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Winter Garden Homes For Sale & Real Estate - 940 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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  • 1906 SHERBOURNE ST, WINTER GARDEN, FL 34787

    $477,00035 Days on yellowkey   MLS ID: S5151079

    For Sale S5151079 - 1906 SHERBOURNE ST, WINTER GARDEN, FL 34787 25 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2029
       Built: 2002
    Monthly Fee: $46
       Tax: $2,815 (2025)
    Community: Stone Creek 44/131
    Single Family


    Estimated Monthly Payment: $2,894 (change assumption)
    Mortgage ($2,614) + Fees ($46) + Taxes in 2025 ($235)


    Taxes:$2,815

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15652 GENTLE RAIN DR, WINTER GARDEN, FL 34787

    $899,00033 Days on yellowkey   MLS ID: O6412120

    REDUCED by $25,999 (2.8%) on 07/01/2026

    For Sale O6412120 - 15652 GENTLE RAIN DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3657
       Built: 2024
    Monthly Fee: $99
       Tax: $12,004 (2025)
    Community: Osprey Ranch-Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,025 (change assumption)
    Mortgage ($4,926) + Fees ($99) + Taxes in 2025 ($1,000)


    Taxes:$12,004

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9611 LOST CREEK DR, WINTER GARDEN, FL 34787

    $765,000174 Days on yellowkey   MLS ID: O6373845

    REDUCED by $30,000 (3.8%) on 07/01/2026

    For Sale O6373845 - 9611 LOST CREEK DR, WINTER GARDEN, FL 34787 57 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2909
       Built: 2021
    Monthly Fee: $260
       Tax: $11,300 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $5,393 (change assumption)
    Mortgage ($4,192) + Fees ($260) + Taxes in 2025 ($942)


    Taxes:$11,300

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1152 PRADO LN, WINTER GARDEN, FL 34787

    $2,615,3207 Days on yellowkey   MLS ID: O6413825

    For Sale O6413825 - 1152 PRADO LN, WINTER GARDEN, FL 34787 13 photos

    Bed: 6   Bath: 6.5   Gar: 2
    Liv Area Sq Ft: 4658
       Built: 2026
    Monthly Fee: $150
       Tax: $399 (2025)
    Community: Grove/Oakland
    Single Family


    Estimated Monthly Payment: $14,513 (change assumption)
    Mortgage ($14,330) + Fees ($150) + Taxes in 2025 ($33)


    Taxes:$399

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15121 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787

    $824,90026 Days on yellowkey   MLS ID: O6416065

    4 Days Off yellowkey (back on 7/1/2026)

    REDUCED by $50,000 (5.7%) on 06/19/2026

    For Sale O6416065 - 15121 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787 43 photos

    Bed: 6   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4042
       Built: 2016
    Monthly Fee: $180
       Tax: $552 (2024)
    Community: Signature Lakes Ph 3B-4
    Single Family


    Estimated Monthly Payment: $4,746 (change assumption)
    Mortgage ($4,520) + Fees ($180) + Taxes in 2024 ($46)


    Taxes:$552

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 1343 CASTLEPORT RD, WINTER GARDEN, FL 34787

    $525,00026 Days on yellowkey   MLS ID: O6414756

    REDUCED by $10,000 (1.9%) on 07/01/2026

    For Sale O6414756 - 1343 CASTLEPORT RD, WINTER GARDEN, FL 34787 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2170
       Built: 2001
    Monthly Fee: $243
       Tax: $4,191 (2025)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,469 (change assumption)
    Mortgage ($2,877) + Fees ($243) + Taxes in 2025 ($349)


    Taxes:$4,191

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 1610 BEULAH RD, WINTER GARDEN, FL 34787

    $450,00019 Days on yellowkey   MLS ID: O6418153

    For Sale O6418153 - 1610 BEULAH RD, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2210
       Built: 1998
    Monthly Fee: $44
       Tax: $2,189 (2025)
    Community: Orange Cove
    Single Family


