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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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  • 7922 WINTER WREN ST, WINTER GARDEN, FL 34787

    $765,90034 Days on yellowkey   MLS ID: O6406681

    For Sale O6406681 - 7922 WINTER WREN ST, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3391
       Built: 2015
    Monthly Fee: $252
       Tax: $10,441 (2025)
    Community: Block Q Summerlake Pd Ph 1B
    Single Family


    Estimated Monthly Payment: $5,319 (change assumption)
    Mortgage ($4,197) + Fees ($252) + Taxes in 2025 ($870)


    Taxes:$10,441

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 6357 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787

    $730,184194 Days on yellowkey   MLS ID: G5105172

    0 Days Off yellowkey (back on 12/3/2025)

    For Sale G5105172 - 6357 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787 2 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,151 (change assumption)
    Mortgage ($4,001) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 5943 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $746,650270 Days on yellowkey   MLS ID: G5102277

    0 Days Off yellowkey (back on 3/17/2026)

    For Sale G5102277 - 5943 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 1 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: $4,241 (change assumption)
    Mortgage ($4,091) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 5217 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787

    $899,000202 Days on yellowkey   MLS ID: O6363382

    For Sale O6363382 - 5217 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787 28 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3144
       Built: 2023
    Monthly Fee: $168
       Tax: $11,569 (2024)
    Community: Silverleaf Reserve
    Single Family


    Estimated Monthly Payment: $6,058 (change assumption)
    Mortgage ($4,926) + Fees ($168) + Taxes in 2024 ($964)


    Taxes:$11,569

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 7104 TICKLEGRASS ST, WINTER GARDEN, FL 34787

    $1,100,000327 Days on yellowkey   MLS ID: O6329696

    REDUCED by $146,000 (11.7%) on 05/12/2026

    For Sale O6329696 - 7104 TICKLEGRASS ST, WINTER GARDEN, FL 34787 43 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3347
       Built: 2014
    Monthly Fee: $195
       Tax: $552 (2024)
    Community: Signature Lakes Parcel 1D
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,268 (change assumption)
    Mortgage ($6,027) + Fees ($195) + Taxes in 2024 ($46)


    Taxes:$552

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 441 COURTLEA OAKS BLVD, WINTER GARDEN, FL 34787

    $1,199,900102 Days on yellowkey   MLS ID: O6385964

    1 Days Off yellowkey (back on 5/9/2026)

    INCREASED by $80,900 (7.2%) on 04/02/2026

    For Sale O6385964 - 441 COURTLEA OAKS BLVD, WINTER GARDEN, FL 34787 63 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4001
       Built: 2000
    Monthly Fee: $83
       Tax: $5,551 (2024)
    Community: Courtlea Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,120 (change assumption)
    Mortgage ($6,575) + Fees ($83) + Taxes in 2024 ($463)


    Taxes:$5,551

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 6153 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $680,03037 Days on yellowkey   MLS ID: G5112171

    0 Days Off yellowkey (back on 5/9/2026)

    For Sale G5112171 - 6153 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 2 photos

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

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $3,876 (change assumption)
    Mortgage ($3,726) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15807 SWEET LEMON WAY, WINTER GARDEN, FL 34787

    $752,000212 Days on yellowkey   MLS ID: O6361039

    For Sale O6361039 - 15807 SWEET LEMON WAY, WINTER GARDEN, FL 34787 35 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2867
       Built: 2018
    Monthly Fee: $58
       Tax: $9,096 (2024)
    Community: Highlands/Summerlake Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $4,936 (change assumption)
    Mortgage ($4,120) + Fees ($58) + Taxes in 2024 ($758)


    Taxes:$9,096

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 17054 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $688,32495 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


  • 16031 PEBBLE BLUFF LOOP, WINTER GARDEN, FL 34787

    $560,00043 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


  • 906 ALLENDALE LN, WINTER GARDEN, FL 34787

    $1,765,000134 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


  • 14834 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787

    $525,00075 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


  • 11253 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $819,10641 Days on yellowkey   MLS ID: O6405126

    REDUCED by $175 (0.0%) on 05/11/2026

    For Sale O6405126 - 11253 HOLLOW BAY DR, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,853 (change assumption)
    Mortgage ($4,488) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1040 MAXEY DR, WINTER GARDEN, FL 34787

