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Winter Garden Homes For Sale & Real Estate - 761 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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  • 14680 BLACK CHERRY TRL, WINTER GARDEN, FL 34787

    $629,00027 Days on yellowkey   MLS ID: O6394614

    For Sale O6394614 - 14680 BLACK CHERRY TRL, WINTER GARDEN, FL 34787 42 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2233
       Built: 2006
    Monthly Fee: $186
       Tax: $8,692 (2025)
    Community: Signature Lakes Prcl 01C
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,357 (change assumption)
    Mortgage ($3,446) + Fees ($186) + Taxes in 2025 ($724)


    Taxes:$8,692

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15828 SHOREBIRD LN, WINTER GARDEN, FL 34787

    $900,00015 Days on yellowkey   MLS ID: O6398059

    1 Days Off yellowkey (back on 4/21/2026)

    For Sale O6398059 - 15828 SHOREBIRD LN, WINTER GARDEN, FL 34787 70 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3058
       Built: 2020
    Monthly Fee: $360
       Tax: $11,042 (2025)
    Community: Lakeshore Preserve Ph 5
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,212 (change assumption)
    Mortgage ($4,931) + Fees ($360) + Taxes in 2025 ($920)


    Taxes:$11,042

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 7104 TICKLEGRASS ST, WINTER GARDEN, FL 34787

    $1,246,000280 Days on yellowkey   MLS ID: O6329696

    For Sale O6329696 - 7104 TICKLEGRASS ST, WINTER GARDEN, FL 34787 43 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3347
       Built: 2014
    Monthly Fee: $195
       Tax: $552 (2024)
    Community: Signature Lakes Parcel 1D
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,068 (change assumption)
    Mortgage ($6,827) + Fees ($195) + Taxes in 2024 ($46)


    Taxes:$552

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 3467 BUOY CIR, WINTER GARDEN, FL 34787

    $629,000115 Days on yellowkey   MLS ID: G5106141

    For Sale G5106141 - 3467 BUOY CIR, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2610
       Built: 2020
    Monthly Fee: $152
       Tax: $5,995 (2025)
    Community: Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $4,098 (change assumption)
    Mortgage ($3,446) + Fees ($152) + Taxes in 2025 ($500)


    Taxes:$5,995

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16632 POINT ROCK DR, WINTER GARDEN, FL 34787

    $550,000121 Days on yellowkey   MLS ID: OM715702

    SHORT SALE OM715702 - 16632 POINT ROCK DR, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2292
       Built: 2023
    Monthly Fee: $281
       Tax: $8,546 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,007 (change assumption)
    Mortgage ($3,014) + Fees ($281) + Taxes in 2024 ($712)


    Taxes:$8,546

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 68 N PARK AVE, WINTER GARDEN, FL 34787

    $1,899,00012 Days on yellowkey   MLS ID: O6400066

    For Sale O6400066 - 68 N PARK AVE, WINTER GARDEN, FL 34787 61 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3555
       Built: 2021
    Monthly Fee: $325
       Tax: $15,594 (2025)
    Community: 30 North Park
    Townhouse


    Estimated Monthly Payment: $12,030 (change assumption)
    Mortgage ($10,405) + Fees ($325) + Taxes in 2025 ($1,300)


    Taxes:$15,594

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3518 TURNINGWIND LN, WINTER GARDEN, FL 34787

    $825,00014 Days on yellowkey   MLS ID: S5147067

    For Sale S5147067 - 3518 TURNINGWIND LN, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2744
       Built: 2003
    Monthly Fee: $115
       Tax: $10,313 (2025)
    Community: Windward Cay 48 125
    Single Family


    Estimated Monthly Payment: $5,495 (change assumption)
    Mortgage ($4,520) + Fees ($115) + Taxes in 2025 ($859)


    Taxes:$10,313

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 9940 BLACK BEAR LN, WINTER GARDEN, FL 34787

    $2,050,000348 Days on yellowkey   MLS ID: O6309917

    For Sale O6309917 - 9940 BLACK BEAR LN, WINTER GARDEN, FL 34787 8 photos

    Bed: 4   Bath: 4.5   Gar: 4
    Liv Area Sq Ft: 3110
       Built: 2025   Tax: $4,423 (2024)
    Community: Acreage & Unrec
    Single Family


    Estimated Monthly Payment: $11,601 (change assumption)
    Mortgage ($11,233) + Taxes in 2024 ($369)


    Taxes:$4,423

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 303 SOUTHERN P CIR #102, WINTER GARDEN, FL 34787

    $228,00069 Days on yellowkey   MLS ID: O6383580

    For Sale O6383580 - 303 SOUTHERN P CIR #102, WINTER GARDEN, FL 34787 20 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 838
       Built: 2005   Tax: $2,540 (2024)
    Community: Southern Pines Condo
    Condo


    Estimated Monthly Payment: $1,461 (change assumption)
    Mortgage ($1,249) + Taxes in 2024 ($212)


    Taxes:$2,540

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 12373 BRACCO ST #12373, WINTER GARDEN, FL 34787

    $500,000166 Days on yellowkey   MLS ID: O6360606

    2 Days Off yellowkey (back on 4/21/2026)

    For Sale O6360606 - 12373 BRACCO ST #12373, WINTER GARDEN, FL 34787 45 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2003
       Built: 2023
    Monthly Fee: $105
       Tax: $7,593 (2024)
    Community: Highland Ridge
    Single Family


    Estimated Monthly Payment: $3,477 (change assumption)
    Mortgage ($2,740) + Fees ($105) + Taxes in 2024 ($633)


    Taxes:$7,593

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 6408 FLAT LEMON DR, WINTER GARDEN, FL 34787

