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Winter Garden Homes For Sale & Real Estate - 915 homes

Winter Garden homes for sale are located in Orange County, Florida. Find homes in Winter Garden for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Garden houses.

Location: Winter Garden

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  • 2227 OAKINGTON ST, WINTER GARDEN, FL 34787

    $489,9902 Days on yellowkey   MLS ID: O6414707

    For Sale O6414707 - 2227 OAKINGTON ST, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1867
       Built: 2002
    Monthly Fee: $240
       Tax: $5,321 (2025)
    Community: Stoneybrook West 47/78
    Single Family


    Estimated Monthly Payment: $3,368 (change assumption)
    Mortgage ($2,685) + Fees ($240) + Taxes in 2025 ($443)


    Taxes:$5,321

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 14903 DRIFTWATER DR, WINTER GARDEN, FL 34787

    $390,0001 Day on yellowkey   MLS ID: S5151359

    For Sale S5151359 - 14903 DRIFTWATER DR, WINTER GARDEN, FL 34787 59 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1745
       Built: 2015
    Monthly Fee: $402
       Tax: $6,152 (2025)
    Community: Signature Lakes Ph 3B-6
    Townhouse


    Estimated Monthly Payment: $3,052 (change assumption)
    Mortgage ($2,137) + Fees ($402) + Taxes in 2025 ($513)


    Taxes:$6,152

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12026 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $596,19035 Days on yellowkey   MLS ID: O6405058

    3 Days Off yellowkey (back on 5/27/2026)

    For Sale O6405058 - 12026 SHINE VIEW LN, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,622 (change assumption)
    Mortgage ($3,267) + Fees ($190) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14494 BREAKWATER WAY, WINTER GARDEN, FL 34787

    $679,000190 Days on yellowkey   MLS ID: S5139023

    INCREASED by $30,000 (4.6%) on 05/11/2026

    For Sale S5139023 - 14494 BREAKWATER WAY, WINTER GARDEN, FL 34787 52 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3638
       Built: 2016
    Monthly Fee: $140
       Tax: $9,261 (2024)
    Community: Black Lake Preserve
    Single Family


    Estimated Monthly Payment: $4,632 (change assumption)
    Mortgage ($3,720) + Fees ($140) + Taxes in 2024 ($772)


    Taxes:$9,261

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 10540 TRIBUTE DR, WINTER GARDEN, FL 34787

    $415,000262 Days on yellowkey   MLS ID: O6346155

    For Sale O6346155 - 10540 TRIBUTE DR, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1636
       Built: 2023
    Monthly Fee: $225
       Tax: $6,096 (2024)
    Community: Storey Grove Ph 4
    Townhouse


    Estimated Monthly Payment: $3,007 (change assumption)
    Mortgage ($2,274) + Fees ($225) + Taxes in 2024 ($508)


    Taxes:$6,096

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 17865 ADRIFT RD, WINTER GARDEN, FL 34787

    $599,000321 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


  • 15907 MARINA BAY DR, WINTER GARDEN, FL 34787

    $443,50058 Days on yellowkey   MLS ID: O6398406

    4 Days Off yellowkey (back on 6/9/2026)

    REDUCED by $6,500 (1.4%) on 05/06/2026

    For Sale O6398406 - 15907 MARINA BAY DR, WINTER GARDEN, FL 34787 58 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1818
       Built: 2020
    Monthly Fee: $286
       Tax: $7,110 (2025)
    Community: Hawksmoor-Ph 1
    Townhouse


    Estimated Monthly Payment: $3,309 (change assumption)
    Mortgage ($2,430) + Fees ($286) + Taxes in 2025 ($593)


    Taxes:$7,110

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13343 SUNNY RETREAT LN, WINTER GARDEN, FL 34787

    $849,000125 Days on yellowkey   MLS ID: O6379591

    REDUCED by $50,900 (5.7%) on 05/04/2026

    For Sale O6379591 - 13343 SUNNY RETREAT LN, WINTER GARDEN, FL 34787 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2214
       Built: 2023
    Monthly Fee: $544
       Tax: $10,256 (2024)
    Community: Del Webb Oasis
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,051 (change assumption)
    Mortgage ($4,652) + Fees ($544) + Taxes in 2024 ($855)


    Taxes:$10,256

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14501 GROVE RESORT AVE #3425, WINTER GARDEN, FL 34787

    $480,0001 Day on yellowkey   MLS ID: O6414956

    For Sale O6414956 - 14501 GROVE RESORT AVE #3425, WINTER GARDEN, FL 34787 21 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1265
       Built: 2018   Tax: $7,044 (2025)
    Community: Grova Residence & Spa Hotel Condo 3
    Condo


    Estimated Monthly Payment: $3,217 (change assumption)
    Mortgage ($2,630) + Taxes in 2025 ($587)


    Taxes:$7,044

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15025 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787

    $505,00018 Days on yellowkey   MLS ID: O6410108

    REDUCED by $5,000 (1.0%) on 06/08/2026

    For Sale O6410108 - 15025 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787 44 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2016
    Monthly Fee: $195
       Tax: $8,019 (2025)
    Community: Signature Lakes Ph 3B-4 3B-5 3B-
    Single Family


    Estimated Monthly Payment: $3,630 (change assumption)
    Mortgage ($2,767) + Fees ($195) + Taxes in 2025 ($668)


    Taxes:$8,019

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12730 GROVEHURST AVE, WINTER GARDEN, FL 34787

    $525,0007 Days on yellowkey   MLS ID: G5113229

    For Sale G5113229 - 12730 GROVEHURST AVE, WINTER GARDEN, FL 34787 27 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2529
       Built: 2005
    Monthly Fee: $111
       Tax: $2,408 (2025)
    Community: Grovehurst A-D
    Single Family


