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Displaying: For Sale

Location: Winter Park

Property Type(s): Single Family

Beds: 4 to 4

Winter Park - 104 properties found

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  • 1090 WILDMEADOW RUN, WINTER PARK, FL 32792

    $845,00038 Days on yellowkey   MLS ID: O6394208

    For Sale O6394208 - 1090 WILDMEADOW RUN, WINTER PARK, FL 32792 35 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2589
       Built: 2021
    Monthly Fee: $243
       Tax: $6,258 (2024)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,394 (change assumption)
    Mortgage ($4,630) + Fees ($243) + Taxes in 2024 ($521)


    Taxes:$6,258

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1800 MAGNOLIA AVE, WINTER PARK, FL 32789

    $1,100,00049 Days on yellowkey   MLS ID: NS1087637

    REDUCED by $47,000 (4.1%) on 04/27/2026

    For Sale NS1087637 - 1800 MAGNOLIA AVE, WINTER PARK, FL 32789 65 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2431
       Built: 1996   Tax: $11,730 (2025)
    Community: Temple Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,005 (change assumption)
    Mortgage ($6,027) + Taxes in 2025 ($978)


    Taxes:$11,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $450,00090 Days on yellowkey   MLS ID: O6379323

    REDUCED by $6,000 (1.3%) on 04/15/2026

    For Sale O6379323 - 2052 LEANNE CT, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2264
       Built: 1969   Tax: $1,581 (2024)
    Community: Eastbrook Sub Unit 15
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,597 (change assumption)
    Mortgage ($2,466) + Taxes in 2024 ($132)


    Taxes:$1,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2217 SUSSEX RD, WINTER PARK, FL 32792

    $520,000164 Days on yellowkey   MLS ID: O6362648

    For Sale O6362648 - 2217 SUSSEX RD, WINTER PARK, FL 32792 56 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2092
       Built: 1968   Tax: $4,939 (2024)
    Community: Winter Woods Unit 01
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,261 (change assumption)
    Mortgage ($2,849) + Taxes in 2024 ($412)


    Taxes:$4,939

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2829 ALOMA, WINTER PARK, FL 32792

    $579,0003 Days on yellowkey   MLS ID: O6404107

    For Sale O6404107 - 2829 ALOMA, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1821
       Built: 1963   Tax: $4,277 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $3,529 (change assumption)
    Mortgage ($3,173) + Taxes in 2025 ($356)


    Taxes:$4,277

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1813 HARLAND PARK DR, WINTER PARK, FL 32789

    $1,995,0003 Days on yellowkey   MLS ID: O6403483

    For Sale O6403483 - 1813 HARLAND PARK DR, WINTER PARK, FL 32789 55 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3551
       Built: 2013
    Monthly Fee: $268
       Tax: $23,539 (2025)
    Community: Windsong-Knowles Place
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,161 (change assumption)
    Mortgage ($10,931) + Fees ($268) + Taxes in 2025 ($1,962)


    Taxes:$23,539

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1565 FOREST AVE, WINTER PARK, FL 32789

    $1,750,00020 Days on yellowkey   MLS ID: O6398694

    For Sale O6398694 - 1565 FOREST AVE, WINTER PARK, FL 32789 37 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2163
       Built: 1925   Tax: $2,803 (2025)
    Community: Ellno Willo
    Single Family


    Estimated Monthly Payment: $9,822 (change assumption)
    Mortgage ($9,589) + Taxes in 2025 ($234)


    Taxes:$2,803

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2015 SUMMERFIELD RD, WINTER PARK, FL 32792

    $1,375,000179 Days on yellowkey   MLS ID: O6357615

    For Sale O6357615 - 2015 SUMMERFIELD RD, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 4.0   Gar: 1
    Liv Area Sq Ft: 3024
       Built: 1957   Tax: $7,243 (2025)
    Community: Kenilworth Shores Sec 07
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,138 (change assumption)
    Mortgage ($7,534) + Taxes in 2025 ($604)


    Taxes:$7,243

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1760 LEGION DR, WINTER PARK, FL 32789

    $2,295,00075 Days on yellowkey   MLS ID: O6383603

    For Sale O6383603 - 1760 LEGION DR, WINTER PARK, FL 32789 66 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4392
       Built: 1964   Tax: $13,622 (2025)
    Community: Green Oaks Rep
    Single Family


    Estimated Monthly Payment: $13,710 (change assumption)
    Mortgage ($12,575) + Taxes in 2025 ($1,135)


    Taxes:$13,622

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1077 MINNESOTA AVE, WINTER PARK, FL 32789

    $1,625,0005 Days on yellowkey   MLS ID: O6403223

    For Sale O6403223 - 1077 MINNESOTA AVE, WINTER PARK, FL 32789 54 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3046
       Built: 2025   Tax: $1,383 (2025)
    Community: Na
    Single Family


