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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Living Area Square Feet: 2500 to 2999

Winter Garden - 155 properties found

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  • 15591 GENTLE RAIN DR, WINTER GARDEN, FL 34787

    $730,00026 Days on yellowkey   MLS ID: O6411803

    For Sale O6411803 - 15591 GENTLE RAIN DR, WINTER GARDEN, FL 34787 68 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2896
       Built: 2025
    Monthly Fee: $99
       Tax: $1,890 (2025)
    Community: Osprey Ranch Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,256 (change assumption)
    Mortgage ($4,000) + Fees ($99) + Taxes in 2025 ($158)


    Taxes:$1,890

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15143 KIRSTY ALY, WINTER GARDEN, FL 34787

    $654,900280 Days on yellowkey   MLS ID: O6344886

    REDUCED by $4,100 (0.6%) on 05/24/2026

    For Sale O6344886 - 15143 KIRSTY ALY, WINTER GARDEN, FL 34787 44 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2934
       Built: 2017
    Monthly Fee: $328
       Tax: $9,868 (2025)
    Community: Overlook 2/Hamlin Ph 2 & 5
    Single Family


    Estimated Monthly Payment: $4,739 (change assumption)
    Mortgage ($3,588) + Fees ($328) + Taxes in 2025 ($822)


    Taxes:$9,868

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 5443 BOWMAN DR, WINTER GARDEN, FL 34787

    $649,00037 Days on yellowkey   MLS ID: O6408812

    0 Days Off yellowkey (back on 5/29/2026)

    For Sale O6408812 - 5443 BOWMAN DR, WINTER GARDEN, FL 34787 73 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2656
       Built: 2015
    Monthly Fee: $339
       Tax: $7,564 (2025)
    Community: Overlook 2/Hamlin
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,525 (change assumption)
    Mortgage ($3,556) + Fees ($339) + Taxes in 2025 ($630)


    Taxes:$7,564

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 1209 CASTLEPORT RD, WINTER GARDEN, FL 34787

    $659,000102 Days on yellowkey   MLS ID: O6390760

    REDUCED by $5,900 (0.9%) on 05/29/2026

    For Sale O6390760 - 1209 CASTLEPORT RD, WINTER GARDEN, FL 34787 36 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2812
       Built: 2001
    Monthly Fee: $243
       Tax: $4,030 (2025)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,190 (change assumption)
    Mortgage ($3,611) + Fees ($243) + Taxes in 2025 ($336)


    Taxes:$4,030

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15043 PIGEON PLUM LN, WINTER GARDEN, FL 34787

    $594,000136 Days on yellowkey   MLS ID: S5143009

    For Sale S5143009 - 15043 PIGEON PLUM LN, WINTER GARDEN, FL 34787 23 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2695
       Built: 2016
    Monthly Fee: $241
       Tax: $8,470 (2024)
    Community: Summerlake Pd Ph 2C 2D 2E
    Single Family


    Estimated Monthly Payment: $4,202 (change assumption)
    Mortgage ($3,255) + Fees ($241) + Taxes in 2024 ($706)


    Taxes:$8,470

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 14345 WABASSO LOOP, WINTER GARDEN, FL 34787

    $735,000139 Days on yellowkey   MLS ID: O6376609

    For Sale O6376609 - 14345 WABASSO LOOP, WINTER GARDEN, FL 34787 31 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2878
       Built: 2022
    Monthly Fee: $192
       Tax: $10,615 (2025)
    Community: Tilden Place/Winter Garden
    Single Family


    Estimated Monthly Payment: $5,104 (change assumption)
    Mortgage ($4,027) + Fees ($192) + Taxes in 2025 ($885)


    Taxes:$10,615

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 18309 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $725,000118 Days on yellowkey   MLS ID: O6386008

    0 Days Off yellowkey (back on 5/27/2026)

    For Sale O6386008 - 18309 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 37 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2832
       Built: 2023
    Monthly Fee: $281
       Tax: $497 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,295 (change assumption)
    Mortgage ($3,973) + Fees ($281) + Taxes in 2024 ($41)


    Taxes:$497

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 15852 SHOREBIRD LN, WINTER GARDEN, FL 34787

    $799,000217 Days on yellowkey   MLS ID: O6361580

    0 Days Off yellowkey (back on 5/27/2026)

    INCREASED by $14,000 (1.8%) on 05/24/2026

    For Sale O6361580 - 15852 SHOREBIRD LN, WINTER GARDEN, FL 34787 71 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2766
       Built: 2019
    Monthly Fee: $385
       Tax: $10,928 (2024)
    Community: Lakeshore Preserve Ph 5
    Single Family


    Estimated Monthly Payment: $5,674 (change assumption)
    Mortgage ($4,378) + Fees ($385) + Taxes in 2024 ($911)


    Taxes:$10,928

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 11271 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $869,99656 Days on yellowkey   MLS ID: O6403252

    3 Days Off yellowkey (back on 5/27/2026)

    For Sale O6403252 - 11271 HOLLOW BAY DR, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2866
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,132 (change assumption)
    Mortgage ($4,767) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7580 SPRING VALLEY ST, WINTER GARDEN, FL 34787

    $693,23061 Days on yellowkey   MLS ID: G5111519

    0 Days Off yellowkey (back on 4/24/2026)

    For Sale G5111519 - 7580 SPRING VALLEY ST, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,920 (change assumption)
    Mortgage ($3,798) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 912 LANDRUM DR, WINTER GARDEN, FL 34787

