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Winter Garden Single Family Homes For Sale - 700 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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  • 16185 TALIESIN ST, WINTER GARDEN, FL 34787

    $660,00034 Days on yellowkey   MLS ID: O6407177

    For Sale O6407177 - 16185 TALIESIN ST, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2372
       Built: 2020
    Monthly Fee: $127
       Tax: $6,048 (2025)
    Community: Hawksmoor
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,247 (change assumption)
    Mortgage ($3,616) + Fees ($127) + Taxes in 2025 ($504)


    Taxes:$6,048

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 11864 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $599,990211 Days on yellowkey   MLS ID: O6361583

    REDUCED by $25,000 (4.0%) on 06/04/2026

    For Sale O6361583 - 11864 SHINE VIEW LN, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2489
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,643 (change assumption)
    Mortgage ($3,288) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1432 MARBLE CREST WAY, WINTER GARDEN, FL 34787

    $824,50065 Days on yellowkey   MLS ID: O6398054

    4 Days Off yellowkey (back on 6/2/2026)

    For Sale O6398054 - 1432 MARBLE CREST WAY, WINTER GARDEN, FL 34787 82 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3734
       Built: 2005
    Monthly Fee: $243
       Tax: $7,963 (2025)
    Community: Stoneybrook West 44/134
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,424 (change assumption)
    Mortgage ($4,518) + Fees ($243) + Taxes in 2025 ($664)


    Taxes:$7,963

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16834 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $599,99056 Days on yellowkey   MLS ID: O6401373

    REDUCED by $25,000 (4.0%) on 06/04/2026

    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: $3,643 (change assumption)
    Mortgage ($3,288) + Fees ($190) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13846 FRESH IVY ST, WINTER GARDEN, FL 34787

    $649,900260 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


  • 8018 BOWERY DR, WINTER GARDEN, FL 34787

    $699,900337 Days on yellowkey   MLS ID: O6325853

    For Sale O6325853 - 8018 BOWERY DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3075
       Built: 2017
    Monthly Fee: $208
       Tax: $5,724 (2024)
    Community: Lake Hancock Preserve
    Single Family


    Estimated Monthly Payment: $4,520 (change assumption)
    Mortgage ($3,835) + Fees ($208) + Taxes in 2024 ($477)


    Taxes:$5,724

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 6100 CYPRESS HILL RD, WINTER GARDEN, FL 34787

    $950,00016 Days on yellowkey   MLS ID: O6412033

    For Sale O6412033 - 6100 CYPRESS HILL RD, WINTER GARDEN, FL 34787 51 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3777
       Built: 2016
    Monthly Fee: $195
       Tax: $11,678 (2025)
    Community: Signature Lakes Ph 3B-4 3B-5 & 3
    Single Family


    Estimated Monthly Payment: $6,374 (change assumption)
    Mortgage ($5,205) + Fees ($195) + Taxes in 2025 ($973)


    Taxes:$11,678

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 2621 SHIREHALL LN, WINTER GARDEN, FL 34787

    $475,000103 Days on yellowkey   MLS ID: O6386585

    0 Days Off yellowkey (back on 5/14/2026)

    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


  • 869 BENDING OAK TRL, WINTER GARDEN, FL 34787

    $520,000219 Days on yellowkey   MLS ID: O6358341

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

    For Sale O6358341 - 869 BENDING OAK TRL, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1975
       Built: 2012
    Monthly Fee: $109
       Tax: $5,262 (2024)
    Community: Oaks/Brandy Lake 01 Rep A & B
    Single Family


    Estimated Monthly Payment: $3,397 (change assumption)
    Mortgage ($2,849) + Fees ($109) + Taxes in 2024 ($438)


    Taxes:$5,262

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16821 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $546,990187 Days on yellowkey   MLS ID: O6367156

    REDUCED by $8,000 (1.4%) on 06/04/2026

    For Sale O6367156 - 16821 HOBE SOUND CT, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,353 (change assumption)
    Mortgage ($2,997) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11223 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $809,990124 Days on yellowkey   MLS ID: O6382359

    1 Days Off yellowkey (back on 6/4/2026)

    REDUCED by $10,000 (1.2%) on 06/04/2026

    For Sale O6382359 - 11223 HOLLOW BAY DR, WINTER GARDEN, FL 34787 10 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2866
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,854 (change assumption)
    Mortgage ($4,438) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6122 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $774,54914 Days on yellowkey   MLS ID: G5113307

