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Winter Garden Homes For Sale & Real Estate - 708 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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  • 15524 AVIATION ALY, WINTER GARDEN, FL 34787

    $569,9008 Days on yellowkey   MLS ID: O6398331

    For Sale O6398331 - 15524 AVIATION ALY, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2414
       Built: 2015
    Monthly Fee: $328
       Tax: $8,711 (2025)
    Community: Overlook 2/Hamlin Ph 1 & 6
    Single Family


    Estimated Monthly Payment: $4,177 (change assumption)
    Mortgage ($3,123) + Fees ($328) + Taxes in 2025 ($726)


    Taxes:$8,711

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 15442 ENCHANTED MELODY WAY, WINTER GARDEN, FL 34787

    $609,85029 Days on yellowkey   MLS ID: S5146095

    REDUCED by $3,050 (0.5%) on 04/13/2026

    For Sale S5146095 - 15442 ENCHANTED MELODY WAY, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2420
       Built: 2024
    Monthly Fee: $95
       Tax: $8,065 (2025)
    Community: Osprey Ranch Ph I
    Single Family


    Estimated Monthly Payment: $4,109 (change assumption)
    Mortgage ($3,342) + Fees ($95) + Taxes in 2025 ($672)


    Taxes:$8,065

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 303 SOUTHERN PECAN CIR #107, WINTER GARDEN, FL 34787

    $234,90070 Days on yellowkey   MLS ID: S5143459

    REDUCED by $5,000 (2.1%) on 04/13/2026

    For Sale S5143459 - 303 SOUTHERN PECAN CIR #107, WINTER GARDEN, FL 34787 15 photos

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

    Condo


    Estimated Monthly Payment: $1,499 (change assumption)
    Mortgage ($1,287) + Taxes in 2024 ($212)


    Taxes:$2,540

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 7680 GREEN MOUNTAIN WAY, WINTER GARDEN, FL 34787

    $658,90010 Days on yellowkey   MLS ID: O6389013

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

    For Sale O6389013 - 7680 GREEN MOUNTAIN WAY, WINTER GARDEN, FL 34787 58 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2385
       Built: 2016
    Monthly Fee: $252
       Tax: $8,915 (2025)
    Community: Summerlake Pd Ph 3A
    Single Family


    Estimated Monthly Payment: $4,605 (change assumption)
    Mortgage ($3,610) + Fees ($252) + Taxes in 2025 ($743)


    Taxes:$8,915

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14058 FRASIER ST, WINTER GARDEN, FL 34787

    $459,00058 Days on yellowkey   MLS ID: V4947394

    For Sale V4947394 - 14058 FRASIER ST, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1996
       Built: 2023
    Monthly Fee: $110
       Tax: $7,893 (2024)
    Community: Highland Rdg
    Single Family


    Estimated Monthly Payment: $3,283 (change assumption)
    Mortgage ($2,515) + Fees ($110) + Taxes in 2024 ($658)


    Taxes:$7,893

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15324 GILLIGAN CT, WINTER GARDEN, FL 34787

    $950,00024 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


  • 14501 GROVE RESORT AVE #1105, WINTER GARDEN, FL 34787

    $304,000135 Days on yellowkey   MLS ID: O6365470

    For Sale O6365470 - 14501 GROVE RESORT AVE #1105, WINTER GARDEN, FL 34787 48 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1265
       Built: 2018
    Monthly Fee: $805
       Tax: $3,954 (2025)
    Community: Grove Resort And Water Park
    Condo


    Estimated Monthly Payment: $2,800 (change assumption)
    Mortgage ($1,666) + Fees ($805) + Taxes in 2025 ($330)


    Taxes:$3,954

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15508 BLACKBEAD ST, WINTER GARDEN, FL 34787

    $430,000102 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

    $799,0007 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


  • 15408 LEBEAU LOOP, WINTER GARDEN, FL 34787

    $580,00060 Days on yellowkey   MLS ID: O6383534

    For Sale O6383534 - 15408 LEBEAU LOOP, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2415
       Built: 2022
    Monthly Fee: $101
       Tax: $7,566 (2024)
    Community: Winding Bay Ph 3
    Single Family


    Estimated Monthly Payment: $3,909 (change assumption)
    Mortgage ($3,178) + Fees ($101) + Taxes in 2024 ($630)


    Taxes:$7,566

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15716 SWEET LEMON WAY, WINTER GARDEN, FL 34787

    $739,00089 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


  • 9256 GRAND ISLAND WAY, WINTER GARDEN, FL 34787

    $750,0009 Days on yellowkey   MLS ID: O6397917

    For Sale O6397917 - 9256 GRAND ISLAND WAY, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2507
       Built: 2017
    Monthly Fee: $164
       Tax: $6,475 (2025)
    Community: Watermark Ph 2C
    Single Family


    Estimated Monthly Payment: $4,813 (change assumption)
    Mortgage ($4,109) + Fees ($164) + Taxes in 2025 ($540)


    Taxes:$6,475

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 5596 THOMAS SQUARE DR, WINTER GARDEN, FL 34787

    $618,00048 Days on yellowkey   MLS ID: O6386791

    For Sale O6386791 - 5596 THOMAS SQUARE DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2458
       Built: 2015
    Monthly Fee: $324
       Tax: $8,569 (2025)
    Community: Overlook At Hamlin
    Single Family


    Estimated Monthly Payment: $4,424 (change assumption)
    Mortgage ($3,386) + Fees ($324) + Taxes in 2025 ($714)


    Taxes:$8,569

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $565,0009 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

    $600,00011 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


  • 1075 CHASE DR, WINTER GARDEN, FL 34787

    $625,00048 Days on yellowkey   MLS ID: O6386607

    For Sale O6386607 - 1075 CHASE DR, WINTER GARDEN, FL 34787 63 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2125
       Built: 2015
    Monthly Fee: $41
       Tax: $2,734 (2024)
    Community: Island Pointe Sub
    Single Family


    Estimated Monthly Payment: $3,693 (change assumption)
    Mortgage ($3,425) + Fees ($41) + Taxes in 2024 ($228)


    Taxes:$2,734

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


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

    $270,000122 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

    $299,000181 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

    $718,79917 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

    $1,499,999181 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




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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.