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Winter Garden Single Family Homes For Sale - 711 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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  • 483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787

    $339,000107 Days on yellowkey   MLS ID: O6398208

    REDUCED by $900 (0.3%) on 07/27/2026

    For Sale O6398208 - 483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1008
       Built: 1988   Tax: $2,702 (2025)
    Community: East Garden Manor Add 03
    Single Family


    Estimated Monthly Payment: $2,083 (change assumption)
    Mortgage ($1,857) + Taxes in 2025 ($225)


    Taxes:$2,702

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 9572 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787

    $859,9009 Days on yellowkey   MLS ID: O6426624

    For Sale O6426624 - 9572 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787 45 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2018
    Monthly Fee: $245
       Tax: $9,486 (2025)
    Community: Waterleigh Ph 2B
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,747 (change assumption)
    Mortgage ($4,712) + Fees ($245) + Taxes in 2025 ($790)


    Taxes:$9,486

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 8275 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $535,000111 Days on yellowkey   MLS ID: TB8496196

    REDUCED by $20,000 (3.6%) on 07/27/2026

    For Sale TB8496196 - 8275 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 96 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2019
       Built: 2017
    Monthly Fee: $312
       Tax: $5,109 (2025)
    Community: Waterleigh Ph 1B
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,669 (change assumption)
    Mortgage ($2,931) + Fees ($312) + Taxes in 2025 ($426)


    Taxes:$5,109

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14543 WHITTRIDGE DR, WINTER GARDEN, FL 34787

    $574,90023 Days on yellowkey   MLS ID: G5114561

    For Sale G5114561 - 14543 WHITTRIDGE DR, WINTER GARDEN, FL 34787 37 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2224
       Built: 2006
    Monthly Fee: $195
       Tax: $8,699 (2025)
    Community: Independence
    Single Family


    Estimated Monthly Payment: $4,070 (change assumption)
    Mortgage ($3,150) + Fees ($195) + Taxes in 2025 ($725)


    Taxes:$8,699

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 9218 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787

    $890,000152 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


  • 1808 WESTERN TRAILWAY DR, WINTER GARDEN, FL 34787

    $589,00023 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

    $929,000103 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

    $1,495,00052 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

    $679,00088 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


  • 4642 PRAIRIE CREEK ST, WINTER GARDEN, FL 34787

    $565,000150 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

    $805,00052 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

    $599,99021 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


  • 16461 OLIVE HILL DR, WINTER GARDEN, FL 34787

    $564,900178 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

    $640,00044 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

    $520,00084 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


  • 16707 SANCTUARY DR, WINTER GARDEN, FL 34787

    $707,00035 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


  • 3447 CURRENT, WINTER GARDEN, FL 34787

    $725,00038 Days on yellowkey   MLS ID: O6417823

    For Sale O6417823 - 3447 CURRENT, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2741
       Built: 2020
    Monthly Fee: $152
       Tax: $5,616 (2025)
    Community: Lakeview Preserve
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,593 (change assumption)
    Mortgage ($3,973) + Fees ($152) + Taxes in 2025 ($468)


    Taxes:$5,616

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14257 LAGOON COVE LN, WINTER GARDEN, FL 34787

    $499,000191 Days on yellowkey   MLS ID: O6375296

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

    REDUCED by $11,000 (2.2%) on 07/23/2026

    For Sale O6375296 - 14257 LAGOON COVE LN, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2365
       Built: 2007
    Monthly Fee: $123
       Tax: $8,178 (2025)
    Community: Black Lake Park Ph 02
    Single Family


    Estimated Monthly Payment: $3,539 (change assumption)
    Mortgage ($2,734) + Fees ($123) + Taxes in 2025 ($682)


    Taxes:$8,178

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13092 SUNRISE HARVEST DR, WINTER GARDEN, FL 34787

    $850,00042 Days on yellowkey   MLS ID: O6417386

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

    For Sale O6417386 - 13092 SUNRISE HARVEST DR, WINTER GARDEN, FL 34787 44 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2993
       Built: 2024
    Monthly Fee: $140
       Tax: $9,934 (2025)
    Community: Harvest/Ovation
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,625 (change assumption)
    Mortgage ($4,657) + Fees ($140) + Taxes in 2025 ($828)


    Taxes:$9,934

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $1,225,000122 Days on yellowkey   MLS ID: O6394059

    REDUCED by $34,000 (2.7%) on 06/17/2026

    For Sale O6394059 - 706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 65 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 4019
       Built: 2018
    Monthly Fee: $298
       Tax: $17,895 (2025)
    Community: Canopy Oaks Ph 1
    Single Family


    Estimated Monthly Payment: $8,501 (change assumption)
    Mortgage ($6,712) + Fees ($298) + Taxes in 2025 ($1,491)


    Taxes:$17,895

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge 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.