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Winter Garden Homes For Sale & Real Estate - 940 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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  • 16031 PEBBLE BLUFF LOOP, WINTER GARDEN, FL 34787

    $560,00065 Days on yellowkey   MLS ID: O6404448

    For Sale O6404448 - 16031 PEBBLE BLUFF LOOP, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2487
       Built: 2018
    Monthly Fee: $257
       Tax: $9,371 (2025)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $4,106 (change assumption)
    Mortgage ($3,068) + Fees ($257) + Taxes in 2025 ($781)


    Taxes:$9,371

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15149 CANOE PL, WINTER GARDEN, FL 34787

    $798,89135 Days on yellowkey   MLS ID: O6412776

    REDUCED by $1 (0.0%) on 06/23/2026

    For Sale O6412776 - 15149 CANOE PL, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3081
       Built: 2019
    Monthly Fee: $385
       Tax: $9,388 (2025)
    Community: Lakeshore Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $5,545 (change assumption)
    Mortgage ($4,377) + Fees ($385) + Taxes in 2025 ($782)


    Taxes:$9,388

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8124 RED CROSSBILL ST, WINTER GARDEN, FL 34787

    $830,000292 Days on yellowkey   MLS ID: O6345400

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

    REDUCED by $10,000 (1.2%) on 06/16/2026

    For Sale O6345400 - 8124 RED CROSSBILL ST, WINTER GARDEN, FL 34787 67 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3708
       Built: 2013
    Monthly Fee: $246
       Tax: $7,515 (2024)
    Community: Summerlake Pd Ph 1A
    Single Family


    Estimated Monthly Payment: $5,420 (change assumption)
    Mortgage ($4,548) + Fees ($246) + Taxes in 2024 ($626)


    Taxes:$7,515

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13086 SUNRISE HARVEST DR, WINTER GARDEN, FL 34787

    $849,00021 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


  • 4863 LACEWING DR, WINTER GARDEN, FL 34787

    $540,00089 Days on yellowkey   MLS ID: O6397857

    For Sale O6397857 - 4863 LACEWING DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1788
       Built: 2023
    Monthly Fee: $171
       Tax: $6,905 (2025)
    Community: Silverleaf Reserve Bungalows
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,705 (change assumption)
    Mortgage ($2,959) + Fees ($171) + Taxes in 2025 ($575)


    Taxes:$6,905

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 2230 ROMANUM DR, WINTER GARDEN, FL 34787

    $565,000117 Days on yellowkey   MLS ID: O6389947

    1 Days Off yellowkey (back on 5/17/2026)

    For Sale O6389947 - 2230 ROMANUM DR, WINTER GARDEN, FL 34787 29 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2562
       Built: 2014
    Monthly Fee: $207
       Tax: $8,425 (2025)
    Community: Alexander Rdg
    Single Family


    Estimated Monthly Payment: $4,005 (change assumption)
    Mortgage ($3,096) + Fees ($207) + Taxes in 2025 ($702)


    Taxes:$8,425

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1338 UNION CLUB DR, WINTER GARDEN, FL 34787

    $890,00028 Days on yellowkey   MLS ID: O6412710

    REDUCED by $10,000 (1.1%) on 06/10/2026

    For Sale O6412710 - 1338 UNION CLUB DR, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2637
       Built: 2014
    Monthly Fee: $208
       Tax: $13,895 (2025)
    Community: Oakland Parka
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,243 (change assumption)
    Mortgage ($4,877) + Fees ($208) + Taxes in 2025 ($1,158)


    Taxes:$13,895

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15143 BLUE PEACOCK LN, WINTER GARDEN, FL 34787

    $595,00029 Days on yellowkey   MLS ID: O6414996

    For Sale O6414996 - 15143 BLUE PEACOCK LN, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2420
       Built: 2024
    Monthly Fee: $96
       Tax: $8,683 (2025)
    Community: Osprey Ranch Ph 1
    Single Family


    Estimated Monthly Payment: $4,080 (change assumption)
    Mortgage ($3,260) + Fees ($96) + Taxes in 2025 ($724)


    Taxes:$8,683

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 914 TROWMAN ALY, WINTER GARDEN, FL 34787

    $649,00042 Days on yellowkey   MLS ID: O6410871

    REDUCED by $26,000 (3.9%) on 06/02/2026

    For Sale O6410871 - 914 TROWMAN ALY, WINTER GARDEN, FL 34787 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1642
       Built: 2022
    Monthly Fee: $356
       Tax: $6,421 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $4,447 (change assumption)
    Mortgage ($3,556) + Fees ($356) + Taxes in 2025 ($535)


    Taxes:$6,421

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15353 OAK APPLE CT, WINTER GARDEN, FL 34787

    $347,500104 Days on yellowkey   MLS ID: O6393663

    REDUCED by $2,500 (0.7%) on 05/27/2026

    For Sale O6393663 - 15353 OAK APPLE CT, WINTER GARDEN, FL 34787 16 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1699
       Built: 2008
    Monthly Fee: $283
       Tax: $1,863 (2025)
    Community: Tucker Oaks Bldg 5
    Townhouse


