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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Winter Garden - 709 properties found

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  • 8018 BOWERY DR, WINTER GARDEN, FL 34787

    $699,900344 Days on yellowkey   MLS ID: O6325853

    For Sale O6325853 - 8018 BOWERY DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3075
       Built: 2017
    Monthly Fee: $208
       Tax: $5,724 (2024)
    Community: Lake Hancock Preserve
    Single Family


    Estimated Monthly Payment: $4,520 (change assumption)
    Mortgage ($3,835) + Fees ($208) + Taxes in 2024 ($477)


    Taxes:$5,724

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 6100 CYPRESS HILL RD, WINTER GARDEN, FL 34787

    $950,00023 Days on yellowkey   MLS ID: O6412033

    For Sale O6412033 - 6100 CYPRESS HILL RD, WINTER GARDEN, FL 34787 51 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3777
       Built: 2016
    Monthly Fee: $195
       Tax: $11,678 (2025)
    Community: Signature Lakes Ph 3B-4 3B-5 & 3
    Single Family


    Estimated Monthly Payment: $6,374 (change assumption)
    Mortgage ($5,205) + Fees ($195) + Taxes in 2025 ($973)


    Taxes:$11,678

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 16821 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $546,990194 Days on yellowkey   MLS ID: O6367156

    REDUCED by $8,000 (1.4%) on 06/04/2026

    For Sale O6367156 - 16821 HOBE SOUND CT, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,353 (change assumption)
    Mortgage ($2,997) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11223 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $809,990131 Days on yellowkey   MLS ID: O6382359

    1 Days Off yellowkey (back on 6/4/2026)

    REDUCED by $10,000 (1.2%) on 06/04/2026

    For Sale O6382359 - 11223 HOLLOW BAY DR, WINTER GARDEN, FL 34787 10 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2866
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,854 (change assumption)
    Mortgage ($4,438) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6122 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $774,54921 Days on yellowkey   MLS ID: G5113307

    0 Days Off yellowkey (back on 6/3/2026)

    For Sale G5113307 - 6122 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2026
    Monthly Fee: $150
       Tax: $298 (2025)
    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,419 (change assumption)
    Mortgage ($4,244) + Fees ($150) + Taxes in 2025 ($25)


    Taxes:$298

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 7531 SILVER VALLEY ST, WINTER GARDEN, FL 34787

    $552,27521 Days on yellowkey   MLS ID: G5113297

    0 Days Off yellowkey (back on 6/3/2026)

    For Sale G5113297 - 7531 SILVER VALLEY ST, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,176 (change assumption)
    Mortgage ($3,026) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17673 LAKE STAR RD, WINTER GARDEN, FL 34787

    $866,86521 Days on yellowkey   MLS ID: TB8515334

    For Sale TB8515334 - 17673 LAKE STAR RD, WINTER GARDEN, FL 34787 9 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2791
       Built: 2026
    Monthly Fee: $84
       Tax: $12,000 (2026)
    Community: Northlake At Ovation
    Single Family


    Estimated Monthly Payment: $5,834 (change assumption)
    Mortgage ($4,750) + Fees ($84) + Taxes in 2026 ($1,000)


    Taxes:$12,000

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 16466 OLIVE HILL DR, WINTER GARDEN, FL 34787

    $660,00021 Days on yellowkey   MLS ID: O6409922

    For Sale O6409922 - 16466 OLIVE HILL DR, WINTER GARDEN, FL 34787 43 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2020
       Built: 2019
    Monthly Fee: $127
       Tax: $8,758 (2025)
    Community: Hawksmoor-Ph 1
    Single Family


    Estimated Monthly Payment: $4,473 (change assumption)
    Mortgage ($3,616) + Fees ($127) + Taxes in 2025 ($730)


    Taxes:$8,758

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 13837 LANYARD WAY, WINTER GARDEN, FL 34787

    $485,000107 Days on yellowkey   MLS ID: O6388993

    REDUCED by $5,000 (1.0%) on 06/03/2026

    For Sale O6388993 - 13837 LANYARD WAY, WINTER GARDEN, FL 34787 38 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1994
       Built: 2023
    Monthly Fee: $225
       Tax: $7,647 (2024)
    Community: Encore/Ovation Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,520 (change assumption)
    Mortgage ($2,657) + Fees ($225) + Taxes in 2024 ($637)


    Taxes:$7,647

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 12595 GOLD HONEYSUCKLE ST #284, WINTER GARDEN, FL 34787

    $844,99090 Days on yellowkey   MLS ID: O6393961

    0 Days Off yellowkey (back on 6/3/2026)

    REDUCED by $25,000 (2.9%) on 06/01/2026

    For Sale O6393961 - 12595 GOLD HONEYSUCKLE ST #284, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3338
       Built: 2026
    Monthly Fee: $96

    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $4,726 (change assumption)
    Mortgage ($4,630) + Fees ($96) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 14645 TULLAMORE LOOP, WINTER GARDEN, FL 34787

    $455,00028 Days on yellowkey   MLS ID: O6409068

    0 Days Off yellowkey (back on 6/2/2026)

    For Sale O6409068 - 14645 TULLAMORE LOOP, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1703
       Built: 2003
    Monthly Fee: $100
       Tax: $3,347 (2025)
    Community: Emerald Rdg H
    Single Family


