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Winter Garden Homes For Sale & Real Estate - 965 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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  • 13856 GLYNSHEL DR, WINTER GARDEN, FL 34787

    $850,00044 Days on yellowkey   MLS ID: O6416757

    For Sale O6416757 - 13856 GLYNSHEL DR, WINTER GARDEN, FL 34787 46 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3538
       Built: 2003
    Monthly Fee: $167
       Tax: $11,261 (2025)
    Community: Glynwood
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,763 (change assumption)
    Mortgage ($4,657) + Fees ($167) + Taxes in 2025 ($938)


    Taxes:$11,261

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16802 OAKBORO ST, WINTER GARDEN, FL 34787

    $500,0008 Days on yellowkey   MLS ID: O6425489

    For Sale O6425489 - 16802 OAKBORO ST, WINTER GARDEN, FL 34787 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1705
       Built: 2020
    Monthly Fee: $257
       Tax: $7,269 (2025)
    Community: Waterleigh Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,602 (change assumption)
    Mortgage ($2,740) + Fees ($257) + Taxes in 2025 ($606)


    Taxes:$7,269

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 2010 BOSS HEWETT ST, WINTER GARDEN, FL 34787

    $1,500,00021 Days on yellowkey   MLS ID: O6423216

    For Sale O6423216 - 2010 BOSS HEWETT ST, WINTER GARDEN, FL 34787 94 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3781
       Built: 2022
    Monthly Fee: $165
       Tax: $11,186 (2025)
    Community: Hull Island/Oakland Ph 2
    Single Family


    Estimated Monthly Payment: $9,316 (change assumption)
    Mortgage ($8,219) + Fees ($165) + Taxes in 2025 ($932)


    Taxes:$11,186

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 8506 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $1,299,00029 Days on yellowkey   MLS ID: O6421255

    For Sale O6421255 - 8506 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 51 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 3966
       Built: 2016
    Monthly Fee: $380
       Tax: $11,330 (2025)
    Community: Waterleigh Ph 1A
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,442 (change assumption)
    Mortgage ($7,118) + Fees ($380) + Taxes in 2025 ($944)


    Taxes:$11,330

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1642 CHANDELLE LN, WINTER GARDEN, FL 34787

    $689,90028 Days on yellowkey   MLS ID: G5114093

    REDUCED by $20,000 (2.8%) on 07/20/2026

    For Sale G5114093 - 1642 CHANDELLE LN, WINTER GARDEN, FL 34787 46 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2918
       Built: 2006
    Monthly Fee: $167
       Tax: $8,474 (2025)
    Community: Belle Meade-Ph I B D & G
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,653 (change assumption)
    Mortgage ($3,780) + Fees ($167) + Taxes in 2025 ($706)


    Taxes:$8,474

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787

    $620,00030 Days on yellowkey   MLS ID: G5114379

    REDUCED by $10,000 (1.6%) on 07/05/2026

    For Sale G5114379 - 17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787 67 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2692
       Built: 2017
    Monthly Fee: $215

    Community: Waterside/Johns Lake Ph 2A
    Single Family


    Estimated Monthly Payment: $3,612 (change assumption)
    Mortgage ($3,397) + Fees ($215) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17035 HARBOR OAK PKWY, WINTER GARDEN, FL 34787

    $485,00058 Days on yellowkey   MLS ID: O6411409

    REDUCED by $14,999 (3.0%) on 07/20/2026

    For Sale O6411409 - 17035 HARBOR OAK PKWY, WINTER GARDEN, FL 34787 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1692
       Built: 2017
    Monthly Fee: $215
       Tax: $3,704 (2025)
    Community: Waterside/Johns Lake Ph 2A
    Single Family


    Estimated Monthly Payment: $3,181 (change assumption)
    Mortgage ($2,657) + Fees ($215) + Taxes in 2025 ($309)


    Taxes:$3,704

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15717 E OAKLAND AVE, WINTER GARDEN, FL 34787

    $1,795,00022 Days on yellowkey   MLS ID: O6419032

    For Sale O6419032 - 15717 E OAKLAND AVE, WINTER GARDEN, FL 34787 82 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3515
       Built: 1997   Tax: $6,623 (2025)
    Community: Oakland
    Single Family


    Estimated Monthly Payment: $10,387 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($552)


    Taxes:$6,623

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 8150 RED STOPPER LN, WINTER GARDEN, FL 34787

    $429,90022 Days on yellowkey   MLS ID: O6416867

    REDUCED by $10,000 (2.3%) on 07/24/2026

    For Sale O6416867 - 8150 RED STOPPER LN, WINTER GARDEN, FL 34787 47 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1738
       Built: 2018
    Monthly Fee: $315
       Tax: $7,091 (2025)
    Community: Summerlake
    Townhouse


    Estimated Monthly Payment: $3,261 (change assumption)
    Mortgage ($2,356) + Fees ($315) + Taxes in 2025 ($591)


    Taxes:$7,091

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 769 HOME GROVE DR, WINTER GARDEN, FL 34787

    $524,50020 Days on yellowkey   MLS ID: O6420766

    0 Days Off yellowkey (back on 7/25/2026)

    REDUCED by $5,500 (1.0%) on 07/24/2026

    For Sale O6420766 - 769 HOME GROVE DR, WINTER GARDEN, FL 34787 62 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2305
       Built: 2005
    Monthly Fee: $99
       Tax: $4,372 (2025)
    Community: Regency Oaks Ph 02 A-C
    Single Family


