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Winter Garden Homes For Sale & Real Estate - 740 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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  • 15324 GILLIGAN CT, WINTER GARDEN, FL 34787

    $950,00028 Days on yellowkey   MLS ID: O6393498

    0 Days Off yellowkey (back on 4/13/2026)

    For Sale O6393498 - 15324 GILLIGAN CT, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2794
       Built: 2020
    Monthly Fee: $102
       Tax: $641 (2025)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $5,361 (change assumption)
    Mortgage ($5,205) + Fees ($102) + Taxes in 2025 ($53)


    Taxes:$641

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15508 BLACKBEAD ST, WINTER GARDEN, FL 34787

    $430,000106 Days on yellowkey   MLS ID: O6371455

    For Sale O6371455 - 15508 BLACKBEAD ST, WINTER GARDEN, FL 34787 21 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1754
       Built: 2017
    Monthly Fee: $313
       Tax: $6,652 (2025)
    Community: Summerlake Pd Ph 2C-2E
    Townhouse


    Estimated Monthly Payment: $3,223 (change assumption)
    Mortgage ($2,356) + Fees ($313) + Taxes in 2025 ($554)


    Taxes:$6,652

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 10224 ATWATER BAY DR, WINTER GARDEN, FL 34787

    $799,00011 Days on yellowkey   MLS ID: S5147252

    For Sale S5147252 - 10224 ATWATER BAY DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3227
       Built: 2018
    Monthly Fee: $230
       Tax: $7,456 (2025)
    Community: Waterleigh Ph 2B
    Single Family


    Estimated Monthly Payment: $5,229 (change assumption)
    Mortgage ($4,378) + Fees ($230) + Taxes in 2025 ($621)


    Taxes:$7,456

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15716 SWEET LEMON WAY, WINTER GARDEN, FL 34787

    $739,00093 Days on yellowkey   MLS ID: O6375190

    REDUCED by $26,000 (3.4%) on 04/13/2026

    For Sale O6375190 - 15716 SWEET LEMON WAY, WINTER GARDEN, FL 34787 63 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2945
       Built: 2021
    Monthly Fee: $118
       Tax: $9,510 (2025)
    Community: Highlands At Summerlake Groves
    Single Family


    Estimated Monthly Payment: $4,960 (change assumption)
    Mortgage ($4,049) + Fees ($118) + Taxes in 2025 ($793)


    Taxes:$9,510

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 8275 BAYVIEW CROSSING DR DR, WINTER GARDEN, FL 34787

    $565,00013 Days on yellowkey   MLS ID: TB8496196

    For Sale TB8496196 - 8275 BAYVIEW CROSSING DR DR, WINTER GARDEN, FL 34787 35 photos

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

    Single Family


    Estimated Monthly Payment: $3,834 (change assumption)
    Mortgage ($3,096) + 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


  • 238 N MAIN ST, WINTER GARDEN, FL 34787

    $600,00015 Days on yellowkey   MLS ID: O6397340

    For Sale O6397340 - 238 N MAIN ST, WINTER GARDEN, FL 34787 21 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1005
       Built: 1950   Tax: $5,389 (2025)
    Community: Orange Grove Sub
    Single Family


    Estimated Monthly Payment: $3,737 (change assumption)
    Mortgage ($3,288) + Taxes in 2025 ($449)


    Taxes:$5,389

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14501 GROVE RESORT AVE #2527, WINTER GARDEN, FL 34787

    $270,000126 Days on yellowkey   MLS ID: O6368187

    SHORT SALE O6368187 - 14501 GROVE RESORT AVE #2527, WINTER GARDEN, FL 34787 36 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1544
       Built: 2018
    Monthly Fee: $1,103
       Tax: $8,868 (2024)
    Community: Grove Residence & Spa Hotel Condo Ii
    Condo


    Estimated Monthly Payment: $3,321 (change assumption)
    Mortgage ($1,479) + Fees ($1,103) + Taxes in 2024 ($739)


    Taxes:$8,868

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14501 GROVE RESORT AVE #1612, WINTER GARDEN, FL 34787

    $299,000185 Days on yellowkey   MLS ID: S5136940

    For Sale S5136940 - 14501 GROVE RESORT AVE #1612, WINTER GARDEN, FL 34787 76 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1375
       Built: 2016
    Monthly Fee: $875
       Tax: $6,828 (2024)
    Community: Grove Resort And Spa Hotel Condo 1
    Condo


    Estimated Monthly Payment: $3,082 (change assumption)
    Mortgage ($1,638) + Fees ($875) + Taxes in 2024 ($569)


    Taxes:$6,828

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 17006 SEVILLE ORANGE RD, WINTER GARDEN, FL 34787

    $718,79921 Days on yellowkey   MLS ID: TB8493597

    For Sale TB8493597 - 17006 SEVILLE ORANGE RD, WINTER GARDEN, FL 34787 11 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2224
       Built: 2026
    Monthly Fee: $84
       Tax: $2,363 (2025)
    Community: Northlake/Ovation Ph 1
    Single Family


