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Displaying: For Sale

Location: Winter Park

Property Type(s): Single Family

Price: $400,000 to $499,000

Winter Park - 48 properties found

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  • 7514 LAUREL SPRINGS DR, WINTER PARK, FL 32792

    $400,000166 Days on yellowkey   MLS ID: O6372653

    1 Days Off yellowkey (back on 6/24/2026)

    For Sale O6372653 - 7514 LAUREL SPRINGS DR, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1677
       Built: 1972   Tax: $1,289 (2024)
    Community: Laurel Spgs
    Single Family


    Estimated Monthly Payment: $2,299 (change assumption)
    Mortgage ($2,192) + Taxes in 2024 ($107)


    Taxes:$1,289

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2231 NAIRN DR, WINTER PARK, FL 32792

    $499,000168 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


  • 230 STRATHY LN, WINTER PARK, FL 32792

    $499,000168 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


  • 1564 LAWNDALE CIR, WINTER PARK, FL 32792

    $450,0001 Day on yellowkey   MLS ID: O6418817

    For Sale O6418817 - 1564 LAWNDALE CIR, WINTER PARK, FL 32792 45 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1980
       Built: 1985
    Monthly Fee: $46
       Tax: $3,124 (2025)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $2,772 (change assumption)
    Mortgage ($2,466) + Fees ($46) + Taxes in 2025 ($260)


    Taxes:$3,124

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 240 ORANGE TERRACE DR, WINTER PARK, FL 32789

    $470,000321 Days on yellowkey   MLS ID: O6330690

    REDUCED by $9,900 (2.1%) on 06/23/2026

    For Sale O6330690 - 240 ORANGE TERRACE DR, WINTER PARK, FL 32789 32 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: $3,093 (change assumption)
    Mortgage ($2,575) + Taxes in 2024 ($518)


    Taxes:$6,210

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: Robinswood Middle


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $440,000141 Days on yellowkey   MLS ID: O6379323

    REDUCED by $5,000 (1.1%) on 06/17/2026

    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: $2,543 (change assumption)
    Mortgage ($2,411) + Taxes in 2024 ($132)


    Taxes:$1,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1840 ASTER DR, WINTER PARK, FL 32792

    $439,90023 Days on yellowkey   MLS ID: O6412364

    REDUCED by $10,000 (2.2%) on 06/21/2026

    For Sale O6412364 - 1840 ASTER DR, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1667
       Built: 1978   Tax: $864 (2025)
    Community: Garden Lake Estates Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,482 (change assumption)
    Mortgage ($2,410) + Taxes in 2025 ($72)


    Taxes:$864

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1023 WORTHING CT, WINTER PARK, FL 32792

    $450,00012 Days on yellowkey   MLS ID: O6416552

    0 Days Off yellowkey (back on 6/23/2026)

    REDUCED by $10,000 (2.2%) on 06/15/2026

    For Sale O6416552 - 1023 WORTHING CT, WINTER PARK, FL 32792 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1184
       Built: 1983   Tax: $1,092 (2025)
    Community: Howell Estates 2Nd Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,557 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($91)


    Taxes:$1,092

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 501 HERITAGE BLVD, WINTER PARK, FL 32792

    $474,900103 Days on yellowkey   MLS ID: S5145746

    REDUCED by $5,000 (1.0%) on 06/23/2026

    For Sale S5145746 - 501 HERITAGE BLVD, WINTER PARK, FL 32792 20 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1376
       Built: 1966   Tax: $10,434 (2025)
    Community: Georgetown Estates
    Single Family


    Estimated Monthly Payment: $3,472 (change assumption)
    Mortgage ($2,602) + Taxes in 2025 ($870)


    Taxes:$10,434

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1521 CAVENDISH RD, WINTER PARK, FL 32789

    $470,00013 Days on yellowkey   MLS ID: O6415985

    For Sale O6415985 - 1521 CAVENDISH RD, WINTER PARK, FL 32789 22 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1036
       Built: 1946   Tax: $2,793 (2025)
    Community: Orwin Manor Westminster
    Single Family


    Estimated Monthly Payment: $2,808 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($233)


    Taxes:$2,793

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 5350 ORANGE AVE, WINTER PARK, FL 32792

    $469,9005 Days on yellowkey   MLS ID: O6415309

    1 Days Off yellowkey (back on 6/23/2026)

    For Sale O6415309 - 5350 ORANGE AVE, WINTER PARK, FL 32792 48 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1863
       Built: 2011   Tax: $5,520 (2025)
    Community: Suburban Homes
    Single Family


