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Winter Garden Homes For Sale & Real Estate - 705 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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  • 7036 TWILIGHT BAY DR, WINTER GARDEN, FL 34787

    $524,900167 Days on yellowkey   MLS ID: S5137842

    For Sale S5137842 - 7036 TWILIGHT BAY DR, WINTER GARDEN, FL 34787 29 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1914
       Built: 2023
    Monthly Fee: $180
       Tax: $750 (2023)
    Community: Mezzano
    Townhouse


    Estimated Monthly Payment: $3,119 (change assumption)
    Mortgage ($2,876) + Fees ($180) + Taxes in 2023 ($63)


    Taxes:$750

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2023

    Middle School: Horizon West Middle School


  • 1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787

    $519,900233 Days on yellowkey   MLS ID: S5133690

    For Sale S5133690 - 1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2035
       Built: 2001
    Monthly Fee: $33
       Tax: $6,403 (2024)
    Community: Tuscany Ph 02
    Single Family


    Estimated Monthly Payment: $3,415 (change assumption)
    Mortgage ($2,849) + Fees ($33) + Taxes in 2024 ($534)


    Taxes:$6,403

    Elementary School: Maxey Elem

    High School: Ocoee High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 3467 BUOY CIR, WINTER GARDEN, FL 34787

    $629,000105 Days on yellowkey   MLS ID: G5106141

    For Sale G5106141 - 3467 BUOY CIR, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2610
       Built: 2020
    Monthly Fee: $152
       Tax: $5,995 (2025)
    Community: Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $4,098 (change assumption)
    Mortgage ($3,446) + Fees ($152) + Taxes in 2025 ($500)


    Taxes:$5,995

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16838 OLD HIGHWAY 50, WINTER GARDEN, FL 34787

    $875,0004 Days on yellowkey   MLS ID: O6399357

    For Sale O6399357 - 16838 OLD HIGHWAY 50, WINTER GARDEN, FL 34787 51 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1795
       Built: 1972   Tax: $4,787 (2025)
    Community: Lake Highlands 23-22-26
    Mobile Home


    Estimated Monthly Payment: $5,193 (change assumption)
    Mortgage ($4,794) + Taxes in 2025 ($399)


    Taxes:$4,787

    Elementary School: Grassy Lake Elementary

    High School: Lake Minneola High

    Tax Year: 2025

    Middle School: East Ridge Middle


  • 671 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $1,325,00041 Days on yellowkey   MLS ID: O6383438

    0 Days Off yellowkey (back on 4/17/2026)

    REDUCED by $25,000 (1.9%) on 04/08/2026

    For Sale O6383438 - 671 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 62 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4490
       Built: 2019
    Monthly Fee: $300
       Tax: $12,519 (2024)
    Community: Canopy Oaks Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,603 (change assumption)
    Mortgage ($7,260) + Fees ($300) + Taxes in 2024 ($1,043)


    Taxes:$12,519

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 628 ORANGE BELT LOOP, WINTER GARDEN, FL 34787

    $525,00039 Days on yellowkey   MLS ID: O6389653

    0 Days Off yellowkey (back on 4/11/2026)

    REDUCED by $4,900 (0.9%) on 04/04/2026

    For Sale O6389653 - 628 ORANGE BELT LOOP, WINTER GARDEN, FL 34787 68 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1850
       Built: 2018
    Monthly Fee: $336
       Tax: $3,620 (2025)
    Community: Heritage At Plant Street Community Assoc
    Spa: No

    Townhouse


    Estimated Monthly Payment: $3,514 (change assumption)
    Mortgage ($2,877) + Fees ($336) + Taxes in 2025 ($302)


    Taxes:$3,620

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14626 BLACK QUILL DR, WINTER GARDEN, FL 34787

