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Winter Garden Homes For Sale & Real Estate - 965 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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  • 5973 CYPRESS HILL RD, WINTER GARDEN, FL 34787

    $719,90059 Days on yellowkey   MLS ID: O6412179

    REDUCED by $15,000 (2.0%) on 07/28/2026

    For Sale O6412179 - 5973 CYPRESS HILL RD, WINTER GARDEN, FL 34787 44 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3532
       Built: 2017
    Monthly Fee: $195
       Tax: $9,630 (2025)
    Community: Independnece
    Single Family


    Estimated Monthly Payment: $4,942 (change assumption)
    Mortgage ($3,945) + Fees ($195) + Taxes in 2025 ($803)


    Taxes:$9,630

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 33 TIMBERCREEK PINES CIR, WINTER GARDEN, FL 34787

    $525,00069 Days on yellowkey   MLS ID: O6408941

    REDUCED by $10,000 (1.9%) on 07/28/2026

    For Sale O6408941 - 33 TIMBERCREEK PINES CIR, WINTER GARDEN, FL 34787 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1600
       Built: 2004
    Monthly Fee: $46
       Tax: $7,326 (2025)
    Community: Timbercreek Pines A B C & D
    Single Family


    Estimated Monthly Payment: $3,533 (change assumption)
    Mortgage ($2,877) + Fees ($46) + Taxes in 2025 ($610)


    Taxes:$7,326

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15419 UGLIS ALY, WINTER GARDEN, FL 34787

    $539,90090 Days on yellowkey   MLS ID: O6403047

    REDUCED by $10,000 (1.8%) on 07/28/2026

    For Sale O6403047 - 15419 UGLIS ALY, WINTER GARDEN, FL 34787 43 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2270
       Built: 2018
    Monthly Fee: $60
       Tax: $8,121 (2025)
    Community: Highlands/Summerlake Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $3,695 (change assumption)
    Mortgage ($2,958) + Fees ($60) + Taxes in 2025 ($677)


    Taxes:$8,121

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15280 MARITIME PINE DR, WINTER GARDEN, FL 34787

    $988,539314 Days on yellowkey   MLS ID: G5102291

    For Sale G5102291 - 15280 MARITIME PINE DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3550
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $5,567 (change assumption)
    Mortgage ($5,417) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15160 TEA TREE DR, WINTER GARDEN, FL 34787

    $879,80646 Days on yellowkey   MLS ID: G5113740

    For Sale G5113740 - 15160 TEA TREE DR, WINTER GARDEN, FL 34787 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2740
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,971 (change assumption)
    Mortgage ($4,821) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 3407 CURRENT AVE, WINTER GARDEN, FL 34787

    $595,000103 Days on yellowkey   MLS ID: O6400102

    2 Days Off yellowkey (back on 7/28/2026)

    REDUCED by $29,000 (4.6%) on 07/22/2026

    For Sale O6400102 - 3407 CURRENT AVE, WINTER GARDEN, FL 34787 46 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3747
       Built: 2020
    Monthly Fee: $152
       Tax: $10,520 (2025)
    Community: Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $4,289 (change assumption)
    Mortgage ($3,260) + Fees ($152) + Taxes in 2025 ($877)


    Taxes:$10,520

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 13019 SERENE GLADE RD, WINTER GARDEN, FL 34787

    $549,99047 Days on yellowkey   MLS ID: G5113698

    REDUCED by $20,000 (3.5%) on 06/17/2026

    For Sale G5113698 - 13019 SERENE GLADE RD, WINTER GARDEN, FL 34787 61 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2078
       Built: 2026
    Monthly Fee: $121

    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $3,135 (change assumption)
    Mortgage ($3,014) + Fees ($121) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14014 SCARLET ASTER ALY, WINTER GARDEN, FL 34787

    $459,00026 Days on yellowkey   MLS ID: O6418814

    REDUCED by $10,000 (2.1%) on 07/28/2026

    For Sale O6418814 - 14014 SCARLET ASTER ALY, WINTER GARDEN, FL 34787 22 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1808
       Built: 2024
    Monthly Fee: $350
       Tax: $6,350 (2025)
    Community: Harvest/Ovation
    Spa: No

    Townhouse


    Estimated Monthly Payment: $3,394 (change assumption)
    Mortgage ($2,515) + Fees ($350) + Taxes in 2025 ($529)


    Taxes:$6,350

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 13295 PEACEFUL MELODY DR, WINTER GARDEN, FL 34787

    $439,99082 Days on yellowkey   MLS ID: G5112136

    For Sale G5112136 - 13295 PEACEFUL MELODY DR, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1715
       Built: 2026
    Monthly Fee: $216

    Community: Serenade At Ovation
    Townhouse


    Estimated Monthly Payment: $2,627 (change assumption)
    Mortgage ($2,411) + Fees ($216) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 12103 EASTMOOR DR, WINTER GARDEN, FL 34787

    $435,00069 Days on yellowkey   MLS ID: O6409071

    REDUCED by $5,000 (1.1%) on 07/28/2026

    For Sale O6409071 - 12103 EASTMOOR DR, WINTER GARDEN, FL 34787 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1604
       Built: 2024
    Monthly Fee: $225
       Tax: $6,795 (2025)
    Community: Encore/Ovation Ph 4B
    Single Family


    Estimated Monthly Payment: $3,175 (change assumption)
    Mortgage ($2,384) + Fees ($225) + Taxes in 2025 ($566)