    Estimated Monthly Payment: $3,035 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($460)


    Taxes:$5,520

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1016 MANCHESTER CIR, WINTER PARK, FL 32792

    $417,50016 Days on yellowkey   MLS ID: O6414031

    0 Days Off yellowkey (back on 6/18/2026)

    For Sale O6414031 - 1016 MANCHESTER CIR, WINTER PARK, FL 32792 23 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1625
       Built: 1976   Tax: $4,388 (2025)
    Community: Howell Estates Rep
    Single Family


    Estimated Monthly Payment: $2,653 (change assumption)
    Mortgage ($2,288) + Taxes in 2025 ($366)


    Taxes:$4,388

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 7134 WRENWOOD WAY, WINTER PARK, FL 32792

    $445,0005 Days on yellowkey   MLS ID: O6418289

    1 Days Off yellowkey (back on 6/22/2026)

    For Sale O6418289 - 7134 WRENWOOD WAY, WINTER PARK, FL 32792 24 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1712
       Built: 1975   Tax: $4,266 (2025)
    Community: Wrenwood Heights Unit 2
    Single Family


    Estimated Monthly Payment: $2,794 (change assumption)
    Mortgage ($2,438) + Taxes in 2025 ($356)


    Taxes:$4,266

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 5530 S LAKE BURKETT LN, WINTER PARK, FL 32792

    $450,00020 Days on yellowkey   MLS ID: O6409433

    REDUCED by $15,000 (3.2%) on 06/22/2026

    For Sale O6409433 - 5530 S LAKE BURKETT LN, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1669
       Built: 1985
    Monthly Fee: $69
       Tax: $3,871 (2025)
    Community: Trinity Bay
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,857 (change assumption)
    Mortgage ($2,466) + Fees ($69) + Taxes in 2025 ($323)


    Taxes:$3,871

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2974 CHANTILLY AVE, WINTER PARK, FL 32789

    $499,00018 Days on yellowkey   MLS ID: O6412851

    REDUCED by $51,000 (9.3%) on 06/15/2026

    For Sale O6412851 - 2974 CHANTILLY AVE, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1433
       Built: 1960   Tax: $1,178 (2025)
    Community: Winter Park Manor
    Single Family


    Estimated Monthly Payment: $2,832 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($98)


    Taxes:$1,178

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 5340 N LAKE BURKETT LN, WINTER PARK, FL 32792

    $489,90019 Days on yellowkey   MLS ID: O6413717

    REDUCED by $5,100 (1.0%) on 06/21/2026

    For Sale O6413717 - 5340 N LAKE BURKETT LN, WINTER PARK, FL 32792 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1746
       Built: 1994
    Monthly Fee: $76
       Tax: $1,591 (2025)
    Community: Trinity Bay Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,893 (change assumption)
    Mortgage ($2,684) + Fees ($76) + Taxes in 2025 ($133)


    Taxes:$1,591

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 5117 CYPRESS CT, WINTER PARK, FL 32792

    $449,99041 Days on yellowkey   MLS ID: O6407713

    1 Days Off yellowkey (back on 6/20/2026)

    For Sale O6407713 - 5117 CYPRESS CT, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1534
       Built: 1972   Tax: $3,877 (2025)
    Community: Wrenwood Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,789 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($323)


    Taxes:$3,877

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3463 ARNEL DR, WINTER PARK, FL 32792

    $429,90099 Days on yellowkey   MLS ID: O6390301

    REDUCED by $20,000 (4.4%) on 06/01/2026

    For Sale O6390301 - 3463 ARNEL DR, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 1967   Tax: $4,648 (2024)
    Community: Eastbrook Sub Unit 11
    Single Family


    Estimated Monthly Payment: $2,743 (change assumption)
    Mortgage ($2,356) + Taxes in 2024 ($387)


    Taxes:$4,648

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792

    $475,00065 Days on yellowkey   MLS ID: O6399199

    0 Days Off yellowkey (back on 5/17/2026)

    REDUCED by $5,000 (1.0%) on 05/06/2026

    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: $3,172 (change assumption)
    Mortgage ($2,603) + 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


  • 1849 VIBURNUM LN, WINTER PARK, FL 32792

    $408,000321 Days on yellowkey   MLS ID: O6333863

    2 Days Off yellowkey (back on 6/17/2026)

    REDUCED by $17,000 (4.0%) on 06/10/2026

    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: $2,539 (change assumption)
    Mortgage ($2,236) + Taxes in 2024 ($304)


    Taxes:$3,645

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


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