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Winter Garden Homes For Sale & Real Estate - 964 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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  • 15111 GROVESIDE RD, WINTER GARDEN, FL 34787

    $495,93521 Days on yellowkey   MLS ID: O6423268

    0 Days Off yellowkey (back on 7/27/2026)

    For Sale O6423268 - 15111 GROVESIDE RD, WINTER GARDEN, FL 34787 5 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2026
    Monthly Fee: $247
       Tax: $1,320 (2025)
    Community: Parkview At Hamlin
    Townhouse


    Estimated Monthly Payment: $3,074 (change assumption)
    Mortgage ($2,717) + Fees ($247) + Taxes in 2025 ($110)


    Taxes:$1,320

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9218 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787

    $890,000151 Days on yellowkey   MLS ID: O6386394

    REDUCED by $9,000 (1.0%) on 07/16/2026

    For Sale O6386394 - 9218 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787 64 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3087
       Built: 2018
    Monthly Fee: $164
       Tax: $11,801 (2025)
    Community: Watermark Ph 2B
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,024 (change assumption)
    Mortgage ($4,877) + Fees ($164) + Taxes in 2025 ($983)


    Taxes:$11,801

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 8113 RED STOPPER LN, WINTER GARDEN, FL 34787

    $434,900149 Days on yellowkey   MLS ID: O6386525

    REDUCED by $9,100 (2.0%) on 06/16/2026

    For Sale O6386525 - 8113 RED STOPPER LN, WINTER GARDEN, FL 34787 62 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1725
       Built: 2017
    Monthly Fee: $315
       Tax: $4,284 (2024)
    Community: Summerlake Pd Ph 2C 2D 2E
    Townhouse


    Estimated Monthly Payment: $3,055 (change assumption)
    Mortgage ($2,383) + Fees ($315) + Taxes in 2024 ($357)


    Taxes:$4,284

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 1808 WESTERN TRAILWAY DR, WINTER GARDEN, FL 34787

    $589,00022 Days on yellowkey   MLS ID: S5152973

    REDUCED by $10,000 (1.7%) on 07/27/2026

    For Sale S5152973 - 1808 WESTERN TRAILWAY DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1860
       Built: 2019
    Monthly Fee: $165
       Tax: $8,389 (2025)
    Community: Hull Island/Oakland
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,091 (change assumption)
    Mortgage ($3,227) + Fees ($165) + Taxes in 2025 ($699)


    Taxes:$8,389

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12928 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787

    $929,000102 Days on yellowkey   MLS ID: O6400451

    0 Days Off yellowkey (back on 7/27/2026)

    REDUCED by $103,000 (10.0%) on 06/15/2026

    For Sale O6400451 - 12928 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3626
       Built: 2026
    Monthly Fee: $80
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $5,364 (change assumption)
    Mortgage ($5,090) + Fees ($80) + Taxes in 2025 ($194)


    Taxes:$2,326

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787

    $1,495,00051 Days on yellowkey   MLS ID: O6414639

    For Sale O6414639 - 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787 69 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4882
       Built: 2016
    Monthly Fee: $168
       Tax: $11,216 (2025)
    Community: Waterside/Johns Lake Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,294 (change assumption)
    Mortgage ($8,192) + Fees ($168) + Taxes in 2025 ($935)


    Taxes:$11,216

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 8721 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $679,00087 Days on yellowkey   MLS ID: G5111855

    REDUCED by $16,000 (2.3%) on 06/08/2026

    For Sale G5111855 - 8721 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2842
       Built: 2015
    Monthly Fee: $342
       Tax: $8,082 (2025)
    Community: Waterleigh Ph 1A
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,736 (change assumption)
    Mortgage ($3,720) + Fees ($342) + Taxes in 2025 ($673)


    Taxes:$8,082

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1711 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787

