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Winter Garden Single Family Homes For Sale - 732 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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  • 11277 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $899,99029 Days on yellowkey   MLS ID: O6419923

    1 Days Off yellowkey (back on 7/23/2026)

    REDUCED by $15,000 (1.6%) on 07/02/2026

    For Sale O6419923 - 11277 HOLLOW BAY DR, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3327
       Built: 2025
    Monthly Fee: $208
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,305 (change assumption)
    Mortgage ($4,931) + Fees ($208) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 20 E DIVISION ST, WINTER GARDEN, FL 34787

    $1,080,00049 Days on yellowkey   MLS ID: O6413659

    REDUCED by $40,000 (3.6%) on 07/23/2026

    For Sale O6413659 - 20 E DIVISION ST, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2729
       Built: 1959   Tax: $7,197 (2025)
    Community: Winter Garden Shores First Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,517 (change assumption)
    Mortgage ($5,918) + Taxes in 2025 ($600)


    Taxes:$7,197

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16827 EVERMORE ALLEY, WINTER GARDEN, FL 34787

    $525,0901 Day on yellowkey   MLS ID: O6427521

    For Sale O6427521 - 16827 EVERMORE ALLEY, WINTER GARDEN, FL 34787 20 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1628
       Built: 2026
    Monthly Fee: $152

    Community: Silverleaf Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,029 (change assumption)
    Mortgage ($2,877) + Fees ($152) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Vista Lakes Elem

    High School: Colonial High

    Tax Year: 2025

    Middle School: Odyssey Middle


  • 16803 EVERMORE ALLEY, WINTER GARDEN, FL 34787

    $537,2901 Day on yellowkey   MLS ID: O6427359

    For Sale O6427359 - 16803 EVERMORE ALLEY, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1896
       Built: 2026
    Monthly Fee: $152
       Tax: $1,372 (2025)
    Community: Silverleaf Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,210 (change assumption)
    Mortgage ($2,944) + Fees ($152) + Taxes in 2025 ($114)


    Taxes:$1,372

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 11341 BOURBON ROSE CIR, WINTER GARDEN, FL 34787

    $936,0631 Day on yellowkey   MLS ID: O6427362

    For Sale O6427362 - 11341 BOURBON ROSE CIR, WINTER GARDEN, FL 34787 15 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 2974
       Built: 2026
    Monthly Fee: $426

    Community: Esplanade At Mckinnon Groves
    Single Family


    Estimated Monthly Payment: $5,555 (change assumption)
    Mortgage ($5,129) + Fees ($426) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 16968 HAMLIN OASIS LOOP, WINTER GARDEN, FL 34787

    $570,0001 Day on yellowkey   MLS ID: O6427350

    For Sale O6427350 - 16968 HAMLIN OASIS LOOP, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2088
       Built: 2025
    Monthly Fee: $210
       Tax: $2,525 (2025)
    Community: Hamlin Pointe
    Single Family


    Estimated Monthly Payment: $3,544 (change assumption)
    Mortgage ($3,123) + Fees ($210) + Taxes in 2025 ($210)


    Taxes:$2,525

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 215 S HIGHLAND AVE, WINTER GARDEN, FL 34787

    $1,099,0002 Days on yellowkey   MLS ID: S5154193

    INCREASED by $1,097,901 (99900.0%) on 07/23/2026

    For Sale S5154193 - 215 S HIGHLAND AVE, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2652
       Built: 2020   Tax: $12,866 (2026)
    Community: Downtown Winter Garden
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,094 (change assumption)
    Mortgage ($6,022) + Taxes in 2026 ($1,072)


    Taxes:$12,866

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2026

    Middle School: Lakeview Middle


  • 17073 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $566,8803 Days on yellowkey   MLS ID: G5115376

    0 Days Off yellowkey (back on 7/21/2026)

    For Sale G5115376 - 17073 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,256 (change assumption)
    Mortgage ($3,106) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


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

    $2,125,0001 Day 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


  • 15367 SHONAN GOLD DR, WINTER GARDEN, FL 34787

    $925,0001 Day on yellowkey   MLS ID: O6426934

    For Sale O6426934 - 15367 SHONAN GOLD DR, WINTER GARDEN, FL 34787 57 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3002
       Built: 2017
    Monthly Fee: $425
       Tax: $10,788 (2025)
    Community: Hamlin Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,392 (change assumption)
    Mortgage ($5,068) + Fees ($425) + Taxes in 2025 ($899)


    Taxes:$10,788

    Elementary School: Keene Crossing Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 15068 LEBEAU LOOP, WINTER GARDEN, FL 34787

    $659,0002 Days on yellowkey   MLS ID: O6424514

    For Sale O6424514 - 15068 LEBEAU LOOP, WINTER GARDEN, FL 34787 92 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3266
       Built: 2022
    Monthly Fee: $101
       Tax: $10,150 (2025)
    Community: Winding Bay Ph 3
    Single Family


    Estimated Monthly Payment: $4,558 (change assumption)
    Mortgage ($3,611) + Fees ($101) + Taxes in 2025 ($846)


