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Winter Garden Single Family Homes For Sale - 502 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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  • 15372 GILLIGAN CT, WINTER GARDEN, FL 34787

    $870,000121 Days on yellowkey   MLS ID: O6367059

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

    For Sale O6367059 - 15372 GILLIGAN CT, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2781
       Built: 2020
    Monthly Fee: $102
       Tax: $8,004 (2023)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $5,536 (change assumption)
    Mortgage ($4,767) + Fees ($102) + Taxes in 2023 ($667)


    Taxes:$8,004

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2023

    Middle School: Water Spring Middle


  • 16105 WATER SPRING BLVD, WINTER GARDEN, FL 34787

    $519,000191 Days on yellowkey   MLS ID: O6348822

    For Sale O6348822 - 16105 WATER SPRING BLVD, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2042
       Built: 2020
    Monthly Fee: $103
       Tax: $4,770 (2024)
    Community: Storey Grove
    Single Family


    Estimated Monthly Payment: $3,344 (change assumption)
    Mortgage ($2,844) + Fees ($103) + Taxes in 2024 ($397)


    Taxes:$4,770

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 1689 CRANLEIGH DR, WINTER GARDEN, FL 34787

    $888,80042 Days on yellowkey   MLS ID: O6387674

    For Sale O6387674 - 1689 CRANLEIGH DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2937
       Built: 2020
    Monthly Fee: $165
       Tax: $7,225 (2025)
    Community: Sanctuary / Twin Waters
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,637 (change assumption)
    Mortgage ($4,870) + Fees ($165) + Taxes in 2025 ($602)


    Taxes:$7,225

    Elementary School: None

    High School: West Orange High

    Tax Year: 2025

    Middle School: None


  • 5431 BOWMAN DR, WINTER GARDEN, FL 34787

    $635,00043 Days on yellowkey   MLS ID: O6386779

    3 Days Off yellowkey (back on 3/12/2026)

    For Sale O6386779 - 5431 BOWMAN DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2458
       Built: 2015
    Monthly Fee: $338
       Tax: $6,296 (2025)
    Community: Overlook 2 Hamlin
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,342 (change assumption)
    Mortgage ($3,479) + Fees ($338) + Taxes in 2025 ($525)


    Taxes:$6,296

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 15060 BRODIE LN, WINTER GARDEN, FL 34787

    $925,000390 Days on yellowkey   MLS ID: O6292102

    3 Days Off yellowkey (back on 2/23/2026)

    For Sale O6292102 - 15060 BRODIE LN, WINTER GARDEN, FL 34787 79 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3256
       Built: 2024
    Monthly Fee: $110
       Tax: $2,642 (2024)
    Community: Westhaven/Ovation
    Single Family


    Estimated Monthly Payment: $5,399 (change assumption)
    Mortgage ($5,068) + Fees ($110) + Taxes in 2024 ($220)


    Taxes:$2,642

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16098 MANGROVE RD, WINTER GARDEN, FL 34787

    $585,00090 Days on yellowkey   MLS ID: O6373125

    For Sale O6373125 - 16098 MANGROVE RD, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2472
       Built: 2021
    Monthly Fee: $257
       Tax: $5,612 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,930 (change assumption)
    Mortgage ($3,205) + Fees ($257) + Taxes in 2025 ($468)


    Taxes:$5,612

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15043 PIGEON PLUM LN, WINTER GARDEN, FL 34787

    $594,00066 Days on yellowkey   MLS ID: S5143009

    For Sale S5143009 - 15043 PIGEON PLUM LN, WINTER GARDEN, FL 34787 23 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2695
       Built: 2016
    Monthly Fee: $241
       Tax: $8,470 (2024)
    Community: Summerlake Pd Ph 2C 2D 2E
    Single Family


    Estimated Monthly Payment: $4,202 (change assumption)
    Mortgage ($3,255) + Fees ($241) + Taxes in 2024 ($706)


    Taxes:$8,470

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 173 DONNER DR, WINTER GARDEN, FL 34787

    $605,000193 Days on yellowkey   MLS ID: O6344303

    1 Days Off yellowkey (back on 3/12/2026)

    For Sale O6344303 - 173 DONNER DR, WINTER GARDEN, FL 34787 47 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3439
       Built: 2005
    Monthly Fee: $57
       Tax: $7,336 (2024)
    Community: Deerfield Place
    Single Family


    Estimated Monthly Payment: $3,983 (change assumption)
    Mortgage ($3,315) + Fees ($57) + Taxes in 2024 ($611)


    Taxes:$7,336

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 4918 WILDWOOD POINTE RD, WINTER GARDEN, FL 34787

    $680,000305 Days on yellowkey   MLS ID: S5129072

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

    For Sale S5129072 - 4918 WILDWOOD POINTE RD, WINTER GARDEN, FL 34787 33 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2868
       Built: 2015
    Monthly Fee: $172
       Tax: $10,554 (2024)
    Community: Orchard Hills Ph 2
    Single Family


    Estimated Monthly Payment: $4,777 (change assumption)
    Mortgage ($3,726) + Fees ($172) + Taxes in 2024 ($880)


    Taxes:$10,554

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 312 SILVERDALE AVE, WINTER GARDEN, FL 34787

    $559,9009 Days on yellowkey   MLS ID: O6396680

    For Sale O6396680 - 312 SILVERDALE AVE, WINTER GARDEN, FL 34787 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 2007
    Monthly Fee: $72
       Tax: $2,473 (2025)
    Community: Covington Park A B D E F G & J
    Single Family