    $1,046,00028 Days on yellowkey   MLS ID: G5114517

    For Sale G5114517 - 1711 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787 72 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3863
       Built: 2017
    Monthly Fee: $187
       Tax: $10,792 (2024)
    Community: Twinwaters
    Single Family


    Estimated Monthly Payment: $6,818 (change assumption)
    Mortgage ($5,731) + Fees ($187) + Taxes in 2024 ($899)


    Taxes:$10,792

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 4642 PRAIRIE CREEK ST, WINTER GARDEN, FL 34787

    $565,000149 Days on yellowkey   MLS ID: S5144794

    REDUCED by $10,000 (1.7%) on 07/15/2026

    For Sale S5144794 - 4642 PRAIRIE CREEK ST, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2149
       Built: 2021
    Monthly Fee: $281
       Tax: $6,500 (2024)
    Community: Enclave At Hamlin
    Single Family


    Estimated Monthly Payment: $3,918 (change assumption)
    Mortgage ($3,096) + Fees ($281) + Taxes in 2024 ($542)


    Taxes:$6,500

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 5024 PALMETTO PARK DR, WINTER GARDEN, FL 34787

    $805,00051 Days on yellowkey   MLS ID: O6414749

    REDUCED by $14,000 (1.7%) on 07/20/2026

    For Sale O6414749 - 5024 PALMETTO PARK DR, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3061
       Built: 2017
    Monthly Fee: $187
       Tax: $10,816 (2025)
    Community: Orchard Hills Ph 3
    Single Family


    Estimated Monthly Payment: $5,499 (change assumption)
    Mortgage ($4,411) + Fees ($187) + Taxes in 2025 ($901)


    Taxes:$10,816

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8180 SAYINGS DR, WINTER GARDEN, FL 34787

    $599,99020 Days on yellowkey   MLS ID: O6423210

    1 Days Off yellowkey (back on 7/27/2026)

    For Sale O6423210 - 8180 SAYINGS DR, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2718
       Built: 2023
    Monthly Fee: $221
       Tax: $9,031 (2025)
    Community: Storey Grove Ph 4
    Single Family


    Estimated Monthly Payment: $4,261 (change assumption)
    Mortgage ($3,288) + Fees ($221) + Taxes in 2025 ($753)


    Taxes:$9,031

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 5079 PALMETTO PARK DR, WINTER GARDEN, FL 34787

    $930,00019 Days on yellowkey   MLS ID: G5114492

    For Sale G5114492 - 5079 PALMETTO PARK DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3866
       Built: 2017
    Monthly Fee: $190
       Tax: $6,877 (2026)
    Community: Orchard Hills Ph 3
    Single Family


    Estimated Monthly Payment: $5,859 (change assumption)
    Mortgage ($5,096) + Fees ($190) + Taxes in 2026 ($573)


    Taxes:$6,877

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2026

    Middle School: Bridgewater Middle


  • 16461 OLIVE HILL DR, WINTER GARDEN, FL 34787

    $564,900177 Days on yellowkey   MLS ID: O6379181

    REDUCED by $5,000 (0.9%) on 07/27/2026

    For Sale O6379181 - 16461 OLIVE HILL DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2008
       Built: 2019
    Monthly Fee: $127
       Tax: $7,241 (2024)
    Community: Hawksmoor
    Single Family


    Estimated Monthly Payment: $3,826 (change assumption)
    Mortgage ($3,095) + Fees ($127) + Taxes in 2024 ($603)


    Taxes:$7,241

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 15587 MURCOTT BLOSSOM BLVD, WINTER GARDEN, FL 34787

    $640,00043 Days on yellowkey   MLS ID: O6415333

    0 Days Off yellowkey (back on 7/27/2026)

    REDUCED by $20,000 (3.0%) on 06/30/2026

    For Sale O6415333 - 15587 MURCOTT BLOSSOM BLVD, WINTER GARDEN, FL 34787 44 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2751
       Built: 2018
    Monthly Fee: $82
       Tax: $8,988 (2025)
    Community: Summerlake Groves
    Single Family