    Taxes:$10,150

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15130 OVATION DR, WINTER GARDEN, FL 34787

    $821,00051 Days on yellowkey   MLS ID: O6413647

    REDUCED by $19,000 (2.3%) on 07/23/2026

    For Sale O6413647 - 15130 OVATION DR, WINTER GARDEN, FL 34787 55 photos

    Bed: 7   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4688
       Built: 2009
    Monthly Fee: $167
       Tax: $6,472 (2025)
    Community: Belle Meade Ph 02 H
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,205 (change assumption)
    Mortgage ($4,499) + Fees ($167) + Taxes in 2025 ($539)


    Taxes:$6,472

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16012 MICELLI DR, WINTER GARDEN, FL 34787

    $599,000165 Days on yellowkey   MLS ID: TB8472370

    REDUCED by $85,000 (12.4%) on 07/10/2026

    For Sale TB8472370 - 16012 MICELLI DR, WINTER GARDEN, FL 34787 77 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2248
       Built: 2021
    Monthly Fee: $101
       Tax: $7,755 (2024)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $4,029 (change assumption)
    Mortgage ($3,282) + Fees ($101) + Taxes in 2024 ($646)


    Taxes:$7,755

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 9572 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787

    $859,9003 Days on yellowkey   MLS ID: O6426624

    For Sale O6426624 - 9572 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787 45 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2018
    Monthly Fee: $245
       Tax: $9,486 (2025)
    Community: Waterleigh Ph 2B
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,747 (change assumption)
    Mortgage ($4,712) + Fees ($245) + Taxes in 2025 ($790)


    Taxes:$9,486

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 217 W BAY ST, WINTER GARDEN, FL 34787

    $1,349,00076 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


  • 15555 PANTHER LAKE DR, WINTER GARDEN, FL 34787

    $2,075,00098 Days on yellowkey   MLS ID: O6400010

    0 Days Off yellowkey (back on 7/22/2026)

    REDUCED by $25,000 (1.2%) on 06/22/2026

    For Sale O6400010 - 15555 PANTHER LAKE DR, WINTER GARDEN, FL 34787 90 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4342
       Built: 2016
    Monthly Fee: $431
       Tax: $28,576 (2025)
    Community: Lakeshore Preserve Ph 1
    Single Family


    Estimated Monthly Payment: $14,182 (change assumption)
    Mortgage ($11,370) + Fees ($431) + Taxes in 2025 ($2,381)


    Taxes:$28,576

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 921 BENDING OAK TRL, WINTER GARDEN, FL 34787

    $529,90077 Days on yellowkey   MLS ID: O6405328

    REDUCED by $15,000 (2.8%) on 07/22/2026

    For Sale O6405328 - 921 BENDING OAK TRL, WINTER GARDEN, FL 34787 66 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2517
       Built: 2012
    Monthly Fee: $125
       Tax: $3,791 (2025)
    Community: Oaks/Brandy Lake 01 Rep A & B
    Single Family


    Estimated Monthly Payment: $3,344 (change assumption)
    Mortgage ($2,903) + Fees ($125) + Taxes in 2025 ($316)


    Taxes:$3,791

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14779 MCCLANE RD, WINTER GARDEN, FL 34787

    $899,0006 Days on yellowkey   MLS ID: O6426346

    For Sale O6426346 - 14779 MCCLANE RD, WINTER GARDEN, FL 34787 39 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3118
       Built: 2018
    Monthly Fee: $212
       Tax: $10,367 (2025)
    Community: Oxford Chase
    Single Family


    Estimated Monthly Payment: $6,002 (change assumption)
    Mortgage ($4,926) + Fees ($212) + Taxes in 2025 ($864)


    Taxes:$10,367

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15537 MANGO ISLE ST, WINTER GARDEN, FL 34787

    $690,00058 Days on yellowkey   MLS ID: S5150619

    REDUCED by $21,000 (3.0%) on 07/09/2026

    For Sale S5150619 - 15537 MANGO ISLE ST, WINTER GARDEN, FL 34787 60 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2909
       Built: 2021
    Monthly Fee: $267
       Tax: $10,430 (2025)
    Community: Waterleigh Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $4,917 (change assumption)
    Mortgage ($3,781) + Fees ($267) + Taxes in 2025 ($869)


    Taxes:$10,430

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 13061 SUNRISE HARVEST DR, WINTER GARDEN, FL 34787

    $779,0009 Days on yellowkey   MLS ID: O6423162

    REDUCED by $20,500 (2.6%) on 07/22/2026

    For Sale O6423162 - 13061 SUNRISE HARVEST DR, WINTER GARDEN, FL 34787 29 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2993
       Built: 2025
    Monthly Fee: $124
       Tax: $9,772 (2025)
    Community: Harvest/Ovation
    Single Family


    Estimated Monthly Payment: $5,207 (change assumption)
    Mortgage ($4,268) + Fees ($124) + Taxes in 2025 ($814)


    Taxes:$9,772

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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.