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Displaying: For Sale

Location: Winter Garden

Property Type(s): Townhomes

Price: $400,000 to $499,000

Winter Garden - 75 properties found

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  • 16329 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787

    $490,000248 Days on yellowkey   MLS ID: O6353551

    For Sale O6353551 - 16329 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787 75 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2070
       Built: 2021
    Monthly Fee: $284
       Tax: $5,869 (2024)
    Community: Hawksmoor Ph 3
    Townhouse


    Estimated Monthly Payment: $3,458 (change assumption)
    Mortgage ($2,685) + Fees ($284) + Taxes in 2024 ($489)


    Taxes:$5,869

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 18167 CIDER MILL LN, WINTER GARDEN, FL 34787

    $469,990117 Days on yellowkey   MLS ID: O6386278

    1 Days Off yellowkey (back on 5/14/2026)

    REDUCED by $5,000 (1.1%) on 04/22/2026

    For Sale O6386278 - 18167 CIDER MILL LN, WINTER GARDEN, FL 34787 15 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1817
       Built: 2025
    Monthly Fee: $205
       Tax: $1,424 (2025)
    Community: Waterleigh
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,899 (change assumption)
    Mortgage ($2,575) + Fees ($205) + Taxes in 2025 ($119)


    Taxes:$1,424

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8156 WOOD SAGE DRIVE, WINTER GARDEN, FL 34787

    $449,000104 Days on yellowkey   MLS ID: V4947783

    REDUCED by $10,000 (2.2%) on 04/30/2026

    For Sale V4947783 - 8156 WOOD SAGE DRIVE, WINTER GARDEN, FL 34787 42 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1853
       Built: 2018
    Monthly Fee: $315
       Tax: $3,792 (2025)
    Community: Summerlake
    Townhouse


    Estimated Monthly Payment: $3,091 (change assumption)
    Mortgage ($2,460) + Fees ($315) + Taxes in 2025 ($316)


    Taxes:$3,792

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 17736 PORTER RD, WINTER GARDEN, FL 34787

    $451,54249 Days on yellowkey   MLS ID: G5112009

    0 Days Off yellowkey (back on 5/6/2026)

    For Sale G5112009 - 17736 PORTER RD, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1715
       Built: 2026
    Monthly Fee: $230

    Community: Serenade At Ovation
    Townhouse


    Estimated Monthly Payment: $2,704 (change assumption)
    Mortgage ($2,474) + Fees ($230) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 17025 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $456,55449 Days on yellowkey   MLS ID: G5112007

    0 Days Off yellowkey (back on 5/6/2026)

    For Sale G5112007 - 17025 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1697
       Built: 2026
    Monthly Fee: $225

    Community: Hamlin Meadows
    Townhouse


    Estimated Monthly Payment: $2,727 (change assumption)
    Mortgage ($2,502) + Fees ($225) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 5755 CYPRESS HILL RD, WINTER GARDEN, FL 34787

    $455,00052 Days on yellowkey   MLS ID: O6404161

    For Sale O6404161 - 5755 CYPRESS HILL RD, WINTER GARDEN, FL 34787 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1797
       Built: 2019
    Monthly Fee: $338
       Tax: $4,506 (2025)
    Community: Orchard Hills Ph 4
    Townhouse


    Estimated Monthly Payment: $3,207 (change assumption)
    Mortgage ($2,493) + Fees ($338) + Taxes in 2025 ($376)


    Taxes:$4,506

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 15038 WINDFLOWER ALY, WINTER GARDEN, FL 34787

    $441,00050 Days on yellowkey   MLS ID: O6405201

    For Sale O6405201 - 15038 WINDFLOWER ALY, WINTER GARDEN, FL 34787 10 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1536
       Built: 2024   Tax: $5,956 (2025)
    Community: Osprey Ranch Ph 1
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,913 (change assumption)
    Mortgage ($2,416) + Taxes in 2025 ($496)


    Taxes:$5,956

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12780 SUNSET WALK DR, WINTER GARDEN, FL 34787

    $465,00074 Days on yellowkey   MLS ID: O6398355

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

    For Sale O6398355 - 12780 SUNSET WALK DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1760
       Built: 2026
    Monthly Fee: $150
       Tax: $400 (2025)
    Community: Westhaven At Ovation
    Townhouse


