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Winter Garden Single Family Homes For Sale - 444 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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  • 107 TRADITIONS DR, WINTER GARDEN, FL 34787

    $499,99519 Days on yellowkey   MLS ID: S5145650

    REDUCED by $24,980 (4.8%) on 04/01/2026

    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: $2,906 (change assumption)
    Mortgage ($2,740) + 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


  • 1710 E BAY ST, WINTER GARDEN, FL 34787

    $254,99533 Days on yellowkey   MLS ID: O6376343

    REDUCED by $19,400 (7.1%) on 04/05/2026

    For Sale O6376343 - 1710 E BAY ST, WINTER GARDEN, FL 34787 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 972
       Built: 1957   Tax: $958 (2025)
    Community: Joe Louis Park First Add
    Single Family


    Estimated Monthly Payment: $1,477 (change assumption)
    Mortgage ($1,397) + Taxes in 2025 ($80)


    Taxes:$958

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2439 BALFORN TOWER WAY, WINTER GARDEN, FL 34787

    $570,00037 Days on yellowkey   MLS ID: O6386373

    For Sale O6386373 - 2439 BALFORN TOWER WAY, WINTER GARDEN, FL 34787 82 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2508
       Built: 2008
    Monthly Fee: $243
       Tax: $3,490 (2025)
    Community: Stoneybrook West D
    Single Family


    Estimated Monthly Payment: $3,657 (change assumption)
    Mortgage ($3,123) + Fees ($243) + Taxes in 2025 ($291)


    Taxes:$3,490

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 5931 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $829,965199 Days on yellowkey   MLS ID: G5102265

    0 Days Off yellowkey (back on 9/18/2025)

    For Sale G5102265 - 5931 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2688
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,698 (change assumption)
    Mortgage ($4,548) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14255 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787

    $1,300,0001 Day on yellowkey   MLS ID: O6395612

    For Sale O6395612 - 14255 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787 73 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4625
       Built: 2003
    Monthly Fee: $141
       Tax: $12,364 (2025)
    Community: Bay Isle 48 17
    Single Family


    Estimated Monthly Payment: $8,294 (change assumption)
    Mortgage ($7,123) + Fees ($141) + Taxes in 2025 ($1,030)


    Taxes:$12,364

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 730 RIVER GRASS LN, WINTER GARDEN, FL 34787

    $649,90070 Days on yellowkey   MLS ID: G5107248

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

    For Sale G5107248 - 730 RIVER GRASS LN, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2647
       Built: 2014
    Monthly Fee: $72
       Tax: $3,572 (2024)
    Community: Covington Chase Ph 2C
    Single Family


    Estimated Monthly Payment: $3,931 (change assumption)
    Mortgage ($3,561) + Fees ($72) + Taxes in 2024 ($298)


    Taxes:$3,572

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787

    $573,00069 Days on yellowkey   MLS ID: NS1087076

    For Sale NS1087076 - 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787 27 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2474
       Built: 2024
    Monthly Fee: $291
       Tax: $2,273 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $3,620 (change assumption)
    Mortgage ($3,140) + Fees ($291) + Taxes in 2024 ($189)


    Taxes:$2,273

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16006 GILDEN WAY, WINTER GARDEN, FL 34787

    $1,150,0009 Days on yellowkey   MLS ID: O6392997

    For Sale O6392997 - 16006 GILDEN WAY, WINTER GARDEN, FL 34787 67 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: $7,604 (change assumption)
    Mortgage ($6,301) + 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


  • 11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $899,990111 Days on yellowkey   MLS ID: O6367437

    For Sale O6367437 - 11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3327
       Built: 2025
    Monthly Fee: $200
       Tax: $1,989 (2024)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $5,297 (change assumption)
    Mortgage ($4,931) + Fees ($200) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11858 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $539,990184 Days on yellowkey   MLS ID: O6349514

    For Sale O6349514 - 11858 SHINE VIEW LN, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,315 (change assumption)
    Mortgage ($2,959) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13846 FRESH IVY ST, WINTER GARDEN, FL 34787

    $649,900187 Days on yellowkey   MLS ID: O6346706

    For Sale O6346706 - 13846 FRESH IVY ST, WINTER GARDEN, FL 34787 51 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2108
       Built: 2024
    Monthly Fee: $534
       Tax: $2,180 (2024)
    Community: Del Webb Oasis Ph 3
    Single Family


    Estimated Monthly Payment: $4,277 (change assumption)
    Mortgage ($3,561) + Fees ($534) + Taxes in 2024 ($182)


    Taxes:$2,180

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 4918 WILDWOOD POINTE RD, WINTER GARDEN, FL 34787

    $680,000295 Days on yellowkey   MLS ID: S5129072

    For Sale S5129072 - 4918 WILDWOOD POINTE RD, WINTER GARDEN, FL 34787 33 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2868
       Built: 2015
    Monthly Fee: $172
       Tax: $10,554 (2024)
    Community: Orchard Hills Ph 2
    Single Family


    Estimated Monthly Payment: $4,777 (change assumption)
    Mortgage ($3,726) + Fees ($172) + Taxes in 2024 ($880)


    Taxes:$10,554

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 9354 LAKE HICKORY NUT DR, WINTER GARDEN, FL 34787

    $1,099,00037 Days on yellowkey   MLS ID: O6385808

    For Sale O6385808 - 9354 LAKE HICKORY NUT DR, WINTER GARDEN, FL 34787 47 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2278
       Built: 1983   Tax: $3,375 (2025)
    Community: Hickory Lake Estates
    Single Family


    Estimated Monthly Payment: $6,303 (change assumption)
    Mortgage ($6,022) + Taxes in 2025 ($281)


    Taxes:$3,375

    Elementary School: Panther Lake Elementary

    High School: None

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14834 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787

    $545,0004 Days on yellowkey   MLS ID: O6395079

    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: $3,557 (change assumption)
    Mortgage ($2,986) + 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


  • 17066 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $765,37719 Days on yellowkey   MLS ID: G5109739

    For Sale G5109739 - 17066 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3038
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,316 (change assumption)
    Mortgage ($4,194) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17060 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $819,39119 Days on yellowkey   MLS ID: G5109737

    For Sale G5109737 - 17060 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 7 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3117
       Built: 2026
    Monthly Fee: $140

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,630 (change assumption)
    Mortgage ($4,490) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17055 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $580,68224 Days on yellowkey   MLS ID: G5109480

    For Sale G5109480 - 17055 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,332 (change assumption)
    Mortgage ($3,182) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17054 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $688,32424 Days on yellowkey   MLS ID: G5109477

    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


  • 14326 MURCOTT BLOSSOM BLVD, WINTER GARDEN, FL 34787

    $511,50036 Days on yellowkey   MLS ID: O6386513

    For Sale O6386513 - 14326 MURCOTT BLOSSOM BLVD, WINTER GARDEN, FL 34787 56 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1936
       Built: 2018
    Monthly Fee: $249
       Tax: $4,788 (2024)
    Community: Lakeview Pointe/Horizon West P
    Single Family


    Estimated Monthly Payment: $3,451 (change assumption)
    Mortgage ($2,803) + Fees ($249) + Taxes in 2024 ($399)


    Taxes:$4,788

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $609,61148 Days on yellowkey   MLS ID: G5108288

    For Sale G5108288 - 17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2520
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,462 (change assumption)
    Mortgage ($3,340) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    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.