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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Living Area Square Feet: 2000 to 2499

Winter Garden - 170 properties found

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  • 9354 MCLAREN ALY, WINTER GARDEN, FL 34787

    $529,50053 Days on yellowkey   MLS ID: O6390060

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

    REDUCED by $15,500 (2.8%) on 04/17/2026

    For Sale O6390060 - 9354 MCLAREN ALY, WINTER GARDEN, FL 34787 59 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2014
       Built: 2020
    Monthly Fee: $257
       Tax: $614 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $3,209 (change assumption)
    Mortgage ($2,901) + Fees ($257) + Taxes in 2025 ($51)


    Taxes:$614

    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

    $975,0002 Days on yellowkey   MLS ID: O6404208

    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: $6,755 (change assumption)
    Mortgage ($5,342) + 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


  • 4122 SHEPPERDS HOLLOW ALY, WINTER GARDEN, FL 34787

    $554,990122 Days on yellowkey   MLS ID: O6370363

    For Sale O6370363 - 4122 SHEPPERDS HOLLOW ALY, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2459
       Built: 2021
    Monthly Fee: $281
       Tax: $8,150 (2024)
    Community: Enclave/Hamlin
    Single Family


    Estimated Monthly Payment: $4,001 (change assumption)
    Mortgage ($3,041) + Fees ($281) + Taxes in 2024 ($679)


    Taxes:$8,150

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 17412 HONEYBELL TANGELO CT, WINTER GARDEN, FL 34787

    $727,0006 Days on yellowkey   MLS ID: O6402876

    For Sale O6402876 - 17412 HONEYBELL TANGELO CT, WINTER GARDEN, FL 34787 42 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2120
       Built: 2026
    Monthly Fee: $82

    Community: Northlake At Ovation
    Single Family


    Estimated Monthly Payment: $4,065 (change assumption)
    Mortgage ($3,983) + Fees ($82) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2026

    Middle School: Water Spring Middle


  • 8031 NAVEL ORANGE LN, WINTER GARDEN, FL 34787

    $659,00019 Days on yellowkey   MLS ID: O6399594

    REDUCED by $10,000 (1.5%) on 05/02/2026

    For Sale O6399594 - 8031 NAVEL ORANGE LN, WINTER GARDEN, FL 34787 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2298
       Built: 2015
    Monthly Fee: $82
       Tax: $8,090 (2025)
    Community: Summerlake Grvs
    Single Family


    Estimated Monthly Payment: $4,367 (change assumption)
    Mortgage ($3,611) + Fees ($82) + Taxes in 2025 ($674)


    Taxes:$8,090

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17058 QUICKSILVER AVE, WINTER GARDEN, FL 34787

    $539,000147 Days on yellowkey   MLS ID: O6365686

    For Sale O6365686 - 17058 QUICKSILVER AVE, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2492
       Built: 2021
    Monthly Fee: $215
       Tax: $7,682 (2024)
    Community: Waterside/Johns Lake Ph 2C
    Single Family


    Estimated Monthly Payment: $3,809 (change assumption)
    Mortgage ($2,953) + Fees ($215) + Taxes in 2024 ($640)


    Taxes:$7,682

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 15162 CANOPY COVER DR, WINTER GARDEN, FL 34787

    $880,000157 Days on yellowkey   MLS ID: S5139203

    REDUCED by $5,000 (0.6%) on 04/29/2026

    For Sale S5139203 - 15162 CANOPY COVER DR, WINTER GARDEN, FL 34787 69 photos

    Bed: 2   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2049
       Built: 2023
    Monthly Fee: $545
       Tax: $1,939 (2023)
    Community: Del Webb Oasis Phase 2
    Single Family


    Estimated Monthly Payment: $5,528 (change assumption)
    Mortgage ($4,822) + Fees ($545) + Taxes in 2023 ($162)


    Taxes:$1,939

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 13846 FRESH IVY ST, WINTER GARDEN, FL 34787

    $649,900216 Days on yellowkey   MLS ID: O6346706

    For Sale O6346706 - 13846 FRESH IVY ST, WINTER GARDEN, FL 34787 51 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2108
       Built: 2024
    Monthly Fee: $534
       Tax: $2,180 (2024)
    Community: Del Webb Oasis Ph 3
    Single Family


    Estimated Monthly Payment: $4,277 (change assumption)
    Mortgage ($3,561) + Fees ($534) + Taxes in 2024 ($182)


    Taxes:$2,180

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 15613 PORTER RD, WINTER GARDEN, FL 34787

    $575,0006 Days on yellowkey   MLS ID: O6397283

    For Sale O6397283 - 15613 PORTER RD, WINTER GARDEN, FL 34787 48 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2089
       Built: 2015
    Monthly Fee: $252
       Tax: $8,171 (2025)
    Community: Summerlake Ph 2C 2D 2E
    Single Family


    Estimated Monthly Payment: $4,084 (change assumption)
    Mortgage ($3,151) + Fees ($252) + Taxes in 2025 ($681)


