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Winter Garden Homes For Sale & Real Estate - 951 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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  • 4231 OAK LODGE WAY, WINTER GARDEN, FL 34787

    $659,9508 Days on yellowkey   MLS ID: O6416590

    For Sale O6416590 - 4231 OAK LODGE WAY, WINTER GARDEN, FL 34787 85 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2821
       Built: 2015
    Monthly Fee: $188
       Tax: $9,739 (2025)
    Community: Orchard Hills Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,616 (change assumption)
    Mortgage ($3,616) + Fees ($188) + Taxes in 2025 ($812)


    Taxes:$9,739

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 638 AUTUMN OAKS LOOP, WINTER GARDEN, FL 34787

    $594,0009 Days on yellowkey   MLS ID: G5113531

    REDUCED by $26,000 (4.2%) on 06/18/2026

    For Sale G5113531 - 638 AUTUMN OAKS LOOP, WINTER GARDEN, FL 34787 55 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2044
       Built: 2005
    Monthly Fee: $146
       Tax: $3,096 (2025)
    Community: Winter Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,659 (change assumption)
    Mortgage ($3,255) + Fees ($146) + Taxes in 2025 ($258)


    Taxes:$3,096

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14252 CREEKBED CIR, WINTER GARDEN, FL 34787

    $799,90010 Days on yellowkey   MLS ID: O6408908

    INCREASED by $900 (0.1%) on 06/17/2026

    For Sale O6408908 - 14252 CREEKBED CIR, WINTER GARDEN, FL 34787 69 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3572
       Built: 2014
    Monthly Fee: $180

    Community: Bradford Creek
    Single Family


    Estimated Monthly Payment: $4,563 (change assumption)
    Mortgage ($4,383) + Fees ($180) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15162 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787

    $639,00010 Days on yellowkey   MLS ID: O6413232

    For Sale O6413232 - 15162 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787 36 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2418
       Built: 2015   Tax: $8,787 (2025)
    Community: Signature Lakes Ph 3B-4, 3B-5 &
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,234 (change assumption)
    Mortgage ($3,501) + Taxes in 2025 ($732)


    Taxes:$8,787

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 11170 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $535,00015 Days on yellowkey   MLS ID: O6414335

    REDUCED by $30,000 (5.3%) on 06/17/2026

    For Sale O6414335 - 11170 HOLLOW BAY DR, WINTER GARDEN, FL 34787 69 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2474
       Built: 2025
    Monthly Fee: $288
       Tax: $2,389 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,419 (change assumption)
    Mortgage ($2,931) + Fees ($288) + Taxes in 2025 ($199)


    Taxes:$2,389

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17167 WRITING ALY, WINTER GARDEN, FL 34787

    $535,00039 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


  • 7841 ICELAND GULL ST, WINTER GARDEN, FL 34787

    $730,00017 Days on yellowkey   MLS ID: O6413079

    REDUCED by $15,000 (2.0%) on 06/14/2026

    For Sale O6413079 - 7841 ICELAND GULL ST, WINTER GARDEN, FL 34787 67 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2765
       Built: 2013
    Monthly Fee: $252
       Tax: $4,898 (2025)
    Community: Summerlake Pd Ph 1B-A Rep
    Single Family


    Estimated Monthly Payment: $4,660 (change assumption)
    Mortgage ($4,000) + Fees ($252) + Taxes in 2025 ($408)


    Taxes:$4,898

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1503 COLUSO DR, WINTER GARDEN, FL 34787

    $473,00028 Days on yellowkey   MLS ID: O6410109

    REDUCED by $7,000 (1.5%) on 06/12/2026

    For Sale O6410109 - 1503 COLUSO DR, WINTER GARDEN, FL 34787 42 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2187
       Built: 1988   Tax: $1,952 (2025)
    Community: Magnolia Wood Fifth Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,754 (change assumption)
    Mortgage ($2,592) + Taxes in 2025 ($163)


    Taxes:$1,952

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14359 MAGNOLIA RIDGE LOOP, WINTER GARDEN, FL 34787

    $1,008,00035 Days on yellowkey   MLS ID: O6408165

    REDUCED by $10,000 (1.0%) on 06/04/2026

    For Sale O6408165 - 14359 MAGNOLIA RIDGE LOOP, WINTER GARDEN, FL 34787 19 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3881
       Built: 2015
    Monthly Fee: $188
       Tax: $13,774 (2025)
    Community: Orchard Hills Phase 1
    Single Family


    Estimated Monthly Payment: $6,859 (change assumption)
    Mortgage ($5,523) + Fees ($188) + Taxes in 2025 ($1,148)


    Taxes:$13,774

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 217 W BAY ST, WINTER GARDEN, FL 34787

    $1,395,00042 Days on yellowkey   MLS ID: S5149527

    REDUCED by $55,000 (3.8%) on 06/15/2026

    For Sale S5149527 - 217 W BAY ST, WINTER GARDEN, FL 34787 79 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: $8,140 (change assumption)
    Mortgage ($7,644) + Taxes in 2025 ($497)


    Taxes:$5,958

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15419 UGLIS ALY, WINTER GARDEN, FL 34787

    $555,00051 Days on yellowkey   MLS ID: O6403047

    REDUCED by $10,000 (1.8%) on 06/12/2026

    For Sale O6403047 - 15419 UGLIS ALY, WINTER GARDEN, FL 34787 47 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2270
       Built: 2018
    Monthly Fee: $60
       Tax: $8,121 (2025)
    Community: Highlands/Summerlake Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $3,778 (change assumption)
    Mortgage ($3,041) + Fees ($60) + Taxes in 2025 ($677)


