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Winter Garden Single Family Homes For Sale - 730 homes

Winter Garden Single Family Homes for Sale are located in Orange County, Florida. Find single family homes for sale in Winter Garden with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Garden single family houses.

Location: Winter Garden

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  • 13856 GLYNSHEL DR, WINTER GARDEN, FL 34787

    $850,00039 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


  • 721 S WOODLAND ST, WINTER GARDEN, FL 34787

    $440,00028 Days on yellowkey   MLS ID: O6419636

    REDUCED by $10,000 (2.2%) on 07/23/2026

    For Sale O6419636 - 721 S WOODLAND ST, WINTER GARDEN, FL 34787 24 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1034
       Built: 1955   Tax: $508 (2025)
    Community: Borders & Woosley Sub
    Single Family


    Estimated Monthly Payment: $2,453 (change assumption)
    Mortgage ($2,411) + Taxes in 2025 ($42)


    Taxes:$508

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 5960 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $597,99674 Days on yellowkey   MLS ID: G5112227

    INCREASED by $40,873 (7.3%) on 06/10/2026

    For Sale G5112227 - 5960 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 5 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: $3,427 (change assumption)
    Mortgage ($3,277) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17631 LAKE STAR RD, WINTER GARDEN, FL 34787

    $830,186Listed 07/24/2026 4:30PM   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


  • 706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $1,225,000116 Days on yellowkey   MLS ID: O6394059

    REDUCED by $34,000 (2.7%) on 06/17/2026

    For Sale O6394059 - 706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 65 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 4019
       Built: 2018
    Monthly Fee: $298
       Tax: $17,895 (2025)
    Community: Canopy Oaks Ph 1
    Single Family


    Estimated Monthly Payment: $8,501 (change assumption)
    Mortgage ($6,712) + Fees ($298) + Taxes in 2025 ($1,491)


    Taxes:$17,895

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 6274 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $1,016,060Listed 07/24/2026 3:59PM   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


  • 2766 BOBCAT CHASE BLVD, WINTER GARDEN, FL 34787

    $520,000Listed 07/24/2026 3:32PM   MLS ID: O6427751

    For Sale O6427751 - 2766 BOBCAT CHASE BLVD, WINTER GARDEN, FL 34787 57 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1811
       Built: 2020
    Monthly Fee: $286
       Tax: $5,482 (2025)
    Community: Longleaf At Oakland
    Single Family


    Estimated Monthly Payment: $3,592 (change assumption)
    Mortgage ($2,849) + Fees ($286) + Taxes in 2025 ($457)


    Taxes:$5,482

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 8768 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $890,00048 Days on yellowkey   MLS ID: O6414519

    For Sale O6414519 - 8768 SONOMA COAST DR, WINTER GARDEN, FL 34787 38 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 3416
       Built: 2022
    Monthly Fee: $275
       Tax: $11,513 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,111 (change assumption)
    Mortgage ($4,877) + Fees ($275) + Taxes in 2024 ($959)


    Taxes:$11,513

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 15665 CITRUS HARVEST RD, WINTER GARDEN, FL 34787

    $699,90083 Days on yellowkey   MLS ID: O6400896

    REDUCED by $20,000 (2.8%) on 07/11/2026

    For Sale O6400896 - 15665 CITRUS HARVEST RD, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2931
       Built: 2016
    Monthly Fee: $235
       Tax: $5,441 (2025)
    Community: Hickory Hammock Ph 2A
    Single Family


    Estimated Monthly Payment: $4,523 (change assumption)
    Mortgage ($3,835) + Fees ($235) + Taxes in 2025 ($453)


    Taxes:$5,441

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 637 GRASSY STONE DR, WINTER GARDEN, FL 34787

    $850,000Listed 07/24/2026 1:39PM   MLS ID: O6427944

    For Sale O6427944 - 637 GRASSY STONE DR, WINTER GARDEN, FL 34787 67 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3241
       Built: 2013
    Monthly Fee: $72
       Tax: $9,999 (2025)
    Community: Covington Chase Ph 2B
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,563 (change assumption)
    Mortgage ($4,657) + Fees ($72) + Taxes in 2025 ($833)


    Taxes:$9,999

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14327 WABASSO LOOP, WINTER GARDEN, FL 34787