    Estimated Monthly Payment: $3,337 (change assumption)
    Mortgage ($2,874) + Fees ($99) + Taxes in 2025 ($364)


    Taxes:$4,372

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15587 HAMLIN BLOSSOM AVE, WINTER GARDEN, FL 34787

    $619,90034 Days on yellowkey   MLS ID: O6418163

    1 Days Off yellowkey (back on 7/25/2026)

    For Sale O6418163 - 15587 HAMLIN BLOSSOM AVE, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1860
       Built: 2015
    Monthly Fee: $235
       Tax: $7,423 (2025)
    Community: Hickory Hammock Ph 2A
    Single Family


    Estimated Monthly Payment: $4,250 (change assumption)
    Mortgage ($3,397) + Fees ($235) + Taxes in 2025 ($619)


    Taxes:$7,423

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 6323 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787

    $560,00049 Days on yellowkey   MLS ID: O6415343

    REDUCED by $10,000 (1.8%) on 06/19/2026

    For Sale O6415343 - 6323 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2177
       Built: 2018
    Monthly Fee: $425
       Tax: $8,526 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $4,204 (change assumption)
    Mortgage ($3,068) + Fees ($425) + Taxes in 2025 ($710)


    Taxes:$8,526

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 17631 LAKE STAR RD, WINTER GARDEN, FL 34787

    $830,1865 Days on yellowkey   MLS ID: TB8532670

    For Sale TB8532670 - 17631 LAKE STAR RD, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3004
       Built: 2026
    Monthly Fee: $84
       Tax: $11,000 (2025)
    Community: Northlake At Ovation
    Single Family


    Estimated Monthly Payment: $5,550 (change assumption)
    Mortgage ($4,549) + Fees ($84) + Taxes in 2025 ($917)


    Taxes:$11,000

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6274 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $1,016,0605 Days on yellowkey   MLS ID: G5115512

    0 Days Off yellowkey (back on 7/24/2026)

    For Sale G5115512 - 6274 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 1 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4236
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $5,717 (change assumption)
    Mortgage ($5,567) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13852 JOMATT LOOP, WINTER GARDEN, FL 34787

    $1,030,0005 Days on yellowkey   MLS ID: O6427925

    For Sale O6427925 - 13852 JOMATT LOOP, WINTER GARDEN, FL 34787 39 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4000
       Built: 2016
    Monthly Fee: $75
       Tax: $7,387 (2025)
    Community: Cypress Reserve Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,334 (change assumption)
    Mortgage ($5,644) + Fees ($75) + Taxes in 2025 ($616)


    Taxes:$7,387

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15190 SUNRISE GROVE CT, WINTER GARDEN, FL 34787

    $435,0005 Days on yellowkey   MLS ID: O6427822

    For Sale O6427822 - 15190 SUNRISE GROVE CT, WINTER GARDEN, FL 34787 61 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1902
       Built: 2018
    Monthly Fee: $346
       Tax: $5,755 (2025)
    Community: Hickory Hammock Phase 2B
    Townhouse


    Estimated Monthly Payment: $3,209 (change assumption)
    Mortgage ($2,384) + Fees ($346) + Taxes in 2025 ($480)


    Taxes:$5,755

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 16130 WIND VIEW LN, WINTER GARDEN, FL 34787

    $550,0005 Days on yellowkey   MLS ID: O6412051

    For Sale O6412051 - 16130 WIND VIEW LN, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2031
       Built: 2016
    Monthly Fee: $344
       Tax: $9,012 (2025)
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $4,109 (change assumption)
    Mortgage ($3,014) + Fees ($344) + Taxes in 2025 ($751)


    Taxes:$9,012

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9718 QUIET LN, WINTER GARDEN, FL 34787

    $1,300,0007 Days on yellowkey   MLS ID: O6427038

    0 Days Off yellowkey (back on 7/24/2026)

    For Sale O6427038 - 9718 QUIET LN, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2738
       Built: 2001
    Monthly Fee: $17
       Tax: $5,389 (2025)
    Community: Valley View
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,589 (change assumption)
    Mortgage ($7,123) + Fees ($17) + Taxes in 2025 ($449)


    Taxes:$5,389

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 11025 SUSPENSE DR, WINTER GARDEN, FL 34787

    $419,90058 Days on yellowkey   MLS ID: G5113196

    REDUCED by $15,100 (3.5%) on 06/14/2026

    For Sale G5113196 - 11025 SUSPENSE DR, WINTER GARDEN, FL 34787 46 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1636
       Built: 2017
    Monthly Fee: $263
       Tax: $5,322 (2025)
    Community: Storey Grove Ph 1B-1
    Townhouse


    Estimated Monthly Payment: $3,007 (change assumption)
    Mortgage ($2,301) + Fees ($263) + Taxes in 2025 ($444)


    Taxes:$5,322

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14411 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787

    $885,00054 Days on yellowkey   MLS ID: O6413972

    REDUCED by $10,000 (1.1%) on 07/24/2026

    For Sale O6413972 - 14411 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787 72 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4010
       Built: 2005
    Monthly Fee: $182
       Tax: $11,924 (2025)
    Community: Bay Isle 48 17
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,025 (change assumption)
    Mortgage ($4,849) + Fees ($182) + Taxes in 2025 ($994)


    Taxes:$11,924

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge 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.