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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Living Area Square Feet: 2500 to 2999

Winter Garden - 130 properties found

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  • 16167 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787

    $699,50060 Days on yellowkey   MLS ID: O6387577

    2 Days Off yellowkey (back on 4/9/2026)

    For Sale O6387577 - 16167 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787 73 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2017
    Monthly Fee: $341
       Tax: $5,669 (2024)
    Community: Waterleigh Ph 1C
    Single Family


    Estimated Monthly Payment: $4,646 (change assumption)
    Mortgage ($3,833) + Fees ($341) + Taxes in 2024 ($472)


    Taxes:$5,669

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 12983 HARVEST RAIN AVE, WINTER GARDEN, FL 34787

    $750,00026 Days on yellowkey   MLS ID: O6397592

    For Sale O6397592 - 12983 HARVEST RAIN AVE, WINTER GARDEN, FL 34787 53 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2858
       Built: 2026
    Monthly Fee: $140

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,249 (change assumption)
    Mortgage ($4,109) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17606 LAKE STAR RD, WINTER GARDEN, FL 34787

    $870,00075 Days on yellowkey   MLS ID: O6382909

    For Sale O6382909 - 17606 LAKE STAR RD, WINTER GARDEN, FL 34787 73 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2605
       Built: 2023
    Monthly Fee: $83
       Tax: $12,316 (2024)
    Community: Northlake/Ovation Ph 1
    Single Family


    Estimated Monthly Payment: $5,876 (change assumption)
    Mortgage ($4,767) + Fees ($83) + Taxes in 2024 ($1,026)


    Taxes:$12,316

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 15372 GILLIGAN CT, WINTER GARDEN, FL 34787

    $870,000140 Days on yellowkey   MLS ID: O6367059

    3 Days Off yellowkey (back on 4/7/2026)

    For Sale O6367059 - 15372 GILLIGAN CT, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2781
       Built: 2020
    Monthly Fee: $102
       Tax: $8,004 (2023)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $5,536 (change assumption)
    Mortgage ($4,767) + Fees ($102) + Taxes in 2023 ($667)


    Taxes:$8,004

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2023

    Middle School: Water Spring Middle


  • 15707 SIGNATURE DR., WINTER GARDEN, FL 34787

    $575,000397 Days on yellowkey   MLS ID: O6295079

    0 Days Off yellowkey (back on 4/6/2026)

    For Sale O6295079 - 15707 SIGNATURE DR., WINTER GARDEN, FL 34787 28 photos

    Bed: 6   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2714
       Built: 2013
    Monthly Fee: $184
       Tax: $8,595 (2024)
    Community: Independence Community
    Single Family


    Estimated Monthly Payment: $4,051 (change assumption)
    Mortgage ($3,151) + Fees ($184) + Taxes in 2024 ($716)


    Taxes:$8,595

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 16071 BARKLY RIDGE CT, WINTER GARDEN, FL 34787

    $1,150,00052 Days on yellowkey   MLS ID: O6390569

    For Sale O6390569 - 16071 BARKLY RIDGE CT, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2986
       Built: 2024
    Monthly Fee: $225
       Tax: $2,420 (2024)
    Community: Avalon Ridge
    Single Family


    Estimated Monthly Payment: $6,728 (change assumption)
    Mortgage ($6,301) + Fees ($225) + Taxes in 2024 ($202)


    Taxes:$2,420

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 5931 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $829,965228 Days on yellowkey   MLS ID: G5102265

    0 Days Off yellowkey (back on 9/18/2025)

    For Sale G5102265 - 5931 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2688
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,698 (change assumption)
    Mortgage ($4,548) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 730 RIVER GRASS LN, WINTER GARDEN, FL 34787

    $649,90099 Days on yellowkey   MLS ID: G5107248

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

    For Sale G5107248 - 730 RIVER GRASS LN, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2647
       Built: 2014
    Monthly Fee: $72
       Tax: $3,572 (2024)
    Community: Covington Chase Ph 2C
    Single Family


    Estimated Monthly Payment: $3,931 (change assumption)
    Mortgage ($3,561) + Fees ($72) + Taxes in 2024 ($298)


    Taxes:$3,572

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 419 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787

    $874,99032 Days on yellowkey   MLS ID: O6395693

    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
    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


  • 17061 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $565,99033 Days on yellowkey   MLS ID: G5110436

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

    For Sale G5110436 - 17061 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,223 (change assumption)
    Mortgage ($3,101) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 5778 LAUREL CHERRY AVE, WINTER GARDEN, FL 34787

    $540,00033 Days on yellowkey   MLS ID: O6395452

    For Sale O6395452 - 5778 LAUREL CHERRY AVE, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2524
       Built: 2016
    Monthly Fee: $195
       Tax: $9,031 (2025)
    Community: Signature Lakes
    Single Family


    Estimated Monthly Payment: $3,906 (change assumption)
    Mortgage ($2,959) + Fees ($195) + Taxes in 2025 ($753)


