REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search

Winter Garden Homes For Sale & Real Estate - 975 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

Sort:
  • 14301 WHITE MOSS WAY, WINTER GARDEN, FL 34787

    $949,99923 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


  • 15037 LAKE BESSIE LOOP, WINTER GARDEN, FL 34787

    $1,045,00033 Days on yellowkey   MLS ID: O6418541

    0 Days Off yellowkey (back on 7/20/2026)

    REDUCED by $55,000 (5.0%) on 07/06/2026

    For Sale O6418541 - 15037 LAKE BESSIE LOOP, WINTER GARDEN, FL 34787 39 photos

    Bed: 7   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3938
       Built: 2022
    Monthly Fee: $160
       Tax: $11,662 (2025)
    Community: Lakeside/Hamlin 60
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,858 (change assumption)
    Mortgage ($5,726) + Fees ($160) + Taxes in 2025 ($972)


    Taxes:$11,662

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 14051 GROVE RESORT AVE #1705, WINTER GARDEN, FL 34787

    $215,000174 Days on yellowkey   MLS ID: O6371816

    For Sale O6371816 - 14051 GROVE RESORT AVE #1705, WINTER GARDEN, FL 34787 15 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1265
       Built: 2016
    Monthly Fee: $904
       Tax: $6,487 (2024)
    Community: The Grove Resort And Spa
    Spa: No

    Condo


    Estimated Monthly Payment: $2,623 (change assumption)
    Mortgage ($1,178) + Fees ($904) + Taxes in 2024 ($541)


    Taxes:$6,487

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 14802 SPEER LAKE DR, WINTER GARDEN, FL 34787

    $1,690,0006 Days on yellowkey   MLS ID: O6425462

    1 Days Off yellowkey (back on 7/20/2026)

    For Sale O6425462 - 14802 SPEER LAKE DR, WINTER GARDEN, FL 34787 76 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3742
       Built: 2014
    Monthly Fee: $195
       Tax: $20,904 (2025)
    Community: Independence
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,197 (change assumption)
    Mortgage ($9,260) + Fees ($195) + Taxes in 2025 ($1,742)


    Taxes:$20,904

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 15806 GEM VIEW ST, WINTER GARDEN, FL 34787

    $495,00050 Days on yellowkey   MLS ID: C7526682

    For Sale C7526682 - 15806 GEM VIEW ST, WINTER GARDEN, FL 34787 37 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1574
       Built: 2024
    Monthly Fee: $725
       Tax: $6,735 (2025)
    Community: Del Webb Oasis Ph 3
    Spa: No

    Villa


    Estimated Monthly Payment: $3,998 (change assumption)
    Mortgage ($2,712) + Fees ($725) + Taxes in 2025 ($561)


    Taxes:$6,735

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7840 WINTER WREN ST, WINTER GARDEN, FL 34787

    $525,90022 Days on yellowkey   MLS ID: O6421167

    REDUCED by $4,000 (0.8%) on 07/20/2026

    For Sale O6421167 - 7840 WINTER WREN ST, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2004
       Built: 2015
    Monthly Fee: $251
       Tax: $7,385 (2025)
    Community: Summerlake Pd Ph 1B Rep
    Single Family


    Estimated Monthly Payment: $3,748 (change assumption)
    Mortgage ($2,882) + Fees ($251) + Taxes in 2025 ($615)


    Taxes:$7,385

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16461 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787

    $400,00046 Days on yellowkey   MLS ID: O6414427

    3 Days Off yellowkey (back on 7/20/2026)

    REDUCED by $15,000 (3.6%) on 07/01/2026

    For Sale O6414427 - 16461 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787 68 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1768
       Built: 2022
    Monthly Fee: $286
       Tax: $7,039 (2025)
    Community: Hawksmoor Ph 3
    Townhouse


    Estimated Monthly Payment: $3,064 (change assumption)
    Mortgage ($2,192) + Fees ($286) + Taxes in 2025 ($587)


    Taxes:$7,039

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14501 GROVE RESORT AVE #3523, WINTER GARDEN, FL 34787

    $200,00055 Days on yellowkey   MLS ID: O6411650

    FORECLOSURE O6411650 - 14501 GROVE RESORT AVE #3523, WINTER GARDEN, FL 34787 78 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1265
       Built: 2018   Tax: $6,847 (2025)
    Community: Grove Resort & Spa
    Spa: Yes

    Condo


    Estimated Monthly Payment: $1,666 (change assumption)
    Mortgage ($1,096) + Taxes in 2025 ($571)


    Taxes:$6,847

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13155 SPRING GROVE WAY, WINTER GARDEN, FL 34787

    $600,00020 Days on yellowkey   MLS ID: O6421867

    For Sale O6421867 - 13155 SPRING GROVE WAY, WINTER GARDEN, FL 34787 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2818
       Built: 2021
    Monthly Fee: $225
       Tax: $7,057 (2025)
    Community: Encore/Ovation Ph 2
    Single Family


    Estimated Monthly Payment: $4,101 (change assumption)
    Mortgage ($3,288) + Fees ($225) + Taxes in 2025 ($588)


    Taxes:$7,057

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $609,611156 Days on yellowkey   MLS ID: G5108288

