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Winter Garden Homes For Sale & Real Estate - 764 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

    $998,0001 Day on yellowkey   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


  • 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $590,000241 Days on yellowkey   MLS ID: O6337436

    For Sale O6337436 - 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787 89 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2292
       Built: 2023
    Monthly Fee: $245
       Tax: $9,031 (2024)
    Community: Waterleigh Ph 4A
    Single Family


    Estimated Monthly Payment: $4,230 (change assumption)
    Mortgage ($3,233) + Fees ($245) + Taxes in 2024 ($753)


    Taxes:$9,031

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 18386 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $724,90049 Days on yellowkey   MLS ID: O6388830

    For Sale O6388830 - 18386 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2924
       Built: 2024
    Monthly Fee: $280
       Tax: $10,366 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $5,116 (change assumption)
    Mortgage ($3,972) + Fees ($280) + Taxes in 2024 ($864)


    Taxes:$10,366

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: None


  • 1670 E SPRING RIDGE CIR, WINTER GARDEN, FL 34787

    $414,90060 Days on yellowkey   MLS ID: O6385776

    REDUCED by $5,000 (1.2%) on 04/07/2026

    For Sale O6385776 - 1670 E SPRING RIDGE CIR, WINTER GARDEN, FL 34787 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1699
       Built: 1995
    Monthly Fee: $50
       Tax: $1,352 (2025)
    Community: Crown Point Springs Ut 2
    Single Family


    Estimated Monthly Payment: $2,436 (change assumption)
    Mortgage ($2,273) + Fees ($50) + Taxes in 2025 ($113)


    Taxes:$1,352

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 5966 CYPRESS HILL RD, WINTER GARDEN, FL 34787

    $695,00093 Days on yellowkey   MLS ID: O6376219

    For Sale O6376219 - 5966 CYPRESS HILL RD, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2839
       Built: 2017
    Monthly Fee: $195
       Tax: $9,648 (2025)
    Community: Signature Lakes Ph 3B-4, 3B-5 & 3B-7 83/27 Lot 184
    Single Family


    Estimated Monthly Payment: $4,807 (change assumption)
    Mortgage ($3,808) + Fees ($195) + Taxes in 2025 ($804)


    Taxes:$9,648

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 1422 BASIN ST, WINTER GARDEN, FL 34787

    $169,00090 Days on yellowkey   MLS ID: O6377176

    3 Days Off yellowkey (back on 3/30/2026)

    For Sale O6377176 - 1422 BASIN ST, WINTER GARDEN, FL 34787 10 photos

    Bed: 4   Bath: 1.0
    Liv Area Sq Ft: 880
       Built: 1966   Tax: $1,800 (2025)
    Community: Joe Louis Park
    Single Family


    Estimated Monthly Payment: $1,076 (change assumption)
    Mortgage ($926) + Taxes in 2025 ($150)


    Taxes:$1,800

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 12513 SCARLETT SAGE CT, WINTER GARDEN, FL 34787

    $875,0004 Days on yellowkey   MLS ID: O6393138

    For Sale O6393138 - 12513 SCARLETT SAGE CT, WINTER GARDEN, FL 34787 45 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3570
       Built: 2001
    Monthly Fee: $104
       Tax: $9,264 (2025)
    Community: Cambridge Crossing Ph 01A 45/21
    Single Family


    Estimated Monthly Payment: $5,670 (change assumption)
    Mortgage ($4,794) + Fees ($104) + Taxes in 2025 ($772)


    Taxes:$9,264

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 12965 HARVEST RAIN AVE, WINTER GARDEN, FL 34787

    $882,93234 Days on yellowkey   MLS ID: O6392975

    1 Days Off yellowkey (back on 4/26/2026)

    For Sale O6392975 - 12965 HARVEST RAIN AVE, WINTER GARDEN, FL 34787 31 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3101
       Built: 2026
    Monthly Fee: $140

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,978 (change assumption)
    Mortgage ($4,838) + Fees ($140) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2026

    Middle School: Water Spring Middle


  • 15391 LEBEAU LOOP, WINTER GARDEN, FL 34787

    $949,00096 Days on yellowkey   MLS ID: O6375228

    1 Days Off yellowkey (back on 4/26/2026)

    For Sale O6375228 - 15391 LEBEAU LOOP, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3042
       Built: 2022
    Monthly Fee: $101
       Tax: $10,724 (2025)
    Community: Winding Bay Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,195 (change assumption)
    Mortgage ($5,200) + Fees ($101) + Taxes in 2025 ($894)


