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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Price: $1,000,000+

Winter Garden - 87 properties found

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  • 15226 SUNSET OVERLOOK CIR, WINTER GARDEN, FL 34787

    $1,100,00046 Days on yellowkey   MLS ID: O6390971

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

    REDUCED by $50,000 (4.3%) on 03/31/2026

    For Sale O6390971 - 15226 SUNSET OVERLOOK CIR, WINTER GARDEN, FL 34787 80 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3556
       Built: 2023
    Monthly Fee: $128
       Tax: $10,299 (2025)
    Community: Johns Lake Pointe
    Single Family


    Estimated Monthly Payment: $7,013 (change assumption)
    Mortgage ($6,027) + Fees ($128) + Taxes in 2025 ($858)


    Taxes:$10,299

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 14766 ELLINGSWORTH LN, WINTER GARDEN, FL 34787

    $1,099,00049 Days on yellowkey   MLS ID: O6390518

    0 Days Off yellowkey (back on 4/23/2026)

    For Sale O6390518 - 14766 ELLINGSWORTH LN, WINTER GARDEN, FL 34787 42 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4661
       Built: 2018
    Monthly Fee: $210
       Tax: $14,115 (2025)
    Community: Oxford Chase
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,408 (change assumption)
    Mortgage ($6,022) + Fees ($210) + Taxes in 2025 ($1,176)


    Taxes:$14,115

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 205 SURPRISE DR, WINTER GARDEN, FL 34787

    $1,200,000151 Days on yellowkey   MLS ID: O6365188

    1 Days Off yellowkey (back on 4/23/2026)

    For Sale O6365188 - 205 SURPRISE DR, WINTER GARDEN, FL 34787 32 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2171
       Built: 1950   Tax: $3,406 (2024)
    Community: Winter Garden Shores Rep
    Single Family


    Estimated Monthly Payment: $6,859 (change assumption)
    Mortgage ($6,575) + Taxes in 2024 ($284)


    Taxes:$3,406

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 7460 JOHN HANCOCK DR, WINTER GARDEN, FL 34787

    $2,445,00013 Days on yellowkey   MLS ID: O6400891

    For Sale O6400891 - 7460 JOHN HANCOCK DR, WINTER GARDEN, FL 34787 89 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4817
       Built: 2020
    Monthly Fee: $210
       Tax: $17,060 (2025)
    Community: Overlook At Hamlin
    Single Family


    Estimated Monthly Payment: $15,029 (change assumption)
    Mortgage ($13,397) + Fees ($210) + Taxes in 2025 ($1,422)


    Taxes:$17,060

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 7104 TICKLEGRASS ST, WINTER GARDEN, FL 34787

    $1,246,000285 Days on yellowkey   MLS ID: O6329696

    For Sale O6329696 - 7104 TICKLEGRASS ST, WINTER GARDEN, FL 34787 43 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3347
       Built: 2014
    Monthly Fee: $195
       Tax: $552 (2024)
    Community: Signature Lakes Parcel 1D
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,068 (change assumption)
    Mortgage ($6,827) + Fees ($195) + Taxes in 2024 ($46)


    Taxes:$552

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 9940 BLACK BEAR LN, WINTER GARDEN, FL 34787

    $2,050,000353 Days on yellowkey   MLS ID: O6309917

    For Sale O6309917 - 9940 BLACK BEAR LN, WINTER GARDEN, FL 34787 8 photos

    Bed: 4   Bath: 4.5   Gar: 4
    Liv Area Sq Ft: 3110
       Built: 2025   Tax: $4,423 (2024)
    Community: Acreage & Unrec
    Single Family


    Estimated Monthly Payment: $11,601 (change assumption)
    Mortgage ($11,233) + Taxes in 2024 ($369)


    Taxes:$4,423

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 617 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $1,190,00053 Days on yellowkey   MLS ID: O6389100

    REDUCED by $10,000 (0.8%) on 04/20/2026

    For Sale O6389100 - 617 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3624
       Built: 2019
    Monthly Fee: $255
       Tax: $16,181 (2025)
    Community: Canopy Oaks Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,124 (change assumption)
    Mortgage ($6,520) + Fees ($255) + Taxes in 2025 ($1,348)


    Taxes:$16,181

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 156 STANTON ESTATES CIR, WINTER GARDEN, FL 34787

    $1,200,00060 Days on yellowkey   MLS ID: O6384801

    For Sale O6384801 - 156 STANTON ESTATES CIR, WINTER GARDEN, FL 34787 64 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: $7,428 (change assumption)
    Mortgage ($6,575) + 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


  • 671 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $1,325,00056 Days on yellowkey   MLS ID: O6383438

    0 Days Off yellowkey (back on 4/17/2026)

    REDUCED by $25,000 (1.9%) on 04/08/2026

    For Sale O6383438 - 671 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 62 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4490
       Built: 2019
    Monthly Fee: $300
       Tax: $12,519 (2024)
    Community: Canopy Oaks Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,603 (change assumption)
    Mortgage ($7,260) + Fees ($300) + Taxes in 2024 ($1,043)


    Taxes:$12,519

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 10067 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787

    $1,170,000165 Days on yellowkey   MLS ID: O6361968

    5 Days Off yellowkey (back on 4/2/2026)

    For Sale O6361968 - 10067 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787 97 photos

    Bed: 6   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4305
       Built: 2020
    Monthly Fee: $159
       Tax: $13,997 (2024)
    Community: Watermark Ph 4
    Single Family


    Estimated Monthly Payment: $7,736 (change assumption)
    Mortgage ($6,411) + Fees ($159) + Taxes in 2024 ($1,166)


    Taxes:$13,997

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 10472 PETRILLO WAY, WINTER GARDEN, FL 34787

