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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Price: $900,000 to $999,000

Winter Garden - 63 properties found

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  • 11277 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $914,990Listed 06/25/2026 10:37AM   MLS ID: O6419923

    For Sale O6419923 - 11277 HOLLOW BAY DR, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3327
       Built: 2025
    Monthly Fee: $208
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,387 (change assumption)
    Mortgage ($5,014) + Fees ($208) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14140 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787

    $996,97575 Days on yellowkey   MLS ID: O6397262

    REDUCED by $25 (0.0%) on 05/28/2026

    For Sale O6397262 - 14140 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787 72 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2346
       Built: 1984
    Monthly Fee: $71
       Tax: $10,303 (2025)
    Community: Country Lakes
    Single Family


    Estimated Monthly Payment: $6,392 (change assumption)
    Mortgage ($5,463) + Fees ($71) + Taxes in 2025 ($859)


    Taxes:$10,303

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17350 WILD DAISY DR, WINTER GARDEN, FL 34787

    $910,5108 Days on yellowkey   MLS ID: G5113976

    For Sale G5113976 - 17350 WILD DAISY DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4236
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $5,139 (change assumption)
    Mortgage ($4,989) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 8216 TOPSAIL PL, WINTER GARDEN, FL 34787

    $949,900100 Days on yellowkey   MLS ID: O6391155

    REDUCED by $25,000 (2.6%) on 06/24/2026

    For Sale O6391155 - 8216 TOPSAIL PL, WINTER GARDEN, FL 34787 67 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3055
       Built: 2022
    Monthly Fee: $360
       Tax: $12,728 (2025)
    Community: Lakeshore Preserve Ph 5
    Single Family


    Estimated Monthly Payment: $6,625 (change assumption)
    Mortgage ($5,205) + Fees ($360) + Taxes in 2025 ($1,061)


    Taxes:$12,728

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14187 JOMATT LOOP, WINTER GARDEN, FL 34787

    $949,90092 Days on yellowkey   MLS ID: O6393373

    0 Days Off yellowkey (back on 6/24/2026)

    For Sale O6393373 - 14187 JOMATT LOOP, WINTER GARDEN, FL 34787 28 photos

    Bed: 6   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4181
       Built: 2019
    Monthly Fee: $70
       Tax: $7,632 (2025)
    Community: Cypress Reserve Ph 2
    Single Family


    Estimated Monthly Payment: $5,911 (change assumption)
    Mortgage ($5,205) + Fees ($70) + Taxes in 2025 ($636)


    Taxes:$7,632

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 13822 JOMATT LOOP, WINTER GARDEN, FL 34787

    $975,00027 Days on yellowkey   MLS ID: O6411926

    REDUCED by $25,000 (2.5%) on 06/24/2026

    For Sale O6411926 - 13822 JOMATT LOOP, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3828
       Built: 2016
    Monthly Fee: $75
       Tax: $12,039 (2025)
    Community: Cypress Reserve Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,421 (change assumption)
    Mortgage ($5,342) + Fees ($75) + Taxes in 2025 ($1,003)


    Taxes:$12,039

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 10264 LOVE STORY ST, WINTER GARDEN, FL 34787

    $915,00037 Days on yellowkey   MLS ID: O6409005

    For Sale O6409005 - 10264 LOVE STORY ST, WINTER GARDEN, FL 34787 35 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3295
       Built: 2018
    Monthly Fee: $228
       Tax: $11,228 (2025)
    Community: Storey Grove Ph 1B-2
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,177 (change assumption)
    Mortgage ($5,014) + Fees ($228) + Taxes in 2025 ($936)


    Taxes:$11,228

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15078 CANOPY COVER DR, WINTER GARDEN, FL 34787

    $969,00054 Days on yellowkey   MLS ID: O6404208

    REDUCED by $5,000 (0.5%) on 06/24/2026

    For Sale O6404208 - 15078 CANOPY COVER DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2270
       Built: 2024
    Monthly Fee: $545
       Tax: $10,412 (2025)
    Community: Del Webb Oasis
    Single Family


    Estimated Monthly Payment: $6,722 (change assumption)
    Mortgage ($5,309) + Fees ($545) + Taxes in 2025 ($868)


    Taxes:$10,412

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9218 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787

    $920,000117 Days on yellowkey   MLS ID: O6386394

    REDUCED by $7,900 (0.9%) on 05/13/2026

    For Sale O6386394 - 9218 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787 64 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3087
       Built: 2018
    Monthly Fee: $164
       Tax: $11,801 (2025)
    Community: Watermark Ph 2B
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,188 (change assumption)
    Mortgage ($5,041) + Fees ($164) + Taxes in 2025 ($983)


    Taxes:$11,801

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1646 HOLCOMB CREEK ST, WINTER GARDEN, FL 34787

    $909,00088 Days on yellowkey   MLS ID: O6394506

    REDUCED by $20,000 (2.2%) on 06/17/2026

    For Sale O6394506 - 1646 HOLCOMB CREEK ST, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3841
       Built: 2017
    Monthly Fee: $184
       Tax: $12,543 (2025)
    Community: Twinwaters
    Single Family


    Estimated Monthly Payment: $6,210 (change assumption)
    Mortgage ($4,981) + Fees ($184) + Taxes in 2025 ($1,045)


    Taxes:$12,543

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15878 CITRUS GROVE LOOP, WINTER GARDEN, FL 34787