    $1,300,00042 Days on yellowkey   MLS ID: O6407616

    0 Days Off yellowkey (back on 5/26/2026)

    For Sale O6407616 - 912 LANDRUM DR, WINTER GARDEN, FL 34787 68 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2834
       Built: 2024
    Monthly Fee: $208
       Tax: $13,517 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $8,458 (change assumption)
    Mortgage ($7,123) + Fees ($208) + Taxes in 2025 ($1,126)


    Taxes:$13,517

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15058 SAWGRASS BLUFF DR, WINTER GARDEN, FL 34787

    $579,90070 Days on yellowkey   MLS ID: O6396640

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

    For Sale O6396640 - 15058 SAWGRASS BLUFF DR, WINTER GARDEN, FL 34787 26 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2626
       Built: 2013
    Monthly Fee: $128
       Tax: $6,746 (2025)
    Community: Johns Lake Pointe A & S
    Single Family


    Estimated Monthly Payment: $3,868 (change assumption)
    Mortgage ($3,177) + Fees ($128) + Taxes in 2025 ($562)


    Taxes:$6,746

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2200 ROMANUM DR, WINTER GARDEN, FL 34787

    $560,00040 Days on yellowkey   MLS ID: O6408190

    For Sale O6408190 - 2200 ROMANUM DR, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2561
       Built: 2015
    Monthly Fee: $211
       Tax: $8,843 (2025)
    Community: Alexander Rdg
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,016 (change assumption)
    Mortgage ($3,068) + Fees ($211) + Taxes in 2025 ($737)


    Taxes:$8,843

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7212 DESERT MANDARIN ST, WINTER GARDEN, FL 34787

    $650,00062 Days on yellowkey   MLS ID: O6401040

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

    For Sale O6401040 - 7212 DESERT MANDARIN ST, WINTER GARDEN, FL 34787 42 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2605
       Built: 2018
    Monthly Fee: $64
       Tax: $5,661 (2025)
    Community: Highlands/Summerlake Grvs Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,097 (change assumption)
    Mortgage ($3,562) + Fees ($64) + Taxes in 2025 ($472)


    Taxes:$5,661

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15480 SANDFIELD LOOP, WINTER GARDEN, FL 34787

    $749,90056 Days on yellowkey   MLS ID: O6399241

    1 Days Off yellowkey (back on 5/22/2026)

    For Sale O6399241 - 15480 SANDFIELD LOOP, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2574
       Built: 2013
    Monthly Fee: $114
       Tax: $7,534 (2025)
    Community: Reserve/Carriage Point Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,851 (change assumption)
    Mortgage ($4,109) + Fees ($114) + Taxes in 2025 ($628)


    Taxes:$7,534

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9942 SUMMERLAKE GROVES ST, WINTER GARDEN, FL 34787

    $899,00055 Days on yellowkey   MLS ID: O6402319

    REDUCED by $20,000 (2.2%) on 05/21/2026

    For Sale O6402319 - 9942 SUMMERLAKE GROVES ST, WINTER GARDEN, FL 34787 94 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2935
       Built: 2019
    Monthly Fee: $164
       Tax: $11,696 (2025)
    Community: Watermark
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,065 (change assumption)
    Mortgage ($4,926) + Fees ($164) + Taxes in 2025 ($975)


    Taxes:$11,696

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17453 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787

    $757,99066 Days on yellowkey   MLS ID: G5111222

    0 Days Off yellowkey (back on 4/19/2026)

    For Sale G5111222 - 17453 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2740
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,303 (change assumption)
    Mortgage ($4,153) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 10187 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787

    $679,00048 Days on yellowkey   MLS ID: O6404599

    0 Days Off yellowkey (back on 5/20/2026)

    REDUCED by $10,000 (1.5%) on 05/11/2026

    For Sale O6404599 - 10187 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787 83 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2020
    Monthly Fee: $250
       Tax: $9,595 (2025)
    Community: Waterleigh Ph 2C-2 & 2C-3
    Single Family


    Estimated Monthly Payment: $4,770 (change assumption)
    Mortgage ($3,720) + Fees ($250) + Taxes in 2025 ($800)


    Taxes:$9,595

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787

    $630,00057 Days on yellowkey   MLS ID: O6403063

    REDUCED by $5,500 (0.9%) on 05/19/2026

    For Sale O6403063 - 17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2692
       Built: 2017
    Monthly Fee: $215
       Tax: $8,922 (2025)
    Community: Waterside/Johns Lake Ph 2A
    Single Family


    Estimated Monthly Payment: $4,410 (change assumption)
    Mortgage ($3,452) + Fees ($215) + Taxes in 2025 ($744)


    Taxes:$8,922

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3518 TURNINGWIND LN, WINTER GARDEN, FL 34787

    $810,00070 Days on yellowkey   MLS ID: S5147067

    3 Days Off yellowkey (back on 5/19/2026)

    REDUCED by $15,000 (1.8%) on 04/30/2026

    For Sale S5147067 - 3518 TURNINGWIND LN, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2744
       Built: 2003
    Monthly Fee: $115
       Tax: $10,313 (2025)
    Community: Windward Cay 48 125
    Single Family


    Estimated Monthly Payment: $5,413 (change assumption)
    Mortgage ($4,438) + Fees ($115) + Taxes in 2025 ($859)


    Taxes:$10,313

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle






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.