    Estimated Monthly Payment: $3,188 (change assumption)
    Mortgage ($2,877) + Fees ($111) + Taxes in 2025 ($201)


    Taxes:$2,408

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7222 SPIKERUSH LN, WINTER GARDEN, FL 34787

    $558,0002 Days on yellowkey   MLS ID: O6414660

    0 Days Off yellowkey (back on 6/8/2026)

    For Sale O6414660 - 7222 SPIKERUSH LN, WINTER GARDEN, FL 34787 37 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2224
       Built: 2006
    Monthly Fee: $195
       Tax: $8,356 (2025)
    Community: Signature Lakes Prcl 01C
    Single Family


    Estimated Monthly Payment: $3,949 (change assumption)
    Mortgage ($3,057) + Fees ($195) + Taxes in 2025 ($696)


    Taxes:$8,356

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5526 TINY RD, WINTER GARDEN, FL 34787

    $1,590,000306 Days on yellowkey   MLS ID: O6334009

    3 Days Off yellowkey (back on 6/8/2026)

    REDUCED by $85,000 (5.1%) on 06/01/2026

    For Sale O6334009 - 5526 TINY RD, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2474
       Built: 2007   Tax: $10,165 (2024)
    Community: None
    Single Family


    Estimated Monthly Payment: $9,559 (change assumption)
    Mortgage ($8,712) + Taxes in 2024 ($847)


    Taxes:$10,165

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15232 FIRELIGHT DR, WINTER GARDEN, FL 34787

    $829,00025 Days on yellowkey   MLS ID: O6408025

    For Sale O6408025 - 15232 FIRELIGHT DR, WINTER GARDEN, FL 34787 65 photos

    Bed: 7   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4612
       Built: 2010
    Monthly Fee: $167
       Tax: $5,873 (2025)
    Community: Belle Meade Ph 02 H
    Single Family


    Estimated Monthly Payment: $5,199 (change assumption)
    Mortgage ($4,542) + Fees ($167) + Taxes in 2025 ($489)


    Taxes:$5,873

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 5545 BOWMAN DR, WINTER GARDEN, FL 34787

    $480,00027 Days on yellowkey   MLS ID: O6407484

    REDUCED by $5,000 (1.0%) on 06/04/2026

    For Sale O6407484 - 5545 BOWMAN DR, WINTER GARDEN, FL 34787 29 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1998
       Built: 2016
    Monthly Fee: $339
       Tax: $7,894 (2025)
    Community: Overlook 2/Hamlin Ph 1 & 6
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,627 (change assumption)
    Mortgage ($2,630) + Fees ($339) + Taxes in 2025 ($658)


    Taxes:$7,894

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1015 WESTSIDE DR, WINTER GARDEN, FL 34787

    $224,00028 Days on yellowkey   MLS ID: O6407229

    For Sale O6407229 - 1015 WESTSIDE DR, WINTER GARDEN, FL 34787 23 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 938
       Built: 1986
    Monthly Fee: $61
       Tax: $360 (2025)
    Community: Westside Twnhms
    Spa: No

    Townhouse


    Estimated Monthly Payment: $1,318 (change assumption)
    Mortgage ($1,227) + Fees ($61) + Taxes in 2025 ($30)


    Taxes:$360

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1544 MISTFLOWER LN, WINTER GARDEN, FL 34787

    $469,9008 Days on yellowkey   MLS ID: O6407815

    0 Days Off yellowkey (back on 6/8/2026)

    For Sale O6407815 - 1544 MISTFLOWER LN, WINTER GARDEN, FL 34787 25 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2348
       Built: 2005
    Monthly Fee: $55
       Tax: $7,220 (2025)
    Community: Winter Garden Trls 01-3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,231 (change assumption)
    Mortgage ($2,575) + Fees ($55) + Taxes in 2025 ($602)


    Taxes:$7,220

    Elementary School: William Frangus Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 279 ZACHARY WADE ST, WINTER GARDEN, FL 34787

    $1,675,00026 Days on yellowkey   MLS ID: O6408014

    For Sale O6408014 - 279 ZACHARY WADE ST, WINTER GARDEN, FL 34787 78 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4473
       Built: 2003
    Monthly Fee: $67
       Tax: $8,609 (2025)
    Community: Lakeview Reserve
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,962 (change assumption)
    Mortgage ($9,178) + Fees ($67) + Taxes in 2025 ($717)


    Taxes:$8,609

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15026 SUMMER HARVEST ST, WINTER GARDEN, FL 34787

    $689,990132 Days on yellowkey   MLS ID: S5142710

    For Sale S5142710 - 15026 SUMMER HARVEST ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2908
       Built: 2024
    Monthly Fee: $202
       Tax: $9,669 (2025)
    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,788 (change assumption)
    Mortgage ($3,781) + Fees ($202) + Taxes in 2025 ($806)


    Taxes:$9,669

    Elementary School: Whispering Oak Elem

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 17406 HONEYBELL TANGELO CT, WINTER GARDEN, FL 34787

    $845,00045 Days on yellowkey   MLS ID: O6402286

    REDUCED by $2,000 (0.2%) on 05/09/2026

    For Sale O6402286 - 17406 HONEYBELL TANGELO CT, WINTER GARDEN, FL 34787 54 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3427
       Built: 2026
    Monthly Fee: $83

    Community: Northlake At Ovation
    Single Family


    Estimated Monthly Payment: $4,713 (change assumption)
    Mortgage ($4,630) + Fees ($83) + Taxes in 2025 ($0)


    Taxes:$0

    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 Homes for Sale and Other Real Estate?

Winter Garden home, townhome, condo, villa, and other listing sales 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 houses for sale in Winter Garden . You can use our website to view Multiple Listing Service (MLS) data on Winter Garden Real Estate. 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 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.