    $910,0006 Days on yellowkey   MLS ID: O6418239

    For Sale O6418239 - 15878 CITRUS GROVE LOOP, WINTER GARDEN, FL 34787 68 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3505
       Built: 2016
    Monthly Fee: $235
       Tax: $6,920 (2025)
    Community: Hickory Hammock Ph 1B
    Single Family


    Estimated Monthly Payment: $5,798 (change assumption)
    Mortgage ($4,986) + Fees ($235) + Taxes in 2025 ($577)


    Taxes:$6,920

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16043 SILVER BROOK WAY, WINTER GARDEN, FL 34787

    $950,0009 Days on yellowkey   MLS ID: O6417421

    For Sale O6417421 - 16043 SILVER BROOK WAY, WINTER GARDEN, FL 34787 86 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3899
       Built: 2024
    Monthly Fee: $168
       Tax: $13,827 (2025)
    Community: Silverleaf Reserve/Hamlin Ph 2
    Single Family


    Estimated Monthly Payment: $6,526 (change assumption)
    Mortgage ($5,205) + Fees ($168) + Taxes in 2025 ($1,152)


    Taxes:$13,827

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14359 MAGNOLIA RIDGE LOOP, WINTER GARDEN, FL 34787

    $998,00040 Days on yellowkey   MLS ID: O6408165

    REDUCED by $10,000 (1.0%) on 06/21/2026

    For Sale O6408165 - 14359 MAGNOLIA RIDGE LOOP, WINTER GARDEN, FL 34787 19 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3881
       Built: 2015
    Monthly Fee: $188
       Tax: $13,774 (2025)
    Community: Orchard Hills Phase 1
    Single Family


    Estimated Monthly Payment: $6,804 (change assumption)
    Mortgage ($5,468) + Fees ($188) + Taxes in 2025 ($1,148)


    Taxes:$13,774

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 14102 LOCHEND WAY, WINTER GARDEN, FL 34787

    $935,00022 Days on yellowkey   MLS ID: O6411646

    REDUCED by $43,800 (4.5%) on 06/19/2026

    For Sale O6411646 - 14102 LOCHEND WAY, WINTER GARDEN, FL 34787 62 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3606
       Built: 2024
    Monthly Fee: $77
       Tax: $11,605 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $6,167 (change assumption)
    Mortgage ($5,123) + Fees ($77) + Taxes in 2025 ($967)


    Taxes:$11,605

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17738 SEDONA ST, WINTER GARDEN, FL 34787

    $905,93942 Days on yellowkey   MLS ID: O6407986

    1 Days Off yellowkey (back on 6/20/2026)

    INCREASED by $3,275 (0.4%) on 06/06/2026

    For Sale O6407986 - 17738 SEDONA ST, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2573
       Built: 2026
    Monthly Fee: $142

    Community: Esplanade At Mckinnon Groves
    Single Family


    Estimated Monthly Payment: $5,106 (change assumption)
    Mortgage ($4,964) + Fees ($142) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 9738 TOWER PINE DR, WINTER GARDEN, FL 34787

    $950,0006 Days on yellowkey   MLS ID: O6417627

    For Sale O6417627 - 9738 TOWER PINE DR, WINTER GARDEN, FL 34787 55 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2526
       Built: 1993   Tax: $7,549 (2025)
    Community: Lake Avalon Rural Settlement
    Single Family


    Estimated Monthly Payment: $5,834 (change assumption)
    Mortgage ($5,205) + Taxes in 2025 ($629)


    Taxes:$7,549

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16827 SANCTUARY DR, WINTER GARDEN, FL 34787

    $998,00061 Days on yellowkey   MLS ID: S5148416

    For Sale S5148416 - 16827 SANCTUARY DR, WINTER GARDEN, FL 34787 64 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2281
       Built: 2020
    Monthly Fee: $165
       Tax: $6,024 (2025)
    Community: Sanctuary/Twin Waters
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,135 (change assumption)
    Mortgage ($5,468) + Fees ($165) + Taxes in 2025 ($502)


    Taxes:$6,024

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9849 LOST CREEK DR, WINTER GARDEN, FL 34787

    $990,000581 Days on yellowkey   MLS ID: O6258009

    1 Days Off yellowkey (back on 6/18/2026)

    For Sale O6258009 - 9849 LOST CREEK DR, WINTER GARDEN, FL 34787 57 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3910
       Built: 2021
    Monthly Fee: $250
       Tax: $10,950 (2023)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,587 (change assumption)
    Mortgage ($5,425) + Fees ($250) + Taxes in 2023 ($913)


    Taxes:$10,950

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2023

    Middle School: Water Spring Middle


  • 10174 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787

    $999,00060 Days on yellowkey   MLS ID: O6402434

    REDUCED by $26,000 (2.5%) on 06/18/2026

    For Sale O6402434 - 10174 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2758
       Built: 2020
    Monthly Fee: $250
       Tax: $7,946 (2025)
    Community: Waterleigh Ph 2C-2 & 2C-3
    Single Family


    Estimated Monthly Payment: $6,386 (change assumption)
    Mortgage ($5,474) + Fees ($250) + Taxes in 2025 ($662)


    Taxes:$7,946

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16175 LEYLAND CYPRESS LN, WINTER GARDEN, FL 34787

    $920,308231 Days on yellowkey   MLS ID: G5104189

    0 Days Off yellowkey (back on 11/6/2025)

    For Sale G5104189 - 16175 LEYLAND CYPRESS LN, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3108
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $5,193 (change assumption)
    Mortgage ($5,043) + 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.