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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Living Area Square Feet: 2000 to 2499

Winter Garden - 200 properties found

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  • 12537 GRAPE CHARDONNAY ALY, WINTER GARDEN, FL 34787

    $647,17226 Days on yellowkey   MLS ID: O6411681

    For Sale O6411681 - 12537 GRAPE CHARDONNAY ALY, WINTER GARDEN, FL 34787 1 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2200
       Built: 2026
    Monthly Fee: $96
       Tax: $9,708 (2026)
    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $4,451 (change assumption)
    Mortgage ($3,546) + Fees ($96) + Taxes in 2026 ($809)


    Taxes:$9,708

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2026

    Middle School: Water Spring Middle


  • 12391 SILK MIMOSA ALY, WINTER GARDEN, FL 34787

    $607,67918 Days on yellowkey   MLS ID: O6414276

    For Sale O6414276 - 12391 SILK MIMOSA ALY, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2200
       Built: 2026
    Monthly Fee: $96
       Tax: $9,115 (2026)
    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $4,185 (change assumption)
    Mortgage ($3,330) + Fees ($96) + Taxes in 2026 ($760)


    Taxes:$9,115

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 16105 WATER SPRING BLVD, WINTER GARDEN, FL 34787

    $499,000260 Days on yellowkey   MLS ID: O6348822

    REDUCED by $20,000 (3.9%) on 04/16/2026

    For Sale O6348822 - 16105 WATER SPRING BLVD, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2042
       Built: 2020
    Monthly Fee: $103
       Tax: $4,770 (2024)
    Community: Storey Grove
    Single Family


    Estimated Monthly Payment: $3,235 (change assumption)
    Mortgage ($2,734) + Fees ($103) + Taxes in 2024 ($397)


    Taxes:$4,770

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 913 BENDING OAK TRL, WINTER GARDEN, FL 34787

    $530,00012 Days on yellowkey   MLS ID: O6409986

    1 Days Off yellowkey (back on 6/14/2026)

    For Sale O6409986 - 913 BENDING OAK TRL, WINTER GARDEN, FL 34787 28 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2212
       Built: 2012
    Monthly Fee: $125
       Tax: $3,860 (2025)
    Community: Oaks/Brandy Lake 01 Rep A & B
    Single Family


    Estimated Monthly Payment: $3,351 (change assumption)
    Mortgage ($2,904) + Fees ($125) + Taxes in 2025 ($322)


    Taxes:$3,860

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1906 SHERBOURNE ST, WINTER GARDEN, FL 34787

    $477,00021 Days on yellowkey   MLS ID: S5151079

    For Sale S5151079 - 1906 SHERBOURNE ST, WINTER GARDEN, FL 34787 25 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2029
       Built: 2002
    Monthly Fee: $46
       Tax: $2,815 (2025)
    Community: Stone Creek 44/131
    Single Family


    Estimated Monthly Payment: $2,894 (change assumption)
    Mortgage ($2,614) + Fees ($46) + Taxes in 2025 ($235)


    Taxes:$2,815

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 1544 MISTFLOWER LN, WINTER GARDEN, FL 34787

    $469,90022 Days on yellowkey   MLS ID: O6407815

    0 Days Off yellowkey (back on 6/8/2026)

    For Sale O6407815 - 1544 MISTFLOWER LN, WINTER GARDEN, FL 34787 25 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2348
       Built: 2005
    Monthly Fee: $55
       Tax: $7,220 (2025)
    Community: Winter Garden Trls 01-3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,231 (change assumption)
    Mortgage ($2,575) + Fees ($55) + Taxes in 2025 ($602)


    Taxes:$7,220

    Elementary School: William Frangus Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 11036 ROBERT FROST DR, WINTER GARDEN, FL 34787

    $649,99025 Days on yellowkey   MLS ID: O6410350

    For Sale O6410350 - 11036 ROBERT FROST DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2136
       Built: 2021
    Monthly Fee: $221
       Tax: $8,394 (2025)
    Community: Storey Grove Ph 3
    Single Family


    Estimated Monthly Payment: $4,482 (change assumption)
    Mortgage ($3,562) + Fees ($221) + Taxes in 2025 ($700)


    Taxes:$8,394

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 7190 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787

    $545,00047 Days on yellowkey   MLS ID: O6402423

    For Sale O6402423 - 7190 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787 24 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2016
    Monthly Fee: $253
       Tax: $5,148 (2025)
    Community: Lakeview Pointe/Horizon West P
    Single Family


    Estimated Monthly Payment: $3,668 (change assumption)
    Mortgage ($2,986) + Fees ($253) + Taxes in 2025 ($429)


    Taxes:$5,148

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 8275 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $555,00074 Days on yellowkey   MLS ID: TB8496196

    REDUCED by $10,000 (1.8%) on 06/09/2026

    For Sale TB8496196 - 8275 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 96 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2019
       Built: 2017
    Monthly Fee: $312
       Tax: $5,109 (2025)
    Community: Waterleigh Ph 1B
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,779 (change assumption)
    Mortgage ($3,041) + Fees ($312) + Taxes in 2025 ($426)


    Taxes:$5,109

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 279 DOE RUN DR, WINTER GARDEN, FL 34787

    $599,00025 Days on yellowkey   MLS ID: TB8513595

    For Sale TB8513595 - 279 DOE RUN DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2435
       Built: 2005
    Monthly Fee: $57
       Tax: $2,489 (2025)
    Community: Deerfield Place 57/1
    Single Family


    Estimated Monthly Payment: $3,547 (change assumption)
    Mortgage ($3,282) + Fees ($57) + Taxes in 2025 ($207)