    Taxes:$8,171

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17055 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $580,68253 Days on yellowkey   MLS ID: G5109480

    0 Days Off yellowkey (back on 4/29/2026)

    For Sale G5109480 - 17055 HAGGERTY HOLLOW DR, 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: $3,332 (change assumption)
    Mortgage ($3,182) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17054 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $688,32453 Days on yellowkey   MLS ID: G5109477

    For Sale G5109477 - 17054 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 1 photos

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

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,922 (change assumption)
    Mortgage ($3,772) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1005 CHASE DR, WINTER GARDEN, FL 34787

    $639,000150 Days on yellowkey   MLS ID: A4674195

    REDUCED by $5,000 (0.8%) on 04/30/2026

    For Sale A4674195 - 1005 CHASE DR, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2319
       Built: 2005
    Monthly Fee: $68
       Tax: $7,086 (2024)
    Community: Island Pointe Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,160 (change assumption)
    Mortgage ($3,501) + Fees ($68) + Taxes in 2024 ($591)


    Taxes:$7,086

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15527 SWEET ORANGE AVE, WINTER GARDEN, FL 34787

    $700,00038 Days on yellowkey   MLS ID: O6394429

    For Sale O6394429 - 15527 SWEET ORANGE AVE, WINTER GARDEN, FL 34787 38 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2383
       Built: 2017
    Monthly Fee: $118
       Tax: $5,959 (2025)
    Community: Highlands/Summerlake Grvs Ph 1
    Single Family


    Estimated Monthly Payment: $4,450 (change assumption)
    Mortgage ($3,836) + Fees ($118) + Taxes in 2025 ($497)


    Taxes:$5,959

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1032 BURLAND CIR, WINTER GARDEN, FL 34787

    $519,9906 Days on yellowkey   MLS ID: O6401764

    For Sale O6401764 - 1032 BURLAND CIR, WINTER GARDEN, FL 34787 58 photos

    Bed: 5   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2487
       Built: 2005
    Monthly Fee: $64
       Tax: $6,728 (2025)
    Community: Fullers Xing Ph 03 A-G
    Single Family


    Estimated Monthly Payment: $3,474 (change assumption)
    Mortgage ($2,849) + Fees ($64) + Taxes in 2025 ($561)


    Taxes:$6,728

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11045 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $749,90037 Days on yellowkey   MLS ID: O6394192

    For Sale O6394192 - 11045 HOLLOW BAY DR, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2025
    Monthly Fee: $295
       Tax: $3,196 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,670 (change assumption)
    Mortgage ($4,109) + Fees ($295) + Taxes in 2025 ($266)


    Taxes:$3,196

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16933 OAKBORO ST, WINTER GARDEN, FL 34787

    $560,00043 Days on yellowkey   MLS ID: R4910916

    For Sale R4910916 - 16933 OAKBORO ST, WINTER GARDEN, FL 34787 32 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2020
    Monthly Fee: $257
       Tax: $3,651 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $3,630 (change assumption)
    Mortgage ($3,068) + Fees ($257) + Taxes in 2025 ($304)


    Taxes:$3,651

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13151 CALMING BREEZE WAY, WINTER GARDEN, FL 34787

    $565,000153 Days on yellowkey   MLS ID: O6363957

    REDUCED by $4,000 (0.7%) on 05/02/2026

    For Sale O6363957 - 13151 CALMING BREEZE WAY, WINTER GARDEN, FL 34787 39 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: $3,867 (change assumption)
    Mortgage ($3,096) + 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


  • 14834 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787

    $525,00033 Days on yellowkey   MLS ID: O6395079

    REDUCED by $10,000 (1.9%) on 05/01/2026

    For Sale O6395079 - 14834 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787 56 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2049
       Built: 2014
    Monthly Fee: $252
       Tax: $3,824 (2025)
    Community: Summerlake Pd Ph 1B-A Rep
    Single Family


    Estimated Monthly Payment: $3,447 (change assumption)
    Mortgage ($2,877) + Fees ($252) + Taxes in 2025 ($319)


    Taxes:$3,824

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16012 MICELLI DR, WINTER GARDEN, FL 34787

    $699,00084 Days on yellowkey   MLS ID: TB8472370

    For Sale TB8472370 - 16012 MICELLI DR, WINTER GARDEN, FL 34787 77 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2428
       Built: 2021
    Monthly Fee: $101
       Tax: $7,755 (2024)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $4,577 (change assumption)
    Mortgage ($3,830) + Fees ($101) + Taxes in 2024 ($646)


    Taxes:$7,755

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16140 HARBOR MIST ALY, WINTER GARDEN, FL 34787

    $565,000151 Days on yellowkey   MLS ID: O6365057

    For Sale O6365057 - 16140 HARBOR MIST ALY, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2018
    Monthly Fee: $245
       Tax: $8,615 (2025)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $4,059 (change assumption)
    Mortgage ($3,096) + Fees ($245) + Taxes in 2025 ($718)


    Taxes:$8,615

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring 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.