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Displaying: For Sale

Location: Winter Park

Property Type(s): Single Family

Living Area Square Feet: 1500 to 1999

Winter Park - 78 properties found

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  • 2333 WESTMINSTER CT, WINTER PARK, FL 32789

    $699,00038 Days on yellowkey   MLS ID: O6407054

    REDUCED by $20,000 (2.8%) on 06/04/2026

    For Sale O6407054 - 2333 WESTMINSTER CT, WINTER PARK, FL 32789 48 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1877
       Built: 1948   Tax: $6,723 (2025)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $4,390 (change assumption)
    Mortgage ($3,830) + Taxes in 2025 ($560)


    Taxes:$6,723

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 330 ELKHORN CT, WINTER PARK, FL 32792

    $549,900150 Days on yellowkey   MLS ID: O6376757

    REDUCED by $5,000 (0.9%) on 06/04/2026

    For Sale O6376757 - 330 ELKHORN CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1570
       Built: 1965   Tax: $2,086 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $3,187 (change assumption)
    Mortgage ($3,013) + Taxes in 2025 ($174)


    Taxes:$2,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 676 DUNBLANE DR, WINTER PARK, FL 32792

    $699,000201 Days on yellowkey   MLS ID: O6365557

    0 Days Off yellowkey (back on 5/26/2026)

    REDUCED by $51,000 (6.8%) on 05/12/2026

    For Sale O6365557 - 676 DUNBLANE DR, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1827
       Built: 1962   Tax: $5,584 (2024)
    Community: Kenilworth Shores Sec 04
    Single Family


    Estimated Monthly Payment: $4,295 (change assumption)
    Mortgage ($3,830) + Taxes in 2024 ($465)


    Taxes:$5,584

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2823 WRIGHT AVE, WINTER PARK, FL 32789

    $899,900103 Days on yellowkey   MLS ID: O6390670

    0 Days Off yellowkey (back on 6/3/2026)

    REDUCED by $30,000 (3.2%) on 05/07/2026

    For Sale O6390670 - 2823 WRIGHT AVE, WINTER PARK, FL 32789 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1536
       Built: 1958   Tax: $9,119 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $5,691 (change assumption)
    Mortgage ($4,931) + Taxes in 2025 ($760)


    Taxes:$9,119

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2758 BANCHORY RD, WINTER PARK, FL 32792

    $598,000331 Days on yellowkey   MLS ID: O6329628

    For Sale O6329628 - 2758 BANCHORY RD, WINTER PARK, FL 32792 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1539
       Built: 1965   Tax: $7,325 (2024)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,887 (change assumption)
    Mortgage ($3,277) + Taxes in 2024 ($610)


    Taxes:$7,325

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 7393 GRAND AVE, WINTER PARK, FL 32792

    $325,00079 Days on yellowkey   MLS ID: S5147029

    INCREASED by $125,000 (62.5%) on 06/01/2026

    SHORT SALE S5147029 - 7393 GRAND AVE, WINTER PARK, FL 32792 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1518
       Built: 1983   Tax: $4,367 (2024)
    Community: Oakcrest-516
    Single Family


    Estimated Monthly Payment: $2,145 (change assumption)
    Mortgage ($1,781) + Taxes in 2024 ($364)


    Taxes:$4,367

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 316 BECKETT CT, WINTER PARK, FL 32792

    $450,00028 Days on yellowkey   MLS ID: O6411108

    For Sale O6411108 - 316 BECKETT CT, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1651
       Built: 1966   Tax: $2,232 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $2,652 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($186)


    Taxes:$2,232

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1780 BRYAN AVE, WINTER PARK, FL 32789

    $849,000196 Days on yellowkey   MLS ID: O6365369

    For Sale O6365369 - 1780 BRYAN AVE, WINTER PARK, FL 32789 8 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1617
       Built: 1952   Tax: $7,345 (2024)
    Community: Lakeview Terrace
    Single Family


    Estimated Monthly Payment: $5,264 (change assumption)
    Mortgage ($4,652) + Taxes in 2024 ($612)


    Taxes:$7,345

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2512 EASTBROOK BLVD, WINTER PARK, FL 32792

    $390,00034 Days on yellowkey   MLS ID: O6409544

    For Sale O6409544 - 2512 EASTBROOK BLVD, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1607
       Built: 1967   Tax: $4,171 (2025)
    Community: Eastbrook Sub Unit 8
    Single Family


    Estimated Monthly Payment: $2,485 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($348)


    Taxes:$4,171

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1960 WINTER PARK RD, WINTER PARK, FL 32789

