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Winter Garden Single Family Homes For Sale - 719 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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  • 5024 PALMETTO PARK DR, WINTER GARDEN, FL 34787

    $805,00050 Days on yellowkey   MLS ID: O6414749

    REDUCED by $14,000 (1.7%) on 07/20/2026

    For Sale O6414749 - 5024 PALMETTO PARK DR, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3061
       Built: 2017
    Monthly Fee: $187
       Tax: $10,816 (2025)
    Community: Orchard Hills Ph 3
    Single Family


    Estimated Monthly Payment: $5,499 (change assumption)
    Mortgage ($4,411) + Fees ($187) + Taxes in 2025 ($901)


    Taxes:$10,816

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8768 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $890,00052 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


  • 12241 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787

    $1,190,00085 Days on yellowkey   MLS ID: O6403198

    For Sale O6403198 - 12241 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787 94 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3693
       Built: 2021
    Monthly Fee: $225
       Tax: $12,882 (2025)
    Community: Encore/Ovation Ph 1
    Single Family


    Estimated Monthly Payment: $7,819 (change assumption)
    Mortgage ($6,520) + Fees ($225) + Taxes in 2025 ($1,074)


    Taxes:$12,882

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1698 JUNIPER HAMMOCK ST, WINTER GARDEN, FL 34787

    $1,399,000102 Days on yellowkey   MLS ID: V4948569

    REDUCED by $51,000 (3.5%) on 06/06/2026

    For Sale V4948569 - 1698 JUNIPER HAMMOCK ST, WINTER GARDEN, FL 34787 50 photos

    Bed: 7   Bath: 4.0   Gar: 4
    Liv Area Sq Ft: 4700
       Built: 2019
    Monthly Fee: $97
       Tax: $9,199 (2025)
    Community: Mcallister Lndg
    Single Family


    Estimated Monthly Payment: $8,529 (change assumption)
    Mortgage ($7,666) + Fees ($97) + Taxes in 2025 ($767)


    Taxes:$9,199

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14301 WHITE MOSS WAY, WINTER GARDEN, FL 34787

    $949,99929 Days on yellowkey   MLS ID: G5114391

    For Sale G5114391 - 14301 WHITE MOSS WAY, WINTER GARDEN, FL 34787 66 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4053
       Built: 2015
    Monthly Fee: $190
       Tax: $9,701 (2026)
    Community: Orchard Hills
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,204 (change assumption)
    Mortgage ($5,205) + Fees ($190) + Taxes in 2026 ($808)


    Taxes:$9,701

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2026

    Middle School: Bridgewater Middle


  • 16149 WIND VIEW LN, WINTER GARDEN, FL 34787

    $495,000137 Days on yellowkey   MLS ID: O6389892

    REDUCED by $3,000 (0.6%) on 05/30/2026

    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: $3,417 (change assumption)
    Mortgage ($2,712) + 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


  • 16038 JOHNS LAKE OVERLOOK DR, WINTER GARDEN, FL 34787

    $2,125,0006 Days on yellowkey   MLS ID: O6426648

    For Sale O6426648 - 16038 JOHNS LAKE OVERLOOK DR, WINTER GARDEN, FL 34787 100 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4139
       Built: 2015
    Monthly Fee: $235
       Tax: $23,164 (2025)
    Community: Hickory Hammock
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,809 (change assumption)
    Mortgage ($11,644) + Fees ($235) + Taxes in 2025 ($1,930)


    Taxes:$23,164

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16004 OLLIVETT ST, WINTER GARDEN, FL 34787

    $834,99931 Days on yellowkey   MLS ID: S5152585

    INCREASED by $5,000 (0.6%) on 06/29/2026

    For Sale S5152585 - 16004 OLLIVETT ST, WINTER GARDEN, FL 34787 45 photos

    Bed: 7   Bath: 4.0   Gar: 4
    Liv Area Sq Ft: 4704
       Built: 2014
    Monthly Fee: $110
       Tax: $9,493 (2024)
    Community: Verde Park Ph 1
    Single Family


