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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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  • 1036 MANCHESTER CIR, WINTER PARK, FL 32792

    $400,00032 Days on yellowkey   MLS ID: O6395138

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

    For Sale O6395138 - 1036 MANCHESTER CIR, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1574
       Built: 1974   Tax: $4,126 (2024)
    Community: Howell Estates Rep
    Single Family


    Estimated Monthly Payment: $2,536 (change assumption)
    Mortgage ($2,192) + Taxes in 2024 ($344)


    Taxes:$4,126

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla 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


  • 1205 VALLEY CREEK RUN, WINTER PARK, FL 32792

    $450,00033 Days on yellowkey   MLS ID: O6394946

    For Sale O6394946 - 1205 VALLEY CREEK RUN, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1815
       Built: 1997
    Monthly Fee: $22
       Tax: $2,237 (2024)
    Community: Lost Creek
    Single Family


    Estimated Monthly Payment: $2,674 (change assumption)
    Mortgage ($2,466) + Fees ($22) + Taxes in 2024 ($186)


    Taxes:$2,237

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 405 LAKE FAIR LN, WINTER PARK, FL 32789

    $459,00040 Days on yellowkey   MLS ID: O6393594

    REDUCED by $999 (0.2%) on 04/25/2026

    For Sale O6393594 - 405 LAKE FAIR LN, WINTER PARK, FL 32789 45 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1491
       Built: 1957   Tax: $1,355 (2025)
    Community: Fairbanks Shores 5Th Add
    Single Family


    Estimated Monthly Payment: $2,628 (change assumption)
    Mortgage ($2,515) + Taxes in 2025 ($113)


    Taxes:$1,355

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2707 TIERRA CIR, WINTER PARK, FL 32792

    $495,0005 Days on yellowkey   MLS ID: O6398979

    For Sale O6398979 - 2707 TIERRA CIR, WINTER PARK, FL 32792 42 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1710
       Built: 1970   Tax: $3,237 (2025)
    Community: Casa Aloma
    Single Family


    Estimated Monthly Payment: $2,982 (change assumption)
    Mortgage ($2,712) + Taxes in 2025 ($270)


    Taxes:$3,237

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 3054 BLUEBROOK DR, WINTER PARK, FL 32792

    $427,50022 Days on yellowkey   MLS ID: O6398450

    For Sale O6398450 - 3054 BLUEBROOK DR, WINTER PARK, FL 32792 27 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1939
       Built: 1973   Tax: $6,422 (2025)
    Community: Laurel Spgs
    Single Family


    Estimated Monthly Payment: $2,878 (change assumption)
    Mortgage ($2,342) + Taxes in 2025 ($535)


    Taxes:$6,422

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2237 WOODCREST DR, WINTER PARK, FL 32792

    $490,0003 Days on yellowkey   MLS ID: O6404115

    0 Days Off yellowkey (back on 5/1/2026)

    For Sale O6404115 - 2237 WOODCREST DR, WINTER PARK, FL 32792 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1492
       Built: 1959   Tax: $1,919 (2025)
    Community: Kenilworth Estates 1St Add
    Single Family


    Estimated Monthly Payment: $2,845 (change assumption)
    Mortgage ($2,685) + Taxes in 2025 ($160)


    Taxes:$1,919

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3440 ALLSTON LN, WINTER PARK, FL 32792

    $420,0008 Days on yellowkey   MLS ID: O6401731

    For Sale O6401731 - 3440 ALLSTON LN, WINTER PARK, FL 32792 37 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1533
       Built: 1993
    Monthly Fee: $65
       Tax: $1,364 (2024)
    Community: Villas Of Casselberry Ph 4
    Single Family


    Estimated Monthly Payment: $2,480 (change assumption)
    Mortgage ($2,301) + Fees ($65) + Taxes in 2024 ($114)


    Taxes:$1,364

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • WINTER PARK, FL 32792

    $430,00053 Days on yellowkey   MLS ID: S5145631

    REDUCED by $10,000 (2.3%) on 04/15/2026

    For Sale S5145631 - WINTER PARK, FL 32792 11 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1296
       Built: 1958   Tax: $4,968 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,770 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($414)


    Taxes:$4,968

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 950 HANOVER AVE, WINTER PARK, FL 32789

    $470,00023 Days on yellowkey   MLS ID: O6398273

    For Sale O6398273 - 950 HANOVER AVE, WINTER PARK, FL 32789 28 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1606
       Built: 1956   Tax: $3,525 (2025)
    Community: Albert Lee Ridge 1St Add
    Single Family


    Estimated Monthly Payment: $2,869 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($294)


    Taxes:$3,525

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7761 FOX KNOLL PL, WINTER PARK, FL 32792

    $425,00011 Days on yellowkey   MLS ID: O6401159

    0 Days Off yellowkey (back on 5/1/2026)

    For Sale O6401159 - 7761 FOX KNOLL PL, WINTER PARK, FL 32792 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1485
       Built: 1989
    Monthly Fee: $20
       Tax: $4,308 (2024)
    Community: Bridgewater
    Single Family


