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Displaying: For Sale

Location: Winter Park

Property Type(s): Single Family

Price: $500,000 to $599,000

Winter Park - 28 properties found

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  • 525 OLOLU DR, WINTER PARK, FL 32789

    $515,00056 Days on yellowkey   MLS ID: S5148431

    For Sale S5148431 - 525 OLOLU DR, WINTER PARK, FL 32789 42 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1786
       Built: 1966   Tax: $2,249 (2025)
    Community: Killarney Circle
    Single Family


    Estimated Monthly Payment: $3,009 (change assumption)
    Mortgage ($2,822) + Taxes in 2025 ($187)


    Taxes:$2,249

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1438 TIERRA CIR, WINTER PARK, FL 32792

    $514,90054 Days on yellowkey   MLS ID: O6403855

    REDUCED by $5,000 (1.0%) on 06/24/2026

    For Sale O6403855 - 1438 TIERRA CIR, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1627
       Built: 1968   Tax: $1,630 (2024)
    Community: Casa Aloma
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,957 (change assumption)
    Mortgage ($2,821) + Taxes in 2024 ($136)


    Taxes:$1,630

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 332 FLEET RD, WINTER PARK, FL 32792

    $595,0007 Days on yellowkey   MLS ID: O6414829

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

    For Sale O6414829 - 332 FLEET RD, WINTER PARK, FL 32792 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2355
       Built: 1966   Tax: $4,919 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $3,670 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($410)


    Taxes:$4,919

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792

    $535,00015 Days on yellowkey   MLS ID: O6414677

    For Sale O6414677 - 528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1656
       Built: 1964   Tax: $6,000 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,431 (change assumption)
    Mortgage ($2,931) + Taxes in 2025 ($500)


    Taxes:$6,000

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1232 VALLEY CREEK RUN, WINTER PARK, FL 32792

    $535,0007 Days on yellowkey   MLS ID: O6417190

    For Sale O6417190 - 1232 VALLEY CREEK RUN, WINTER PARK, FL 32792 48 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2071
       Built: 1994
    Monthly Fee: $22
       Tax: $2,283 (2025)
    Community: Lost Creek
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,144 (change assumption)
    Mortgage ($2,931) + Fees ($22) + Taxes in 2025 ($190)


    Taxes:$2,283

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 641 W LYMAN AVE, WINTER PARK, FL 32789

    $509,00023 Days on yellowkey   MLS ID: O6408078

    0 Days Off yellowkey (back on 6/21/2026)

    For Sale O6408078 - 641 W LYMAN AVE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1120
       Built: 2003   Tax: $6,342 (2025)
    Community: Town/Winter Park
    Single Family


    Estimated Monthly Payment: $3,317 (change assumption)
    Mortgage ($2,789) + Taxes in 2025 ($529)


    Taxes:$6,342

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 333 CORNWALL RD, WINTER PARK, FL 32792

    $579,00034 Days on yellowkey   MLS ID: O6409379

    For Sale O6409379 - 333 CORNWALL RD, WINTER PARK, FL 32792 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1660
       Built: 1963
    Monthly Fee: $5
       Tax: $2,654 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,399 (change assumption)
    Mortgage ($3,173) + Fees ($5) + Taxes in 2025 ($221)


    Taxes:$2,654

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2718 SANDWELL DR, WINTER PARK, FL 32792

    $525,0007 Days on yellowkey   MLS ID: O6410283

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

    For Sale O6410283 - 2718 SANDWELL DR, WINTER PARK, FL 32792 56 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1597
       Built: 1968
    Monthly Fee: $5
       Tax: $2,105 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,057 (change assumption)
    Mortgage ($2,877) + Fees ($5) + Taxes in 2025 ($175)


    Taxes:$2,105

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2715 PRINCE JOHN RD, WINTER PARK, FL 32792

    $504,90017 Days on yellowkey   MLS ID: O6415084

    REDUCED by $15,000 (2.9%) on 06/19/2026

    For Sale O6415084 - 2715 PRINCE JOHN RD, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1565
       Built: 1963   Tax: $7,101 (2025)
    Community: Winter Park Pines Rep
    Single Family


    Estimated Monthly Payment: $3,358 (change assumption)
    Mortgage ($2,767) + Taxes in 2025 ($592)


    Taxes:$7,101

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2054 EASTBROOK BLVD, WINTER PARK, FL 32792