    Estimated Monthly Payment: $3,346 (change assumption)
    Mortgage ($3,068) + Fees ($72) + Taxes in 2025 ($206)


    Taxes:$2,473

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 7266 DESERT MANDARIN ST, WINTER GARDEN, FL 34787

    $595,0009 Days on yellowkey   MLS ID: O6395920

    For Sale O6395920 - 7266 DESERT MANDARIN ST, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2365
       Built: 2018
    Monthly Fee: $110
       Tax: $9,154 (2025)
    Community: Highlands/Summerlake Grove Ph 2
    Single Family


    Estimated Monthly Payment: $4,133 (change assumption)
    Mortgage ($3,260) + Fees ($110) + Taxes in 2025 ($763)


    Taxes:$9,154

    Elementary School: Water Spring Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 14038 JOMATT LOOP, WINTER GARDEN, FL 34787

    $1,059,0009 Days on yellowkey   MLS ID: O6394977

    For Sale O6394977 - 14038 JOMATT LOOP, WINTER GARDEN, FL 34787 67 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4105
       Built: 2018
    Monthly Fee: $70
       Tax: $7,306 (2025)
    Community: Cypress Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,481 (change assumption)
    Mortgage ($5,803) + Fees ($70) + Taxes in 2025 ($609)


    Taxes:$7,306

    Elementary School: Sunrise Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 723 SUNBURST COVE LN, WINTER GARDEN, FL 34787

    $555,0009 Days on yellowkey   MLS ID: S5145002

    For Sale S5145002 - 723 SUNBURST COVE LN, WINTER GARDEN, FL 34787 77 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2189
       Built: 2000
    Monthly Fee: $44
       Tax: $4,217 (2025)
    Community: Orange Cove
    Single Family


    Estimated Monthly Payment: $3,436 (change assumption)
    Mortgage ($3,041) + Fees ($44) + Taxes in 2025 ($351)


    Taxes:$4,217

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787

    $819,00061 Days on yellowkey   MLS ID: O6380281

    REDUCED by $30,000 (3.5%) on 04/06/2026

    For Sale O6380281 - 2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787 58 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3747
       Built: 2000
    Monthly Fee: $90
       Tax: $10,152 (2025)
    Community: Wintermere Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,424 (change assumption)
    Mortgage ($4,488) + Fees ($90) + Taxes in 2025 ($846)


    Taxes:$10,152

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 8906 DODDINGTON WAY, WINTER GARDEN, FL 34787

    $550,00076 Days on yellowkey   MLS ID: O6377538

    For Sale O6377538 - 8906 DODDINGTON WAY, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2352
       Built: 2016
    Monthly Fee: $115
       Tax: $9,036 (2025)
    Community: Latham Park North
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,882 (change assumption)
    Mortgage ($3,014) + Fees ($115) + Taxes in 2025 ($753)


    Taxes:$9,036

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13147 SUBURBAN TER, WINTER GARDEN, FL 34787

    $245,00014 Days on yellowkey   MLS ID: G5110298

    For Sale G5110298 - 13147 SUBURBAN TER, WINTER GARDEN, FL 34787 41 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1479
       Built: 1971
    Monthly Fee: $15
       Tax: $4,142 (2025)
    Community: Suburban Shores
    Single Family


    Estimated Monthly Payment: $1,703 (change assumption)
    Mortgage ($1,342) + Fees ($15) + Taxes in 2025 ($345)


    Taxes:$4,142

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15707 SIGNATURE DR., WINTER GARDEN, FL 34787

    $575,000378 Days on yellowkey   MLS ID: O6295079

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

    For Sale O6295079 - 15707 SIGNATURE DR., WINTER GARDEN, FL 34787 28 photos

    Bed: 6   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2714
       Built: 2013
    Monthly Fee: $184
       Tax: $8,595 (2024)
    Community: Independence Community
    Single Family


    Estimated Monthly Payment: $4,051 (change assumption)
    Mortgage ($3,151) + Fees ($184) + Taxes in 2024 ($716)


    Taxes:$8,595

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 5374 LAKE VIRGINIA ST, WINTER GARDEN, FL 34787

    $571,90048 Days on yellowkey   MLS ID: O6385721

    REDUCED by $8,100 (1.4%) on 04/06/2026

    For Sale O6385721 - 5374 LAKE VIRGINIA ST, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2038
       Built: 2023
    Monthly Fee: $160
       Tax: $7,532 (2024)
    Community: Lakeside/Hamlin
    Single Family


    Estimated Monthly Payment: $3,921 (change assumption)
    Mortgage ($3,134) + Fees ($160) + Taxes in 2024 ($628)


    Taxes:$7,532

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 16933 OAKBORO ST, WINTER GARDEN, FL 34787

    $560,00024 Days on yellowkey   MLS ID: R4910916

    For Sale R4910916 - 16933 OAKBORO ST, WINTER GARDEN, FL 34787 32 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2014
       Built: 2020
    Monthly Fee: $257
       Tax: $3,651 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $3,630 (change assumption)
    Mortgage ($3,068) + Fees ($257) + Taxes in 2025 ($304)


    Taxes:$3,651

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17098 WATER SPRING BLVD, WINTER GARDEN, FL 34787

    $580,000156 Days on yellowkey   MLS ID: O6357599

    For Sale O6357599 - 17098 WATER SPRING BLVD, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2484
       Built: 2023
    Monthly Fee: $271
       Tax: $9,199 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,216 (change assumption)
    Mortgage ($3,178) + Fees ($271) + Taxes in 2024 ($767)


    Taxes:$9,199

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring 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.