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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Price: $400,000 to $499,000

Winter Garden - 36 properties found

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  • 16385 ADMIRALS COVE LN, WINTER GARDEN, FL 34787

    $469,90040 Days on yellowkey   MLS ID: O6393056

    REDUCED by $100 (0.0%) on 04/27/2026

    For Sale O6393056 - 16385 ADMIRALS COVE LN, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1705
       Built: 2020
    Monthly Fee: $257
       Tax: $4,805 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,232 (change assumption)
    Mortgage ($2,575) + Fees ($257) + Taxes in 2025 ($400)


    Taxes:$4,805

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 107 TRADITIONS DR, WINTER GARDEN, FL 34787

    $474,97548 Days on yellowkey   MLS ID: S5145650

    REDUCED by $25,020 (5.0%) on 04/20/2026

    For Sale S5145650 - 107 TRADITIONS DR, WINTER GARDEN, FL 34787 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1582
       Built: 1999
    Monthly Fee: $45
       Tax: $1,458 (2024)
    Community: Traditions Sub
    Single Family


    Estimated Monthly Payment: $2,769 (change assumption)
    Mortgage ($2,603) + Fees ($45) + Taxes in 2024 ($121)


    Taxes:$1,458

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 9355 TYRELLA PINE TRL, WINTER GARDEN, FL 34787

    $475,00040 Days on yellowkey   MLS ID: O6391856

    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: $2,805 (change assumption)
    Mortgage ($2,603) + 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


  • 16229 PEBBLE BLUFF LOOP, WINTER GARDEN, FL 34787

    $479,0004 Days on yellowkey   MLS ID: O6403777

    For Sale O6403777 - 16229 PEBBLE BLUFF LOOP, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1685
       Built: 2018   Tax: $7,243 (2025)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $3,228 (change assumption)
    Mortgage ($2,625) + Taxes in 2025 ($604)


    Taxes:$7,243

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2154 OAKINGTON ST, WINTER GARDEN, FL 34787

    $469,9004 Days on yellowkey   MLS ID: O6402495

    For Sale O6402495 - 2154 OAKINGTON ST, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1585
       Built: 2002
    Monthly Fee: $243
       Tax: $5,166 (2025)
    Community: Stoneybrook West
    Single Family


    Estimated Monthly Payment: $3,248 (change assumption)
    Mortgage ($2,575) + Fees ($243) + Taxes in 2025 ($431)


    Taxes:$5,166

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 115 ZACHARY WADE ST, WINTER GARDEN, FL 34787

    $496,000177 Days on yellowkey   MLS ID: O6356997

    For Sale O6356997 - 115 ZACHARY WADE ST, WINTER GARDEN, FL 34787 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1780
       Built: 2001
    Monthly Fee: $58
       Tax: $5,467 (2024)
    Community: Lakeview Reserve 46/149
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,231 (change assumption)
    Mortgage ($2,718) + Fees ($58) + Taxes in 2024 ($456)


    Taxes:$5,467

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 1836 WINGED ELM PL, WINTER GARDEN, FL 34787

    $435,00050 Days on yellowkey   MLS ID: O6390771

    REDUCED by $4,000 (0.9%) on 04/30/2026

    For Sale O6390771 - 1836 WINGED ELM PL, WINTER GARDEN, FL 34787 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1712
       Built: 2005
    Monthly Fee: $55
       Tax: $6,075 (2025)
    Community: Winter Garden Trls 01-3
    Single Family


    Estimated Monthly Payment: $2,945 (change assumption)
    Mortgage ($2,384) + Fees ($55) + Taxes in 2025 ($506)


    Taxes:$6,075

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 236 DONALD DR, WINTER GARDEN, FL 34787

    $465,00010 Days on yellowkey   MLS ID: O6401940

    2 Days Off yellowkey (back on 4/30/2026)

    For Sale O6401940 - 236 DONALD DR, WINTER GARDEN, FL 34787 12 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1080
       Built: 1930   Tax: $410 (2025)
    Community: Showalter Park
    Single Family


    Estimated Monthly Payment: $2,582 (change assumption)
    Mortgage ($2,548) + Taxes in 2025 ($34)


    Taxes:$410

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 16105 WATER SPRING BLVD, WINTER GARDEN, FL 34787

    $499,000210 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


  • 1670 E SPRING RIDGE CIR, WINTER GARDEN, FL 34787

    $425,0006 Days on yellowkey   MLS ID: O6403033

    For Sale O6403033 - 1670 E SPRING RIDGE CIR, WINTER GARDEN, FL 34787 5 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1699
       Built: 1995
    Monthly Fee: $50
       Tax: $1,352 (2025)
    Community: Crown Point Springs Ut 2
    Single Family


    Estimated Monthly Payment: $2,491 (change assumption)
    Mortgage ($2,329) + Fees ($50) + Taxes in 2025 ($113)


    Taxes:$1,352

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 2281 OAKINGTON ST, WINTER GARDEN, FL 34787

    $475,00011 Days on yellowkey   MLS ID: S5148475

    REDUCED by $20,000 (4.0%) on 04/29/2026

    For Sale S5148475 - 2281 OAKINGTON ST, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1628
       Built: 2003
    Monthly Fee: $240
       Tax: $5,033 (2025)
    Community: Stoneybrook West 47/78
    Single Family