    Estimated Monthly Payment: $5,476 (change assumption)
    Mortgage ($4,575) + Fees ($110) + Taxes in 2024 ($791)


    Taxes:$9,493

    Elementary School: Grassy Lake Elementary

    High School: Lake Minneola High

    Tax Year: 2024

    Middle School: East Ridge Middle


  • 15139 CANOPY COVER DR, WINTER GARDEN, FL 34787

    $699,00043 Days on yellowkey   MLS ID: O6415871

    For Sale O6415871 - 15139 CANOPY COVER DR, WINTER GARDEN, FL 34787 65 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2000
       Built: 2023
    Monthly Fee: $642
       Tax: $5,682 (2025)
    Community: Del Webb Oasis
    Single Family


    Estimated Monthly Payment: $4,946 (change assumption)
    Mortgage ($3,830) + Fees ($642) + Taxes in 2025 ($474)


    Taxes:$5,682

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15143 BLUE PEACOCK LN, WINTER GARDEN, FL 34787

    $589,00050 Days on yellowkey   MLS ID: O6414996

    REDUCED by $6,000 (1.0%) on 07/16/2026

    For Sale O6414996 - 15143 BLUE PEACOCK LN, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2420
       Built: 2024
    Monthly Fee: $96
       Tax: $8,683 (2025)
    Community: Osprey Ranch Ph 1
    Single Family


    Estimated Monthly Payment: $4,047 (change assumption)
    Mortgage ($3,227) + Fees ($96) + Taxes in 2025 ($724)


    Taxes:$8,683

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 217 W BAY ST, WINTER GARDEN, FL 34787

    $1,349,00080 Days on yellowkey   MLS ID: S5149527

    REDUCED by $46,000 (3.3%) on 07/21/2026

    For Sale S5149527 - 217 W BAY ST, WINTER GARDEN, FL 34787 89 photos

    Bed: 5   Bath: 4.0
    Liv Area Sq Ft: 2800
       Built: 2025   Tax: $5,958 (2025)
    Community: Cooper & Sewell Add
    Single Family


    Estimated Monthly Payment: $7,888 (change assumption)
    Mortgage ($7,392) + Taxes in 2025 ($497)


    Taxes:$5,958

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9218 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787

    $890,000150 Days on yellowkey   MLS ID: O6386394

    REDUCED by $9,000 (1.0%) on 07/16/2026

    For Sale O6386394 - 9218 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787 64 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3087
       Built: 2018
    Monthly Fee: $164
       Tax: $11,801 (2025)
    Community: Watermark Ph 2B
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,024 (change assumption)
    Mortgage ($4,877) + Fees ($164) + Taxes in 2025 ($983)


    Taxes:$11,801

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13856 GLYNSHEL DR, WINTER GARDEN, FL 34787

    $850,00043 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


  • 2031 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787

    $589,0004 Days on yellowkey   MLS ID: O6428109

    For Sale O6428109 - 2031 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2048
       Built: 2000
    Monthly Fee: $109
       Tax: $4,516 (2025)
    Community: Wintermere Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,713 (change assumption)
    Mortgage ($3,227) + Fees ($109) + Taxes in 2025 ($376)


    Taxes:$4,516

    Elementary School: Wheatley Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: None


  • 16802 OAKBORO ST, WINTER GARDEN, FL 34787

    $500,0007 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

    $1,500,00020 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

    $1,299,00028 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

    $689,90027 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

    $620,00029 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


  • 132 ZACHARY WADE ST, WINTER GARDEN, FL 34787

    $515,00032 Days on yellowkey   MLS ID: O6411394

    REDUCED by $10,000 (1.9%) on 07/22/2026

    For Sale O6411394 - 132 ZACHARY WADE ST, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1708
       Built: 2002
    Monthly Fee: $67
       Tax: $3,813 (2025)
    Community: Lakeview Reserve 46/149
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,207 (change assumption)
    Mortgage ($2,822) + Fees ($67) + Taxes in 2025 ($318)


    Taxes:$3,813

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview 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.