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Displaying: For Sale

Location: Winter Park

Property Type(s): Single Family

Beds: 3 to 3

Winter Park - 103 properties found

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  • 1082 WILDMEADOW RUN, WINTER PARK, FL 32792

    $650,00035 Days on yellowkey   MLS ID: O6408825

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

    For Sale O6408825 - 1082 WILDMEADOW RUN, WINTER PARK, FL 32792 40 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2021
    Monthly Fee: $170
       Tax: $5,154 (2025)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,161 (change assumption)
    Mortgage ($3,562) + Fees ($170) + Taxes in 2025 ($430)


    Taxes:$5,154

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1926 NATALEN RD, WINTER PARK, FL 32792

    $638,900111 Days on yellowkey   MLS ID: O6388308

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

    REDUCED by $1,000 (0.2%) on 05/22/2026

    For Sale O6388308 - 1926 NATALEN RD, WINTER PARK, FL 32792 44 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1469
       Built: 1957   Tax: $7,308 (2024)
    Community: Kenilworth Shores Sec 07
    Single Family


    Estimated Monthly Payment: $4,110 (change assumption)
    Mortgage ($3,501) + Taxes in 2024 ($609)


    Taxes:$7,308

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 418 GILBERT RD, WINTER PARK, FL 32792

    $710,00091 Days on yellowkey   MLS ID: O6385950

    REDUCED by $9,000 (1.3%) on 06/02/2026

    For Sale O6385950 - 418 GILBERT RD, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1680
       Built: 1964   Tax: $9,094 (2025)
    Community: Winter Park Pines Ut 5
    Single Family


    Estimated Monthly Payment: $4,648 (change assumption)
    Mortgage ($3,890) + Taxes in 2025 ($758)


    Taxes:$9,094

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 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


  • 1052 MANCHESTER CIR, WINTER PARK, FL 32792

    $460,000152 Days on yellowkey   MLS ID: O6376260

    REDUCED by $10,000 (2.1%) on 05/28/2026

    For Sale O6376260 - 1052 MANCHESTER CIR, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1703
       Built: 1983   Tax: $5,216 (2025)
    Community: Howell Estates 1St Add
    Single Family


    Estimated Monthly Payment: $2,955 (change assumption)
    Mortgage ($2,520) + Taxes in 2025 ($435)


    Taxes:$5,216

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 622 PENN PL, WINTER PARK, FL 32789

    $1,895,00035 Days on yellowkey   MLS ID: TB8511228

    For Sale TB8511228 - 622 PENN PL, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2767
       Built: 2001
    Monthly Fee: $222
       Tax: $12,624 (2025)
    Community: Pennsylvania Place Rep
    Single Family


    Estimated Monthly Payment: $11,657 (change assumption)
    Mortgage ($10,383) + Fees ($222) + Taxes in 2025 ($1,052)


    Taxes:$12,624

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 950 HANOVER AVE, WINTER PARK, FL 32789

    $460,00075 Days on yellowkey   MLS ID: O6398273

    REDUCED by $10,000 (2.1%) on 06/01/2026

    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: $2,814 (change assumption)
    Mortgage ($2,520) + Taxes in 2025 ($294)


    Taxes:$3,525

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 121 STEFANIK RD, WINTER PARK, FL 32792

    $317,500246 Days on yellowkey   MLS ID: A4669103

    0 Days Off yellowkey (back on 6/7/2026)

    For Sale A4669103 - 121 STEFANIK RD, WINTER PARK, FL 32792 11 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1392
       Built: 1949   Tax: $3,581 (2024)
    Community: Slovak Village
    Single Family


    Estimated Monthly Payment: $2,038 (change assumption)
    Mortgage ($1,740) + Taxes in 2024 ($298)


    Taxes:$3,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 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


  • 318 VITORIA AVE, WINTER PARK, FL 32789

    $1,980,00090 Days on yellowkey   MLS ID: O6388489

    REDUCED by $220,000 (10.0%) on 06/02/2026

    For Sale O6388489 - 318 VITORIA AVE, WINTER PARK, FL 32789 66 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2433
       Built: 1922   Tax: $2,960 (2024)
    Community: College Quarter
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,096 (change assumption)
    Mortgage ($10,849) + Taxes in 2024 ($247)


    Taxes:$2,960

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1120 WISCONSIN AVE, WINTER PARK, FL 32789

    $1,095,00030 Days on yellowkey   MLS ID: O6406800

    For Sale O6406800 - 1120 WISCONSIN AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 2213
       Built: 2021   Tax: $10,451 (2025)
    Community: Henkel Add
    Single Family


    Estimated Monthly Payment: $6,871 (change assumption)
    Mortgage ($6,000) + Taxes in 2025 ($871)


    Taxes:$10,451

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1407 MILLER AVE, WINTER PARK, FL 32789

    $899,00042 Days on yellowkey   MLS ID: O6406408

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

    For Sale O6406408 - 1407 MILLER AVE, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1884
       Built: 2023
    Monthly Fee: $200
       Tax: $6,818 (2025)
    Community: H Vanwies Sub
    Single Family


    Estimated Monthly Payment: $5,694 (change assumption)
    Mortgage ($4,926) + Fees ($200) + Taxes in 2025 ($568)


    Taxes:$6,818

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 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


  • 1707 HARMON AVE, WINTER PARK, FL 32789

    $687,00037 Days on yellowkey   MLS ID: O6409180

    REDUCED by $8,000 (1.2%) on 06/05/2026

    For Sale O6409180 - 1707 HARMON AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1669
       Built: 1927   Tax: $4,658 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $4,152 (change assumption)
    Mortgage ($3,764) + Taxes in 2025 ($388)


    Taxes:$4,658

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2779 SANBINA ST, WINTER PARK, FL 32789

    $429,000104 Days on yellowkey   MLS ID: O6388746

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

    REDUCED by $10,000 (2.3%) on 05/29/2026

    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: $2,820 (change assumption)
    Mortgage ($2,351) + Taxes in 2024 ($469)


    Taxes:$5,629

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 330 ELKHORN CT, WINTER PARK, FL 32792

    $549,900151 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

    $699,000202 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

    $899,900104 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

    $598,000332 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

    $325,00080 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






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