimated Monthly Payment: $2,258 (change assumption)
    Mortgage ($1,862) + Fees ($40) + Taxes in 2025 ($356)


    Taxes:$4,266

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15025 PIGEON PLUM LN, WINTER GARDEN, FL 34787

    $599,99033 Days on yellowkey   MLS ID: O6404948

    1 Days Off yellowkey (back on 5/16/2026)

    For Sale O6404948 - 15025 PIGEON PLUM LN, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2605
       Built: 2016
    Monthly Fee: $252
       Tax: $6,086 (2025)
    Community: Summerlake Pd Ph 2C
    Single Family


    Estimated Monthly Payment: $4,047 (change assumption)
    Mortgage ($3,288) + Fees ($252) + Taxes in 2025 ($507)


    Taxes:$6,086

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 3362 HANGING TIDE ST, WINTER GARDEN, FL 34787

    $929,00013 Days on yellowkey   MLS ID: O6412485

    For Sale O6412485 - 3362 HANGING TIDE ST, WINTER GARDEN, FL 34787 76 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4495
       Built: 2022
    Monthly Fee: $208
       Tax: $12,674 (2025)
    Community: Lakeview Preserve Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,354 (change assumption)
    Mortgage ($5,090) + Fees ($208) + Taxes in 2025 ($1,056)


    Taxes:$12,674

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 8016 SWEET ORANGE AVE, WINTER GARDEN, FL 34787

    $549,90023 Days on yellowkey   MLS ID: TB8511160

    For Sale TB8511160 - 8016 SWEET ORANGE AVE, WINTER GARDEN, FL 34787 24 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2084
       Built: 2018
    Monthly Fee: $55
       Tax: $7,636 (2025)
    Community: Summerlake Groves
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,704 (change assumption)
    Mortgage ($3,013) + Fees ($55) + Taxes in 2025 ($636)


    Taxes:$7,636

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 3367 HANGING TIDE ST, WINTER GARDEN, FL 34787

    $774,90030 Days on yellowkey   MLS ID: O6408299

    REDUCED by $25,000 (3.1%) on 06/03/2026

    For Sale O6408299 - 3367 HANGING TIDE ST, WINTER GARDEN, FL 34787 50 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4440
       Built: 2021
    Monthly Fee: $152
       Tax: $12,253 (2025)
    Community: Lakeview Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $5,419 (change assumption)
    Mortgage ($4,246) + Fees ($152) + Taxes in 2025 ($1,021)


    Taxes:$12,253

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13332 SUBURBAN TER, WINTER GARDEN, FL 34787

    $699,50044 Days on yellowkey   MLS ID: O6402778

    REDUCED by $15,400 (2.2%) on 05/29/2026

    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: $4,070 (change assumption)
    Mortgage ($3,833) + Taxes in 2024 ($237)


    Taxes:$2,841

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 9218 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787

    $920,000106 Days on yellowkey   MLS ID: O6386394

    REDUCED by $7,900 (0.9%) on 05/13/2026

    For Sale O6386394 - 9218 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787 64 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3087
       Built: 2018
    Monthly Fee: $164
       Tax: $11,801 (2025)
    Community: Watermark Ph 2B
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,188 (change assumption)
    Mortgage ($5,041) + Fees ($164) + Taxes in 2025 ($983)


    Taxes:$11,801

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 914 TROWMAN ALY, WINTER GARDEN, FL 34787

    $649,00019 Days on yellowkey   MLS ID: O6410871

    REDUCED by $26,000 (3.9%) on 06/02/2026

    For Sale O6410871 - 914 TROWMAN ALY, WINTER GARDEN, FL 34787 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1642
       Built: 2022
    Monthly Fee: $356
       Tax: $6,421 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $4,447 (change assumption)
    Mortgage ($3,556) + Fees ($356) + Taxes in 2025 ($535)


    Taxes:$6,421

    Elementary School: Tildenville Elem

    High School: West Orange High

    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.