    Taxes:$2,489

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5460 BOWMAN DR, WINTER GARDEN, FL 34787

    $585,00046 Days on yellowkey   MLS ID: O6402308

    REDUCED by $30,000 (4.9%) on 06/10/2026

    For Sale O6402308 - 5460 BOWMAN DR, WINTER GARDEN, FL 34787 69 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2474
       Built: 2016
    Monthly Fee: $328
       Tax: $8,917 (2025)
    Community: Overlook At Hamlin
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,276 (change assumption)
    Mortgage ($3,205) + Fees ($328) + Taxes in 2025 ($743)


    Taxes:$8,917

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 5754 SURPRISE LILY DR, WINTER GARDEN, FL 34787

    $515,00011 Days on yellowkey   MLS ID: S5151845

    For Sale S5151845 - 5754 SURPRISE LILY DR, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2128
       Built: 2021
    Monthly Fee: $91
       Tax: $8,266 (2025)
    Community: Hamilton Gardens Ph 2A 2B
    Single Family


    Estimated Monthly Payment: $3,602 (change assumption)
    Mortgage ($2,822) + Fees ($91) + Taxes in 2025 ($689)


    Taxes:$8,266

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 6475 BREEZE FILLED LN, WINTER GARDEN, FL 34787

    $585,00011 Days on yellowkey   MLS ID: O6416512

    For Sale O6416512 - 6475 BREEZE FILLED LN, WINTER GARDEN, FL 34787 43 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2231
       Built: 2025
    Monthly Fee: $147
       Tax: $2,107 (2025)
    Community: Silverleaf Oaks At Hamlin Phase 3A
    Single Family


    Estimated Monthly Payment: $3,528 (change assumption)
    Mortgage ($3,205) + Fees ($147) + Taxes in 2025 ($176)


    Taxes:$2,107

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 7808 WINTER WREN ST, WINTER GARDEN, FL 34787

    $579,00061 Days on yellowkey   MLS ID: O6400269

    0 Days Off yellowkey (back on 6/12/2026)

    REDUCED by $9,000 (1.5%) on 06/04/2026

    For Sale O6400269 - 7808 WINTER WREN ST, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2274
       Built: 2015
    Monthly Fee: $252
       Tax: $8,119 (2025)
    Community: Summerlake
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,101 (change assumption)
    Mortgage ($3,173) + Fees ($252) + Taxes in 2025 ($677)


    Taxes:$8,119

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17090 HARBOR OAK PKWY, WINTER GARDEN, FL 34787

    $534,90055 Days on yellowkey   MLS ID: G5111718

    1 Days Off yellowkey (back on 6/12/2026)

    REDUCED by $5,000 (0.9%) on 06/02/2026

    For Sale G5111718 - 17090 HARBOR OAK PKWY, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2148
       Built: 2019
    Monthly Fee: $215
       Tax: $7,499 (2025)
    Community: Waterside/Johns Lk-Ph 2A
    Single Family


    Estimated Monthly Payment: $3,771 (change assumption)
    Mortgage ($2,931) + Fees ($215) + Taxes in 2025 ($625)


    Taxes:$7,499

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17125 STILLNESS ALY, WINTER GARDEN, FL 34787

    $580,93312 Days on yellowkey   MLS ID: G5113666

    For Sale G5113666 - 17125 STILLNESS ALY, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2083
       Built: 2026
    Monthly Fee: $121

    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $3,304 (change assumption)
    Mortgage ($3,183) + Fees ($121) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 611 SIGLER DR, WINTER GARDEN, FL 34787

    $899,76014 Days on yellowkey   MLS ID: O6415005

    For Sale O6415005 - 611 SIGLER DR, WINTER GARDEN, FL 34787 14 photos

    Bed: 4   Bath: 3.5   Gar: 22
    Liv Area Sq Ft: 2432
       Built: 2026
    Monthly Fee: $155
       Tax: $993 (2025)
    Community: Lakeview Village Estates
    Single Family


    Estimated Monthly Payment: $5,168 (change assumption)
    Mortgage ($4,930) + Fees ($155) + Taxes in 2025 ($83)


    Taxes:$993

    Elementary School: Dillard Street Elem

    High School: None

    Tax Year: 2025

    Middle School: Lakeview Middle


  • WINTER GARDEN, FL 34787

    $558,99012 Days on yellowkey   MLS ID: G5113611

    0 Days Off yellowkey (back on 6/11/2026)

    For Sale G5113611 - 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: $3,213 (change assumption)
    Mortgage ($3,063) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1343 CASTLEPORT RD, WINTER GARDEN, FL 34787

    $535,00012 Days on yellowkey   MLS ID: O6414756

    For Sale O6414756 - 1343 CASTLEPORT RD, WINTER GARDEN, FL 34787 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2170
       Built: 2001
    Monthly Fee: $243
       Tax: $4,191 (2025)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,524 (change assumption)
    Mortgage ($2,931) + Fees ($243) + Taxes in 2025 ($349)


    Taxes:$4,191

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 13343 SUNNY RETREAT LN, WINTER GARDEN, FL 34787

    $799,900139 Days on yellowkey   MLS ID: O6379591

    REDUCED by $49,100 (5.8%) on 06/11/2026

    For Sale O6379591 - 13343 SUNNY RETREAT LN, WINTER GARDEN, FL 34787 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2214
       Built: 2023
    Monthly Fee: $544
       Tax: $10,256 (2024)
    Community: Del Webb Oasis
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,782 (change assumption)
    Mortgage ($4,383) + Fees ($544) + Taxes in 2024 ($855)


    Taxes:$10,256

    Elementary School: None

    High School: None

    Tax Year: 2024

    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.