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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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  • 8266 PURPLE SANDPIPER AVE, WINTER GARDEN, FL 34787

    $639,00022 Days on yellowkey   MLS ID: O6411387

    For Sale O6411387 - 8266 PURPLE SANDPIPER AVE, WINTER GARDEN, FL 34787 57 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2274
       Built: 2018
    Monthly Fee: $252
       Tax: $5,852 (2025)
    Community: Summerlake Pd Ph 4B
    Single Family


    Estimated Monthly Payment: $4,241 (change assumption)
    Mortgage ($3,501) + Fees ($252) + Taxes in 2025 ($488)


    Taxes:$5,852

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 11 WINDTREE LN #B, WINTER GARDEN, FL 34787

    $195,00032 Days on yellowkey   MLS ID: O6409169

    1 Days Off yellowkey (back on 6/18/2026)

    For Sale O6409169 - 11 WINDTREE LN #B, WINTER GARDEN, FL 34787 33 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 918
       Built: 1983
    Monthly Fee: $300
       Tax: $2,664 (2025)
    Community: Windtree Gardens Condo Ph 01
    Condo


    Estimated Monthly Payment: $1,590 (change assumption)
    Mortgage ($1,068) + Fees ($300) + Taxes in 2025 ($222)


    Taxes:$2,664

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9652 AMBER CHESTNUT WAY, WINTER GARDEN, FL 34787

    $430,00031 Days on yellowkey   MLS ID: O6409704

    REDUCED by $5,000 (1.1%) on 06/18/2026

    For Sale O6409704 - 9652 AMBER CHESTNUT WAY, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1948
       Built: 2019
    Monthly Fee: $245
       Tax: $5,389 (2024)
    Community: Watermark Ph 3
    Townhouse


    Estimated Monthly Payment: $3,050 (change assumption)
    Mortgage ($2,356) + Fees ($245) + Taxes in 2024 ($449)


    Taxes:$5,389

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 22 WINDTREE LN #203, WINTER GARDEN, FL 34787

    $169,900193 Days on yellowkey   MLS ID: S5139914

    REDUCED by $10,000 (5.6%) on 06/18/2026

    For Sale S5139914 - 22 WINDTREE LN #203, WINTER GARDEN, FL 34787 30 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 918
       Built: 1983
    Monthly Fee: $300
       Tax: $875 (2025)
    Community: Windtree Gardens Condo Ph 01
    Condo


    Estimated Monthly Payment: $1,304 (change assumption)
    Mortgage ($931) + Fees ($300) + Taxes in 2025 ($73)


    Taxes:$875

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16776 BROADWATER AVE, WINTER GARDEN, FL 34787

    $1,299,90038 Days on yellowkey   MLS ID: O6407043

    1 Days Off yellowkey (back on 6/18/2026)

    REDUCED by $24,100 (1.8%) on 05/27/2026

    For Sale O6407043 - 16776 BROADWATER AVE, WINTER GARDEN, FL 34787 75 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3713
       Built: 2018
    Monthly Fee: $383
       Tax: $9,438 (2025)
    Community: Waterside/Johns Lk-Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,292 (change assumption)
    Mortgage ($7,123) + Fees ($383) + Taxes in 2025 ($787)


    Taxes:$9,438

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 6316 MANUSCRIPT ST, WINTER GARDEN, FL 34787

    $619,0007 Days on yellowkey   MLS ID: O6409661

    For Sale O6409661 - 6316 MANUSCRIPT ST, WINTER GARDEN, FL 34787 32 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2608
       Built: 2011
    Monthly Fee: $195
       Tax: $8,654 (2025)
    Community: Signature Lakes Ph 02 A B H I J
    Single Family


    Estimated Monthly Payment: $4,308 (change assumption)
    Mortgage ($3,392) + Fees ($195) + Taxes in 2025 ($721)


