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Winter Garden Single Family Homes For Sale - 697 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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  • 8807 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $780,00012 Days on yellowkey   MLS ID: O6419920

    For Sale O6419920 - 8807 SONOMA COAST DR, WINTER GARDEN, FL 34787 25 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2022
    Monthly Fee: $261
       Tax: $9,520 (2025)
    Community: Waterleigh Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,328 (change assumption)
    Mortgage ($4,274) + Fees ($261) + Taxes in 2025 ($793)


    Taxes:$9,520

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17167 WRITING ALY, WINTER GARDEN, FL 34787

    $535,00056 Days on yellowkey   MLS ID: O6406920

    For Sale O6406920 - 17167 WRITING ALY, WINTER GARDEN, FL 34787 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2486
       Built: 2020
    Monthly Fee: $110
       Tax: $7,916 (2025)
    Community: Storey Grove Ph 1B
    Single Family


    Estimated Monthly Payment: $3,701 (change assumption)
    Mortgage ($2,931) + Fees ($110) + Taxes in 2025 ($660)


    Taxes:$7,916

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14280 BRAEMAR ST, WINTER GARDEN, FL 34787

    $499,00076 Days on yellowkey   MLS ID: TB8500322

    REDUCED by $40,000 (7.4%) on 06/12/2026

    For Sale TB8500322 - 14280 BRAEMAR ST, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1964
       Built: 2023
    Monthly Fee: $100
       Tax: $7,928 (2025)
    Community: Highland Rdg
    Single Family


    Estimated Monthly Payment: $3,495 (change assumption)
    Mortgage ($2,734) + Fees ($100) + Taxes in 2025 ($661)


    Taxes:$7,928

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6323 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787

    $560,00027 Days on yellowkey   MLS ID: O6415343

    REDUCED by $10,000 (1.8%) on 06/19/2026

    For Sale O6415343 - 6323 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2177
       Built: 2018
    Monthly Fee: $425
       Tax: $8,526 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $4,204 (change assumption)
    Mortgage ($3,068) + Fees ($425) + Taxes in 2025 ($710)


    Taxes:$8,526

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12959 HARVEST RAIN AVE, WINTER GARDEN, FL 34787

    $750,00021 Days on yellowkey   MLS ID: O6417449

    1 Days Off yellowkey (back on 6/28/2026)

    For Sale O6417449 - 12959 HARVEST RAIN AVE, WINTER GARDEN, FL 34787 13 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2858
       Built: 2026
    Monthly Fee: $140

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,249 (change assumption)
    Mortgage ($4,109) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 2106 BLACK LAKE BLVD, WINTER GARDEN, FL 34787

    $980,00010 Days on yellowkey   MLS ID: TB8523029

    For Sale TB8523029 - 2106 BLACK LAKE BLVD, WINTER GARDEN, FL 34787 10 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4111
       Built: 2007
    Monthly Fee: $223
       Tax: $13,870 (2025)
    Community: Stoneybrook West D
    Single Family


    Estimated Monthly Payment: $6,749 (change assumption)
    Mortgage ($5,370) + Fees ($223) + Taxes in 2025 ($1,156)


    Taxes:$13,870

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3399 BUOY CIR, WINTER GARDEN, FL 34787

    $1,224,90013 Days on yellowkey   MLS ID: O6419829

    For Sale O6419829 - 3399 BUOY CIR, WINTER GARDEN, FL 34787 34 photos

    Bed: 6   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 5277
       Built: 2020
    Monthly Fee: $128
       Tax: $17,116 (2025)
    Community: Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $8,266 (change assumption)
    Mortgage ($6,712) + Fees ($128) + Taxes in 2025 ($1,426)


    Taxes:$17,116

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14542 BLACK CHERRY TRL, WINTER GARDEN, FL 34787

    $589,90042 Days on yellowkey   MLS ID: O6410574

    REDUCED by $10,100 (1.7%) on 06/16/2026

    For Sale O6410574 - 14542 BLACK CHERRY TRL, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2234
       Built: 2008
    Monthly Fee: $184
       Tax: $5,498 (2025)
    Community: Signature Lks-Pcl 01D Ph 01
    Single Family


    Estimated Monthly Payment: $3,874 (change assumption)
    Mortgage ($3,232) + Fees ($184) + Taxes in 2025 ($458)


    Taxes:$5,498

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9506 BOLERO RD, WINTER GARDEN, FL 34787

    $749,00013 Days on yellowkey   MLS ID: O6419794

    For Sale O6419794 - 9506 BOLERO RD, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2117
       Built: 2020
    Monthly Fee: $267
       Tax: $6,938 (2025)
    Community: Waterleigh Ph 3A
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,949 (change assumption)
    Mortgage ($4,104) + Fees ($267) + Taxes in 2025 ($578)


    Taxes:$6,938

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 13780 FRESH IVY ST, WINTER GARDEN, FL 34787

    $865,00062 Days on yellowkey   MLS ID: O6403387

    REDUCED by $30,000 (3.4%) on 06/06/2026

    For Sale O6403387 - 13780 FRESH IVY ST, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2862
       Built: 2025
    Monthly Fee: $642
       Tax: $2,578 (2025)
    Community: Del Webb Oasis Ph 3
    Single Family


    Estimated Monthly Payment: $5,596 (change assumption)
    Mortgage ($4,740) + Fees ($642) + Taxes in 2025 ($215)


    Taxes:$2,578

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14140 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787

