REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search


Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Winter Garden - 581 properties found

Sort:
  • 15543 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787

    $645,900563 Days on yellowkey   MLS ID: O6250356

    2 Days Off yellowkey (back on 4/23/2026)

    REDUCED by $3,900 (0.6%) on 04/17/2026

    For Sale O6250356 - 15543 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3359
       Built: 2001
    Monthly Fee: $233
       Tax: $8,538 (2023)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,484 (change assumption)
    Mortgage ($3,539) + Fees ($233) + Taxes in 2023 ($712)


    Taxes:$8,538

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2023

    Middle School: SunRidge Middle


  • 328 BAYSIDE AVE, WINTER GARDEN, FL 34787

    $445,00017 Days on yellowkey   MLS ID: O6396654

    1 Days Off yellowkey (back on 4/23/2026)

    For Sale O6396654 - 328 BAYSIDE AVE, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1235
       Built: 1986
    Monthly Fee: $7
       Tax: $5,354 (2025)
    Community: Kings Bay
    Single Family


    Estimated Monthly Payment: $2,891 (change assumption)
    Mortgage ($2,438) + Fees ($7) + Taxes in 2025 ($446)


    Taxes:$5,354

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15327 GILLIGAN CT, WINTER GARDEN, FL 34787

    $664,80018 Days on yellowkey   MLS ID: O6398756

    2 Days Off yellowkey (back on 4/23/2026)

    For Sale O6398756 - 15327 GILLIGAN CT, WINTER GARDEN, FL 34787 63 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2506
       Built: 2021
    Monthly Fee: $103
       Tax: $7,266 (2025)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $4,351 (change assumption)
    Mortgage ($3,643) + Fees ($103) + Taxes in 2025 ($606)


    Taxes:$7,266

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 13386 PEACEFUL MELODY DR, WINTER GARDEN, FL 34787

    $799,99066 Days on yellowkey   MLS ID: S5144786

    5 Days Off yellowkey (back on 4/23/2026)

    For Sale S5144786 - 13386 PEACEFUL MELODY DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2856
       Built: 2026
    Monthly Fee: $125
       Tax: $500 (2025)
    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $4,550 (change assumption)
    Mortgage ($4,383) + Fees ($125) + Taxes in 2025 ($42)


    Taxes:$500

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 3439 BUOY CIR, WINTER GARDEN, FL 34787

    $734,99048 Days on yellowkey   MLS ID: O6386482

    REDUCED by $13,010 (1.7%) on 04/23/2026

    For Sale O6386482 - 3439 BUOY CIR, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 2920
       Built: 2019
    Monthly Fee: $152
       Tax: $7,013 (2025)
    Community: Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $4,764 (change assumption)
    Mortgage ($4,027) + Fees ($152) + Taxes in 2025 ($584)


    Taxes:$7,013

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 16467 OLIVE HILL DR, WINTER GARDEN, FL 34787

    $599,900600 Days on yellowkey   MLS ID: O6240446

    2 Days Off yellowkey (back on 6/27/2025)

    For Sale O6240446 - 16467 OLIVE HILL DR, WINTER GARDEN, FL 34787 67 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2355
       Built: 2019
    Monthly Fee: $115
       Tax: $7,249 (2023)
    Community: Hawksmoor Ph 1
    Single Family


    Estimated Monthly Payment: $4,006 (change assumption)
    Mortgage ($3,287) + Fees ($115) + Taxes in 2023 ($604)


    Taxes:$7,249

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 205 SURPRISE DR, WINTER GARDEN, FL 34787

    $1,200,000151 Days on yellowkey   MLS ID: O6365188

    1 Days Off yellowkey (back on 4/23/2026)

    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


  • 15408 LEBEAU LOOP, WINTER GARDEN, FL 34787

    $580,00075 Days on yellowkey   MLS ID: O6383534

    1 Days Off yellowkey (back on 4/23/2026)

    For Sale O6383534 - 15408 LEBEAU LOOP, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2415
       Built: 2022
    Monthly Fee: $101
       Tax: $7,566 (2024)
    Community: Winding Bay Ph 3
    Single Family


    Estimated Monthly Payment: $3,909 (change assumption)
    Mortgage ($3,178) + Fees ($101) + Taxes in 2024 ($630)


    Taxes:$7,566

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15306 LEBEAU LOOP, WINTER GARDEN, FL 34787

    $568,00073 Days on yellowkey   MLS ID: O6384014

    1 Days Off yellowkey (back on 4/23/2026)

    For Sale O6384014 - 15306 LEBEAU LOOP, WINTER GARDEN, FL 34787 52 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2482
       Built: 2021
    Monthly Fee: $101
       Tax: $6,339 (2024)
    Community: Winding Bay Ph 3
    Single Family


    Estimated Monthly Payment: $3,741 (change assumption)
    Mortgage ($3,112) + Fees ($101) + Taxes in 2024 ($528)


    Taxes:$6,339

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16856 HYPATIA ALY, WINTER GARDEN, FL 34787

