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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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  • 17054 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $688,32462 Days on yellowkey   MLS ID: G5109477

    0 Days Off yellowkey (back on 5/11/2026)

    For Sale G5109477 - 17054 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2235
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,922 (change assumption)
    Mortgage ($3,772) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 2609 SLAGROVE CT, WINTER GARDEN, FL 34787

    $539,000134 Days on yellowkey   MLS ID: O6369515

    REDUCED by $5,000 (0.9%) on 05/11/2026

    For Sale O6369515 - 2609 SLAGROVE CT, WINTER GARDEN, FL 34787 44 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2383
       Built: 2003
    Monthly Fee: $205
       Tax: $4,293 (2024)
    Community: Stoneybrook West Ut 04 Rep 49 121
    Single Family


    Estimated Monthly Payment: $3,516 (change assumption)
    Mortgage ($2,953) + Fees ($205) + Taxes in 2024 ($358)


    Taxes:$4,293

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787

    $750,00029 Days on yellowkey   MLS ID: O6398720

    For Sale O6398720 - 2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3747
       Built: 2000
    Monthly Fee: $90
       Tax: $10,152 (2025)
    Community: Wintermere Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,045 (change assumption)
    Mortgage ($4,109) + Fees ($90) + Taxes in 2025 ($846)


    Taxes:$10,152

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 9549 BOLERO RD, WINTER GARDEN, FL 34787

    $997,000253 Days on yellowkey   MLS ID: O6340193

    For Sale O6340193 - 9549 BOLERO RD, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3910
       Built: 2021
    Monthly Fee: $271
       Tax: $13,484 (2024)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $6,858 (change assumption)
    Mortgage ($5,463) + Fees ($271) + Taxes in 2024 ($1,124)


    Taxes:$13,484

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 10187 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787

    $679,0006 Days on yellowkey   MLS ID: O6404599

    REDUCED by $10,000 (1.5%) on 05/11/2026

    For Sale O6404599 - 10187 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787 83 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2020
    Monthly Fee: $250
       Tax: $9,595 (2025)
    Community: Waterleigh Ph 2C-2 & 2C-3
    Single Family


    Estimated Monthly Payment: $4,770 (change assumption)
    Mortgage ($3,720) + Fees ($250) + Taxes in 2025 ($800)


    Taxes:$9,595

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 3208 SAILING PIER AVE, WINTER GARDEN, FL 34787

    $1,049,90018 Days on yellowkey   MLS ID: O6402332

    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


  • 17005 ARROWHEAD BLVD, WINTER GARDEN, FL 34787

    $615,00022 Days on yellowkey   MLS ID: O6401039

    For Sale O6401039 - 17005 ARROWHEAD BLVD, WINTER GARDEN, FL 34787 53 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1655
       Built: 1983   Tax: $5,400 (2025)
    Community: Arrowhead Lakes
    Single Family


    Estimated Monthly Payment: $3,820 (change assumption)
    Mortgage ($3,370) + Taxes in 2025 ($450)


    Taxes:$5,400

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6221 ARGENT WOOD DR, WINTER GARDEN, FL 34787

    $930,00065 Days on yellowkey   MLS ID: O6388355

    REDUCED by $66,000 (6.6%) on 05/11/2026

    For Sale O6388355 - 6221 ARGENT WOOD DR, WINTER GARDEN, FL 34787 54 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3878
       Built: 2025
    Monthly Fee: $55
       Tax: $1,647 (2024)
    Community: Silverleaf Oaks
    Single Family


    Estimated Monthly Payment: $5,288 (change assumption)
    Mortgage ($5,096) + Fees ($55) + Taxes in 2024 ($137)


    Taxes:$1,647

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16031 PEBBLE BLUFF LOOP, WINTER GARDEN, FL 34787

    $560,00010 Days on yellowkey   MLS ID: O6404448

    For Sale O6404448 - 16031 PEBBLE BLUFF LOOP, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2487
       Built: 2018
    Monthly Fee: $257
       Tax: $9,371 (2025)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $4,106 (change assumption)
    Mortgage ($3,068) + Fees ($257) + Taxes in 2025 ($781)


    Taxes:$9,371

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15527 SWEET ORANGE AVE, WINTER GARDEN, FL 34787

    $685,00047 Days on yellowkey   MLS ID: O6394429

    REDUCED by $15,000 (2.1%) on 05/11/2026

    For Sale O6394429 - 15527 SWEET ORANGE AVE, WINTER GARDEN, FL 34787 38 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2383
       Built: 2017
    Monthly Fee: $118
       Tax: $5,959 (2025)
    Community: Highlands/Summerlake Grvs Ph 1
    Single Family


    Estimated Monthly Payment: $4,368 (change assumption)
    Mortgage ($3,753) + Fees ($118) + Taxes in 2025 ($497)


    Taxes:$5,959

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 906 ALLENDALE LN, WINTER GARDEN, FL 34787

    $1,765,000101 Days on yellowkey   MLS ID: G5107489

    REDUCED by $20,000 (1.1%) on 04/01/2026

    For Sale G5107489 - 906 ALLENDALE LN, WINTER GARDEN, FL 34787 67 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3784
       Built: 2023
    Monthly Fee: $203
       Tax: $17,228 (2024)
    Community: Oakland Park B-2
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,310 (change assumption)
    Mortgage ($9,671) + Fees ($203) + Taxes in 2024 ($1,436)