    Estimated Monthly Payment: $4,338 (change assumption)
    Mortgage ($3,507) + Fees ($82) + Taxes in 2025 ($749)


    Taxes:$8,988

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16754 OAKBORO ST, WINTER GARDEN, FL 34787

    $520,00083 Days on yellowkey   MLS ID: O6404652

    1 Days Off yellowkey (back on 7/27/2026)

    REDUCED by $9,000 (1.7%) on 07/19/2026

    For Sale O6404652 - 16754 OAKBORO ST, WINTER GARDEN, FL 34787 85 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2020
    Monthly Fee: $254
       Tax: $8,808 (2025)
    Community: Waterleigh Ph 3B 3C 3D
    Single Family


    Estimated Monthly Payment: $3,837 (change assumption)
    Mortgage ($2,849) + Fees ($254) + Taxes in 2025 ($734)


    Taxes:$8,808

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 2766 BOBCAT CHASE BLVD, WINTER GARDEN, FL 34787

    $520,0005 Days on yellowkey   MLS ID: O6427751

    For Sale O6427751 - 2766 BOBCAT CHASE BLVD, WINTER GARDEN, FL 34787 57 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1811
       Built: 2020
    Monthly Fee: $286
       Tax: $5,482 (2025)
    Community: Longleaf At Oakland
    Single Family


    Estimated Monthly Payment: $3,592 (change assumption)
    Mortgage ($2,849) + Fees ($286) + Taxes in 2025 ($457)


    Taxes:$5,482

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 16209 ADMIRALS COVE LN, WINTER GARDEN, FL 34787

    $409,990125 Days on yellowkey   MLS ID: S5145675

    REDUCED by $5,005 (1.2%) on 07/27/2026

    For Sale S5145675 - 16209 ADMIRALS COVE LN, WINTER GARDEN, FL 34787 51 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1568
       Built: 2020
    Monthly Fee: $275
       Tax: $6,070 (2025)
    Community: Waterleigh
    Townhouse


    Estimated Monthly Payment: $3,027 (change assumption)
    Mortgage ($2,246) + Fees ($275) + Taxes in 2025 ($506)


    Taxes:$6,070

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1815 AMERICUS MINOR DR, WINTER GARDEN, FL 34787

    $499,99014 Days on yellowkey   MLS ID: O6425157

    For Sale O6425157 - 1815 AMERICUS MINOR DR, WINTER GARDEN, FL 34787 9 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2199
       Built: 2002
    Monthly Fee: $44
       Tax: $6,178 (2025)
    Community: Fullers Crossing Ph 02 49 31
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,298 (change assumption)
    Mortgage ($2,740) + Fees ($44) + Taxes in 2025 ($515)


    Taxes:$6,178

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 16707 SANCTUARY DR, WINTER GARDEN, FL 34787

    $707,00034 Days on yellowkey   MLS ID: O6419784

    REDUCED by $5,000 (0.7%) on 07/27/2026

    For Sale O6419784 - 16707 SANCTUARY DR, WINTER GARDEN, FL 34787 22 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2516
       Built: 2020
    Monthly Fee: $165

    Community: Sanctuary/Twin Waters
    Single Family


    Estimated Monthly Payment: $4,039 (change assumption)
    Mortgage ($3,874) + Fees ($165) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 330 SOUTHERN PECAN CIR #205, WINTER GARDEN, FL 34787

    $289,00072 Days on yellowkey   MLS ID: S5150108

    REDUCED by $11,000 (3.7%) on 07/18/2026

    For Sale S5150108 - 330 SOUTHERN PECAN CIR #205, WINTER GARDEN, FL 34787 62 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1453
       Built: 2005   Tax: $3,719 (2025)
    Community: Southern Pines Condo
    Condo


    Estimated Monthly Payment: $1,893 (change assumption)
    Mortgage ($1,584) + Taxes in 2025 ($310)


    Taxes:$3,719

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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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.