    $459,99960 Days on yellowkey   MLS ID: O6387941

    0 Days Off yellowkey (back on 4/23/2026)

    For Sale O6387941 - 16856 HYPATIA ALY, WINTER GARDEN, FL 34787 74 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1705
       Built: 2019
    Monthly Fee: $250
       Tax: $6,769 (2024)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $3,335 (change assumption)
    Mortgage ($2,520) + Fees ($250) + Taxes in 2024 ($564)


    Taxes:$6,769

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 17865 ADRIFT RD, WINTER GARDEN, FL 34787

    $599,000285 Days on yellowkey   MLS ID: O6329586

    For Sale O6329586 - 17865 ADRIFT RD, WINTER GARDEN, FL 34787 26 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2484
       Built: 2023
    Monthly Fee: $277
       Tax: $9,155 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,322 (change assumption)
    Mortgage ($3,282) + Fees ($277) + Taxes in 2024 ($763)


    Taxes:$9,155

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16834 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $634,99012 Days on yellowkey   MLS ID: O6401373

    For Sale O6401373 - 16834 HOBE SOUND CT, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2494
       Built: 2026
    Monthly Fee: $190
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,835 (change assumption)
    Mortgage ($3,479) + Fees ($190) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13837 LANYARD WAY, WINTER GARDEN, FL 34787

    $490,00056 Days on yellowkey   MLS ID: O6388993

    REDUCED by $5,000 (1.0%) on 04/22/2026

    For Sale O6388993 - 13837 LANYARD WAY, WINTER GARDEN, FL 34787 38 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1994
       Built: 2023
    Monthly Fee: $225
       Tax: $7,647 (2024)
    Community: Encore/Ovation Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,547 (change assumption)
    Mortgage ($2,685) + Fees ($225) + Taxes in 2024 ($637)


    Taxes:$7,647

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 7343 TWILIGHT BAY DR, WINTER GARDEN, FL 34787

    $599,99920 Days on yellowkey   MLS ID: S5147747

    0 Days Off yellowkey (back on 4/22/2026)

    For Sale S5147747 - 7343 TWILIGHT BAY DR, WINTER GARDEN, FL 34787 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1975
       Built: 2017
    Monthly Fee: $249
       Tax: $5,164 (2025)
    Community: Lakeview Pointe/Horizon West P
    Single Family


    Estimated Monthly Payment: $3,967 (change assumption)
    Mortgage ($3,288) + Fees ($249) + Taxes in 2025 ($430)


    Taxes:$5,164

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15401 PORTER RD, WINTER GARDEN, FL 34787

    $558,000125 Days on yellowkey   MLS ID: S5140743

    For Sale S5140743 - 15401 PORTER RD, WINTER GARDEN, FL 34787 59 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2455
       Built: 2015
    Monthly Fee: $242
       Tax: $8,271 (2024)
    Community: Summerlake
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,989 (change assumption)
    Mortgage ($3,057) + Fees ($242) + Taxes in 2024 ($689)


    Taxes:$8,271

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 2621 SHIREHALL LN, WINTER GARDEN, FL 34787

    $475,00059 Days on yellowkey   MLS ID: O6386585

    REDUCED by $25,000 (5.0%) on 04/17/2026

    For Sale O6386585 - 2621 SHIREHALL LN, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1960
       Built: 2003
    Monthly Fee: $243
       Tax: $3,181 (2024)
    Community: Stoneybrook West Ut 04 48 48
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,111 (change assumption)
    Mortgage ($2,603) + Fees ($243) + Taxes in 2024 ($265)


    Taxes:$3,181

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 650 SETTING SUN DR, WINTER GARDEN, FL 34787

    $740,00047 Days on yellowkey   MLS ID: O6390644

    1 Days Off yellowkey (back on 4/22/2026)

    For Sale O6390644 - 650 SETTING SUN DR, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3605
       Built: 2006
    Monthly Fee: $123
       Tax: $9,067 (2025)
    Community: Black Lake Park Ph 01
    Single Family


    Estimated Monthly Payment: $4,933 (change assumption)
    Mortgage ($4,055) + Fees ($123) + Taxes in 2025 ($756)


    Taxes:$9,067

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 276 SUMMER PINE ST, WINTER GARDEN, FL 34787

    $875,00072 Days on yellowkey   MLS ID: O6384565

    REDUCED by $5,000 (0.6%) on 04/22/2026

    For Sale O6384565 - 276 SUMMER PINE ST, WINTER GARDEN, FL 34787 25 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3147
       Built: 2025
    Monthly Fee: $240
       Tax: $1,914 (2024)
    Community: Winter Grove
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,194 (change assumption)
    Mortgage ($4,794) + Fees ($240) + Taxes in 2024 ($160)


    Taxes:$1,914

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $609,61177 Days on yellowkey   MLS ID: G5108288

    0 Days Off yellowkey (back on 4/7/2026)

    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


  • 9008 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $824,950287 Days on yellowkey   MLS ID: O6328849

    For Sale O6328849 - 9008 SONOMA COAST DR, WINTER GARDEN, FL 34787 51 photos

    Bed: 3   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2348
       Built: 2022
    Monthly Fee: $258
       Tax: $10,553 (2024)
    Community: Waterleigh Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $5,658 (change assumption)
    Mortgage ($4,520) + Fees ($258) + Taxes in 2024 ($879)


    Taxes:$10,553

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle






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.