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Displaying: For Sale

Location: Winter Park

Property Type(s): Single Family

Price: $400,000 to $499,000

Winter Park - 42 properties found

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  • 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792

    $480,00014 Days on yellowkey   MLS ID: O6399199

    For Sale O6399199 - 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 1984
    Monthly Fee: $49
       Tax: $6,243 (2024)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $3,199 (change assumption)
    Mortgage ($2,630) + Fees ($49) + Taxes in 2024 ($520)


    Taxes:$6,243

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2020 COCOS CT, WINTER PARK, FL 32792

    $458,99052 Days on yellowkey   MLS ID: O6389901

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

    REDUCED by $1,000 (0.2%) on 04/17/2026

    For Sale O6389901 - 2020 COCOS CT, WINTER PARK, FL 32792 22 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1715
       Built: 1966   Tax: $1,410 (2024)
    Community: Eastbrook Sub Unit 8
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,632 (change assumption)
    Mortgage ($2,515) + Taxes in 2024 ($117)


    Taxes:$1,410

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3207 LOWNDES DR, WINTER PARK, FL 32792

    $485,00094 Days on yellowkey   MLS ID: O6362285

    REDUCED by $10,000 (2.0%) on 04/23/2026

    For Sale O6362285 - 3207 LOWNDES DR, WINTER PARK, FL 32792 31 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2028
       Built: 1967   Tax: $4,172 (2024)
    Community: Georgetown Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,005 (change assumption)
    Mortgage ($2,657) + Taxes in 2024 ($348)


    Taxes:$4,172

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 665 LYMAN AVE, WINTER PARK, FL 32789

    $450,00017 Days on yellowkey   MLS ID: O6400200

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

    For Sale O6400200 - 665 LYMAN AVE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1119
       Built: 1994   Tax: $5,851 (2025)
    Community: Town Of Winter Park
    Single Family


    Estimated Monthly Payment: $2,953 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($488)


    Taxes:$5,851

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1849 VIBURNUM LN, WINTER PARK, FL 32792

    $425,000270 Days on yellowkey   MLS ID: O6333863

    For Sale O6333863 - 1849 VIBURNUM LN, WINTER PARK, FL 32792 27 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1627
       Built: 1961   Tax: $3,645 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,632 (change assumption)
    Mortgage ($2,329) + Taxes in 2024 ($304)


    Taxes:$3,645

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1905 BONANZA CT, WINTER PARK, FL 32792

    $490,00018 Days on yellowkey   MLS ID: O6398772

    0 Days Off yellowkey (back on 4/20/2026)

    For Sale O6398772 - 1905 BONANZA CT, WINTER PARK, FL 32792 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1774
       Built: 1968   Tax: $5,015 (2024)
    Community: Eastbrook Sub Unit 13
    Single Family


    Estimated Monthly Payment: $3,103 (change assumption)
    Mortgage ($2,685) + Taxes in 2024 ($418)


    Taxes:$5,015

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1052 MANCHESTER CIR, WINTER PARK, FL 32792

    $470,000100 Days on yellowkey   MLS ID: O6376260

    REDUCED by $5,000 (1.1%) on 04/13/2026

    For Sale O6376260 - 1052 MANCHESTER CIR, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1703
       Built: 1983   Tax: $5,216 (2025)
    Community: Howell Estates 1St Add
    Single Family


    Estimated Monthly Payment: $3,010 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($435)


    Taxes:$5,216

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 240 ORANGE TERRACE DR, WINTER PARK, FL 32789

    $484,000270 Days on yellowkey   MLS ID: O6330690

    REDUCED by $1,000 (0.2%) on 04/15/2026

    For Sale O6330690 - 240 ORANGE TERRACE DR, WINTER PARK, FL 32789 30 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1718
       Built: 1955   Tax: $6,210 (2024)
    Community: Orange Terrace
    Single Family


    Estimated Monthly Payment: $3,169 (change assumption)
    Mortgage ($2,652) + Taxes in 2024 ($518)


    Taxes:$6,210

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: Robinswood Middle


  • 1354 TIERRA CIR, WINTER PARK, FL 32792

    $425,000476 Days on yellowkey   MLS ID: O6271121

    For Sale O6271121 - 1354 TIERRA CIR, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1827
       Built: 1969
    Monthly Fee: $2
       Tax: $3,812 (2023)
    Community: Casa Aloma
    Single Family


    Estimated Monthly Payment: $2,648 (change assumption)
    Mortgage ($2,329) + Fees ($2) + Taxes in 2023 ($318)


    Taxes:$3,812

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2023

    Middle School: Tuskawilla Middle


  • 814 DENSMORE DR, WINTER PARK, FL 32792

    $425,00018 Days on yellowkey   MLS ID: O6399773

    For Sale O6399773 - 814 DENSMORE DR, WINTER PARK, FL 32792 24 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1610
       Built: 1960   Tax: $5,402 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,779 (change assumption)
    Mortgage ($2,329) + Taxes in 2025 ($450)