    Estimated Monthly Payment: $2,731 (change assumption)
    Mortgage ($2,548) + Fees ($150) + Taxes in 2025 ($33)


    Taxes:$400

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15140 WINDFLOWER ALY, WINTER GARDEN, FL 34787

    $410,00051 Days on yellowkey   MLS ID: S5149180

    For Sale S5149180 - 15140 WINDFLOWER ALY, WINTER GARDEN, FL 34787 34 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1536
       Built: 2024
    Monthly Fee: $200
       Tax: $5,304 (2025)
    Community: Osprey Ranch Ph I
    Townhouse


    Estimated Monthly Payment: $2,889 (change assumption)
    Mortgage ($2,247) + Fees ($200) + Taxes in 2025 ($442)


    Taxes:$5,304

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 5413 NEW INDEPENDENCE PKWY, WINTER GARDEN, FL 34787

    $488,00084 Days on yellowkey   MLS ID: S5146601

    For Sale S5146601 - 5413 NEW INDEPENDENCE PKWY, WINTER GARDEN, FL 34787 28 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2131
       Built: 2012
    Monthly Fee: $264
       Tax: $5,449 (2025)
    Community: Signature Lakes Ph 02 A B H I J
    Townhouse


    Estimated Monthly Payment: $3,392 (change assumption)
    Mortgage ($2,674) + Fees ($264) + Taxes in 2025 ($454)


    Taxes:$5,449

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15659 JUNGLE ALY, WINTER GARDEN, FL 34787

    $435,00095 Days on yellowkey   MLS ID: S5143684

    INCREASED by $75,000 (20.8%) on 04/23/2026

    For Sale S5143684 - 15659 JUNGLE ALY, WINTER GARDEN, FL 34787 16 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1732
       Built: 2021
    Monthly Fee: $203
       Tax: $6,265 (2024)
    Community: Winding Bay Ph 2
    Townhouse


    Estimated Monthly Payment: $3,109 (change assumption)
    Mortgage ($2,384) + Fees ($203) + Taxes in 2024 ($522)


    Taxes:$6,265

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 12036 HOLYSTONE ST, WINTER GARDEN, FL 34787

    $455,000202 Days on yellowkey   MLS ID: S5139531

    For Sale S5139531 - 12036 HOLYSTONE ST, WINTER GARDEN, FL 34787 43 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1817
       Built: 2022
    Monthly Fee: $256
       Tax: $6,116 (2024)
    Community: Waterleigh Ph 4A
    Townhouse


    Estimated Monthly Payment: $3,259 (change assumption)
    Mortgage ($2,493) + Fees ($256) + Taxes in 2024 ($510)


    Taxes:$6,116

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16209 ADMIRALS COVE LN, WINTER GARDEN, FL 34787

    $414,99590 Days on yellowkey   MLS ID: S5145675

    For Sale S5145675 - 16209 ADMIRALS COVE LN, WINTER GARDEN, FL 34787 51 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1568
       Built: 2020
    Monthly Fee: $275
       Tax: $6,070 (2025)
    Community: Waterleigh
    Townhouse


    Estimated Monthly Payment: $3,055 (change assumption)
    Mortgage ($2,274) + Fees ($275) + Taxes in 2025 ($506)


    Taxes:$6,070

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 5706 CYPRESS HILL RD, WINTER GARDEN, FL 34787

    $460,000   MLS ID: O6386620

    For Sale O6386620 - 5706 CYPRESS HILL RD, WINTER GARDEN, FL 34787 21 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1712
       Built: 2018
    Community: Orchard Hills Ph 4
    Townhouse


    Estimated Monthly Payment: $2,520 (change assumption)
    Mortgage ($2,520)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 13278 SERENE GLADE RD, WINTER GARDEN, FL 34787

    $434,990   MLS ID: G5105229

    For Sale G5105229 - 13278 SERENE GLADE RD, WINTER GARDEN, FL 34787 36 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1715
       Built: 2025
    Community: Serenade At Ovation
    Townhouse


    Estimated Monthly Payment: $2,383 (change assumption)
    Mortgage ($2,383)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None






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.