    Taxes:$8,121

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14280 BRAEMAR ST, WINTER GARDEN, FL 34787

    $499,00059 Days on yellowkey   MLS ID: TB8500322

    REDUCED by $40,000 (7.4%) on 06/12/2026

    For Sale TB8500322 - 14280 BRAEMAR ST, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1964
       Built: 2023
    Monthly Fee: $100
       Tax: $7,928 (2025)
    Community: Highland Rdg
    Single Family


    Estimated Monthly Payment: $3,495 (change assumption)
    Mortgage ($2,734) + Fees ($100) + Taxes in 2025 ($661)


    Taxes:$7,928

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2450 DAHLGREN WAY, WINTER GARDEN, FL 34787

    $1,700,000110 Days on yellowkey   MLS ID: TB8481106

    REDUCED by $250,000 (12.8%) on 05/20/2026

    For Sale TB8481106 - 2450 DAHLGREN WAY, WINTER GARDEN, FL 34787 68 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4365
       Built: 2007
    Monthly Fee: $225
       Tax: $8,970 (2024)
    Community: Bronsons Lndgs F & M
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,287 (change assumption)
    Mortgage ($9,315) + Fees ($225) + Taxes in 2024 ($748)


    Taxes:$8,970

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 15037 LAKE BESSIE LOOP, WINTER GARDEN, FL 34787

    $1,100,000Listed 06/19/2026 5:35PM   MLS ID: O6418541

    For Sale O6418541 - 15037 LAKE BESSIE LOOP, WINTER GARDEN, FL 34787 35 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: $7,159 (change assumption)
    Mortgage ($6,027) + 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


  • 15813 SWEET LEMON WAY, WINTER GARDEN, FL 34787

    $569,000Listed 06/19/2026 5:46PM   MLS ID: O6418559

    For Sale O6418559 - 15813 SWEET LEMON WAY, WINTER GARDEN, FL 34787 64 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2119
       Built: 2018
    Monthly Fee: $125
       Tax: $8,371 (2025)
    Community: Highlands/Summerlake Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $3,940 (change assumption)
    Mortgage ($3,118) + Fees ($125) + Taxes in 2025 ($698)


    Taxes:$8,371

    Elementary School: Summerlake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16627 SILVER BROOK WAY, WINTER GARDEN, FL 34787

    $805,2601 Day on yellowkey   MLS ID: O6418338

    0 Days Off yellowkey (back on 6/19/2026)

    For Sale O6418338 - 16627 SILVER BROOK WAY, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2656
       Built: 2026
    Monthly Fee: $152

    Community: Silverleaf
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,564 (change assumption)
    Mortgage ($4,412) + Fees ($152) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Vista Lakes Elem

    High School: Colonial High

    Tax Year: 2025

    Middle School: Odyssey Middle


  • 13086 SUNRISE HARVEST DR, WINTER GARDEN, FL 34787

    $849,0004 Days on yellowkey   MLS ID: O6415942

    For Sale O6415942 - 13086 SUNRISE HARVEST DR, WINTER GARDEN, FL 34787 57 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2835
       Built: 2025
    Monthly Fee: $140
       Tax: $2,829 (2025)
    Community: Harvest/Ovation
    Single Family


    Estimated Monthly Payment: $5,028 (change assumption)
    Mortgage ($4,652) + Fees ($140) + Taxes in 2025 ($236)


    Taxes:$2,829

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 2241 WHITE FEATHER LOOP, WINTER GARDEN, FL 34787

    $525,00020 Days on yellowkey   MLS ID: O6411576

    For Sale O6411576 - 2241 WHITE FEATHER LOOP, WINTER GARDEN, FL 34787 55 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2152
       Built: 2018
    Monthly Fee: $105
       Tax: $4,991 (2025)
    Community: Oakland Trls Ph 1
    Single Family


    Estimated Monthly Payment: $3,398 (change assumption)
    Mortgage ($2,877) + Fees ($105) + Taxes in 2025 ($416)


    Taxes:$4,991

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 16186 HONEY HARVEST ST, WINTER GARDEN, FL 34787

    $610,00023 Days on yellowkey   MLS ID: O6411495

    REDUCED by $20,000 (3.2%) on 06/12/2026

    For Sale O6411495 - 16186 HONEY HARVEST ST, WINTER GARDEN, FL 34787 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2445
       Built: 2025
    Monthly Fee: $229
       Tax: $1,614 (2025)
    Community: Harvest/Ovation Ph 2
    Single Family


    Estimated Monthly Payment: $3,706 (change assumption)
    Mortgage ($3,342) + Fees ($229) + Taxes in 2025 ($134)


    Taxes:$1,614

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 33 TIMBERCREEK PINES CIR, WINTER GARDEN, FL 34787

    $555,00030 Days on yellowkey   MLS ID: O6408941

    REDUCED by $7,000 (1.2%) on 06/13/2026

    For Sale O6408941 - 33 TIMBERCREEK PINES CIR, WINTER GARDEN, FL 34787 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1584
       Built: 2004
    Monthly Fee: $46
       Tax: $7,326 (2025)
    Community: Timbercreek Pines A B C & D
    Single Family


    Estimated Monthly Payment: $3,698 (change assumption)
    Mortgage ($3,041) + Fees ($46) + Taxes in 2025 ($610)


    Taxes:$7,326

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview 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.