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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Living Area Square Feet: 1500 to 1999

Winter Garden - 65 properties found

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  • 2281 OAKINGTON ST, WINTER GARDEN, FL 34787

    $475,00012 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


  • 14542 GOLDEN HARBOR LN, WINTER GARDEN, FL 34787

    $500,00035 Days on yellowkey   MLS ID: O6395116

    0 Days Off yellowkey (back on 4/28/2026)

    For Sale O6395116 - 14542 GOLDEN HARBOR LN, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1904
       Built: 2016
    Monthly Fee: $164
       Tax: $4,822 (2025)
    Community: Watermark
    Single Family


    Estimated Monthly Payment: $3,305 (change assumption)
    Mortgage ($2,740) + Fees ($164) + Taxes in 2025 ($402)


    Taxes:$4,822

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 312 SILVERDALE AVE, WINTER GARDEN, FL 34787

    $559,90029 Days on yellowkey   MLS ID: O6396680

    0 Days Off yellowkey (back on 4/27/2026)

    For Sale O6396680 - 312 SILVERDALE AVE, WINTER GARDEN, FL 34787 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 2007
    Monthly Fee: $72
       Tax: $2,473 (2025)
    Community: Covington Park A B D E F G & J
    Single Family


    Estimated Monthly Payment: $3,346 (change assumption)
    Mortgage ($3,068) + Fees ($72) + Taxes in 2025 ($206)


    Taxes:$2,473

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 869 BENDING OAK TRL, WINTER GARDEN, FL 34787

    $530,000176 Days on yellowkey   MLS ID: O6358341

    REDUCED by $5,000 (0.9%) on 04/27/2026

    For Sale O6358341 - 869 BENDING OAK TRL, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1975
       Built: 2012
    Monthly Fee: $109
       Tax: $5,262 (2024)
    Community: Oaks/Brandy Lake 01 Rep A & B
    Single Family


    Estimated Monthly Payment: $3,451 (change assumption)
    Mortgage ($2,904) + Fees ($109) + Taxes in 2024 ($438)


    Taxes:$5,262

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4863 LACEWING DR, WINTER GARDEN, FL 34787

    $540,00026 Days on yellowkey   MLS ID: O6397857

    For Sale O6397857 - 4863 LACEWING DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1788
       Built: 2023
    Monthly Fee: $171
       Tax: $6,905 (2025)
    Community: Silverleaf Reserve Bungalows
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,705 (change assumption)
    Mortgage ($2,959) + Fees ($171) + Taxes in 2025 ($575)


    Taxes:$6,905

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 3276 SAILING PIER AVE, WINTER GARDEN, FL 34787

    $525,00013 Days on yellowkey   MLS ID: O6401195

    For Sale O6401195 - 3276 SAILING PIER AVE, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1990
       Built: 2020
    Monthly Fee: $152
       Tax: $7,081 (2025)
    Community: Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $3,619 (change assumption)
    Mortgage ($2,877) + Fees ($152) + Taxes in 2025 ($590)


    Taxes:$7,081

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 6321 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787

    $654,990158 Days on yellowkey   MLS ID: G5105005

    0 Days Off yellowkey (back on 11/28/2025)

    For Sale G5105005 - 6321 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787 2 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1772
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $3,739 (change assumption)
    Mortgage ($3,589) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16716 WINGSPREAD LOOP, WINTER GARDEN, FL 34787

    $495,00026 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

    $479,00012 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


  • 16856 HYPATIA ALY, WINTER GARDEN, FL 34787

    $459,99961 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

    $490,00057 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


  • 7343 TWILIGHT BAY DR, WINTER GARDEN, FL 34787

    $599,99921 Days on yellowkey   MLS ID: S5147747

    0 Days Off yellowkey (back on 4/22/2026)

    For Sale S5147747 - 7343 TWILIGHT BAY DR, WINTER GARDEN, FL 34787 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1975
       Built: 2017
    Monthly Fee: $249
       Tax: $5,164 (2025)
    Community: Lakeview Pointe/Horizon West P
    Single Family


    Estimated Monthly Payment: $3,967 (change assumption)
    Mortgage ($3,288) + Fees ($249) + Taxes in 2025 ($430)


    Taxes:$5,164

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 2621 SHIREHALL LN, WINTER GARDEN, FL 34787

    $475,00060 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


  • 12055 BRACCO ST, WINTER GARDEN, FL 34787

    $429,000146 Days on yellowkey   MLS ID: O6366675

    3 Days Off yellowkey (back on 4/21/2026)

    REDUCED by $11,000 (2.5%) on 04/14/2026

    For Sale O6366675 - 12055 BRACCO ST, WINTER GARDEN, FL 34787 31 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1668
       Built: 2023
    Monthly Fee: $105
       Tax: $6,881 (2024)
    Community: Highland Ridge
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,029 (change assumption)
    Mortgage ($2,351) + Fees ($105) + Taxes in 2024 ($573)


    Taxes:$6,881

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6408 FLAT LEMON DR, WINTER GARDEN, FL 34787

    $550,00028 Days on yellowkey   MLS ID: O6396757

    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


  • 14446 WHITTRIDGE DR, WINTER GARDEN, FL 34787

    $450,00069 Days on yellowkey   MLS ID: O6378698

    2 Days Off yellowkey (back on 4/21/2026)

    For Sale O6378698 - 14446 WHITTRIDGE DR, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1650
       Built: 2005
    Monthly Fee: $195
       Tax: $5,006 (2024)
    Community: Signature Lks-Pcl 01B
    Single Family


    Estimated Monthly Payment: $3,078 (change assumption)
    Mortgage ($2,466) + Fees ($195) + Taxes in 2024 ($417)


    Taxes:$5,006

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 17682 NORTHLAKE GROVE DR, WINTER GARDEN, FL 34787

    $540,00079 Days on yellowkey   MLS ID: O6382844

    For Sale O6382844 - 17682 NORTHLAKE GROVE DR, WINTER GARDEN, FL 34787 28 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1906
       Built: 2023
    Monthly Fee: $83
       Tax: $5,705 (2024)
    Community: Northlake/Ovation Ph 1
    Single Family


    Estimated Monthly Payment: $3,517 (change assumption)
    Mortgage ($2,959) + Fees ($83) + Taxes in 2024 ($475)


    Taxes:$5,705

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 12050 BRACCO ST, WINTER GARDEN, FL 34787

    $489,90017 Days on yellowkey   MLS ID: O6398494

    For Sale O6398494 - 12050 BRACCO ST, WINTER GARDEN, FL 34787 73 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2023
    Monthly Fee: $110
       Tax: $7,195 (2025)
    Community: Highland Ridge
    Single Family


    Estimated Monthly Payment: $3,394 (change assumption)
    Mortgage ($2,684) + Fees ($110) + Taxes in 2025 ($600)


    Taxes:$7,195

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1261 E FULLERS CROSS RD, WINTER GARDEN, FL 34787

    $675,00026 Days on yellowkey   MLS ID: O6397098

    For Sale O6397098 - 1261 E FULLERS CROSS RD, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1832
       Built: 1991   Tax: $2,367 (2025)
    Community: 0000
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,896 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($197)


    Taxes:$2,367

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 1035 CHASE DR, WINTER GARDEN, FL 34787

    $465,00025 Days on yellowkey   MLS ID: O6396474

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale O6396474 - 1035 CHASE DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1793
       Built: 1995
    Monthly Fee: $44
       Tax: $3,337 (2025)
    Community: Island Pointe Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,870 (change assumption)
    Mortgage ($2,548) + Fees ($44) + Taxes in 2025 ($278)


    Taxes:$3,337

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview 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.