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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Beds: 5 to 5

Winter Garden - 175 properties found

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  • 1209 CASTLEPORT RD, WINTER GARDEN, FL 34787

    $659,000101 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


  • 15606 SHOREBIRD LN, WINTER GARDEN, FL 34787

    $1,625,000187 Days on yellowkey   MLS ID: O6367956

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

    REDUCED by $74,000 (4.4%) on 05/14/2026

    For Sale O6367956 - 15606 SHOREBIRD LN, WINTER GARDEN, FL 34787 55 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4300
       Built: 2020
    Monthly Fee: $360
       Tax: $21,186 (2025)
    Community: Lakeshore Preserve Ph 4
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,029 (change assumption)
    Mortgage ($8,904) + Fees ($360) + Taxes in 2025 ($1,766)


    Taxes:$21,186

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 276 SUMMER PINE ST, WINTER GARDEN, FL 34787

    $874,000122 Days on yellowkey   MLS ID: O6384565

    REDUCED by $1,000 (0.1%) on 05/28/2026

    For Sale O6384565 - 276 SUMMER PINE ST, WINTER GARDEN, FL 34787 25 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3147
       Built: 2025
    Monthly Fee: $240
       Tax: $1,914 (2024)
    Community: Winter Grove
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,188 (change assumption)
    Mortgage ($4,789) + Fees ($240) + Taxes in 2024 ($160)


    Taxes:$1,914

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 12469 WESTFIELD LAKES CIR, WINTER GARDEN, FL 34787

    $1,039,00034 Days on yellowkey   MLS ID: O6409038

    0 Days Off yellowkey (back on 5/28/2026)

    For Sale O6409038 - 12469 WESTFIELD LAKES CIR, WINTER GARDEN, FL 34787 72 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3451
       Built: 2004
    Monthly Fee: $85
       Tax: $7,873 (2025)
    Community: Westfield Lakes
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,434 (change assumption)
    Mortgage ($5,693) + Fees ($85) + Taxes in 2025 ($656)


    Taxes:$7,873

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 13542 SUNSET LAKES CIR, WINTER GARDEN, FL 34787

    $3,799,00040 Days on yellowkey   MLS ID: O6402896

    For Sale O6402896 - 13542 SUNSET LAKES CIR, WINTER GARDEN, FL 34787 78 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5450
       Built: 2022
    Monthly Fee: $69
       Tax: $25,701 (2025)
    Community: Sunset Lakes
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $23,027 (change assumption)
    Mortgage ($20,816) + Fees ($69) + Taxes in 2025 ($2,142)


    Taxes:$25,701

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 638 ENGLISH LAKE DR, WINTER GARDEN, FL 34787

    $949,00033 Days on yellowkey   MLS ID: O6409735

    1 Days Off yellowkey (back on 5/28/2026)

    For Sale O6409735 - 638 ENGLISH LAKE DR, WINTER GARDEN, FL 34787 58 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3708
       Built: 2005
    Monthly Fee: $85
       Tax: $6,353 (2025)
    Community: Westfield Lakes
    Single Family


    Estimated Monthly Payment: $5,814 (change assumption)
    Mortgage ($5,200) + Fees ($85) + Taxes in 2025 ($529)


    Taxes:$6,353

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 14345 WABASSO LOOP, WINTER GARDEN, FL 34787

    $735,000138 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


  • 3035 IRISH PEACH DR, WINTER GARDEN, FL 34787

    $1,099,000133 Days on yellowkey   MLS ID: O6381190

    0 Days Off yellowkey (back on 5/28/2026)

    For Sale O6381190 - 3035 IRISH PEACH DR, WINTER GARDEN, FL 34787 97 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3788
       Built: 2018
    Monthly Fee: $190
       Tax: $7,815 (2024)
    Community: Orchard Pk/Stillwater Xing Ph
    Single Family


    Estimated Monthly Payment: $6,863 (change assumption)
    Mortgage ($6,022) + Fees ($190) + Taxes in 2024 ($651)


    Taxes:$7,815

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 16323 BRIGHT LEAF RD, WINTER GARDEN, FL 34787

    $998,00040 Days on yellowkey   MLS ID: O6407909

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

    For Sale O6407909 - 16323 BRIGHT LEAF RD, WINTER GARDEN, FL 34787 38 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3676
       Built: 2026
    Monthly Fee: $152
       Tax: $1,981 (2025)
    Community: Silverleaf Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,785 (change assumption)
    Mortgage ($5,468) + Fees ($152) + Taxes in 2025 ($165)


    Taxes:$1,981

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 18309 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $725,000117 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


  • 11271 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $869,99655 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


  • 1157 VINSETTA CIR, WINTER GARDEN, FL 34787

    $800,00039 Days on yellowkey   MLS ID: O6403597

    0 Days Off yellowkey (back on 5/24/2026)

    For Sale O6403597 - 1157 VINSETTA CIR, WINTER GARDEN, FL 34787 64 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3598
       Built: 2014
    Monthly Fee: $112
       Tax: $6,599 (2025)
    Community: Avalon Reserve Village 1
    Single Family


