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Displaying: For Sale

Location: Winter Park

Property Type(s): Single Family

Winter Park - 306 properties found

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  • 525 S LAKEMONT AVE, WINTER PARK, FL 32792

    $2,199,90017 Days on yellowkey   MLS ID: O6414770

    For Sale O6414770 - 525 S LAKEMONT AVE, WINTER PARK, FL 32792 76 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3330
       Built: 2026   Tax: $7,133 (2024)
    Community: Kenilworth Shores Sec 01
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,648 (change assumption)
    Mortgage ($12,054) + Taxes in 2024 ($594)


    Taxes:$7,133

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1320 GLADIOLAS DR, WINTER PARK, FL 32792

    $475,00027 Days on yellowkey   MLS ID: O6412139

    REDUCED by $5,000 (1.0%) on 06/15/2026

    For Sale O6412139 - 1320 GLADIOLAS DR, WINTER PARK, FL 32792 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1624
       Built: 1983   Tax: $1,380 (2025)
    Community: Garden Lake Estates Unit 3
    Single Family


    Estimated Monthly Payment: $2,718 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($115)


    Taxes:$1,380

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 3641 OAK VISTA LN, WINTER PARK, FL 32792

    $475,00017 Days on yellowkey   MLS ID: O6412855

    0 Days Off yellowkey (back on 6/15/2026)

    For Sale O6412855 - 3641 OAK VISTA LN, WINTER PARK, FL 32792 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1645
       Built: 1981   Tax: $1,562 (2025)
    Community: Garden Lake Estates Unit 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,733 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($130)


    Taxes:$1,562

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1724 PINE AVE, WINTER PARK, FL 32789

    $3,095,00020 Days on yellowkey   MLS ID: O6414263

    4 Days Off yellowkey (back on 6/15/2026)

    For Sale O6414263 - 1724 PINE AVE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 4.0   Gar: 4
    Liv Area Sq Ft: 4425
       Built: 2012   Tax: $32,133 (2025)
    Community: Conwill Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $19,636 (change assumption)
    Mortgage ($16,958) + Taxes in 2025 ($2,678)


    Taxes:$32,133

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1701 GOODRICH AVE, WINTER PARK, FL 32789

    $709,00066 Days on yellowkey   MLS ID: O6400278

    0 Days Off yellowkey (back on 6/15/2026)

    REDUCED by $30,000 (4.1%) on 06/05/2026

    For Sale O6400278 - 1701 GOODRICH AVE, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1528
       Built: 1950   Tax: $5,023 (2025)
    Community: Sylvan Hgts
    Single Family


    Estimated Monthly Payment: $4,303 (change assumption)
    Mortgage ($3,885) + Taxes in 2025 ($419)


    Taxes:$5,023

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2222 MARSH SEDGE LN, WINTER PARK, FL 32792

    $739,000323 Days on yellowkey   MLS ID: O6333145

    REDUCED by $25,900 (3.4%) on 06/13/2026

    For Sale O6333145 - 2222 MARSH SEDGE LN, WINTER PARK, FL 32792 60 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2192
       Built: 2019
    Monthly Fee: $243
       Tax: $7,847 (2024)
    Community: Preserve At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,946 (change assumption)
    Mortgage ($4,049) + Fees ($243) + Taxes in 2024 ($654)


    Taxes:$7,847

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 5503 ALBERT DR, WINTER PARK, FL 32792

    $402,50022 Days on yellowkey   MLS ID: S5151098

    REDUCED by $2,500 (0.6%) on 06/15/2026

    For Sale S5151098 - 5503 ALBERT DR, WINTER PARK, FL 32792 57 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1366
       Built: 1978   Tax: $4,123 (2025)
    Community: Howell Branch Woods
    Single Family


    Estimated Monthly Payment: $2,549 (change assumption)
    Mortgage ($2,205) + Taxes in 2025 ($344)


    Taxes:$4,123

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2708 LION HEART RD, WINTER PARK, FL 32792

    $617,500113 Days on yellowkey   MLS ID: O6387685

    REDUCED by $2,400 (0.4%) on 06/15/2026

    For Sale O6387685 - 2708 LION HEART RD, WINTER PARK, FL 32792 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1785
       Built: 1963   Tax: $7,007 (2024)
    Community: Winter Park Pines Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,967 (change assumption)
    Mortgage ($3,383) + Taxes in 2024 ($584)


    Taxes:$7,007

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 721 PANSY AVE, WINTER PARK, FL 32789

    $1,850,000247 Days on yellowkey   MLS ID: O6352857

    REDUCED by $75,000 (3.9%) on 06/10/2026

    For Sale O6352857 - 721 PANSY AVE, WINTER PARK, FL 32789 29 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2653
       Built: 2018   Tax: $15,480 (2025)
    Community: Villa View Park
    Single Family


    Estimated Monthly Payment: $11,427 (change assumption)
    Mortgage ($10,137) + Taxes in 2025 ($1,290)