    Taxes:$5,402

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3720 JONQUIL LN, WINTER PARK, FL 32792

    $445,00019 Days on yellowkey   MLS ID: O6399628

    0 Days Off yellowkey (back on 4/16/2026)

    For Sale O6399628 - 3720 JONQUIL LN, WINTER PARK, FL 32792 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1647
       Built: 1982   Tax: $1,835 (2024)
    Community: Garden Lake Estates Unit 2
    Single Family


    Estimated Monthly Payment: $2,591 (change assumption)
    Mortgage ($2,438) + Taxes in 2024 ($153)


    Taxes:$1,835

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1280 GLADIOLAS DR, WINTER PARK, FL 32792

    $489,000123 Days on yellowkey   MLS ID: O6370371

    1 Days Off yellowkey (back on 4/14/2026)

    For Sale O6370371 - 1280 GLADIOLAS DR, WINTER PARK, FL 32792 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1624
       Built: 1983   Tax: $5,162 (2024)
    Community: Garden Lake Estates Unit 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,110 (change assumption)
    Mortgage ($2,679) + Taxes in 2024 ($430)


    Taxes:$5,162

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 518 SHOREVIEW AVE, WINTER PARK, FL 32789

    $490,09041 Days on yellowkey   MLS ID: O6392797

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

    For Sale O6392797 - 518 SHOREVIEW AVE, WINTER PARK, FL 32789 35 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1609
       Built: 1920   Tax: $3,919 (2025)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $3,012 (change assumption)
    Mortgage ($2,685) + Taxes in 2025 ($327)


    Taxes:$3,919

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 7445 BETTY ST, WINTER PARK, FL 32792

    $435,00033 Days on yellowkey   MLS ID: OM721366

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

    For Sale OM721366 - 7445 BETTY ST, WINTER PARK, FL 32792 76 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1576
       Built: 1983   Tax: $3,769 (2025)
    Community: Wrenwood Unit 3 4Th Add
    Single Family


    Estimated Monthly Payment: $2,698 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($314)


    Taxes:$3,769

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 3642 PERIWINKLE DR, WINTER PARK, FL 32792

    $440,000242 Days on yellowkey   MLS ID: O6341725

    For Sale O6341725 - 3642 PERIWINKLE DR, WINTER PARK, FL 32792 28 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 1945
       Built: 1964   Tax: $5,131 (2024)
    Community: Eastbrook Sub
    Single Family


    Estimated Monthly Payment: $2,838 (change assumption)
    Mortgage ($2,411) + Taxes in 2024 ($428)


    Taxes:$5,131

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 837 APPALACHEE AVE, WINTER PARK, FL 32792

    $439,00038 Days on yellowkey   MLS ID: O6393151

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

    For Sale O6393151 - 837 APPALACHEE AVE, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1771
       Built: 1968   Tax: $6,834 (2025)
    Community: Winter Park Forest
    Single Family


    Estimated Monthly Payment: $2,975 (change assumption)
    Mortgage ($2,405) + Taxes in 2025 ($570)


    Taxes:$6,834

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 230 STRATHY LN, WINTER PARK, FL 32792

    $499,000117 Days on yellowkey   MLS ID: O6371054

    For Sale O6371054 - 230 STRATHY LN, WINTER PARK, FL 32792 12 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 920
       Built: 1957   Tax: $4,071 (2024)
    Community: Aloma
    Single Family


    Estimated Monthly Payment: $3,073 (change assumption)
    Mortgage ($2,734) + Taxes in 2024 ($339)


    Taxes:$4,071

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2231 NAIRN DR, WINTER PARK, FL 32792

    $499,000117 Days on yellowkey   MLS ID: O6369016

    For Sale O6369016 - 2231 NAIRN DR, WINTER PARK, FL 32792 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1088
       Built: 1956   Tax: $3,793 (2025)
    Community: Aloma
    Single Family


    Estimated Monthly Payment: $3,050 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($316)


    Taxes:$3,793

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3127 ASH PARK LOOP, WINTER PARK, FL 32792

    $400,00059 Days on yellowkey   MLS ID: O6388568

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

    For Sale O6388568 - 3127 ASH PARK LOOP, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1518
       Built: 1986
    Monthly Fee: $37
       Tax: $3,995 (2025)
    Community: Hyde Park
    Single Family


    Estimated Monthly Payment: $2,562 (change assumption)
    Mortgage ($2,192) + Fees ($37) + Taxes in 2025 ($333)


    Taxes:$3,995

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1914 BONANZA CT, WINTER PARK, FL 32792

    $430,000149 Days on yellowkey   MLS ID: O6365516

    For Sale O6365516 - 1914 BONANZA CT, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1727
       Built: 1968   Tax: $4,503 (2025)
    Community: Eastbrook Sub Unit 13
    Single Family


    Estimated Monthly Payment: $2,731 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($375)


    Taxes:$4,503

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


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