    $869,990301 Days on yellowkey   MLS ID: O6347454

    REDUCED by $30,000 (3.3%) on 07/24/2026

    For Sale O6347454 - 14327 WABASSO LOOP, WINTER GARDEN, FL 34787 48 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3710
       Built: 2022
    Monthly Fee: $200
       Tax: $12,141 (2024)
    Community: Tilden Place/Winter Garden
    Single Family


    Estimated Monthly Payment: $5,979 (change assumption)
    Mortgage ($4,767) + Fees ($200) + Taxes in 2024 ($1,012)


    Taxes:$12,141

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 10067 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787

    $1,160,000246 Days on yellowkey   MLS ID: O6361968

    REDUCED by $10,000 (0.9%) on 07/21/2026

    For Sale O6361968 - 10067 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787 97 photos

    Bed: 6   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4305
       Built: 2020
    Monthly Fee: $159
       Tax: $13,997 (2024)
    Community: Watermark Ph 4
    Single Family


    Estimated Monthly Payment: $7,681 (change assumption)
    Mortgage ($6,356) + Fees ($159) + Taxes in 2024 ($1,166)


    Taxes:$13,997

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 2200 ROMANUM DR, WINTER GARDEN, FL 34787

    $550,00070 Days on yellowkey   MLS ID: O6408190

    0 Days Off yellowkey (back on 6/29/2026)

    REDUCED by $10,000 (1.8%) on 06/24/2026

    For Sale O6408190 - 2200 ROMANUM DR, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2561
       Built: 2015
    Monthly Fee: $211
       Tax: $8,843 (2025)
    Community: Alexander Rdg
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,962 (change assumption)
    Mortgage ($3,014) + Fees ($211) + Taxes in 2025 ($737)


    Taxes:$8,843

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7190 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787

    $535,00078 Days on yellowkey   MLS ID: O6402423

    REDUCED by $10,000 (1.8%) on 06/25/2026

    For Sale O6402423 - 7190 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787 17 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2016
    Monthly Fee: $253
       Tax: $5,148 (2025)
    Community: Lakeview Pointe/Horizon West P
    Single Family


    Estimated Monthly Payment: $3,613 (change assumption)
    Mortgage ($2,931) + Fees ($253) + Taxes in 2025 ($429)


    Taxes:$5,148

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 7052 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787

    $775,0001 Day on yellowkey   MLS ID: S5154077

    For Sale S5154077 - 7052 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787 65 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3264
       Built: 2016
    Monthly Fee: $270
       Tax: $6,080 (2025)
    Community: Lakeview Pointe At Horizon West
    Single Family


    Estimated Monthly Payment: $5,023 (change assumption)
    Mortgage ($4,246) + Fees ($270) + Taxes in 2025 ($507)


    Taxes:$6,080

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13852 JOMATT LOOP, WINTER GARDEN, FL 34787

    $1,030,000Listed 07/24/2026 1:09PM   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


  • 15717 E OAKLAND AVE, WINTER GARDEN, FL 34787

    $1,795,00017 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


  • 15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787

    $765,000120 Days on yellowkey   MLS ID: O6393987

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

    REDUCED by $30,000 (3.8%) on 05/08/2026

    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: $4,778 (change assumption)
    Mortgage ($4,192) + 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


  • 16936 TRADEWIND PT, WINTER GARDEN, FL 34787

    $645,00010 Days on yellowkey   MLS ID: O6424578

    For Sale O6424578 - 16936 TRADEWIND PT, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2930
       Built: 2019
    Monthly Fee: $215
       Tax: $7,616 (2025)
    Community: Waterside/Johns Lake Ph 2A
    Single Family


    Estimated Monthly Payment: $4,384 (change assumption)
    Mortgage ($3,534) + Fees ($215) + Taxes in 2025 ($635)


    Taxes:$7,616

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14140 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787

    $996,975104 Days on yellowkey   MLS ID: O6397262

    REDUCED by $25 (0.0%) on 05/28/2026

    For Sale O6397262 - 14140 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787 71 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2346
       Built: 1984
    Monthly Fee: $71
       Tax: $10,303 (2025)
    Community: Country Lakes
    Single Family


    Estimated Monthly Payment: $6,392 (change assumption)
    Mortgage ($5,463) + Fees ($71) + Taxes in 2025 ($859)


    Taxes:$10,303

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle




Why Bother Searching Elsewhere for Winter Garden Single Family Homes for Sale?

Winter Garden home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Garden . You can use our website to view Multiple Listing Service (MLS) data on Winter Garden single family homes. 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 single family home 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.