    Taxes:$6,795

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1324 VIC KAY CT, WINTER GARDEN, FL 34787

    $1,390,0007 Days on yellowkey   MLS ID: O6427278

    For Sale O6427278 - 1324 VIC KAY CT, WINTER GARDEN, FL 34787 78 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3749
       Built: 1999   Tax: $4,286 (2025)
    Community: Hillcrest
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,973 (change assumption)
    Mortgage ($7,616) + Taxes in 2025 ($357)


    Taxes:$4,286

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16185 TALIESIN ST, WINTER GARDEN, FL 34787

    $649,99076 Days on yellowkey   MLS ID: O6407177

    REDUCED by $10,010 (1.5%) on 06/25/2026

    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: $4,192 (change assumption)
    Mortgage ($3,562) + 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


  • 914 TROWMAN ALY, WINTER GARDEN, FL 34787

    $625,00064 Days on yellowkey   MLS ID: O6410871

    REDUCED by $24,000 (3.7%) on 07/14/2026

    For Sale O6410871 - 914 TROWMAN ALY, WINTER GARDEN, FL 34787 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1642
       Built: 2022
    Monthly Fee: $356
       Tax: $6,421 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $4,316 (change assumption)
    Mortgage ($3,425) + Fees ($356) + Taxes in 2025 ($535)


    Taxes:$6,421

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 215 S HIGHLAND AVE, WINTER GARDEN, FL 34787

    $1,099,0007 Days on yellowkey   MLS ID: S5154193

    INCREASED by $1,097,901 (99900.0%) on 07/23/2026

    For Sale S5154193 - 215 S HIGHLAND AVE, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2700
       Built: 2020   Tax: $12,866 (2026)
    Community: Downtown Winter Garden
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,094 (change assumption)
    Mortgage ($6,022) + Taxes in 2026 ($1,072)


    Taxes:$12,866

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2026

    Middle School: Lakeview Middle


  • 1005 CHASE DR, WINTER GARDEN, FL 34787

    $599,99962 Days on yellowkey   MLS ID: O6411451

    5 Days Off yellowkey (back on 7/28/2026)

    REDUCED by $1 (0.0%) on 07/09/2026

    For Sale O6411451 - 1005 CHASE DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2319
       Built: 2005
    Monthly Fee: $68
       Tax: $7,087 (2025)
    Community: Island Pointe Sub
    Single Family


    Estimated Monthly Payment: $3,946 (change assumption)
    Mortgage ($3,288) + Fees ($68) + Taxes in 2025 ($591)


    Taxes:$7,087

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 7687 BOWERY DR, WINTER GARDEN, FL 34787

    $799,90051 Days on yellowkey   MLS ID: O6415123

    REDUCED by $90 (0.0%) on 07/28/2026

    For Sale O6415123 - 7687 BOWERY DR, WINTER GARDEN, FL 34787 40 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3179
       Built: 2020
    Monthly Fee: $134
       Tax: $9,576 (2025)
    Community: Ravenna Ph 1
    Single Family


    Estimated Monthly Payment: $5,315 (change assumption)
    Mortgage ($4,383) + Fees ($134) + Taxes in 2025 ($798)


    Taxes:$9,576

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14784 FIELD DAISY DR, WINTER GARDEN, FL 34787

    $635,69975 Days on yellowkey   MLS ID: O6408277

    REDUCED by $54,301 (7.9%) on 07/21/2026

    For Sale O6408277 - 14784 FIELD DAISY DR, WINTER GARDEN, FL 34787 45 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2841
       Built: 2026
    Monthly Fee: $229

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $3,712 (change assumption)
    Mortgage ($3,483) + Fees ($229) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14780 FIELD DAISY DR, WINTER GARDEN, FL 34787

    $653,118134 Days on yellowkey   MLS ID: O6391463

    INCREASED by $10,118 (1.6%) on 07/21/2026

    For Sale O6391463 - 14780 FIELD DAISY DR, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2441
       Built: 2026
    Monthly Fee: $229

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $3,808 (change assumption)
    Mortgage ($3,579) + Fees ($229) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15514 CAMPDEN ST, WINTER GARDEN, FL 34787

    $375,0006 Days on yellowkey   MLS ID: O6425709

    For Sale O6425709 - 15514 CAMPDEN ST, WINTER GARDEN, FL 34787 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1917
       Built: 2011
    Monthly Fee: $369
       Tax: $3,518 (2025)
    Community: Stoneybrook West I
    Townhouse


    Estimated Monthly Payment: $2,717 (change assumption)
    Mortgage ($2,055) + Fees ($369) + Taxes in 2025 ($293)


    Taxes:$3,518

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15183 BRIDGEWATER CROSSINGS BLVD, WINTER GARDEN, FL 34787

    $520,00037 Days on yellowkey   MLS ID: O6416462

    For Sale O6416462 - 15183 BRIDGEWATER CROSSINGS BLVD, WINTER GARDEN, FL 34787 47 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1998
       Built: 2017
    Monthly Fee: $195
       Tax: $6,636 (2025)
    Community: Signature Lakes Ph 3B-4, 3B-5 &
    Single Family


    Estimated Monthly Payment: $3,597 (change assumption)
    Mortgage ($2,849) + Fees ($195) + Taxes in 2025 ($553)


    Taxes:$6,636

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater 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.