    Estimated Monthly Payment: $4,219 (change assumption)
    Mortgage ($3,939) + Fees ($84) + Taxes in 2025 ($197)


    Taxes:$2,363

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 241 N DILLARD ST, WINTER GARDEN, FL 34787

    $1,499,999185 Days on yellowkey   MLS ID: O6353975

    REDUCED by $100,001 (6.3%) on 04/13/2026

    For Sale O6353975 - 241 N DILLARD ST, WINTER GARDEN, FL 34787 51 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 3507
       Built: 1953   Tax: $2,959 (2024)
    Community: J L Dillard Sub 3
    Single Family


    Estimated Monthly Payment: $8,466 (change assumption)
    Mortgage ($8,219) + Taxes in 2024 ($247)


    Taxes:$2,959

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 12915 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787

    $594,00073 Days on yellowkey   MLS ID: O6381156

    For Sale O6381156 - 12915 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2143
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $3,526 (change assumption)
    Mortgage ($3,255) + Fees ($77) + 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


  • 12911 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787

    $548,00078 Days on yellowkey   MLS ID: O6379918

    5 Days Off yellowkey (back on 4/13/2026)

    For Sale O6379918 - 12911 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2062
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $3,273 (change assumption)
    Mortgage ($3,003) + Fees ($77) + 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


  • 15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787

    $795,00028 Days on yellowkey   MLS ID: O6393987

    For Sale O6393987 - 15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787 20 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4307
       Built: 2014
    Monthly Fee: $114
       Tax: $5,670 (2025)
    Community: Reserve/Carriage Pointe Ph 1
    Single Family


    Estimated Monthly Payment: $4,943 (change assumption)
    Mortgage ($4,356) + Fees ($114) + Taxes in 2025 ($472)


    Taxes:$5,670

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9728 NANCY DREW ALY, WINTER GARDEN, FL 34787

    $524,990178 Days on yellowkey   MLS ID: O6355911

    3 Days Off yellowkey (back on 4/13/2026)

    For Sale O6355911 - 9728 NANCY DREW ALY, WINTER GARDEN, FL 34787 39 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2475
       Built: 2020
    Monthly Fee: $108
       Tax: $8,203 (2024)
    Community: Storey Grove Ph 2
    Single Family


    Estimated Monthly Payment: $3,668 (change assumption)
    Mortgage ($2,877) + Fees ($108) + Taxes in 2024 ($684)


    Taxes:$8,203

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 17031 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $646,09011 Days on yellowkey   MLS ID: G5110934

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale G5110934 - 17031 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2680
       Built: 2026
    Monthly Fee: $140

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,680 (change assumption)
    Mortgage ($3,540) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17428 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787

    $740,20511 Days on yellowkey   MLS ID: G5110933

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale G5110933 - 17428 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3412
       Built: 2026
    Monthly Fee: $140

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,196 (change assumption)
    Mortgage ($4,056) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 5637 TIGER WAY, WINTER GARDEN, FL 34787

    $765,00011 Days on yellowkey   MLS ID: O6398378

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale O6398378 - 5637 TIGER WAY, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2917
       Built: 2018
    Monthly Fee: $214
       Tax: $12,077 (2025)
    Community: Overlook 2/Hamlin Ph 3
    Single Family


    Estimated Monthly Payment: $5,412 (change assumption)
    Mortgage ($4,192) + Fees ($214) + Taxes in 2025 ($1,006)


    Taxes:$12,077

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 6309 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787

    $709,990217 Days on yellowkey   MLS ID: G5102289

    0 Days Off yellowkey (back on 9/18/2025)

    For Sale G5102289 - 6309 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,040 (change assumption)
    Mortgage ($3,890) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 8150 GRAY KINGBIRD DR, WINTER GARDEN, FL 34787

    $649,99912 Days on yellowkey   MLS ID: O6396729

    For Sale O6396729 - 8150 GRAY KINGBIRD DR, WINTER GARDEN, FL 34787 54 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2706
       Built: 2018
    Monthly Fee: $252
       Tax: $6,076 (2025)
    Community: Summerlake Pd Ph 4B
    Single Family


    Estimated Monthly Payment: $4,320 (change assumption)
    Mortgage ($3,562) + Fees ($252) + Taxes in 2025 ($506)


    Taxes:$6,076

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 11714 FLYNN CT, WINTER GARDEN, FL 34787

    $1,349,000154 Days on yellowkey   MLS ID: O6361446

    1 Days Off yellowkey (back on 4/12/2026)

    For Sale O6361446 - 11714 FLYNN CT, WINTER GARDEN, FL 34787 62 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 4370
       Built: 1994   Tax: $4,944 (2025)
    Community: Acreage
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,804 (change assumption)
    Mortgage ($7,392) + Taxes in 2025 ($412)


    Taxes:$4,944

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle




Why Bother Searching Elsewhere for Winter Garden Homes for Sale and Other Real Estate?

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.