    Estimated Monthly Payment: $2,708 (change assumption)
    Mortgage ($2,329) + Fees ($20) + Taxes in 2024 ($359)


    Taxes:$4,308

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2779 SANBINA ST, WINTER PARK, FL 32789

    $449,00052 Days on yellowkey   MLS ID: O6388746

    REDUCED by $11,000 (2.4%) on 04/29/2026

    For Sale O6388746 - 2779 SANBINA ST, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1405
       Built: 1960   Tax: $5,629 (2024)
    Community: Howell Heights
    Single Family


    Estimated Monthly Payment: $2,929 (change assumption)
    Mortgage ($2,460) + Taxes in 2024 ($469)


    Taxes:$5,629

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 841 W SWOOPE AVE, WINTER PARK, FL 32789

    $499,00095 Days on yellowkey   MLS ID: O6373287

    0 Days Off yellowkey (back on 4/30/2026)

    REDUCED by $241,000 (32.6%) on 04/13/2026

    For Sale O6373287 - 841 W SWOOPE AVE, WINTER PARK, FL 32789 31 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1396
       Built: 1930   Tax: $3,824 (2024)
    Community: Capens Add
    Single Family


    Estimated Monthly Payment: $3,053 (change assumption)
    Mortgage ($2,734) + Taxes in 2024 ($319)


    Taxes:$3,824

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1832 E CHERYL DR, WINTER PARK, FL 32792

    $439,99510 Days on yellowkey   MLS ID: O6402209

    0 Days Off yellowkey (back on 4/30/2026)

    INCREASED by $10,000 (2.3%) on 04/27/2026

    For Sale O6402209 - 1832 E CHERYL DR, WINTER PARK, FL 32792 22 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1808
       Built: 1983
    Monthly Fee: $8
       Tax: $1,847 (2024)
    Community: Carolyn Estates
    Single Family


    Estimated Monthly Payment: $2,573 (change assumption)
    Mortgage ($2,411) + Fees ($8) + Taxes in 2024 ($154)


    Taxes:$1,847

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3463 ARNEL DR, WINTER PARK, FL 32792

    $449,90048 Days on yellowkey   MLS ID: O6390301

    REDUCED by $10,000 (2.2%) on 04/29/2026

    For Sale O6390301 - 3463 ARNEL DR, WINTER PARK, FL 32792 58 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: $2,852 (change assumption)
    Mortgage ($2,465) + Taxes in 2024 ($387)


    Taxes:$4,648

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1367 TIERRA CIR, WINTER PARK, FL 32792

    $424,900104 Days on yellowkey   MLS ID: O6375221

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

    For Sale O6375221 - 1367 TIERRA CIR, WINTER PARK, FL 32792 62 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2083
       Built: 1969   Tax: $4,948 (2024)
    Community: Casa Aloma
    Single Family


    Estimated Monthly Payment: $2,740 (change assumption)
    Mortgage ($2,328) + Taxes in 2024 ($412)


    Taxes:$4,948

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 5503 ALBERT DR, WINTER PARK, FL 32792

    $405,00035 Days on yellowkey   MLS ID: S5146768

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

    For Sale S5146768 - 5503 ALBERT DR, WINTER PARK, FL 32792 55 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1366
       Built: 1978   Tax: $4,241 (2024)
    Community: Howell Branch Woods
    Single Family


    Estimated Monthly Payment: $2,573 (change assumption)
    Mortgage ($2,219) + Taxes in 2024 ($353)


    Taxes:$4,241

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5331 OAK CT, WINTER PARK, FL 32792

    $460,000292 Days on yellowkey   MLS ID: S5130868

    For Sale S5130868 - 5331 OAK CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1263
       Built: 1976   Tax: $2,311 (2024)
    Community: Wrenwood Heights Unit 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,713 (change assumption)
    Mortgage ($2,520) + Taxes in 2024 ($193)


    Taxes:$2,311

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1923 LINDEN RD, WINTER PARK, FL 32792

    $475,00035 Days on yellowkey   MLS ID: O6393643

    REDUCED by $24,999 (5.0%) on 04/17/2026

    For Sale O6393643 - 1923 LINDEN RD, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2117
       Built: 1955   Tax: $340 (2024)
    Community: Tanglewood Sec 4
    Single Family


    Estimated Monthly Payment: $2,631 (change assumption)
    Mortgage ($2,603) + Taxes in 2024 ($28)


    Taxes:$340

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 501 HERITAGE BLVD, WINTER PARK, FL 32792

    $489,99052 Days on yellowkey   MLS ID: S5145746

    REDUCED by $10,000 (2.0%) on 04/15/2026

    For Sale S5145746 - 501 HERITAGE BLVD, WINTER PARK, FL 32792 17 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: $3,554 (change assumption)
    Mortgage ($2,685) + Taxes in 2025 ($870)


    Taxes:$10,434

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


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