    $996,97587 Days on yellowkey   MLS ID: O6397262

    REDUCED by $25 (0.0%) on 05/28/2026

    For Sale O6397262 - 14140 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787 72 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2346
       Built: 1984
    Monthly Fee: $71
       Tax: $10,303 (2025)
    Community: Country Lakes
    Single Family


    Estimated Monthly Payment: $6,392 (change assumption)
    Mortgage ($5,463) + Fees ($71) + Taxes in 2025 ($859)


    Taxes:$10,303

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17056 RED BIRD RD, WINTER GARDEN, FL 34787

    $795,00015 Days on yellowkey   MLS ID: G5113999

    0 Days Off yellowkey (back on 6/27/2026)

    For Sale G5113999 - 17056 RED BIRD RD, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1709
       Built: 1981   Tax: $1,474 (2025)
    Community: N/A
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,479 (change assumption)
    Mortgage ($4,356) + Taxes in 2025 ($123)


    Taxes:$1,474

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 4958 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787

    $540,00024 Days on yellowkey   MLS ID: S5151791

    For Sale S5151791 - 4958 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1788
       Built: 2023
    Monthly Fee: $166
       Tax: $7,028 (2025)
    Community: Silverleaf Reserve
    Single Family


    Estimated Monthly Payment: $3,710 (change assumption)
    Mortgage ($2,959) + Fees ($166) + Taxes in 2025 ($586)


    Taxes:$7,028

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: None


  • 9481 EMERALD BERRY DR, WINTER GARDEN, FL 34787

    $789,99026 Days on yellowkey   MLS ID: O6414779

    For Sale O6414779 - 9481 EMERALD BERRY DR, WINTER GARDEN, FL 34787 38 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2569
       Built: 2023
    Monthly Fee: $99
       Tax: $9,756 (2025)
    Community: Summerlake Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,241 (change assumption)
    Mortgage ($4,329) + Fees ($99) + Taxes in 2025 ($813)


    Taxes:$9,756

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14240 COLONIAL POINTE DR, WINTER GARDEN, FL 34787

    $1,250,00036 Days on yellowkey   MLS ID: O6412255

    REDUCED by $25,000 (2.0%) on 06/06/2026

    For Sale O6412255 - 14240 COLONIAL POINTE DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4816
       Built: 2018
    Monthly Fee: $209
       Tax: $10,516 (2025)
    Community: West Lake Hancock Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,934 (change assumption)
    Mortgage ($6,849) + Fees ($209) + Taxes in 2025 ($876)


    Taxes:$10,516

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16277 HONEY HARVEST ST, WINTER GARDEN, FL 34787

    $668,00039 Days on yellowkey   MLS ID: O6411737

    For Sale O6411737 - 16277 HONEY HARVEST ST, WINTER GARDEN, FL 34787 38 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2930
       Built: 2024
    Monthly Fee: $228
       Tax: $9,784 (2025)
    Community: Harvest/Ovation
    Single Family


    Estimated Monthly Payment: $4,704 (change assumption)
    Mortgage ($3,660) + Fees ($228) + Taxes in 2025 ($815)


    Taxes:$9,784

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 3286 MAINSAIL CT, WINTER GARDEN, FL 34787

    $889,00042 Days on yellowkey   MLS ID: O6411073

    For Sale O6411073 - 3286 MAINSAIL CT, WINTER GARDEN, FL 34787 65 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4293
       Built: 2023
    Monthly Fee: $208
       Tax: $12,028 (2024)
    Community: Ests/Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $6,081 (change assumption)
    Mortgage ($4,871) + Fees ($208) + Taxes in 2024 ($1,002)


    Taxes:$12,028

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2024

    Middle School: Windy Hill Middle


  • 7190 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787

    $535,00061 Days on yellowkey   MLS ID: O6402423

    REDUCED by $10,000 (1.8%) on 06/25/2026

    For Sale O6402423 - 7190 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787 28 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2016
    Monthly Fee: $253
       Tax: $5,148 (2025)
    Community: Lakeview Pointe/Horizon West P
    Single Family


    Estimated Monthly Payment: $3,613 (change assumption)
    Mortgage ($2,931) + Fees ($253) + Taxes in 2025 ($429)


    Taxes:$5,148

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14005 ALDFORD DR, WINTER GARDEN, FL 34787

    $639,00075 Days on yellowkey   MLS ID: O6401397

    REDUCED by $11,000 (1.7%) on 06/26/2026

    For Sale O6401397 - 14005 ALDFORD DR, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2334
       Built: 2017
    Monthly Fee: $115
       Tax: $9,241 (2025)
    Community: Latham Park North
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,386 (change assumption)
    Mortgage ($3,501) + Fees ($115) + Taxes in 2025 ($770)


    Taxes:$9,241

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 8216 TOPSAIL PL, WINTER GARDEN, FL 34787

    $949,900112 Days on yellowkey   MLS ID: O6391155

    REDUCED by $25,000 (2.6%) on 06/24/2026

    For Sale O6391155 - 8216 TOPSAIL PL, WINTER GARDEN, FL 34787 67 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3055
       Built: 2022
    Monthly Fee: $360
       Tax: $12,728 (2025)
    Community: Lakeshore Preserve Ph 5
    Single Family


    Estimated Monthly Payment: $6,625 (change assumption)
    Mortgage ($5,205) + Fees ($360) + Taxes in 2025 ($1,061)


    Taxes:$12,728

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    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.