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Winter Garden Homes For Sale & Real Estate - 763 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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  • 16827 SANCTUARY DR, WINTER GARDEN, FL 34787

    $998,000Listed 04/25/2026 1:15PM   MLS ID: S5148416

    For Sale S5148416 - 16827 SANCTUARY DR, WINTER GARDEN, FL 34787 64 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2281
       Built: 2020
    Monthly Fee: $165
       Tax: $6,024 (2025)
    Community: Sanctuary/Twin Waters
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,135 (change assumption)
    Mortgage ($5,468) + Fees ($165) + Taxes in 2025 ($502)


    Taxes:$6,024

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1021 TEMPLE GROVE PL, WINTER GARDEN, FL 34787

    $1,895,00052 Days on yellowkey   MLS ID: O6387876

    REDUCED by $100,000 (5.0%) on 04/25/2026

    For Sale O6387876 - 1021 TEMPLE GROVE PL, WINTER GARDEN, FL 34787 59 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3185
       Built: 2020   Tax: $17,100 (2025)
    Community: Emerald Acres
    Single Family


    Estimated Monthly Payment: $11,808 (change assumption)
    Mortgage ($10,383) + Taxes in 2025 ($1,425)


    Taxes:$17,100

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15508 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787

    $695,000Listed 04/25/2026 8:51AM   MLS ID: O6402010

    For Sale O6402010 - 15508 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787 59 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2763
       Built: 2001
    Monthly Fee: $243
       Tax: $6,075 (2025)
    Community: Stoneybrook West 44/134
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,557 (change assumption)
    Mortgage ($3,808) + Fees ($243) + Taxes in 2025 ($506)


    Taxes:$6,075

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 9201 GRAN TEATRO DR, WINTER GARDEN, FL 34787

    $525,000Listed 04/25/2026 8:24AM   MLS ID: O6401827

    For Sale O6401827 - 9201 GRAN TEATRO DR, WINTER GARDEN, FL 34787 32 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1715
       Built: 2024
    Monthly Fee: $292
       Tax: $6,402 (2025)
    Community: Tribute/Ovation
    Townhouse


    Estimated Monthly Payment: $3,702 (change assumption)
    Mortgage ($2,877) + Fees ($292) + Taxes in 2025 ($534)


    Taxes:$6,402

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6165 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $745,130Listed 04/25/2026 11:33AM   MLS ID: G5111538

    0 Days Off yellowkey (back on 4/25/2026)

    For Sale G5111538 - 6165 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3038
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,233 (change assumption)
    Mortgage ($4,083) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 505 E GULLEY AVE, WINTER GARDEN, FL 34787

    $899,0001 Day on yellowkey   MLS ID: O6400317

    For Sale O6400317 - 505 E GULLEY AVE, WINTER GARDEN, FL 34787 83 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3399
       Built: 2006
    Monthly Fee: $73
       Tax: $6,649 (2025)
    Community: Winters Landing
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,553 (change assumption)
    Mortgage ($4,926) + Fees ($73) + Taxes in 2025 ($554)


    Taxes:$6,649

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 9433 EMERALD BERRY DR, WINTER GARDEN, FL 34787

    $729,8002 Days on yellowkey   MLS ID: O6401775

    For Sale O6401775 - 9433 EMERALD BERRY DR, WINTER GARDEN, FL 34787 62 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2063
       Built: 2024
    Monthly Fee: $99
       Tax: $8,457 (2025)
    Community: Summerlake Reserve
    Single Family


    Estimated Monthly Payment: $4,803 (change assumption)
    Mortgage ($3,999) + Fees ($99) + Taxes in 2025 ($705)


    Taxes:$8,457

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 8170 BLUEJACK OAK DR, WINTER GARDEN, FL 34787

    $465,0009 Days on yellowkey   MLS ID: O6399484

    For Sale O6399484 - 8170 BLUEJACK OAK DR, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1853
       Built: 2016
    Monthly Fee: $315
       Tax: $4,738 (2025)
    Community: Summerlake Pd Ph 2C 2D 2E
    Townhouse


    Estimated Monthly Payment: $3,258 (change assumption)
    Mortgage ($2,548) + Fees ($315) + Taxes in 2025 ($395)


    Taxes:$4,738

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16029 TOLLINGTON ALY, WINTER GARDEN, FL 34787

    $619,5008 Days on yellowkey   MLS ID: P4938378

    For Sale P4938378 - 16029 TOLLINGTON ALY, WINTER GARDEN, FL 34787 55 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2341
       Built: 2020
    Monthly Fee: $225
       Tax: $8,643 (2025)
    Community: Encore/Ovation Ph 1
    Single Family


    Estimated Monthly Payment: $4,340 (change assumption)
    Mortgage ($3,394) + Fees ($225) + Taxes in 2025 ($720)


    Taxes:$8,643

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16396 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787

    $484,99015 Days on yellowkey   MLS ID: O6396532

    For Sale O6396532 - 16396 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2070
       Built: 2021
    Monthly Fee: $286
       Tax: $7,102 (2025)
    Community: Hawksmoor Ph 3
    Townhouse


    Estimated Monthly Payment: $3,535 (change assumption)
    Mortgage ($2,657) + Fees ($286) + Taxes in 2025 ($592)


    Taxes:$7,102

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16149 WIND VIEW LN, WINTER GARDEN, FL 34787