    $500,00023 Days on yellowkey   MLS ID: V4949389

    For Sale V4949389 - 2054 EASTBROOK BLVD, WINTER PARK, FL 32792 5 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2031
       Built: 1966   Tax: $5,054 (2025)
    Community: Eastbrook Sub Unit 8
    Single Family


    Estimated Monthly Payment: $3,161 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($421)


    Taxes:$5,054

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2008 HOUNDSLAKE DR, WINTER PARK, FL 32792

    $515,00010 Days on yellowkey   MLS ID: O6414369

    For Sale O6414369 - 2008 HOUNDSLAKE DR, WINTER PARK, FL 32792 27 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2250
       Built: 1980   Tax: $5,253 (2025)
    Community: Cedar Ridge
    Single Family


    Estimated Monthly Payment: $3,260 (change assumption)
    Mortgage ($2,822) + Taxes in 2025 ($438)


    Taxes:$5,253

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla 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


  • 1822 YORKSHIRE DR, WINTER PARK, FL 32792

    $598,00062 Days on yellowkey   MLS ID: O6401364

    REDUCED by $26,000 (4.2%) on 05/20/2026

    For Sale O6401364 - 1822 YORKSHIRE DR, WINTER PARK, FL 32792 42 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1620
       Built: 1957   Tax: $5,959 (2025)
    Community: Park Manor
    Single Family


    Estimated Monthly Payment: $3,773 (change assumption)
    Mortgage ($3,277) + Taxes in 2025 ($497)


    Taxes:$5,959

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1741 WESTCHESTER AVE, WINTER PARK, FL 32789

    $595,00070 Days on yellowkey   MLS ID: O6399014

    REDUCED by $14,900 (2.4%) on 05/04/2026

    For Sale O6399014 - 1741 WESTCHESTER AVE, WINTER PARK, FL 32789 24 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1434
       Built: 1964   Tax: $8,945 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $4,006 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($745)


    Taxes:$8,945

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1944 NATALEN RD, WINTER PARK, FL 32792

    $519,00024 Days on yellowkey   MLS ID: O6405802

    0 Days Off yellowkey (back on 6/11/2026)

    For Sale O6405802 - 1944 NATALEN RD, WINTER PARK, FL 32792 27 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1380
       Built: 1957   Tax: $7,067 (2025)
    Community: Kenilworth Shores Sec 07
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,433 (change assumption)
    Mortgage ($2,844) + Taxes in 2025 ($589)


    Taxes:$7,067

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 650 DOUGLAS AVE, WINTER PARK, FL 32789

    $550,00017 Days on yellowkey   MLS ID: O6414807

    0 Days Off yellowkey (back on 6/8/2026)

    For Sale O6414807 - 650 DOUGLAS AVE, WINTER PARK, FL 32789 2 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1280
       Built: 2003   Tax: $7,799 (2025)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $3,664 (change assumption)
    Mortgage ($3,014) + Taxes in 2025 ($650)


    Taxes:$7,799

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1319 BESSMOR RD, WINTER PARK, FL 32789

    $589,00065 Days on yellowkey   MLS ID: O6400395

    REDUCED by $6,000 (1.0%) on 06/08/2026

    For Sale O6400395 - 1319 BESSMOR RD, WINTER PARK, FL 32789 13 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1126
       Built: 1956   Tax: $5,626 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,696 (change assumption)
    Mortgage ($3,227) + Taxes in 2025 ($469)


    Taxes:$5,626

    Elementary School: Dream Lake Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2756 SHERIFF WAY, WINTER PARK, FL 32792

    $595,00058 Days on yellowkey   MLS ID: O6402570

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

    REDUCED by $30,000 (4.8%) on 06/05/2026

    For Sale O6402570 - 2756 SHERIFF WAY, WINTER PARK, FL 32792 48 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1812
       Built: 1965   Tax: $5,547 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,722 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($462)


    Taxes:$5,547

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2829 ALOMA, WINTER PARK, FL 32792

    $579,00055 Days on yellowkey   MLS ID: O6404107

    2 Days Off yellowkey (back on 6/5/2026)

    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


  • 508 DUNRAVEN DR, WINTER PARK, FL 32792

    $595,00023 Days on yellowkey   MLS ID: O6412363

    0 Days Off yellowkey (back on 6/5/2026)

    For Sale O6412363 - 508 DUNRAVEN DR, WINTER PARK, FL 32792 34 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1370
       Built: 1958   Tax: $2,281 (2025)
    Community: Kenilworth Shores Sec 03
    Single Family


    Estimated Monthly Payment: $3,450 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($190)


    Taxes:$2,281

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


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