    Estimated Monthly Payment: $9,019 (change assumption)
    Mortgage ($8,904) + Taxes in 2025 ($115)


    Taxes:$1,383

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2361 MULBRY DR, WINTER PARK, FL 32789

    $2,395,00018 Days on yellowkey   MLS ID: O6396840

    For Sale O6396840 - 2361 MULBRY DR, WINTER PARK, FL 32789 82 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3111
       Built: 2026   Tax: $6,436 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $13,659 (change assumption)
    Mortgage ($13,123) + Taxes in 2025 ($536)


    Taxes:$6,436

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 102 BELL PL, WINTER PARK, FL 32792

    $1,399,00020 Days on yellowkey   MLS ID: O6398118

    For Sale O6398118 - 102 BELL PL, WINTER PARK, FL 32792 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2459
       Built: 2025   Tax: $4,224 (2025)
    Community: Eastgate Sub
    Single Family


    Estimated Monthly Payment: $8,018 (change assumption)
    Mortgage ($7,666) + Taxes in 2025 ($352)


    Taxes:$4,224

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2408 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,495,00024 Days on yellowkey   MLS ID: O6397694

    For Sale O6397694 - 2408 LAFAYETTE AVE, WINTER PARK, FL 32789 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2838
       Built: 2024   Tax: $3,770 (2024)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,506 (change assumption)
    Mortgage ($8,192) + Taxes in 2024 ($314)


    Taxes:$3,770

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 234 DETMAR DR, WINTER PARK, FL 32789

    $1,599,00083 Days on yellowkey   MLS ID: O6379927

    REDUCED by $46,000 (2.8%) on 04/29/2026

    For Sale O6379927 - 234 DETMAR DR, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 5.5   Gar: 1
    Liv Area Sq Ft: 3609
       Built: 1935   Tax: $13,664 (2025)
    Community: Osceola Shores Sec 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,900 (change assumption)
    Mortgage ($8,761) + Taxes in 2025 ($1,139)


    Taxes:$13,664

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1611 CHESTNUT AVE, WINTER PARK, FL 32789

    $1,100,0004 Days on yellowkey   MLS ID: O6402502

    For Sale O6402502 - 1611 CHESTNUT AVE, WINTER PARK, FL 32789 45 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2916
       Built: 1973   Tax: $3,590 (2025)
    Community: Lake Knowles Terrace
    Single Family


    Estimated Monthly Payment: $6,326 (change assumption)
    Mortgage ($6,027) + Taxes in 2025 ($299)


    Taxes:$3,590

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1660 WALNUT AVE, WINTER PARK, FL 32789

    $1,650,0007 Days on yellowkey   MLS ID: O6395277

    For Sale O6395277 - 1660 WALNUT AVE, WINTER PARK, FL 32789 43 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2249
       Built: 2026   Tax: $6,297 (2025)
    Community: Lake Knowles Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,566 (change assumption)
    Mortgage ($9,041) + Taxes in 2025 ($525)


    Taxes:$6,297

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 363 N PHELPS AVE, WINTER PARK, FL 32789

    $1,249,00011 Days on yellowkey   MLS ID: O6401811

    For Sale O6401811 - 363 N PHELPS AVE, WINTER PARK, FL 32789 38 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2871
       Built: 1950   Tax: $8,856 (2025)
    Community: Sylvan Park
    Single Family


    Estimated Monthly Payment: $7,582 (change assumption)
    Mortgage ($6,844) + Taxes in 2025 ($738)


    Taxes:$8,856

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 688 BRECHIN DR, WINTER PARK, FL 32792

    $724,9004 Days on yellowkey   MLS ID: O6403080

    For Sale O6403080 - 688 BRECHIN DR, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1599
       Built: 1961   Tax: $6,760 (2025)
    Community: Kenilworth Shores Sec 04
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,535 (change assumption)
    Mortgage ($3,972) + Taxes in 2025 ($563)


    Taxes:$6,760

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1981 BLUE RIDGE RD, WINTER PARK, FL 32789

    $1,150,0003 Days on yellowkey   MLS ID: O6402961

    For Sale O6402961 - 1981 BLUE RIDGE RD, WINTER PARK, FL 32789 52 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2750
       Built: 1963   Tax: $11,270 (2025)
    Community: Timberlane Shores
    Single Family


    Estimated Monthly Payment: $7,240 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($939)


    Taxes:$11,270

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 2922 REEF KNOT PL, WINTER PARK, FL 32792

    $1,149,000330 Days on yellowkey   MLS ID: O6316445

    0 Days Off yellowkey (back on 5/2/2026)

    For Sale O6316445 - 2922 REEF KNOT PL, WINTER PARK, FL 32792 49 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3153
       Built: 2019
    Monthly Fee: $186
       Tax: $10,521 (2024)
    Community: Lake Florence Preserve
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,358 (change assumption)
    Mortgage ($6,296) + Fees ($186) + Taxes in 2024 ($877)


    Taxes:$10,521

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle






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