    Estimated Monthly Payment: $2,872 (change assumption)
    Mortgage ($2,493) + Fees ($100) + Taxes in 2025 ($279)


    Taxes:$3,347

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13023 INKWELL ALY, WINTER GARDEN, FL 34787

    $515,00035 Days on yellowkey   MLS ID: O6409443

    0 Days Off yellowkey (back on 6/3/2026)

    For Sale O6409443 - 13023 INKWELL ALY, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2042
       Built: 2020
    Monthly Fee: $268
       Tax: $5,162 (2025)
    Community: Storey Grove
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,520 (change assumption)
    Mortgage ($2,822) + Fees ($268) + Taxes in 2025 ($430)


    Taxes:$5,162

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 156 STANTON ESTATES CIR, WINTER GARDEN, FL 34787

    $1,149,950111 Days on yellowkey   MLS ID: O6384801

    REDUCED by $50,050 (4.2%) on 06/03/2026

    For Sale O6384801 - 156 STANTON ESTATES CIR, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3170
       Built: 2018
    Monthly Fee: $188
       Tax: $7,979 (2024)
    Community: Stanton Estates
    Single Family


    Estimated Monthly Payment: $7,154 (change assumption)
    Mortgage ($6,301) + Fees ($188) + Taxes in 2024 ($665)


    Taxes:$7,979

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 13151 CALMING BREEZE WAY, WINTER GARDEN, FL 34787

    $553,000204 Days on yellowkey   MLS ID: O6363957

    REDUCED by $12,000 (2.1%) on 06/01/2026

    For Sale O6363957 - 13151 CALMING BREEZE WAY, WINTER GARDEN, FL 34787 30 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2096
       Built: 2024
    Monthly Fee: $125
       Tax: $7,757 (2025)
    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $3,801 (change assumption)
    Mortgage ($3,030) + Fees ($125) + Taxes in 2025 ($646)


    Taxes:$7,757

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16161 BARKLY RIDGE CT, WINTER GARDEN, FL 34787

    $1,690,00055 Days on yellowkey   MLS ID: O6402785

    REDUCED by $110,000 (6.1%) on 06/03/2026

    For Sale O6402785 - 16161 BARKLY RIDGE CT, WINTER GARDEN, FL 34787 53 photos

    Bed: 6   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 5284
       Built: 2024
    Monthly Fee: $225
       Tax: $2,826 (2025)
    Community: Avalon Rdg
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,721 (change assumption)
    Mortgage ($9,260) + Fees ($225) + Taxes in 2025 ($236)


    Taxes:$2,826

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 2640 GROVE VIEW DR, WINTER GARDEN, FL 34787

    $784,90061 Days on yellowkey   MLS ID: O6401215

    REDUCED by $5,000 (0.6%) on 05/31/2026

    For Sale O6401215 - 2640 GROVE VIEW DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3738
       Built: 2001
    Monthly Fee: $90
       Tax: $10,261 (2025)
    Community: Wintermere Pointe Ph 02 46/141
    Single Family


    Estimated Monthly Payment: $5,246 (change assumption)
    Mortgage ($4,301) + Fees ($90) + Taxes in 2025 ($855)


    Taxes:$10,261

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 46 W VINING ST, WINTER GARDEN, FL 34787

    $549,90037 Days on yellowkey   MLS ID: O6408720

    REDUCED by $20,000 (3.5%) on 06/03/2026

    For Sale O6408720 - 46 W VINING ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1273
       Built: 1938   Tax: $6,287 (2025)
    Community: Ellman Park
    Single Family


    Estimated Monthly Payment: $3,537 (change assumption)
    Mortgage ($3,013) + Taxes in 2025 ($524)


    Taxes:$6,287

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 16461 OLIVE HILL DR, WINTER GARDEN, FL 34787

    $569,900142 Days on yellowkey   MLS ID: O6379181

    REDUCED by $19,000 (3.2%) on 06/03/2026

    For Sale O6379181 - 16461 OLIVE HILL DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2008
       Built: 2019
    Monthly Fee: $127
       Tax: $7,241 (2024)
    Community: Hawksmoor
    Single Family


    Estimated Monthly Payment: $3,853 (change assumption)
    Mortgage ($3,123) + Fees ($127) + Taxes in 2024 ($603)


    Taxes:$7,241

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 338 WINDFORD CT, WINTER GARDEN, FL 34787

    $330,00022 Days on yellowkey   MLS ID: O6413058

    For Sale O6413058 - 338 WINDFORD CT, WINTER GARDEN, FL 34787 29 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1050
       Built: 1996
    Monthly Fee: $40
       Tax: $2,089 (2025)
    Community: Park Ave Estates
    Single Family


    Estimated Monthly Payment: $2,022 (change assumption)
    Mortgage ($1,808) + Fees ($40) + Taxes in 2025 ($174)


    Taxes:$2,089

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 5937 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $674,475279 Days on yellowkey   MLS ID: G5102276

    0 Days Off yellowkey (back on 3/16/2026)

    For Sale G5102276 - 5937 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2235
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $3,846 (change assumption)
    Mortgage ($3,696) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin 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.