    Estimated Monthly Payment: $2,692 (change assumption)
    Mortgage ($2,466) + Fees ($44) + Taxes in 2025 ($182)


    Taxes:$2,189

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17372 GLOSSY POMELO WAY, WINTER GARDEN, FL 34787

    $1,749,89058 Days on yellowkey   MLS ID: O6406639

    REDUCED by $40,110 (2.2%) on 07/01/2026

    For Sale O6406639 - 17372 GLOSSY POMELO WAY, WINTER GARDEN, FL 34787 78 photos

    Bed: 5   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 4977
       Built: 2025
    Monthly Fee: $86

    Community: Lake Star/Ovation Ph 1B
    Single Family


    Estimated Monthly Payment: $9,674 (change assumption)
    Mortgage ($9,588) + Fees ($86) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 434 SAND LIME RD, WINTER GARDEN, FL 34787

    $249,90013 Days on yellowkey   MLS ID: O6416074

    For Sale O6416074 - 434 SAND LIME RD, WINTER GARDEN, FL 34787 22 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1302
       Built: 1984
    Monthly Fee: $63
       Tax: $401 (2025)
    Community: Village Grove Ph 01
    Townhouse


    Estimated Monthly Payment: $1,466 (change assumption)
    Mortgage ($1,369) + Fees ($63) + Taxes in 2025 ($33)


    Taxes:$401

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13822 JOMATT LOOP, WINTER GARDEN, FL 34787

    $975,00039 Days on yellowkey   MLS ID: O6411926

    0 Days Off yellowkey (back on 7/1/2026)

    REDUCED by $25,000 (2.5%) on 06/24/2026

    For Sale O6411926 - 13822 JOMATT LOOP, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3828
       Built: 2016
    Monthly Fee: $75
       Tax: $12,039 (2025)
    Community: Cypress Reserve Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,421 (change assumption)
    Mortgage ($5,342) + Fees ($75) + Taxes in 2025 ($1,003)


    Taxes:$12,039

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15672 SHOREBIRD LN, WINTER GARDEN, FL 34787

    $849,900165 Days on yellowkey   MLS ID: O6375411

    REDUCED by $10,000 (1.2%) on 06/29/2026

    For Sale O6375411 - 15672 SHOREBIRD LN, WINTER GARDEN, FL 34787 79 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2800
       Built: 2017
    Monthly Fee: $360
       Tax: $6,887 (2025)
    Community: Lakeshore Preserve
    Single Family


    Estimated Monthly Payment: $5,591 (change assumption)
    Mortgage ($4,657) + Fees ($360) + Taxes in 2025 ($574)


    Taxes:$6,887

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1144 HULL ISLAND DR, WINTER GARDEN, FL 34787

    $1,749,00012 Days on yellowkey   MLS ID: O6418306

    REDUCED by $50,000 (2.8%) on 07/01/2026

    For Sale O6418306 - 1144 HULL ISLAND DR, WINTER GARDEN, FL 34787 64 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4102
       Built: 2021
    Monthly Fee: $165
       Tax: $13,885 (2025)
    Community: Hull Island/Oakland
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,905 (change assumption)
    Mortgage ($9,583) + Fees ($165) + Taxes in 2025 ($1,157)


    Taxes:$13,885

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14501 GROVE RESORT AVE #3303, WINTER GARDEN, FL 34787

    $215,0007 Days on yellowkey   MLS ID: O6421329

    For Sale O6421329 - 14501 GROVE RESORT AVE #3303, WINTER GARDEN, FL 34787 30 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1265
       Built: 2018
    Monthly Fee: $904
       Tax: $6,178 (2025)
    Community: Grove Residence & Spa Hotel Condo 3
    Condo


    Estimated Monthly Payment: $2,597 (change assumption)
    Mortgage ($1,178) + Fees ($904) + Taxes in 2025 ($515)


    Taxes:$6,178

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12597 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787

    $475,00051 Days on yellowkey   MLS ID: O6407413

    REDUCED by $45,000 (8.7%) on 07/01/2026

    For Sale O6407413 - 12597 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2322
       Built: 2021
    Monthly Fee: $225
       Tax: $8,365 (2025)
    Community: Encore At Ovation
    Single Family