    $1,065,00080 Days on yellowkey   MLS ID: O6382263

    For Sale O6382263 - 10472 PETRILLO WAY, WINTER GARDEN, FL 34787 53 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 4025
       Built: 2022
    Monthly Fee: $102
       Tax: $12,049 (2025)
    Community: Winding Bay Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,942 (change assumption)
    Mortgage ($5,835) + Fees ($102) + Taxes in 2025 ($1,004)


    Taxes:$12,049

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 441 COURTLEA OAKS BLVD, WINTER GARDEN, FL 34787

    $1,199,90060 Days on yellowkey   MLS ID: O6385964

    INCREASED by $80,900 (7.2%) on 04/02/2026

    For Sale O6385964 - 441 COURTLEA OAKS BLVD, WINTER GARDEN, FL 34787 63 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4001
       Built: 2000
    Monthly Fee: $83
       Tax: $5,551 (2024)
    Community: Courtlea Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,120 (change assumption)
    Mortgage ($6,575) + Fees ($83) + Taxes in 2024 ($463)


    Taxes:$5,551

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 16788 MUSKGRASS DR, WINTER GARDEN, FL 34787

    $1,600,00059 Days on yellowkey   MLS ID: O6388174

    For Sale O6388174 - 16788 MUSKGRASS DR, WINTER GARDEN, FL 34787 77 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4733
       Built: 2025
    Monthly Fee: $86

    Community: Lake Star At Ovation Phase 1B
    Single Family


    Estimated Monthly Payment: $8,853 (change assumption)
    Mortgage ($8,767) + Fees ($86) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16669 VARONE COVE CT, WINTER GARDEN, FL 34787

    $1,399,90091 Days on yellowkey   MLS ID: O6375749

    For Sale O6375749 - 16669 VARONE COVE CT, WINTER GARDEN, FL 34787 81 photos

    Bed: 7   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 5613
       Built: 2016
    Monthly Fee: $185
       Tax: $15,548 (2024)
    Community: Twinwaters
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,151 (change assumption)
    Mortgage ($7,670) + Fees ($185) + Taxes in 2024 ($1,296)


    Taxes:$15,548

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 13536 SUNSET LAKES CIR, WINTER GARDEN, FL 34787

    $1,200,00018 Days on yellowkey   MLS ID: O6399227

    For Sale O6399227 - 13536 SUNSET LAKES CIR, WINTER GARDEN, FL 34787 68 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3389
       Built: 1998
    Monthly Fee: $69
       Tax: $10,940 (2025)
    Community: Sunset Lakes
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,556 (change assumption)
    Mortgage ($6,575) + Fees ($69) + Taxes in 2025 ($912)


    Taxes:$10,940

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 1675 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787

    $1,149,90046 Days on yellowkey   MLS ID: O6392108

    For Sale O6392108 - 1675 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4299
       Built: 2017
    Monthly Fee: $184
       Tax: $12,008 (2024)
    Community: Twinwaters
    Single Family


    Estimated Monthly Payment: $7,485 (change assumption)
    Mortgage ($6,301) + Fees ($184) + Taxes in 2024 ($1,001)


    Taxes:$12,008

    Elementary School: Whispering Oak Elem

    High School: None

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 17144 PHIL C PETERS RD, WINTER GARDEN, FL 34787

    $2,550,000507 Days on yellowkey   MLS ID: O6260561

    For Sale O6260561 - 17144 PHIL C PETERS RD, WINTER GARDEN, FL 34787 10 photos

    Bed: 4   Bath: 4.5
    Liv Area Sq Ft: 4633
       Built: 1982   Tax: $1,591 (2023)
    Community: Lake Avalon Groves Rep
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,105 (change assumption)
    Mortgage ($13,972) + Taxes in 2023 ($133)


    Taxes:$1,591

    Elementary School: Hamlin Elementary

    High School: Windermere High School

    Tax Year: 2023

    Middle School: Hamlin Middle


  • 15195 LAKE CLAIRE OVERLOOK DR, WINTER GARDEN, FL 34787

    $1,295,00052 Days on yellowkey   MLS ID: O6389732

    5 Days Off yellowkey (back on 4/16/2026)

    For Sale O6389732 - 15195 LAKE CLAIRE OVERLOOK DR, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3844
       Built: 2016
    Monthly Fee: $235
       Tax: $8,393 (2025)
    Community: Hickory Hammock Ph 2B
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,030 (change assumption)
    Mortgage ($7,096) + Fees ($235) + Taxes in 2025 ($699)


    Taxes:$8,393

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15161 CANOE PL, WINTER GARDEN, FL 34787

    $1,200,00020 Days on yellowkey   MLS ID: O6398949

    For Sale O6398949 - 15161 CANOE PL, WINTER GARDEN, FL 34787 63 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3816
       Built: 2019
    Monthly Fee: $385
       Tax: $13,235 (2025)
    Community: Lakeshore Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $8,063 (change assumption)
    Mortgage ($6,575) + Fees ($385) + Taxes in 2025 ($1,103)


    Taxes:$13,235

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 5401 BOWMAN DR, WINTER GARDEN, FL 34787

    $1,250,00023 Days on yellowkey   MLS ID: O6390128

    0 Days Off yellowkey (back on 4/14/2026)

    For Sale O6390128 - 5401 BOWMAN DR, WINTER GARDEN, FL 34787 99 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4044
       Built: 2015
    Monthly Fee: $214
       Tax: $9,108 (2025)
    Community: Overlook At Hamlin
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,822 (change assumption)
    Mortgage ($6,849) + Fees ($214) + Taxes in 2025 ($759)


    Taxes:$9,108

    Elementary School: None

    High School: None

    Tax Year: 2025

    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.