    Taxes:$15,480

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 7577 DOCKSIDE ST, WINTER PARK, FL 32792

    $370,00023 Days on yellowkey   MLS ID: O6412514

    For Sale O6412514 - 7577 DOCKSIDE ST, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1245
       Built: 1977   Tax: $3,722 (2025)
    Community: Woodcrest Unit 6
    Single Family


    Estimated Monthly Payment: $2,338 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($310)


    Taxes:$3,722

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2803 BANCHORY RD, WINTER PARK, FL 32792

    $495,00027 Days on yellowkey   MLS ID: O6404011

    For Sale O6404011 - 2803 BANCHORY RD, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1596
       Built: 1965
    Monthly Fee: $5
       Tax: $2,458 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,922 (change assumption)
    Mortgage ($2,712) + Fees ($5) + Taxes in 2025 ($205)


    Taxes:$2,458

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2217 SUSSEX RD, WINTER PARK, FL 32792

    $519,999216 Days on yellowkey   MLS ID: O6362648

    For Sale O6362648 - 2217 SUSSEX RD, WINTER PARK, FL 32792 34 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


  • 731 BONGART ROAD, WINTER PARK, FL 32792

    $499,00049 Days on yellowkey   MLS ID: O6406004

    For Sale O6406004 - 731 BONGART ROAD, WINTER PARK, FL 32792 44 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1526
       Built: 1961   Tax: $5,910 (2025)
    Community: Winter Park Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,227 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($493)


    Taxes:$5,910

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2215 WOODCREST DR, WINTER PARK, FL 32792

    $695,00042 Days on yellowkey   MLS ID: O6407540

    REDUCED by $24,000 (3.3%) on 06/14/2026

    For Sale O6407540 - 2215 WOODCREST DR, WINTER PARK, FL 32792 39 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1688
       Built: 1960   Tax: $4,090 (2025)
    Community: Kenilworth Estates 1St Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,149 (change assumption)
    Mortgage ($3,808) + Taxes in 2025 ($341)


    Taxes:$4,090

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1850 ASTER DR, WINTER PARK, FL 32792

    $485,00023 Days on yellowkey   MLS ID: TB8513990

    REDUCED by $15,000 (3.0%) on 06/13/2026

    For Sale TB8513990 - 1850 ASTER DR, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1656
       Built: 1978   Tax: $1,584 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,789 (change assumption)
    Mortgage ($2,657) + Taxes in 2025 ($132)


    Taxes:$1,584

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1090 WILDMEADOW RUN, WINTER PARK, FL 32792

    $835,00090 Days on yellowkey   MLS ID: O6394208

    REDUCED by $10,000 (1.2%) on 06/02/2026

    For Sale O6394208 - 1090 WILDMEADOW RUN, WINTER PARK, FL 32792 37 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: $5,340 (change assumption)
    Mortgage ($4,575) + 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


  • 1441 CARDINAL CT, WINTER PARK, FL 32789

    $4,285,00071 Days on yellowkey   MLS ID: O6399395

    For Sale O6399395 - 1441 CARDINAL CT, WINTER PARK, FL 32789 85 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4066
       Built: 2022   Tax: $47,740 (2025)
    Community: Winflor Court
    Spa: No

    Single Family


    Estimated Monthly Payment: $27,457 (change assumption)
    Mortgage ($23,479) + Taxes in 2025 ($3,978)


    Taxes:$47,740

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 4469 OLD BEAR RUN, WINTER PARK, FL 32792

    $1,799,999136 Days on yellowkey   MLS ID: O6375415

    REDUCED by $50,001 (2.7%) on 05/22/2026

    For Sale O6375415 - 4469 OLD BEAR RUN, WINTER PARK, FL 32792 77 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4288
       Built: 1978   Tax: $10,710 (2024)
    Community: Pervis Survey For R E
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,755 (change assumption)
    Mortgage ($9,863) + Taxes in 2024 ($893)


    Taxes:$10,710

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1611 CHESTNUT AVE, WINTER PARK, FL 32789

    $1,070,00056 Days on yellowkey   MLS ID: O6402502

    REDUCED by $30,000 (2.7%) on 06/10/2026

    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: $6,162 (change assumption)
    Mortgage ($5,863) + Taxes in 2025 ($299)


    Taxes:$3,590

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1760 PERUVIAN LN, WINTER PARK, FL 32792

    $324,000110 Days on yellowkey   MLS ID: A4685217

    REDUCED by $15,000 (4.4%) on 06/09/2026

    For Sale A4685217 - 1760 PERUVIAN LN, WINTER PARK, FL 32792 21 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1160
       Built: 1960   Tax: $3,470 (2025)
    Community: Eastbrook Sub Unit 06
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,064 (change assumption)
    Mortgage ($1,775) + Taxes in 2025 ($289)


    Taxes:$3,470

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None






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