    $498,00043 Days on yellowkey   MLS ID: O6389892

    REDUCED by $7,000 (1.4%) on 04/15/2026

    For Sale O6389892 - 16149 WIND VIEW LN, WINTER GARDEN, FL 34787 46 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2036
       Built: 2016
    Monthly Fee: $332
       Tax: $4,472 (2025)
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $3,433 (change assumption)
    Mortgage ($2,729) + Fees ($332) + Taxes in 2025 ($373)


    Taxes:$4,472

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 12731 GROVEHURST AVE, WINTER GARDEN, FL 34787

    $620,00080 Days on yellowkey   MLS ID: O6379203

    REDUCED by $24,900 (3.9%) on 04/20/2026

    For Sale O6379203 - 12731 GROVEHURST AVE, WINTER GARDEN, FL 34787 59 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3474
       Built: 2006
    Monthly Fee: $111
       Tax: $8,378 (2025)
    Community: Grovehurst A-D
    Single Family


    Estimated Monthly Payment: $4,206 (change assumption)
    Mortgage ($3,397) + Fees ($111) + Taxes in 2025 ($698)


    Taxes:$8,378

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 8124 RED CROSSBILL ST, WINTER GARDEN, FL 34787

    $840,000219 Days on yellowkey   MLS ID: O6345400

    REDUCED by $10,000 (1.2%) on 04/21/2026

    For Sale O6345400 - 8124 RED CROSSBILL ST, WINTER GARDEN, FL 34787 67 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3708
       Built: 2013
    Monthly Fee: $246
       Tax: $7,515 (2024)
    Community: Summerlake Pd Ph 1A
    Single Family


    Estimated Monthly Payment: $5,475 (change assumption)
    Mortgage ($4,603) + Fees ($246) + Taxes in 2024 ($626)


    Taxes:$7,515

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5416 GOLDEN APPLE DR, WINTER GARDEN, FL 34787

    $949,99962 Days on yellowkey   MLS ID: O6384645

    REDUCED by $25,001 (2.6%) on 04/20/2026

    For Sale O6384645 - 5416 GOLDEN APPLE DR, WINTER GARDEN, FL 34787 58 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3104
       Built: 2021
    Monthly Fee: $115
       Tax: $8,275 (2024)
    Community: Wincey Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $6,010 (change assumption)
    Mortgage ($5,205) + Fees ($115) + Taxes in 2024 ($690)


    Taxes:$8,275

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 15594 SHOREBIRD LN, WINTER GARDEN, FL 34787

    $1,258,00019 Days on yellowkey   MLS ID: S5147208

    For Sale S5147208 - 15594 SHOREBIRD LN, WINTER GARDEN, FL 34787 84 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3022
       Built: 2020
    Monthly Fee: $360
       Tax: $17,905 (2025)
    Community: Lakeshore Preserve Ph 4
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,745 (change assumption)
    Mortgage ($6,893) + Fees ($360) + Taxes in 2025 ($1,492)


    Taxes:$17,905

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9409 EMERALD BERRY DR, WINTER GARDEN, FL 34787

    $875,00053 Days on yellowkey   MLS ID: S5144953

    0 Days Off yellowkey (back on 4/25/2026)

    For Sale S5144953 - 9409 EMERALD BERRY DR, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2923
       Built: 2024
    Monthly Fee: $85

    Community: Summerlake Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,879 (change assumption)
    Mortgage ($4,794) + Fees ($85) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 17549 SEIDNER RD, WINTER GARDEN, FL 34787

    $950,00028 Days on yellowkey   MLS ID: O6392430

    1 Days Off yellowkey (back on 4/18/2026)

    For Sale O6392430 - 17549 SEIDNER RD, WINTER GARDEN, FL 34787 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2130
       Built: 1985
    Monthly Fee: $3
       Tax: $3,947 (2025)
    Community: Lake Avalon Heights
    Single Family


    Estimated Monthly Payment: $5,537 (change assumption)
    Mortgage ($5,205) + Fees ($3) + Taxes in 2025 ($329)


    Taxes:$3,947

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 317 SOUTHERN PECAN CIR #102, WINTER GARDEN, FL 34787

    $228,00060 Days on yellowkey   MLS ID: O6384866

    REDUCED by $4,000 (1.7%) on 04/23/2026

    For Sale O6384866 - 317 SOUTHERN PECAN CIR #102, WINTER GARDEN, FL 34787 42 photos

    Bed: 1   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 738
       Built: 2005
    Monthly Fee: $309
       Tax: $245 (2025)
    Community: Southern Pines Condominium
    Condo


    Estimated Monthly Payment: $1,579 (change assumption)
    Mortgage ($1,249) + Fees ($309) + Taxes in 2025 ($20)


    Taxes:$245

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 17737 DEER ISLE CIR, WINTER GARDEN, FL 34787

    $2,950,00068 Days on yellowkey   MLS ID: O6381953

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

    For Sale O6381953 - 17737 DEER ISLE CIR, WINTER GARDEN, FL 34787 76 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4886
       Built: 2015
    Monthly Fee: $207
       Tax: $24,540 (2024)
    Community: Deer Island
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $18,416 (change assumption)
    Mortgage ($16,164) + Fees ($207) + Taxes in 2024 ($2,045)


    Taxes:$24,540

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 6321 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787

    $654,990148 Days on yellowkey   MLS ID: G5105005

    0 Days Off yellowkey (back on 11/28/2025)

    For Sale G5105005 - 6321 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787 2 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1772
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $3,739 (change assumption)
    Mortgage ($3,589) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin 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.