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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Living Area Square Feet: 1500 to 1999

Winter Garden - 76 properties found

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  • 1681 E SPRING RIDGE CIR, WINTER GARDEN, FL 34787

    $469,00043 Days on yellowkey   MLS ID: B4902258

    REDUCED by $10,000 (2.1%) on 06/10/2026

    For Sale B4902258 - 1681 E SPRING RIDGE CIR, WINTER GARDEN, FL 34787 70 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1858
       Built: 1990
    Monthly Fee: $25
       Tax: $2,403 (2025)
    Community: Crown Point Spgs
    Single Family


    Estimated Monthly Payment: $2,795 (change assumption)
    Mortgage ($2,570) + Fees ($25) + Taxes in 2025 ($200)


    Taxes:$2,403

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9338 TYRELLA PINE TRL, WINTER GARDEN, FL 34787

    $435,000261 Days on yellowkey   MLS ID: O6349881

    REDUCED by $10,000 (2.2%) on 06/10/2026

    For Sale O6349881 - 9338 TYRELLA PINE TRL, WINTER GARDEN, FL 34787 21 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1696
       Built: 2018
    Monthly Fee: $142
       Tax: $7,556 (2024)
    Community: Watermark Ph 2B
    Single Family


    Estimated Monthly Payment: $3,155 (change assumption)
    Mortgage ($2,384) + Fees ($142) + Taxes in 2024 ($630)


    Taxes:$7,556

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 708 ORANGE BELT LOOP, WINTER GARDEN, FL 34787

    $745,00043 Days on yellowkey   MLS ID: G5112211

    3 Days Off yellowkey (back on 6/9/2026)

    For Sale G5112211 - 708 ORANGE BELT LOOP, WINTER GARDEN, FL 34787 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1916
       Built: 2019
    Monthly Fee: $280
       Tax: $8,412 (2025)
    Community: Heritage/Plant Street
    Single Family


    Estimated Monthly Payment: $5,063 (change assumption)
    Mortgage ($4,082) + Fees ($280) + Taxes in 2025 ($701)


    Taxes:$8,412

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2227 OAKINGTON ST, WINTER GARDEN, FL 34787

    $489,99016 Days on yellowkey   MLS ID: O6414707

    For Sale O6414707 - 2227 OAKINGTON ST, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1867
       Built: 2002
    Monthly Fee: $240
       Tax: $5,321 (2025)
    Community: Stoneybrook West 47/78
    Single Family


    Estimated Monthly Payment: $3,368 (change assumption)
    Mortgage ($2,685) + Fees ($240) + Taxes in 2025 ($443)


    Taxes:$5,321

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 13043 SANDCASTLE DRIVE, WINTER GARDEN, FL 34787

    $899,00069 Days on yellowkey   MLS ID: O6399529

    1 Days Off yellowkey (back on 6/7/2026)

    INCREASED by $23,000 (2.6%) on 05/09/2026

    For Sale O6399529 - 13043 SANDCASTLE DRIVE, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1943
       Built: 2022
    Monthly Fee: $534
       Tax: $10,109 (2025)
    Community: Del Webb Oasis
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,302 (change assumption)
    Mortgage ($4,926) + Fees ($534) + Taxes in 2025 ($842)


    Taxes:$10,109

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12410 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787

    $639,99032 Days on yellowkey   MLS ID: O6409937

    For Sale O6409937 - 12410 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1860
       Built: 2022
    Monthly Fee: $225
       Tax: $7,966 (2025)
    Community: Encore At Ovation
    Single Family


    Estimated Monthly Payment: $4,396 (change assumption)
    Mortgage ($3,507) + Fees ($225) + Taxes in 2025 ($664)


    Taxes:$7,966

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 6408 FLAT LEMON DR, WINTER GARDEN, FL 34787