    $899,00048 Days on yellowkey   MLS ID: O6406091

    0 Days Off yellowkey (back on 5/20/2026)

    For Sale O6406091 - 1960 WINTER PARK RD, WINTER PARK, FL 32789 47 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1864
       Built: 1948   Tax: $7,103 (2025)
    Community: Charmont
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,518 (change assumption)
    Mortgage ($4,926) + Taxes in 2025 ($592)


    Taxes:$7,103

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 346 S RANGER BLVD, WINTER PARK, FL 32792

    $475,000283 Days on yellowkey   MLS ID: S5134662

    For Sale S5134662 - 346 S RANGER BLVD, WINTER PARK, FL 32792 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1592
       Built: 1965   Tax: $5,339 (2024)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,048 (change assumption)
    Mortgage ($2,603) + Taxes in 2024 ($445)


    Taxes:$5,339

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 3054 BLUEBROOK DR, WINTER PARK, FL 32792

    $410,00073 Days on yellowkey   MLS ID: O6398450

    REDUCED by $17,500 (4.1%) on 05/15/2026

    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: $2,782 (change assumption)
    Mortgage ($2,247) + Taxes in 2025 ($535)


    Taxes:$6,422

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 423 OLOLU DR, WINTER PARK, FL 32789

    $549,000167 Days on yellowkey   MLS ID: O6369976

    REDUCED by $40,000 (6.8%) on 05/14/2026

    For Sale O6369976 - 423 OLOLU DR, WINTER PARK, FL 32789 51 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1920
       Built: 1981   Tax: $4,030 (2024)
    Community: Killarney Circle
    Single Family


    Estimated Monthly Payment: $3,344 (change assumption)
    Mortgage ($3,008) + Taxes in 2024 ($336)


    Taxes:$4,030

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 814 DENSMORE DR, WINTER PARK, FL 32792

    $425,00069 Days on yellowkey   MLS ID: O6399773

    2 Days Off yellowkey (back on 5/13/2026)

    For Sale O6399773 - 814 DENSMORE DR, WINTER PARK, FL 32792 24 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1610
       Built: 1960   Tax: $5,402 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,779 (change assumption)
    Mortgage ($2,329) + Taxes in 2025 ($450)


    Taxes:$5,402

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 517 ROUGHBEARD RD, WINTER PARK, FL 32792

    $565,00071 Days on yellowkey   MLS ID: O6399029

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

    For Sale O6399029 - 517 ROUGHBEARD RD, WINTER PARK, FL 32792 53 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1873
       Built: 1971   Tax: $4,323 (2025)
    Community: Winter Park Pines Unit 17
    Single Family


    Estimated Monthly Payment: $3,456 (change assumption)
    Mortgage ($3,096) + Taxes in 2025 ($360)


    Taxes:$4,323

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2627 AMBERGATE RD, WINTER PARK, FL 32792

    $510,0001198 Days on yellowkey   MLS ID: O6093816

    For Sale O6093816 - 2627 AMBERGATE RD, WINTER PARK, FL 32792 19 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 1805
       Built: 1959   Tax: $4,750 (2022)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $3,190 (change assumption)
    Mortgage ($2,794) + Taxes in 2022 ($396)


    Taxes:$4,750

    Elementary School: None

    High School: None

    Tax Year: 2022

    Middle School: None


  • 2020 COCOS CT, WINTER PARK, FL 32792

    $458,990103 Days on yellowkey   MLS ID: O6389901

    1 Days Off yellowkey (back on 4/24/2026)

    REDUCED by $1,000 (0.2%) on 04/17/2026

    For Sale O6389901 - 2020 COCOS CT, WINTER PARK, FL 32792 22 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1715
       Built: 1966   Tax: $1,410 (2024)
    Community: Eastbrook Sub Unit 8
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,632 (change assumption)
    Mortgage ($2,515) + Taxes in 2024 ($117)


    Taxes:$1,410

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 5233 LAKE HOWELL RD, WINTER PARK, FL 32792

    $562,0001028 Days on yellowkey   MLS ID: O6137445

    1 Days Off yellowkey (back on 10/24/2023)

    For Sale O6137445 - 5233 LAKE HOWELL RD, WINTER PARK, FL 32792 45 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1778
       Built: 1956   Tax: $4,888 (2022)
    Community: Tanglewood Sec 3 Rep
    Single Family


    Estimated Monthly Payment: $3,487 (change assumption)
    Mortgage ($3,079) + Taxes in 2022 ($407)


    Taxes:$4,888

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2022

    Middle School: Tuskawilla Middle






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