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Winter Garden Homes For Sale & Real Estate - 984 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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  • 1286 WINTER GREEN WAY, WINTER GARDEN, FL 34787

    $219,900251 Days on yellowkey   MLS ID: G5104510

    REDUCED by $10,000 (4.3%) on 07/21/2026

    For Sale G5104510 - 1286 WINTER GREEN WAY, WINTER GARDEN, FL 34787 30 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1144
       Built: 1985
    Monthly Fee: $63
       Tax: $1,159 (2024)
    Community: Village Grove Ph 02
    Townhouse


    Estimated Monthly Payment: $1,364 (change assumption)
    Mortgage ($1,205) + Fees ($63) + Taxes in 2024 ($97)


    Taxes:$1,159

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16161 MANGROVE RD, WINTER GARDEN, FL 34787

    $499,90017 Days on yellowkey   MLS ID: O6420311

    REDUCED by $15,100 (2.9%) on 07/21/2026

    For Sale O6420311 - 16161 MANGROVE RD, WINTER GARDEN, FL 34787 48 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2200
       Built: 2021
    Monthly Fee: $257
       Tax: $6,775 (2025)
    Community: Waterleigh Ph 3B 3C &3D
    Single Family


    Estimated Monthly Payment: $3,561 (change assumption)
    Mortgage ($2,739) + Fees ($257) + Taxes in 2025 ($565)


    Taxes:$6,775

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 353 LAKE AMBERLEIGH DR, WINTER GARDEN, FL 34787

    $730,0004 Days on yellowkey   MLS ID: O6426485

    For Sale O6426485 - 353 LAKE AMBERLEIGH DR, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2762
       Built: 2003
    Monthly Fee: $117
       Tax: $8,064 (2025)
    Community: Amberleigh 47/7
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,789 (change assumption)
    Mortgage ($4,000) + Fees ($117) + Taxes in 2025 ($672)


    Taxes:$8,064

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 13043 SERENE GLADE RD, WINTER GARDEN, FL 34787

    $589,0006 Days on yellowkey   MLS ID: G5115242

    For Sale G5115242 - 13043 SERENE GLADE RD, WINTER GARDEN, FL 34787 25 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2083
       Built: 2024
    Monthly Fee: $160
       Tax: $2,147 (2025)
    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $3,566 (change assumption)
    Mortgage ($3,227) + Fees ($160) + Taxes in 2025 ($179)


    Taxes:$2,147

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: None


  • 15372 SUGAR CITRUS DR, WINTER GARDEN, FL 34787

    $750,0004 Days on yellowkey   MLS ID: O6425356

    For Sale O6425356 - 15372 SUGAR CITRUS DR, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3100
       Built: 2019
    Monthly Fee: $142
       Tax: $9,789 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $5,067 (change assumption)
    Mortgage ($4,109) + Fees ($142) + Taxes in 2025 ($816)


    Taxes:$9,789

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 7531 SPRING VALLEY ST, WINTER GARDEN, FL 34787

    $551,27544 Days on yellowkey   MLS ID: G5113580

    2 Days Off yellowkey (back on 6/12/2026)

    For Sale G5113580 - 7531 SPRING VALLEY ST, 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: $3,171 (change assumption)
    Mortgage ($3,021) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9218 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787

    $890,000146 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


  • 18344 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $660,000214 Days on yellowkey   MLS ID: S5140531

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

    REDUCED by $65,000 (9.0%) on 07/14/2026

    SHORT SALE S5140531 - 18344 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2924
       Built: 2023
    Monthly Fee: $300
       Tax: $1,706 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,059 (change assumption)
    Mortgage ($3,616) + Fees ($300) + Taxes in 2024 ($142)


    Taxes:$1,706

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 8114 SAYINGS DR, WINTER GARDEN, FL 34787

    $699,99092 Days on yellowkey   MLS ID: O6401941

    REDUCED by $29,010 (4.0%) on 07/20/2026

    For Sale O6401941 - 8114 SAYINGS DR, WINTER GARDEN, FL 34787 56 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3284
       Built: 2023
    Monthly Fee: $221
       Tax: $9,107 (2025)
    Community: Storey Grove Ph 4
    Single Family


    Estimated Monthly Payment: $4,815 (change assumption)
    Mortgage ($3,835) + Fees ($221) + Taxes in 2025 ($759)


    Taxes:$9,107

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 925 EASLEY AVE, WINTER GARDEN, FL 34787

    $1,165,00039 Days on yellowkey   MLS ID: O6412977

    REDUCED by $10,000 (0.9%) on 07/20/2026

    For Sale O6412977 - 925 EASLEY AVE, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2667
       Built: 2016
    Monthly Fee: $208
       Tax: $12,692 (2025)
    Community: Oakland Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,649 (change assumption)
    Mortgage ($6,383) + Fees ($208) + Taxes in 2025 ($1,058)


    Taxes:$12,692

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15037 LAKE BESSIE LOOP, WINTER GARDEN, FL 34787

    $1,045,00035 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

    $215,000176 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

    $1,690,0008 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


  • 7840 WINTER WREN ST, WINTER GARDEN, FL 34787

    $525,90024 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

    $400,00048 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

    $200,00057 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


  • 17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $609,611158 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

    $649,90036 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

    $779,9006 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


  • 8170 BLUEJACK OAK DR, WINTER GARDEN, FL 34787

    $445,00099 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




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.