    $799,9003 Days on yellowkey   MLS ID: O6399975

    For Sale O6399975 - 14626 BLACK QUILL DR, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2907
       Built: 2016
    Monthly Fee: $215
       Tax: $6,816 (2025)
    Community: Overlook At Hamlin
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,166 (change assumption)
    Mortgage ($4,383) + Fees ($215) + Taxes in 2025 ($568)


    Taxes:$6,816

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 213 W TILDEN ST, WINTER GARDEN, FL 34787

    $765,00067 Days on yellowkey   MLS ID: O6381848

    0 Days Off yellowkey (back on 3/2/2026)

    For Sale O6381848 - 213 W TILDEN ST, WINTER GARDEN, FL 34787 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2151
       Built: 1972   Tax: $8,105 (2025)
    Community: Westlake Manor 1St Add
    Single Family


    Estimated Monthly Payment: $4,867 (change assumption)
    Mortgage ($4,192) + Taxes in 2025 ($675)


    Taxes:$8,105

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12043 HOLYSTONE ST, WINTER GARDEN, FL 34787

    $385,000224 Days on yellowkey   MLS ID: O6339950

    1 Days Off yellowkey (back on 4/17/2026)

    REDUCED by $5,000 (1.3%) on 04/01/2026

    For Sale O6339950 - 12043 HOLYSTONE ST, WINTER GARDEN, FL 34787 38 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1568
       Built: 2023
    Monthly Fee: $259
       Tax: $6,198 (2024)
    Community: Waterleigh Ph 4A
    Townhouse


    Estimated Monthly Payment: $2,885 (change assumption)
    Mortgage ($2,110) + Fees ($259) + Taxes in 2024 ($516)


    Taxes:$6,198

    Elementary School: Waterbridge Elem

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 2202 ROMANUM DR, WINTER GARDEN, FL 34787

    $585,0003 Days on yellowkey   MLS ID: O6398743

    For Sale O6398743 - 2202 ROMANUM DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1889
       Built: 2015
    Monthly Fee: $211
       Tax: $3,839 (2025)
    Community: Alexander Ridge
    Single Family


    Estimated Monthly Payment: $3,736 (change assumption)
    Mortgage ($3,205) + Fees ($211) + Taxes in 2025 ($320)


    Taxes:$3,839

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15543 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787

    $645,900548 Days on yellowkey   MLS ID: O6250356

    REDUCED by $3,900 (0.6%) on 04/17/2026

    For Sale O6250356 - 15543 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3359
       Built: 2001
    Monthly Fee: $233
       Tax: $8,538 (2023)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,484 (change assumption)
    Mortgage ($3,539) + Fees ($233) + Taxes in 2023 ($712)


    Taxes:$8,538

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2023

    Middle School: SunRidge Middle


  • 9936 GOLDEN LAGOON ALY, WINTER GARDEN, FL 34787

    $475,00039 Days on yellowkey   MLS ID: O6390052

    1 Days Off yellowkey (back on 4/16/2026)

    For Sale O6390052 - 9936 GOLDEN LAGOON ALY, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1816
       Built: 2018
    Monthly Fee: $292
       Tax: $3,994 (2025)
    Community: Waterleigh Phase 2B
    Townhouse


    Estimated Monthly Payment: $3,228 (change assumption)
    Mortgage ($2,603) + Fees ($292) + Taxes in 2025 ($333)


    Taxes:$3,994

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1670 E SPRING RIDGE CIR, WINTER GARDEN, FL 34787

    $414,90053 Days on yellowkey   MLS ID: O6385776

    0 Days Off yellowkey (back on 4/17/2026)

    REDUCED by $5,000 (1.2%) on 04/07/2026

    For Sale O6385776 - 1670 E SPRING RIDGE CIR, WINTER GARDEN, FL 34787 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1699
       Built: 1995
    Monthly Fee: $50
       Tax: $1,352 (2025)
    Community: Crown Point Springs Ut 2
    Single Family


    Estimated Monthly Payment: $2,436 (change assumption)
    Mortgage ($2,273) + Fees ($50) + Taxes in 2025 ($113)