    $225,00086 Days on yellowkey   MLS ID: O6391395

    REDUCED by $25,000 (10.0%) on 05/10/2026

    For Sale O6391395 - 1040 MAXEY DR, WINTER GARDEN, FL 34787 22 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1184
       Built: 1968   Tax: $1,671 (2025)
    Community: Bay St Park
    Single Family


    Estimated Monthly Payment: $1,372 (change assumption)
    Mortgage ($1,233) + Taxes in 2025 ($139)


    Taxes:$1,671

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15200 LAKE CLAIRE OVERLOOK DR, WINTER GARDEN, FL 34787

    $1,325,00054 Days on yellowkey   MLS ID: O6401205

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

    For Sale O6401205 - 15200 LAKE CLAIRE OVERLOOK DR, WINTER GARDEN, FL 34787 70 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3904
       Built: 2016
    Monthly Fee: $235
       Tax: $8,218 (2025)
    Community: Hickory Hammock
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,180 (change assumption)
    Mortgage ($7,260) + Fees ($235) + Taxes in 2025 ($685)


    Taxes:$8,218

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1032 BURLAND CIR, WINTER GARDEN, FL 34787

    $529,99048 Days on yellowkey   MLS ID: O6401764

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

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

    For Sale O6401764 - 1032 BURLAND CIR, WINTER GARDEN, FL 34787 58 photos

    Bed: 5   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2487
       Built: 2005
    Monthly Fee: $64
       Tax: $6,728 (2025)
    Community: Fullers Xing Ph 03 A-G
    Single Family


    Estimated Monthly Payment: $3,529 (change assumption)
    Mortgage ($2,904) + Fees ($64) + Taxes in 2025 ($561)


    Taxes:$6,728

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17224 OLD COUNTRY LN, WINTER GARDEN, FL 34787

    $1,999,999110 Days on yellowkey   MLS ID: O6384075

    REDUCED by $200,001 (9.1%) on 04/16/2026

    For Sale O6384075 - 17224 OLD COUNTRY LN, WINTER GARDEN, FL 34787 41 photos

    Bed: 6   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3629
       Built: 1980   Tax: $9,822 (2024)
    Community: Lake Avalon Groves Rep
    Single Family


    Estimated Monthly Payment: $11,777 (change assumption)
    Mortgage ($10,959) + Taxes in 2024 ($819)


    Taxes:$9,822

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 12971 HARVEST RAIN AVE, WINTER GARDEN, FL 34787

    $787,562110 Days on yellowkey   MLS ID: O6385596

    REDUCED by $50,000 (6.0%) on 05/09/2026

    For Sale O6385596 - 12971 HARVEST RAIN AVE, WINTER GARDEN, FL 34787 53 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2858
       Built: 2026
    Monthly Fee: $140

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,455 (change assumption)
    Mortgage ($4,315) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15686 PANTHER LAKE DR, WINTER GARDEN, FL 34787

    $1,220,00094 Days on yellowkey   MLS ID: O6390015

    REDUCED by $80,000 (6.2%) on 05/08/2026

    For Sale O6390015 - 15686 PANTHER LAKE DR, WINTER GARDEN, FL 34787 38 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3094
       Built: 2019
    Monthly Fee: $456
       Tax: $11,351 (2025)
    Community: Lakeshore Preserve Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,087 (change assumption)
    Mortgage ($6,685) + Fees ($456) + Taxes in 2025 ($946)


    Taxes:$11,351

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787

    $765,00081 Days on yellowkey   MLS ID: O6393987

    REDUCED by $30,000 (3.8%) on 05/08/2026

    For Sale O6393987 - 15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787 20 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4307
       Built: 2014
    Monthly Fee: $114
       Tax: $5,670 (2025)
    Community: Reserve/Carriage Pointe Ph 1
    Single Family


    Estimated Monthly Payment: $4,778 (change assumption)
    Mortgage ($4,192) + Fees ($114) + Taxes in 2025 ($472)


    Taxes:$5,670

    Elementary School: Hamlin Elementary

    High School: West Orange High

    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.