    Estimated Monthly Payment: $3,525 (change assumption)
    Mortgage ($2,603) + Fees ($225) + Taxes in 2025 ($697)


    Taxes:$8,365

    Elementary School: Water Spring Elementary

    High School: Lake Nona High

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14031 PICARD ALY, WINTER GARDEN, FL 34787

    $406,0007 Days on yellowkey   MLS ID: O6421215

    For Sale O6421215 - 14031 PICARD ALY, WINTER GARDEN, FL 34787 49 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1789
       Built: 2018
    Monthly Fee: $241
       Tax: $6,527 (2025)
    Community: Watermark
    Townhouse


    Estimated Monthly Payment: $3,010 (change assumption)
    Mortgage ($2,225) + Fees ($241) + Taxes in 2025 ($544)


    Taxes:$6,527

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15264 SHONAN GOLD DR, WINTER GARDEN, FL 34787

    $1,399,9997 Days on yellowkey   MLS ID: O6418870

    For Sale O6418870 - 15264 SHONAN GOLD DR, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4000
       Built: 2017
    Monthly Fee: $210
       Tax: $8,796 (2025)
    Community: Overlook 2/Hamlin Ph 2 & 5
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,614 (change assumption)
    Mortgage ($7,671) + Fees ($210) + Taxes in 2025 ($733)


    Taxes:$8,796

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 6207 SUNNY TIME AVENUE, WINTER GARDEN, FL 34787

    $547,1907 Days on yellowkey   MLS ID: O6421162

    For Sale O6421162 - 6207 SUNNY TIME AVENUE, WINTER GARDEN, FL 34787 23 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1628
       Built: 2026
    Monthly Fee: $286
       Tax: $1,373 (2024)
    Community: Silverleaf Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,399 (change assumption)
    Mortgage ($2,998) + Fees ($286) + Taxes in 2024 ($114)


    Taxes:$1,373

    Elementary School: Vista Lakes Elem

    High School: Colonial High

    Tax Year: 2024

    Middle School: Odyssey Middle


  • 13617 SALAMANDER ST, WINTER GARDEN, FL 34787

    $530,000110 Days on yellowkey   MLS ID: O6391534

    REDUCED by $19,900 (3.6%) on 05/03/2026

    For Sale O6391534 - 13617 SALAMANDER ST, WINTER GARDEN, FL 34787 59 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2022
    Monthly Fee: $291
       Tax: $7,653 (2025)
    Community: Waterleigh Ph 4A
    Single Family


    Estimated Monthly Payment: $3,833 (change assumption)
    Mortgage ($2,904) + Fees ($291) + Taxes in 2025 ($638)


    Taxes:$7,653

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 4620 GLIDING WAVE ST, WINTER GARDEN, FL 34787

    $539,000165 Days on yellowkey   MLS ID: O6370772

    REDUCED by $36,000 (6.3%) on 06/18/2026

    For Sale O6370772 - 4620 GLIDING WAVE ST, WINTER GARDEN, FL 34787 86 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2184
       Built: 2021
    Monthly Fee: $136
       Tax: $8,224 (2025)
    Community: Lakeview Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $3,775 (change assumption)
    Mortgage ($2,953) + Fees ($136) + Taxes in 2025 ($685)


    Taxes:$8,224

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 14536 GOLDEN HARBOR LN, WINTER GARDEN, FL 34787

    $450,000369 Days on yellowkey   MLS ID: O6320739

    SHORT SALE O6320739 - 14536 GOLDEN HARBOR LN, WINTER GARDEN, FL 34787 23 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1904
       Built: 2016
    Monthly Fee: $159
       Tax: $7,554 (2024)
    Community: Watermark Ph 2C
    Single Family


    Estimated Monthly Payment: $3,254 (change assumption)
    Mortgage ($2,466) + Fees ($159) + Taxes in 2024 ($630)


    Taxes:$7,554

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin 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.