    Taxes:$1,352

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 7343 TWILIGHT BAY DR, WINTER GARDEN, FL 34787

    $599,9995 Days on yellowkey   MLS ID: S5147747

    For Sale S5147747 - 7343 TWILIGHT BAY DR, WINTER GARDEN, FL 34787 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1975
       Built: 2017
    Monthly Fee: $249
       Tax: $5,164 (2025)
    Community: Lakeview Pointe/Horizon West P
    Single Family


    Estimated Monthly Payment: $3,967 (change assumption)
    Mortgage ($3,288) + Fees ($249) + Taxes in 2025 ($430)


    Taxes:$5,164

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787

    $568,00083 Days on yellowkey   MLS ID: NS1087076

    REDUCED by $5,000 (0.9%) on 04/17/2026

    For Sale NS1087076 - 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787 23 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2474
       Built: 2024
    Monthly Fee: $291
       Tax: $2,273 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $3,593 (change assumption)
    Mortgage ($3,112) + Fees ($291) + Taxes in 2024 ($189)


    Taxes:$2,273

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • WINTER GARDEN, FL 34787

    $619,0003 Days on yellowkey   MLS ID: O6399369

    For Sale O6399369 - WINTER GARDEN, FL 34787 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1827
       Built: 2001
    Monthly Fee: $320
       Tax: $4,811 (2025)
    Community: Woodbridge On Green
    Single Family


    Estimated Monthly Payment: $4,113 (change assumption)
    Mortgage ($3,392) + Fees ($320) + Taxes in 2025 ($401)


    Taxes:$4,811

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 16788 MUSKGRASS DR, WINTER GARDEN, FL 34787

    $1,600,00044 Days on yellowkey   MLS ID: O6388174

    For Sale O6388174 - 16788 MUSKGRASS DR, WINTER GARDEN, FL 34787 77 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4733
       Built: 2025
    Monthly Fee: $86

    Community: Lake Star At Ovation Phase 1B
    Single Family


    Estimated Monthly Payment: $8,853 (change assumption)
    Mortgage ($8,767) + Fees ($86) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 4918 WILDWOOD POINTE RD, WINTER GARDEN, FL 34787

    $680,000309 Days on yellowkey   MLS ID: S5129072

    For Sale S5129072 - 4918 WILDWOOD POINTE RD, WINTER GARDEN, FL 34787 33 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2868
       Built: 2015
    Monthly Fee: $172
       Tax: $10,554 (2024)
    Community: Orchard Hills Ph 2
    Single Family


    Estimated Monthly Payment: $4,777 (change assumption)
    Mortgage ($3,726) + Fees ($172) + Taxes in 2024 ($880)


    Taxes:$10,554

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 14680 BLACK CHERRY TRL, WINTER GARDEN, FL 34787

    $629,00017 Days on yellowkey   MLS ID: O6394614

    0 Days Off yellowkey (back on 4/17/2026)

    For Sale O6394614 - 14680 BLACK CHERRY TRL, WINTER GARDEN, FL 34787 42 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2233
       Built: 2006
    Monthly Fee: $186
       Tax: $8,692 (2025)
    Community: Signature Lakes Prcl 01C
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,357 (change assumption)
    Mortgage ($3,446) + Fees ($186) + Taxes in 2025 ($724)


    Taxes:$8,692

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14501 GROVE RESORT AVE #1742, WINTER GARDEN, FL 34787

    $209,900207 Days on yellowkey   MLS ID: O6346817

    For Sale O6346817 - 14501 GROVE RESORT AVE #1742, WINTER GARDEN, FL 34787 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1396
       Built: 2016
    Monthly Fee: $997
       Tax: $6,945 (2024)
    Community: Grove Resort And Spa
    Condo


    Estimated Monthly Payment: $2,726 (change assumption)
    Mortgage ($1,150) + Fees ($997) + Taxes in 2024 ($579)


    Taxes:$6,945

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




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.