    0 Days Off yellowkey (back on 4/7/2026)

    For Sale G5108288 - 17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2520
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,462 (change assumption)
    Mortgage ($3,340) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16131 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787

    $649,90034 Days on yellowkey   MLS ID: O6417701

    For Sale O6417701 - 16131 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2117
       Built: 2017
    Monthly Fee: $342
       Tax: $6,366 (2025)
    Community: Waterleigh Ph 1C
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,433 (change assumption)
    Mortgage ($3,561) + Fees ($342) + Taxes in 2025 ($530)


    Taxes:$6,366

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 944 KYLEE ALY, WINTER GARDEN, FL 34787

    $779,9004 Days on yellowkey   MLS ID: O6425976

    0 Days Off yellowkey (back on 7/20/2026)

    For Sale O6425976 - 944 KYLEE ALY, WINTER GARDEN, FL 34787 60 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2831
       Built: 2022
    Monthly Fee: $401
       Tax: $11,438 (2026)
    Community: Oakland Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,627 (change assumption)
    Mortgage ($4,273) + Fees ($401) + Taxes in 2026 ($953)


    Taxes:$11,438

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2026

    Middle School: Lakeview Middle


  • 8530 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $1,375,00047 Days on yellowkey   MLS ID: O6413249

    REDUCED by $124,000 (8.3%) on 07/20/2026

    For Sale O6413249 - 8530 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4130
       Built: 2018
    Monthly Fee: $266
       Tax: $2,479 (2025)
    Community: Waterleigh Ph 1A
    Single Family


    Estimated Monthly Payment: $8,007 (change assumption)
    Mortgage ($7,534) + Fees ($266) + Taxes in 2025 ($207)


    Taxes:$2,479

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8170 BLUEJACK OAK DR, WINTER GARDEN, FL 34787

    $445,00097 Days on yellowkey   MLS ID: O6399484

    0 Days Off yellowkey (back on 7/20/2026)

    REDUCED by $15,000 (3.3%) on 07/02/2026

    For Sale O6399484 - 8170 BLUEJACK OAK DR, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1853
       Built: 2016
    Monthly Fee: $315
       Tax: $4,738 (2025)
    Community: Summerlake Pd Ph 2C 2D 2E
    Townhouse


    Estimated Monthly Payment: $3,148 (change assumption)
    Mortgage ($2,438) + Fees ($315) + Taxes in 2025 ($395)


    Taxes:$4,738

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13019 SERENE GLADE RD, WINTER GARDEN, FL 34787

    $549,99040 Days on yellowkey   MLS ID: G5113698

    REDUCED by $20,000 (3.5%) on 06/17/2026

    For Sale G5113698 - 13019 SERENE GLADE RD, WINTER GARDEN, FL 34787 61 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2078
       Built: 2026
    Monthly Fee: $121

    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $3,135 (change assumption)
    Mortgage ($3,014) + Fees ($121) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 5320 LAKE VIRGINIA ST, WINTER GARDEN, FL 34787

    $695,9907 Days on yellowkey   MLS ID: O6424081

    For Sale O6424081 - 5320 LAKE VIRGINIA ST, WINTER GARDEN, FL 34787 67 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3366
       Built: 2024
    Monthly Fee: $176
       Tax: $10,233 (2025)
    Community: Lakeside/Hamlin
    Single Family


    Estimated Monthly Payment: $4,842 (change assumption)
    Mortgage ($3,814) + Fees ($176) + Taxes in 2025 ($853)


    Taxes:$10,233

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1642 CHANDELLE LN, WINTER GARDEN, FL 34787

    $689,90021 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


  • 17167 WRITING ALY, WINTER GARDEN, FL 34787

    $535,00071 Days on yellowkey   MLS ID: O6406920

    For Sale O6406920 - 17167 WRITING ALY, WINTER GARDEN, FL 34787 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2486
       Built: 2020
    Monthly Fee: $110
       Tax: $7,916 (2025)
    Community: Storey Grove Ph 1B
    Single Family


    Estimated Monthly Payment: $3,701 (change assumption)
    Mortgage ($2,931) + Fees ($110) + Taxes in 2025 ($660)


    Taxes:$7,916

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14629 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787

    $484,90020 Days on yellowkey   MLS ID: O6421797

    REDUCED by $8,000 (1.6%) on 07/20/2026

    For Sale O6421797 - 14629 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2223
       Built: 2012
    Monthly Fee: $242
       Tax: $8,151 (2025)
    Community: Summerlake Pd Ph 01B
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,578 (change assumption)
    Mortgage ($2,657) + Fees ($242) + Taxes in 2025 ($679)


    Taxes:$8,151

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14755 MASTHEAD LANDING CIR, WINTER GARDEN, FL 34787

    $549,90069 Days on yellowkey   MLS ID: O6408082

    REDUCED by $15,100 (2.7%) on 07/20/2026

    For Sale O6408082 - 14755 MASTHEAD LANDING CIR, WINTER GARDEN, FL 34787 17 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2258
       Built: 2004
    Monthly Fee: $253
       Tax: $8,397 (2025)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,966 (change assumption)
    Mortgage ($3,013) + Fees ($253) + Taxes in 2025 ($700)


    Taxes:$8,397

    Elementary School: Whispering Oak Elem

    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.