    Estimated Monthly Payment: $2,342 (change assumption)
    Mortgage ($1,904) + Fees ($283) + Taxes in 2025 ($155)


    Taxes:$1,863

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2006 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787

    $750,0007 Days on yellowkey   MLS ID: O6420951

    For Sale O6420951 - 2006 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787 50 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3011
       Built: 1999
    Monthly Fee: $90
       Tax: $5,441 (2025)
    Community: Wintermere Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,653 (change assumption)
    Mortgage ($4,109) + Fees ($90) + Taxes in 2025 ($453)


    Taxes:$5,441

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 33 TIMBERCREEK PINES CIR, WINTER GARDEN, FL 34787

    $535,00047 Days on yellowkey   MLS ID: O6408941

    REDUCED by $10,000 (1.8%) on 07/03/2026

    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: $3,588 (change assumption)
    Mortgage ($2,931) + 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


  • 15340 OAK APPLE COURT CT #16B, WINTER GARDEN, FL 34787

    $350,00012 Days on yellowkey   MLS ID: O6419809

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

    For Sale O6419809 - 15340 OAK APPLE COURT CT #16B, WINTER GARDEN, FL 34787 42 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1544
       Built: 2008
    Monthly Fee: $282
       Tax: $4,127 (2025)
    Community: Tucker Oaks Condo Ph 4
    Condo


    Estimated Monthly Payment: $2,544 (change assumption)
    Mortgage ($1,918) + Fees ($282) + Taxes in 2025 ($344)


    Taxes:$4,127

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15025 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787

    $490,00046 Days on yellowkey   MLS ID: O6410108

    REDUCED by $15,000 (3.0%) on 07/03/2026

    For Sale O6410108 - 15025 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787 44 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2016
    Monthly Fee: $195
       Tax: $8,019 (2025)
    Community: Signature Lakes Ph 3B-4 3B-5 3B-
    Single Family


    Estimated Monthly Payment: $3,548 (change assumption)
    Mortgage ($2,685) + Fees ($195) + Taxes in 2025 ($668)


    Taxes:$8,019

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 844 OAKLAND PARK BLVD, WINTER GARDEN, FL 34787

    $1,225,0006 Days on yellowkey   MLS ID: O6419976

    For Sale O6419976 - 844 OAKLAND PARK BLVD, WINTER GARDEN, FL 34787 74 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3525
       Built: 2012
    Monthly Fee: $208
       Tax: $14,087 (2025)
    Community: Oakland Parkb-1B A
    Single Family


    Estimated Monthly Payment: $8,094 (change assumption)
    Mortgage ($6,712) + Fees ($208) + Taxes in 2025 ($1,174)


    Taxes:$14,087

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7467 JOHN HANCOCK DR, WINTER GARDEN, FL 34787

    $1,350,0005 Days on yellowkey   MLS ID: O6421848

    For Sale O6421848 - 7467 JOHN HANCOCK DR, WINTER GARDEN, FL 34787 90 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3964
       Built: 2019
    Monthly Fee: $215
       Tax: $16,560 (2025)
    Community: West Lake Hancock Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,992 (change assumption)
    Mortgage ($7,397) + Fees ($215) + Taxes in 2025 ($1,380)


    Taxes:$16,560

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 417 SOUTHERN PECAN CIR #201, WINTER GARDEN, FL 34787

    $275,0005 Days on yellowkey   MLS ID: O6421941

    For Sale O6421941 - 417 SOUTHERN PECAN CIR #201, WINTER GARDEN, FL 34787 19 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1264
       Built: 2005
    Monthly Fee: $489
       Tax: $3,366 (2025)
    Community: Southern Pines Condo
    Condo


    Estimated Monthly Payment: $2,276 (change assumption)
    Mortgage ($1,507) + Fees ($489) + Taxes in 2025 ($281)


    Taxes:$3,366

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 689 BETHUNE AVE, WINTER GARDEN, FL 34787

    $434,0005 Days on yellowkey   MLS ID: O6421715

    For Sale O6421715 - 689 BETHUNE AVE, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1434
       Built: 1950   Tax: $2,330 (2025)
    Community: Joe Louis Park Q162
    Single Family


    Estimated Monthly Payment: $2,572 (change assumption)
    Mortgage ($2,378) + Taxes in 2025 ($194)


    Taxes:$2,330

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6843 POINT HANCOCK DR, WINTER GARDEN, FL 34787

    $435,0005 Days on yellowkey   MLS ID: G5114589

    For Sale G5114589 - 6843 POINT HANCOCK DR, WINTER GARDEN, FL 34787 16 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1720
       Built: 2013
    Monthly Fee: $195
       Tax: $6,895 (2025)
    Community: Signature Lakes Ph 2
    Single Family


    Estimated Monthly Payment: $3,153 (change assumption)
    Mortgage ($2,384) + Fees ($195) + Taxes in 2025 ($575)


    Taxes:$6,895

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14629 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787

    $492,9005 Days on yellowkey   MLS ID: O6421797

    For Sale O6421797 - 14629 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787 14 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: $3,622 (change assumption)
    Mortgage ($2,701) + Fees ($242) + Taxes in 2025 ($679)


    Taxes:$8,151

    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.