    Estimated Monthly Payment: $3,262 (change assumption)
    Mortgage ($2,603) + Fees ($240) + Taxes in 2025 ($419)


    Taxes:$5,033

    Elementary School: Whispering Oak Elem

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1419 HUNTERMAN LN, WINTER GARDEN, FL 34787

    $479,90053 Days on yellowkey   MLS ID: O6390064

    1 Days Off yellowkey (back on 3/20/2026)

    For Sale O6390064 - 1419 HUNTERMAN LN, WINTER GARDEN, FL 34787 27 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 2840
       Built: 2005
    Monthly Fee: $42
       Tax: $7,786 (2025)
    Community: Chapin Station A
    Single Family


    Estimated Monthly Payment: $3,320 (change assumption)
    Mortgage ($2,630) + Fees ($42) + Taxes in 2025 ($649)


    Taxes:$7,786

    Elementary School: Maxey Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15187 HARROWGATE WAY, WINTER GARDEN, FL 34787

    $450,00018 Days on yellowkey   MLS ID: TB8497081

    For Sale TB8497081 - 15187 HARROWGATE WAY, WINTER GARDEN, FL 34787 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1296
       Built: 2003
    Monthly Fee: $46
       Tax: $5,808 (2025)
    Community: Stone Crk
    Single Family


    Estimated Monthly Payment: $2,996 (change assumption)
    Mortgage ($2,466) + Fees ($46) + Taxes in 2025 ($484)


    Taxes:$5,808

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16149 WIND VIEW LN, WINTER GARDEN, FL 34787

    $498,00052 Days on yellowkey   MLS ID: O6389892

    REDUCED by $7,000 (1.4%) on 04/15/2026

    For Sale O6389892 - 16149 WIND VIEW LN, WINTER GARDEN, FL 34787 46 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2036
       Built: 2016
    Monthly Fee: $332
       Tax: $4,472 (2025)
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $3,433 (change assumption)
    Mortgage ($2,729) + Fees ($332) + Taxes in 2025 ($373)


    Taxes:$4,472

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16716 WINGSPREAD LOOP, WINTER GARDEN, FL 34787

    $495,00025 Days on yellowkey   MLS ID: O6397108

    1 Days Off yellowkey (back on 4/24/2026)

    For Sale O6397108 - 16716 WINGSPREAD LOOP, WINTER GARDEN, FL 34787 56 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 2019
    Monthly Fee: $127
       Tax: $5,006 (2025)
    Community: Hawksmoor-Ph 1
    Single Family


    Estimated Monthly Payment: $3,256 (change assumption)
    Mortgage ($2,712) + Fees ($127) + Taxes in 2025 ($417)


    Taxes:$5,006

    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

    $479,00011 Days on yellowkey   MLS ID: O6400571

    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: $2,823 (change assumption)
    Mortgage ($2,625) + Fees ($60) + Taxes in 2025 ($138)


    Taxes:$1,662

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 328 BAYSIDE AVE, WINTER GARDEN, FL 34787

    $445,00017 Days on yellowkey   MLS ID: O6396654

    1 Days Off yellowkey (back on 4/23/2026)

    For Sale O6396654 - 328 BAYSIDE AVE, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1235
       Built: 1986
    Monthly Fee: $7
       Tax: $5,354 (2025)
    Community: Kings Bay
    Single Family


    Estimated Monthly Payment: $2,891 (change assumption)
    Mortgage ($2,438) + Fees ($7) + Taxes in 2025 ($446)


    Taxes:$5,354

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 16856 HYPATIA ALY, WINTER GARDEN, FL 34787

    $459,99960 Days on yellowkey   MLS ID: O6387941

    0 Days Off yellowkey (back on 4/23/2026)

    For Sale O6387941 - 16856 HYPATIA ALY, WINTER GARDEN, FL 34787 74 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1705
       Built: 2019
    Monthly Fee: $250
       Tax: $6,769 (2024)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $3,335 (change assumption)
    Mortgage ($2,520) + Fees ($250) + Taxes in 2024 ($564)


    Taxes:$6,769

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13837 LANYARD WAY, WINTER GARDEN, FL 34787

    $490,00056 Days on yellowkey   MLS ID: O6388993

    REDUCED by $5,000 (1.0%) on 04/22/2026

    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: $3,547 (change assumption)
    Mortgage ($2,685) + Fees ($225) + Taxes in 2024 ($637)


    Taxes:$7,647

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2621 SHIREHALL LN, WINTER GARDEN, FL 34787

    $475,00059 Days on yellowkey   MLS ID: O6386585

    REDUCED by $25,000 (5.0%) on 04/17/2026

    For Sale O6386585 - 2621 SHIREHALL LN, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1960
       Built: 2003
    Monthly Fee: $243
       Tax: $3,181 (2024)
    Community: Stoneybrook West Ut 04 48 48
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,111 (change assumption)
    Mortgage ($2,603) + Fees ($243) + Taxes in 2024 ($265)


    Taxes:$3,181

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


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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.