    0 Days Off yellowkey (back on 6/3/2026)

    For Sale G5113307 - 6122 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2026
    Monthly Fee: $150
       Tax: $298 (2025)
    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,419 (change assumption)
    Mortgage ($4,244) + Fees ($150) + Taxes in 2025 ($25)


    Taxes:$298

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 7531 SILVER VALLEY ST, WINTER GARDEN, FL 34787

    $552,27514 Days on yellowkey   MLS ID: G5113297

    0 Days Off yellowkey (back on 6/3/2026)

    For Sale G5113297 - 7531 SILVER VALLEY ST, 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: $3,176 (change assumption)
    Mortgage ($3,026) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17673 LAKE STAR RD, WINTER GARDEN, FL 34787

    $866,86514 Days on yellowkey   MLS ID: TB8515334

    For Sale TB8515334 - 17673 LAKE STAR RD, WINTER GARDEN, FL 34787 9 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2791
       Built: 2026
    Monthly Fee: $84
       Tax: $12,000 (2026)
    Community: Northlake At Ovation
    Single Family


    Estimated Monthly Payment: $5,834 (change assumption)
    Mortgage ($4,750) + Fees ($84) + Taxes in 2026 ($1,000)


    Taxes:$12,000

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 745 MARSH REED DR, WINTER GARDEN, FL 34787

    $635,00014 Days on yellowkey   MLS ID: TB8514854

    For Sale TB8514854 - 745 MARSH REED DR, WINTER GARDEN, FL 34787 7 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2596
       Built: 2015
    Monthly Fee: $132
       Tax: $8,274 (2025)
    Community: John Lake Pointe
    Single Family


    Estimated Monthly Payment: $4,301 (change assumption)
    Mortgage ($3,479) + Fees ($132) + Taxes in 2025 ($690)


    Taxes:$8,274

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16466 OLIVE HILL DR, WINTER GARDEN, FL 34787

    $660,00014 Days on yellowkey   MLS ID: O6409922

    For Sale O6409922 - 16466 OLIVE HILL DR, WINTER GARDEN, FL 34787 43 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2020
       Built: 2019
    Monthly Fee: $127
       Tax: $8,758 (2025)
    Community: Hawksmoor-Ph 1
    Single Family


    Estimated Monthly Payment: $4,473 (change assumption)
    Mortgage ($3,616) + Fees ($127) + Taxes in 2025 ($730)


    Taxes:$8,758

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 13837 LANYARD WAY, WINTER GARDEN, FL 34787

    $485,000100 Days on yellowkey   MLS ID: O6388993

    REDUCED by $5,000 (1.0%) on 06/03/2026

    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: $3,520 (change assumption)
    Mortgage ($2,657) + Fees ($225) + Taxes in 2024 ($637)


    Taxes:$7,647

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 12595 GOLD HONEYSUCKLE ST #284, WINTER GARDEN, FL 34787

    $844,99083 Days on yellowkey   MLS ID: O6393961

    0 Days Off yellowkey (back on 6/3/2026)

    REDUCED by $25,000 (2.9%) on 06/01/2026

    For Sale O6393961 - 12595 GOLD HONEYSUCKLE ST #284, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3338
       Built: 2026
    Monthly Fee: $96

    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $4,726 (change assumption)
    Mortgage ($4,630) + Fees ($96) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 14645 TULLAMORE LOOP, WINTER GARDEN, FL 34787

    $455,00021 Days on yellowkey   MLS ID: O6409068

    0 Days Off yellowkey (back on 6/2/2026)

    For Sale O6409068 - 14645 TULLAMORE LOOP, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1703
       Built: 2003
    Monthly Fee: $100
       Tax: $3,347 (2025)
    Community: Emerald Rdg H
    Single Family


    Estimated Monthly Payment: $2,872 (change assumption)
    Mortgage ($2,493) + Fees ($100) + Taxes in 2025 ($279)


    Taxes:$3,347

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13023 INKWELL ALY, WINTER GARDEN, FL 34787

    $515,00028 Days on yellowkey   MLS ID: O6409443

    0 Days Off yellowkey (back on 6/3/2026)

    For Sale O6409443 - 13023 INKWELL ALY, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2042
       Built: 2020
    Monthly Fee: $268
       Tax: $5,162 (2025)
    Community: Storey Grove
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,520 (change assumption)
    Mortgage ($2,822) + Fees ($268) + Taxes in 2025 ($430)


    Taxes:$5,162

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring 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.