    $550,00077 Days on yellowkey   MLS ID: O6396757

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

    REDUCED by $20,000 (3.5%) on 04/21/2026

    For Sale O6396757 - 6408 FLAT LEMON DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1979
       Built: 2019
    Monthly Fee: $142
       Tax: $8,155 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $3,835 (change assumption)
    Mortgage ($3,014) + Fees ($142) + Taxes in 2025 ($680)


    Taxes:$8,155

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 914 TROWMAN ALY, WINTER GARDEN, FL 34787

    $649,00028 Days on yellowkey   MLS ID: O6410871

    REDUCED by $26,000 (3.9%) on 06/02/2026

    For Sale O6410871 - 914 TROWMAN ALY, WINTER GARDEN, FL 34787 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1642
       Built: 2022
    Monthly Fee: $356
       Tax: $6,421 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $4,447 (change assumption)
    Mortgage ($3,556) + Fees ($356) + Taxes in 2025 ($535)


    Taxes:$6,421

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 2123 PORTCASTLE CIR, WINTER GARDEN, FL 34787

    $389,00021 Days on yellowkey   MLS ID: O6412643

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

    For Sale O6412643 - 2123 PORTCASTLE CIR, WINTER GARDEN, FL 34787 39 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1606
       Built: 2006
    Monthly Fee: $46
       Tax: $5,857 (2025)
    Community: Stone Creek Unit 4
    Single Family


    Estimated Monthly Payment: $2,666 (change assumption)
    Mortgage ($2,131) + Fees ($46) + Taxes in 2025 ($488)


    Taxes:$5,857

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 9468 KOMIKA LN, WINTER GARDEN, FL 34787

    $459,90027 Days on yellowkey   MLS ID: S5150415

    0 Days Off yellowkey (back on 6/5/2026)

    FORECLOSURE S5150415 - 9468 KOMIKA LN, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1705
       Built: 2020
    Monthly Fee: $300
       Tax: $7,605 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $3,454 (change assumption)
    Mortgage ($2,520) + Fees ($300) + Taxes in 2025 ($634)


    Taxes:$7,605

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9355 TYRELLA PINE TRL, WINTER GARDEN, FL 34787

    $459,00090 Days on yellowkey   MLS ID: O6391856

    0 Days Off yellowkey (back on 6/5/2026)

    REDUCED by $8,000 (1.7%) on 05/30/2026

    For Sale O6391856 - 9355 TYRELLA PINE TRL, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1670
       Built: 2016
    Monthly Fee: $148
       Tax: $657 (2025)
    Community: Watermark Ph 1B
    Single Family


    Estimated Monthly Payment: $2,718 (change assumption)
    Mortgage ($2,515) + Fees ($148) + Taxes in 2025 ($55)


    Taxes:$657

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14451 WINDSOR HALL WAY, WINTER GARDEN, FL 34787

    $510,00036 Days on yellowkey   MLS ID: O6408731

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

    For Sale O6408731 - 14451 WINDSOR HALL WAY, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1814
       Built: 2016
    Monthly Fee: $192
       Tax: $5,900 (2025)
    Community: Lake Hancock Preserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,478 (change assumption)
    Mortgage ($2,794) + Fees ($192) + Taxes in 2025 ($492)


    Taxes:$5,900

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13837 LANYARD WAY, WINTER GARDEN, FL 34787

    $485,000106 Days on yellowkey   MLS ID: O6388993

    REDUCED by $5,000 (1.0%) on 06/03/2026

    For Sale O6388993 - 13837 LANYARD WAY, WINTER GARDEN, FL 34787 38 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1994
       Built: 2023
    Monthly Fee: $225
       Tax: $7,647 (2024)
    Community: Encore/Ovation Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,520 (change assumption)
    Mortgage ($2,657) + Fees ($225) + Taxes in 2024 ($637)


    Taxes:$7,647

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14645 TULLAMORE LOOP, WINTER GARDEN, FL 34787

    $455,00027 Days on yellowkey   MLS ID: O6409068

    0 Days Off yellowkey (back on 6/2/2026)

    For Sale O6409068 - 14645 TULLAMORE LOOP, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1703
       Built: 2003
    Monthly Fee: $100
       Tax: $3,347 (2025)
    Community: Emerald Rdg H
    Single Family