    $550,00022 Days on yellowkey   MLS ID: O6396757

    REDUCED by $20,000 (3.5%) on 04/21/2026

    For Sale O6396757 - 6408 FLAT LEMON DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1979
       Built: 2019
    Monthly Fee: $142
       Tax: $8,155 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $3,835 (change assumption)
    Mortgage ($3,014) + Fees ($142) + Taxes in 2025 ($680)


    Taxes:$8,155

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 87 WINDTREE LN #K, WINTER GARDEN, FL 34787

    $205,00061 Days on yellowkey   MLS ID: G5108773

    REDUCED by $15,000 (6.8%) on 04/21/2026

    For Sale G5108773 - 87 WINDTREE LN #K, WINTER GARDEN, FL 34787 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 918
       Built: 1984
    Monthly Fee: $300
       Tax: $587 (2024)
    Community: Windtree Gardens Condo Ph 03
    Condo


    Estimated Monthly Payment: $1,472 (change assumption)
    Mortgage ($1,123) + Fees ($300) + Taxes in 2024 ($49)


    Taxes:$587

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 14446 WHITTRIDGE DR, WINTER GARDEN, FL 34787

    $450,00063 Days on yellowkey   MLS ID: O6378698

    2 Days Off yellowkey (back on 4/21/2026)

    For Sale O6378698 - 14446 WHITTRIDGE DR, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1650
       Built: 2005
    Monthly Fee: $195
       Tax: $5,006 (2024)
    Community: Signature Lks-Pcl 01B
    Single Family


    Estimated Monthly Payment: $3,078 (change assumption)
    Mortgage ($2,466) + Fees ($195) + Taxes in 2024 ($417)


    Taxes:$5,006

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 15456 GILLIGAN CT, WINTER GARDEN, FL 34787

    $600,000272 Days on yellowkey   MLS ID: A4660262

    REDUCED by $20,000 (3.2%) on 04/21/2026

    For Sale A4660262 - 15456 GILLIGAN CT, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2571
       Built: 2020
    Monthly Fee: $102
       Tax: $8,702 (2024)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $4,115 (change assumption)
    Mortgage ($3,288) + Fees ($102) + Taxes in 2024 ($725)


    Taxes:$8,702

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15162 SPINNAKER COVE LN, WINTER GARDEN, FL 34787

    $823,90033 Days on yellowkey   MLS ID: O6393190

    REDUCED by $1,000 (0.1%) on 04/19/2026

    For Sale O6393190 - 15162 SPINNAKER COVE LN, WINTER GARDEN, FL 34787 82 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3902
       Built: 2005
    Monthly Fee: $243
       Tax: $7,653 (2025)
    Community: Stoneybrook West
    Single Family


    Estimated Monthly Payment: $5,395 (change assumption)
    Mortgage ($4,514) + Fees ($243) + Taxes in 2025 ($638)


    Taxes:$7,653

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 515 9TH ST, WINTER GARDEN, FL 34787

    $279,90071 Days on yellowkey   MLS ID: O6383185

    5 Days Off yellowkey (back on 4/21/2026)

    For Sale O6383185 - 515 9TH ST, WINTER GARDEN, FL 34787 32 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 770
       Built: 1951   Tax: $1,285 (2024)
    Community: Merchants Sub
    Single Family


    Estimated Monthly Payment: $1,641 (change assumption)
    Mortgage ($1,534) + Taxes in 2024 ($107)


    Taxes:$1,285

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1286 WINTER GREEN WAY, WINTER GARDEN, FL 34787

    $239,900165 Days on yellowkey   MLS ID: G5104510

    For Sale G5104510 - 1286 WINTER GREEN WAY, WINTER GARDEN, FL 34787 30 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1144
       Built: 1985
    Monthly Fee: $63
       Tax: $1,159 (2024)
    Community: Village Grove Ph 02
    Townhouse


    Estimated Monthly Payment: $1,474 (change assumption)
    Mortgage ($1,314) + Fees ($63) + Taxes in 2024 ($97)


    Taxes:$1,159

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5618 WATER ROSE RD, WINTER GARDEN, FL 34787

    $395,0009 Days on yellowkey   MLS ID: O6400788

    For Sale O6400788 - 5618 WATER ROSE RD, WINTER GARDEN, FL 34787 27 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1755
       Built: 2016
    Monthly Fee: $402
       Tax: $6,527 (2025)
    Community: Signature Lakes Ph 3B-6
    Townhouse


    Estimated Monthly Payment: $3,110 (change assumption)
    Mortgage ($2,164) + Fees ($402) + Taxes in 2025 ($544)


    Taxes:$6,527

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12529 DALLINGTON TER, WINTER GARDEN, FL 34787

    $884,9909 Days on yellowkey   MLS ID: O6400678

    For Sale O6400678 - 12529 DALLINGTON TER, WINTER GARDEN, FL 34787 66 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3519
       Built: 2006
    Monthly Fee: $130
       Tax: $6,735 (2025)
    Community: Foxcrest A-N & P
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,540 (change assumption)
    Mortgage ($4,849) + Fees ($130) + Taxes in 2025 ($561)


    Taxes:$6,735

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 13067 TOLLCROSS WAY, WINTER GARDEN, FL 34787

    $599,000107 Days on yellowkey   MLS ID: O6367311

    For Sale O6367311 - 13067 TOLLCROSS WAY, WINTER GARDEN, FL 34787 64 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1906
       Built: 2024
    Monthly Fee: $96
       Tax: $2,239 (2024)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $3,565 (change assumption)
    Mortgage ($3,282) + Fees ($96) + Taxes in 2024 ($187)


    Taxes:$2,239

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    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.