    Taxes:$9,031

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13001 HARVEST RAIN AVE, WINTER GARDEN, FL 34787

    $750,00048 Days on yellowkey   MLS ID: O6391387

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

    For Sale O6391387 - 13001 HARVEST RAIN AVE, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2858
       Built: 2026
    Monthly Fee: $140

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,249 (change assumption)
    Mortgage ($4,109) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1112 JUNIPER HAMMOCK CT, WINTER GARDEN, FL 34787

    $520,00055 Days on yellowkey   MLS ID: O6388013

    REDUCED by $5,000 (1.0%) on 04/01/2026

    For Sale O6388013 - 1112 JUNIPER HAMMOCK CT, WINTER GARDEN, FL 34787 28 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2545
       Built: 2002
    Monthly Fee: $44
       Tax: $6,455 (2024)
    Community: Fullers Crossing Ph 02 49 31
    Single Family


    Estimated Monthly Payment: $3,431 (change assumption)
    Mortgage ($2,849) + Fees ($44) + Taxes in 2024 ($538)


    Taxes:$6,455

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 7832 FREESTYLE LN, WINTER GARDEN, FL 34787

    $1,100,00090 Days on yellowkey   MLS ID: G5107680

    For Sale G5107680 - 7832 FREESTYLE LN, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2650
       Built: 2018
    Monthly Fee: $300
       Tax: $16,616 (2025)
    Community: Isles Of Lake Hancock
    Single Family


    Estimated Monthly Payment: $7,712 (change assumption)
    Mortgage ($6,027) + Fees ($300) + Taxes in 2025 ($1,385)


    Taxes:$16,616

    Elementary School: Independence Elementary

    High School: None

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 3439 CURRENT AVE, WINTER GARDEN, FL 34787

    $729,90055 Days on yellowkey   MLS ID: S5145475

    2 Days Off yellowkey (back on 3/30/2026)

    For Sale S5145475 - 3439 CURRENT AVE, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 4.5
    Liv Area Sq Ft: 2920
       Built: 2020
    Monthly Fee: $152
       Tax: $9,431 (2025)
    Community: Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $4,937 (change assumption)
    Mortgage ($3,999) + Fees ($152) + Taxes in 2025 ($786)


    Taxes:$9,431

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 12554 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787

    $599,000222 Days on yellowkey   MLS ID: O6346537

    For Sale O6346537 - 12554 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787 42 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 2743
       Built: 2025
    Monthly Fee: $96
       Tax: $1,862 (2024)
    Community: Osprey Ranch-Ph 1
    Single Family


    Estimated Monthly Payment: $3,533 (change assumption)
    Mortgage ($3,282) + Fees ($96) + Taxes in 2024 ($155)


    Taxes:$1,862

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11400 LOVERS LN, WINTER GARDEN, FL 34787

    $1,250,000397 Days on yellowkey   MLS ID: O6295587

    1 Days Off yellowkey (back on 3/28/2026)

    For Sale O6295587 - 11400 LOVERS LN, WINTER GARDEN, FL 34787 48 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2517
       Built: 1999   Tax: $6,673 (2024)
    Community: Avalon Estates
    Single Family


    Estimated Monthly Payment: $7,405 (change assumption)
    Mortgage ($6,849) + Taxes in 2024 ($556)


    Taxes:$6,673

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2024

    Middle School: Windy Hill Middle


  • 1226 PORTMOOR WAY, WINTER GARDEN, FL 34787

    $650,00079 Days on yellowkey   MLS ID: O6381941

    For Sale O6381941 - 1226 PORTMOOR WAY, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 2856
       Built: 2003
    Monthly Fee: $243
       Tax: $7,279 (2024)
    Community: Stoneybrook West 44/134
    Single Family


    Estimated Monthly Payment: $4,411 (change assumption)
    Mortgage ($3,562) + Fees ($243) + Taxes in 2024 ($607)


    Taxes:$7,279

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 8256 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $675,000218 Days on yellowkey   MLS ID: O6346538

    For Sale O6346538 - 8256 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 64 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 2557
       Built: 2016
    Monthly Fee: $290
       Tax: $10,027 (2024)
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $4,824 (change assumption)
    Mortgage ($3,699) + Fees ($290) + Taxes in 2024 ($836)


    Taxes:$10,027

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 8066 BOWERY DR, WINTER GARDEN, FL 34787

    $589,90073 Days on yellowkey   MLS ID: O6384210

    For Sale O6384210 - 8066 BOWERY DR, WINTER GARDEN, FL 34787 29 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 2579
       Built: 2017
    Monthly Fee: $195
       Tax: $5,185 (2024)
    Community: Lake Hancock Preserve
    Single Family


    Estimated Monthly Payment: $3,859 (change assumption)
    Mortgage ($3,232) + Fees ($195) + Taxes in 2024 ($432)


    Taxes:$5,185

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    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.