    Taxes:$10,724

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 6177 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $729,385Listed 04/25/2026 8:42PM   MLS ID: G5111566

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

    For Sale G5111566 - 6177 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2688
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,147 (change assumption)
    Mortgage ($3,997) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 6165 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $745,1301 Day on yellowkey   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


  • 15508 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787

    $695,0001 Day on yellowkey   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

    $525,0001 Day on yellowkey   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


  • 9354 MEADOW HUNT WAY, WINTER GARDEN, FL 34787

    $525,0001 Day on yellowkey   MLS ID: O6400695

    For Sale O6400695 - 9354 MEADOW HUNT WAY, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2079
       Built: 2017
    Monthly Fee: $164
       Tax: $4,974 (2025)
    Community: Watermark
    Single Family


    Estimated Monthly Payment: $3,455 (change assumption)
    Mortgage ($2,877) + Fees ($164) + Taxes in 2025 ($415)


    Taxes:$4,974

    Elementary School: Panther Lake 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 82 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


  • 16256 MISTY HILLS AVE, WINTER GARDEN, FL 34787

    $648,000116 Days on yellowkey   MLS ID: O6369818

    REDUCED by $2,000 (0.3%) on 04/25/2026

    For Sale O6369818 - 16256 MISTY HILLS AVE, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2240
       Built: 2020
    Monthly Fee: $115
       Tax: $9,333 (2024)
    Community: Wincey Grvs Ph 1
    Single Family


    Estimated Monthly Payment: $4,443 (change assumption)
    Mortgage ($3,551) + Fees ($115) + Taxes in 2024 ($778)


    Taxes:$9,333

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 648 ORANGE BELT LOOP, WINTER GARDEN, FL 34787

    $499,99059 Days on yellowkey   MLS ID: S5144591

    REDUCED by $25,010 (4.8%) on 04/06/2026

    For Sale S5144591 - 648 ORANGE BELT LOOP, WINTER GARDEN, FL 34787 49 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1688
       Built: 2018
    Monthly Fee: $338
       Tax: $4,171 (2024)
    Community: Heritage/Plant Street
    Townhouse


    Estimated Monthly Payment: $3,425 (change assumption)
    Mortgage ($2,740) + Fees ($338) + Taxes in 2024 ($348)


    Taxes:$4,171

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 199 E CREST AVE, WINTER GARDEN, FL 34787

    $525,0003 Days on yellowkey   MLS ID: O6401923

    For Sale O6401923 - 199 E CREST AVE, WINTER GARDEN, FL 34787 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1659
       Built: 1984   Tax: $6,857 (2025)
    Community: Garden Heights Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,448 (change assumption)
    Mortgage ($2,877) + Taxes in 2025 ($571)


    Taxes:$6,857

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17588 LAKE STAR RD, WINTER GARDEN, FL 34787

    $1,185,00045 Days on yellowkey   MLS ID: O6387269

    REDUCED by $10,000 (0.8%) on 04/25/2026

    For Sale O6387269 - 17588 LAKE STAR RD, WINTER GARDEN, FL 34787 54 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4026
       Built: 2024
    Monthly Fee: $84
       Tax: $3,806 (2024)
    Community: Northlake At Ovation
    Single Family


    Estimated Monthly Payment: $6,894 (change assumption)
    Mortgage ($6,493) + Fees ($84) + Taxes in 2024 ($317)


    Taxes:$3,806

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 636 S PARK AVE, WINTER GARDEN, FL 34787

    $298,9008 Days on yellowkey   MLS ID: O6400433

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

    For Sale O6400433 - 636 S PARK AVE, WINTER GARDEN, FL 34787 14 photos

    Bed: 4   Bath: 1.5   Gar: 2
    Liv Area Sq Ft: 1272
       Built: 1953   Tax: $3,751 (2025)
    Community: Burchshire
    Single Family


    Estimated Monthly Payment: $1,950 (change assumption)
    Mortgage ($1,638) + Taxes in 2025 ($313)


    Taxes:$3,751

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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.