    Taxes:$8,654

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 14501 GROVE RESORT AVE #1114, WINTER GARDEN, FL 34787

    $239,50062 Days on yellowkey   MLS ID: O6400258

    REDUCED by $30,000 (11.1%) on 06/18/2026

    For Sale O6400258 - 14501 GROVE RESORT AVE #1114, WINTER GARDEN, FL 34787 51 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1544
       Built: 2016
    Monthly Fee: $904
       Tax: $7,003 (2025)
    Community: Grove Resort And Spa
    Condo


    Estimated Monthly Payment: $2,800 (change assumption)
    Mortgage ($1,312) + Fees ($904) + Taxes in 2025 ($584)


    Taxes:$7,003

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16827 SANCTUARY DR, WINTER GARDEN, FL 34787

    $998,00056 Days on yellowkey   MLS ID: S5148416

    For Sale S5148416 - 16827 SANCTUARY DR, WINTER GARDEN, FL 34787 64 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2281
       Built: 2020
    Monthly Fee: $165
       Tax: $6,024 (2025)
    Community: Sanctuary/Twin Waters
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,135 (change assumption)
    Mortgage ($5,468) + Fees ($165) + Taxes in 2025 ($502)


    Taxes:$6,024

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 420 E CYPRESS ST, WINTER GARDEN, FL 34787

    $420,00019 Days on yellowkey   MLS ID: O6412414

    REDUCED by $5,000 (1.2%) on 06/18/2026

    For Sale O6412414 - 420 E CYPRESS ST, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1616
       Built: 1950   Tax: $5,517 (2025)
    Community: Overstreet Crate
    Single Family


    Estimated Monthly Payment: $2,761 (change assumption)
    Mortgage ($2,301) + Taxes in 2025 ($460)


    Taxes:$5,517

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 4620 GLIDING WAVE ST, WINTER GARDEN, FL 34787

    $539,000148 Days on yellowkey   MLS ID: O6370772

    REDUCED by $36,000 (6.3%) on 06/18/2026

    For Sale O6370772 - 4620 GLIDING WAVE ST, WINTER GARDEN, FL 34787 86 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2184
       Built: 2021
    Monthly Fee: $136
       Tax: $8,224 (2025)
    Community: Lakeview Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $3,775 (change assumption)
    Mortgage ($2,953) + Fees ($136) + Taxes in 2025 ($685)


    Taxes:$8,224

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 15506 HONEY MANDARIN WAY, WINTER GARDEN, FL 34787

    $894,000281 Days on yellowkey   MLS ID: O6343579

    REDUCED by $5,000 (0.6%) on 06/05/2026

    For Sale O6343579 - 15506 HONEY MANDARIN WAY, WINTER GARDEN, FL 34787 42 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3408
       Built: 2018
    Monthly Fee: $110
       Tax: $8,619 (2024)
    Community: Highlands/Summerlake Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $5,727 (change assumption)
    Mortgage ($4,899) + Fees ($110) + Taxes in 2024 ($718)


    Taxes:$8,619

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 214 S WOODLAND ST, WINTER GARDEN, FL 34787

    $800,00017 Days on yellowkey   MLS ID: O6413395

    For Sale O6413395 - 214 S WOODLAND ST, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2868
       Built: 1925   Tax: $2,450 (2025)
    Community: Fries Winter Garden
    Single Family


    Estimated Monthly Payment: $4,588 (change assumption)
    Mortgage ($4,383) + Taxes in 2025 ($204)


    Taxes:$2,450

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 3262 HANGING TIDE ST, WINTER GARDEN, FL 34787

    $750,000158 Days on yellowkey   MLS ID: S5141634

    For Sale S5141634 - 3262 HANGING TIDE ST, WINTER GARDEN, FL 34787 63 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3663
       Built: 2021
    Monthly Fee: $132
       Tax: $10,508 (2025)
    Community: Lakeview Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $5,117 (change assumption)
    Mortgage ($4,109) + Fees ($132) + Taxes in 2025 ($876)