    Taxes:$17,228

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 9827 BEACH PORT DR, WINTER GARDEN, FL 34787

    $1,374,9906 Days on yellowkey   MLS ID: O6405480

    For Sale O6405480 - 9827 BEACH PORT DR, WINTER GARDEN, FL 34787 68 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3910
       Built: 2020
    Monthly Fee: $259
       Tax: $11,122 (2025)
    Community: Waterleigh Ph 2C-2 & 2C-3
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,720 (change assumption)
    Mortgage ($7,534) + Fees ($259) + Taxes in 2025 ($927)


    Taxes:$11,122

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 931 KYLEE ALY, WINTER GARDEN, FL 34787

    $799,9008 Days on yellowkey   MLS ID: O6404673

    REDUCED by $25,100 (3.0%) on 05/11/2026

    For Sale O6404673 - 931 KYLEE ALY, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2831
       Built: 2022
    Monthly Fee: $393
       Tax: $9,637 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $5,579 (change assumption)
    Mortgage ($4,383) + Fees ($393) + Taxes in 2025 ($803)


    Taxes:$9,637

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 4842 LIME RICKEY ALY, WINTER GARDEN, FL 34787

    $534,90090 Days on yellowkey   MLS ID: O6381954

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

    REDUCED by $4,600 (0.9%) on 04/30/2026

    For Sale O6381954 - 4842 LIME RICKEY ALY, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2114
       Built: 2023
    Monthly Fee: $148
       Tax: $8,002 (2024)
    Community: Silverleaf Reserve/Haml Ph 2A
    Single Family


    Estimated Monthly Payment: $3,746 (change assumption)
    Mortgage ($2,931) + Fees ($148) + Taxes in 2024 ($667)


    Taxes:$8,002

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16256 MISTY HILLS AVE, WINTER GARDEN, FL 34787

    $629,000133 Days on yellowkey   MLS ID: O6369818

    2 Days Off yellowkey (back on 5/11/2026)

    REDUCED by $19,000 (2.9%) on 05/08/2026

    For Sale O6369818 - 16256 MISTY HILLS AVE, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2240
       Built: 2020
    Monthly Fee: $115
       Tax: $9,333 (2024)
    Community: Wincey Grvs Ph 1
    Single Family


    Estimated Monthly Payment: $4,339 (change assumption)
    Mortgage ($3,446) + Fees ($115) + Taxes in 2024 ($778)


    Taxes:$9,333

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 14834 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787

    $525,00042 Days on yellowkey   MLS ID: O6395079

    0 Days Off yellowkey (back on 5/11/2026)

    REDUCED by $10,000 (1.9%) on 05/01/2026

    For Sale O6395079 - 14834 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787 56 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2049
       Built: 2014
    Monthly Fee: $252
       Tax: $3,824 (2025)
    Community: Summerlake Pd Ph 1B-A Rep
    Single Family


    Estimated Monthly Payment: $3,447 (change assumption)
    Mortgage ($2,877) + Fees ($252) + Taxes in 2025 ($319)


    Taxes:$3,824

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 897 LANDRUM DR, WINTER GARDEN, FL 34787

    $899,9006 Days on yellowkey   MLS ID: O6404632

    For Sale O6404632 - 897 LANDRUM DR, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3012
       Built: 2013
    Monthly Fee: $208
       Tax: $6,263 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $5,661 (change assumption)
    Mortgage ($4,931) + Fees ($208) + Taxes in 2025 ($522)


    Taxes:$6,263

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 16006 GILDEN WAY, WINTER GARDEN, FL 34787

    $1,084,99947 Days on yellowkey   MLS ID: O6392997

    REDUCED by $1 (0.0%) on 05/01/2026

    For Sale O6392997 - 16006 GILDEN WAY, WINTER GARDEN, FL 34787 68 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3617
       Built: 2023
    Monthly Fee: $225
       Tax: $12,929 (2025)
    Community: Encore At Ovation
    Single Family


    Estimated Monthly Payment: $7,247 (change assumption)
    Mortgage ($5,945) + Fees ($225) + Taxes in 2025 ($1,077)


    Taxes:$12,929

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17422 CHANNEL WAY, WINTER GARDEN, FL 34787

    $767,00078 Days on yellowkey   MLS ID: G5108709

    REDUCED by $7,000 (0.9%) on 05/11/2026

    For Sale G5108709 - 17422 CHANNEL WAY, WINTER GARDEN, FL 34787 44 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3261
       Built: 2019
    Monthly Fee: $215
       Tax: $9,958 (2025)
    Community: Waterside On Johns Lake
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,247 (change assumption)
    Mortgage ($4,203) + Fees ($215) + Taxes in 2025 ($830)


    Taxes:$9,958

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14280 BRAEMAR ST, WINTER GARDEN, FL 34787

    $559,90021 Days on yellowkey   MLS ID: TB8500322

    For Sale TB8500322 - 14280 BRAEMAR ST, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1964
       Built: 2023
    Monthly Fee: $100
       Tax: $7,928 (2025)
    Community: Highland Rdg
    Single Family


    Estimated Monthly Payment: $3,829 (change assumption)
    Mortgage ($3,068) + Fees ($100) + Taxes in 2025 ($661)


    Taxes:$7,928

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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.