    Estimated Monthly Payment: $2,872 (change assumption)
    Mortgage ($2,493) + Fees ($100) + Taxes in 2025 ($279)


    Taxes:$3,347

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6174 WHISPERING GLEN, WINTER GARDEN, FL 34787

    $518,29041 Days on yellowkey   MLS ID: O6407807

    REDUCED by $28,000 (5.1%) on 06/02/2026

    For Sale O6407807 - 6174 WHISPERING GLEN, WINTER GARDEN, FL 34787 20 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1628
       Built: 2026
    Monthly Fee: $152
       Tax: $1,373 (2024)
    Community: Silverleaf Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,106 (change assumption)
    Mortgage ($2,840) + Fees ($152) + Taxes in 2024 ($114)


    Taxes:$1,373

    Elementary School: Vista Lakes Elem

    High School: Colonial High

    Tax Year: 2024

    Middle School: Odyssey Middle


  • 17035 HARBOR OAK PKWY, WINTER GARDEN, FL 34787

    $499,99922 Days on yellowkey   MLS ID: O6411409

    For Sale O6411409 - 17035 HARBOR OAK PKWY, WINTER GARDEN, FL 34787 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1692
       Built: 2017
    Monthly Fee: $215
       Tax: $3,704 (2025)
    Community: Waterside/Johns Lake Ph 2A
    Single Family


    Estimated Monthly Payment: $3,263 (change assumption)
    Mortgage ($2,740) + Fees ($215) + Taxes in 2025 ($309)


    Taxes:$3,704

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17124 BEACHGRASS ALY, WINTER GARDEN, FL 34787

    $559,99036 Days on yellowkey   MLS ID: O6408024

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

    For Sale O6408024 - 17124 BEACHGRASS ALY, WINTER GARDEN, FL 34787 4 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1983
       Built: 2026
    Monthly Fee: $112
       Tax: $6,874 (2025)
    Community: Lake Star At Ovation
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,753 (change assumption)
    Mortgage ($3,068) + Fees ($112) + Taxes in 2025 ($573)


    Taxes:$6,874

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 837 GRANDE REGAL PT, WINTER GARDEN, FL 34787

    $450,00061 Days on yellowkey   MLS ID: O6400571

    3 Days Off yellowkey (back on 5/29/2026)

    REDUCED by $19,000 (4.1%) on 05/20/2026

    For Sale O6400571 - 837 GRANDE REGAL PT, WINTER GARDEN, FL 34787 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1874
       Built: 2002
    Monthly Fee: $60
       Tax: $1,662 (2025)
    Community: Regal Pointe Ph 02 47/133
    Single Family


    Estimated Monthly Payment: $2,664 (change assumption)
    Mortgage ($2,466) + Fees ($60) + Taxes in 2025 ($138)


    Taxes:$1,662

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 516 S HIGHLAND AVE, WINTER GARDEN, FL 34787

    $500,00029 Days on yellowkey   MLS ID: O6409675

    1 Days Off yellowkey (back on 5/29/2026)

    For Sale O6409675 - 516 S HIGHLAND AVE, WINTER GARDEN, FL 34787 22 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1716
       Built: 1955   Tax: $709 (2025)
    Community: Rep Pt Pleasant Park Sub
    Single Family


    Estimated Monthly Payment: $2,799 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($59)


    Taxes:$709

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11072 SILVER SURFER ALY, WINTER GARDEN, FL 34787

    $450,00044 Days on yellowkey   MLS ID: O6406656

    REDUCED by $10,000 (2.2%) on 05/28/2026

    For Sale O6406656 - 11072 SILVER SURFER ALY, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2018
    Monthly Fee: $108
       Tax: $3,977 (2025)
    Community: Storey Grove Ph 1B-2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,905 (change assumption)
    Mortgage ($2,466) + Fees ($108) + Taxes in 2025 ($331)


    Taxes:$3,977

    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.