    Taxes:$10,508

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 9849 LOST CREEK DR, WINTER GARDEN, FL 34787

    $990,000576 Days on yellowkey   MLS ID: O6258009

    1 Days Off yellowkey (back on 6/18/2026)

    For Sale O6258009 - 9849 LOST CREEK DR, WINTER GARDEN, FL 34787 57 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3910
       Built: 2021
    Monthly Fee: $250
       Tax: $10,950 (2023)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,587 (change assumption)
    Mortgage ($5,425) + Fees ($250) + Taxes in 2023 ($913)


    Taxes:$10,950

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2023

    Middle School: Water Spring Middle


  • 12959 HARVEST RAIN AVE, WINTER GARDEN, FL 34787

    $750,0004 Days on yellowkey   MLS ID: O6417449

    For Sale O6417449 - 12959 HARVEST RAIN AVE, WINTER GARDEN, FL 34787 13 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2858
       Built: 2026
    Monthly Fee: $140

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,249 (change assumption)
    Mortgage ($4,109) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14788 FIELD DAISY DR, WINTER GARDEN, FL 34787

    $579,99968 Days on yellowkey   MLS ID: O6398754

    REDUCED by $37,501 (6.1%) on 06/16/2026

    For Sale O6398754 - 14788 FIELD DAISY DR, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1992
       Built: 2026
    Monthly Fee: $229

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $3,407 (change assumption)
    Mortgage ($3,178) + Fees ($229) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14784 FIELD DAISY DR, WINTER GARDEN, FL 34787

    $690,00036 Days on yellowkey   MLS ID: O6408277

    For Sale O6408277 - 14784 FIELD DAISY DR, WINTER GARDEN, FL 34787 45 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2841
       Built: 2026
    Monthly Fee: $229

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,010 (change assumption)
    Mortgage ($3,781) + Fees ($229) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 745 MARSH REED DR, WINTER GARDEN, FL 34787

    $598,00017 Days on yellowkey   MLS ID: TB8514854

    REDUCED by $37,000 (5.8%) on 06/18/2026

    For Sale TB8514854 - 745 MARSH REED DR, WINTER GARDEN, FL 34787 7 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2596
       Built: 2015
    Monthly Fee: $132
       Tax: $8,274 (2025)
    Community: John Lake Pointe
    Single Family


    Estimated Monthly Payment: $4,098 (change assumption)
    Mortgage ($3,277) + Fees ($132) + Taxes in 2025 ($690)


    Taxes:$8,274

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 14531 CEDAR HILL DR, WINTER GARDEN, FL 34787

    $699,00036 Days on yellowkey   MLS ID: O6408070

    0 Days Off yellowkey (back on 6/18/2026)

    REDUCED by $50,000 (6.7%) on 06/03/2026

    For Sale O6408070 - 14531 CEDAR HILL DR, WINTER GARDEN, FL 34787 51 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3510
       Built: 2014
    Monthly Fee: $187
       Tax: $6,330 (2025)
    Community: Orchard Hills Ph 1
    Single Family


    Estimated Monthly Payment: $4,545 (change assumption)
    Mortgage ($3,830) + Fees ($187) + Taxes in 2025 ($528)


    Taxes:$6,330

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 10174 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787

    $999,00055 Days on yellowkey   MLS ID: O6402434

    REDUCED by $26,000 (2.5%) on 06/18/2026

    For Sale O6402434 - 10174 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2758
       Built: 2020
    Monthly Fee: $250
       Tax: $7,946 (2025)
    Community: Waterleigh Ph 2C-2 & 2C-3
    Single Family


    Estimated Monthly Payment: $6,386 (change assumption)
    Mortgage ($5,474) + Fees ($250) + Taxes in 2025 ($662)


    Taxes:$7,946

    Elementary School: None

    High School: None

    Tax Year: 2025

    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.