    Estimated Monthly Payment: $5,045 (change assumption)
    Mortgage ($4,383) + Fees ($112) + Taxes in 2025 ($550)


    Taxes:$6,599

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 12529 DALLINGTON TER, WINTER GARDEN, FL 34787

    $869,99064 Days on yellowkey   MLS ID: O6400678

    0 Days Off yellowkey (back on 5/24/2026)

    REDUCED by $15,000 (1.7%) on 05/12/2026

    For Sale O6400678 - 12529 DALLINGTON TER, WINTER GARDEN, FL 34787 66 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3519
       Built: 2006
    Monthly Fee: $130
       Tax: $6,735 (2025)
    Community: Foxcrest A-N & P
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,458 (change assumption)
    Mortgage ($4,767) + Fees ($130) + Taxes in 2025 ($561)


    Taxes:$6,735

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16548 RAVEN ROCK PL, WINTER GARDEN, FL 34787

    $1,399,900120 Days on yellowkey   MLS ID: S5144064

    REDUCED by $60,000 (4.1%) on 05/23/2026

    For Sale S5144064 - 16548 RAVEN ROCK PL, WINTER GARDEN, FL 34787 36 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4263
       Built: 2017
    Monthly Fee: $178
       Tax: $16,938 (2024)
    Community: Twinwaters
    Single Family


    Estimated Monthly Payment: $9,260 (change assumption)
    Mortgage ($7,670) + Fees ($178) + Taxes in 2024 ($1,411)


    Taxes:$16,938

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13613 LARSEN LN, WINTER GARDEN, FL 34787

    $825,00032 Days on yellowkey   MLS ID: O6410121

    For Sale O6410121 - 13613 LARSEN LN, WINTER GARDEN, FL 34787 25 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3812
       Built: 2005
    Monthly Fee: $189
       Tax: $10,378 (2025)
    Community: Lake Forest Sec 10A
    Single Family


    Estimated Monthly Payment: $5,574 (change assumption)
    Mortgage ($4,520) + Fees ($189) + Taxes in 2025 ($865)


    Taxes:$10,378

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 325 CRYSTAL WOOD DR, WINTER GARDEN, FL 34787

    $1,600,00033 Days on yellowkey   MLS ID: O6408089

    For Sale O6408089 - 325 CRYSTAL WOOD DR, WINTER GARDEN, FL 34787 96 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4442
       Built: 2025
    Monthly Fee: $240
       Tax: $1,955 (2025)
    Community: Winter Grv
    Single Family


    Estimated Monthly Payment: $9,170 (change assumption)
    Mortgage ($8,767) + Fees ($240) + Taxes in 2025 ($163)


    Taxes:$1,955

    Elementary School: None

    High School: West Orange High

    Tax Year: 2025

    Middle School: None


  • 13813 PEACH ORCHARD WAY, WINTER GARDEN, FL 34787

    $850,00077 Days on yellowkey   MLS ID: O6392351

    0 Days Off yellowkey (back on 5/21/2026)

    For Sale O6392351 - 13813 PEACH ORCHARD WAY, WINTER GARDEN, FL 34787 40 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3793
       Built: 2018
    Monthly Fee: $190
       Tax: $7,249 (2025)
    Community: Orchard Pk/Stillwater Xing Ph
    Single Family


    Estimated Monthly Payment: $5,452 (change assumption)
    Mortgage ($4,657) + Fees ($190) + Taxes in 2025 ($604)


    Taxes:$7,249

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 419 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787

    $874,99082 Days on yellowkey   MLS ID: O6395693

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

    For Sale O6395693 - 419 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787 35 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2650
       Built: 2026
    Monthly Fee: $240
       Tax: $1,955 (2025)
    Community: Winter Grove
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,197 (change assumption)
    Mortgage ($4,794) + Fees ($240) + Taxes in 2025 ($163)


    Taxes:$1,955

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 11265 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $870,33148 Days on yellowkey   MLS ID: O6405351

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

    For Sale O6405351 - 11265 HOLLOW BAY DR, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3225
       Built: 2025
    Monthly Fee: $200
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,135 (change assumption)
    Mortgage ($4,769) + Fees ($200) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13412 FOX GLOVE ST, WINTER GARDEN, FL 34787

    $849,90085 Days on yellowkey   MLS ID: G5110319

    REDUCED by $43,000 (4.8%) on 04/16/2026

    For Sale G5110319 - 13412 FOX GLOVE ST, WINTER GARDEN, FL 34787 31 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3954
       Built: 2005
    Monthly Fee: $243
       Tax: $5,889 (2025)
    Community: Stoneybrook West Un 06
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,391 (change assumption)
    Mortgage ($4,657) + Fees ($243) + Taxes in 2025 ($491)


    Taxes:$5,889

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge 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.