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Displaying: For Sale

Location: Winter Park

Property Type(s): Single Family

Beds: 4 to 4

Winter Park - 126 properties found

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  • 723 SYMONDS AVE, WINTER PARK, FL 32789

    $1,800,00028 Days on yellowkey   MLS ID: O6406823

    For Sale O6406823 - 723 SYMONDS AVE, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3065
       Built: 2023   Tax: $15,884 (2025)
    Community: Horton Aaron
    Single Family


    Estimated Monthly Payment: $11,186 (change assumption)
    Mortgage ($9,863) + Taxes in 2025 ($1,324)


    Taxes:$15,884

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2430 CHANTILLY AVE, WINTER PARK, FL 32789

    $1,665,00042 Days on yellowkey   MLS ID: O6401352

    For Sale O6401352 - 2430 CHANTILLY AVE, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2916
       Built: 2026   Tax: $4,730 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,517 (change assumption)
    Mortgage ($9,123) + Taxes in 2025 ($394)


    Taxes:$4,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1316 BLUE STEM LN, WINTER PARK, FL 32792

    $725,00011 Days on yellowkey   MLS ID: O6416828

    For Sale O6416828 - 1316 BLUE STEM LN, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2196
       Built: 2022
    Monthly Fee: $243
       Tax: $6,788 (2025)
    Community: Landings At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,781 (change assumption)
    Mortgage ($3,973) + Fees ($243) + Taxes in 2025 ($566)


    Taxes:$6,788

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2831 MULFORD AVE, WINTER PARK, FL 32789

    $735,00018 Days on yellowkey   MLS ID: O6414319

    For Sale O6414319 - 2831 MULFORD AVE, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 1647
       Built: 1952   Tax: $3,192 (2025)
    Community: Orangewood Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,293 (change assumption)
    Mortgage ($4,027) + Taxes in 2025 ($266)


    Taxes:$3,192

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2625 PARK PLACE DR, WINTER PARK, FL 32789

    $1,950,0006 Days on yellowkey   MLS ID: O6413031

    For Sale O6413031 - 2625 PARK PLACE DR, WINTER PARK, FL 32789 55 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3460
       Built: 2002
    Monthly Fee: $146
       Tax: $9,695 (2025)
    Community: Winter Park Place 45/148
    Single Family


    Estimated Monthly Payment: $11,639 (change assumption)
    Mortgage ($10,685) + Fees ($146) + Taxes in 2025 ($808)


    Taxes:$9,695

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 1287 VERDANT GLADE PL, WINTER PARK, FL 32792

    $825,00062 Days on yellowkey   MLS ID: O6400331

    REDUCED by $22,000 (2.6%) on 06/19/2026

    For Sale O6400331 - 1287 VERDANT GLADE PL, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3020
       Built: 2020
    Monthly Fee: $413
       Tax: $6,133 (2025)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,444 (change assumption)
    Mortgage ($4,520) + Fees ($413) + Taxes in 2025 ($511)


    Taxes:$6,133

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1946 STRATHAVEN RD, WINTER PARK, FL 32792

    $650,00029 Days on yellowkey   MLS ID: O6411329

    REDUCED by $25,000 (3.7%) on 06/19/2026

    For Sale O6411329 - 1946 STRATHAVEN RD, WINTER PARK, FL 32792 37 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 1960   Tax: $8,540 (2025)
    Community: Kenilworth Shores Sec 07
    Single Family


    Estimated Monthly Payment: $4,273 (change assumption)
    Mortgage ($3,562) + Taxes in 2025 ($712)


    Taxes:$8,540

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1434 VIA SANGRO PL, WINTER PARK, FL 32792

    $1,300,00012 Days on yellowkey   MLS ID: O6416325

    0 Days Off yellowkey (back on 6/13/2026)

    For Sale O6416325 - 1434 VIA SANGRO PL, WINTER PARK, FL 32792 1 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3063
       Built: 2016
    Monthly Fee: $182
       Tax: $9,764 (2025)
    Community: Lakeside Estates
    Single Family


    Estimated Monthly Payment: $8,119 (change assumption)
    Mortgage ($7,123) + Fees ($182) + Taxes in 2025 ($814)


    Taxes:$9,764

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2614 PARKLAND DR, WINTER PARK, FL 32789

    $1,890,000431 Days on yellowkey   MLS ID: O6301489

    REDUCED by $34,450 (1.8%) on 06/18/2026

    For Sale O6301489 - 2614 PARKLAND DR, WINTER PARK, FL 32789 54 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3307
       Built: 2007   Tax: $12,712 (2024)
    Community: Parklando 03
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,415 (change assumption)
    Mortgage ($10,356) + Taxes in 2024 ($1,059)


    Taxes:$12,712

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 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


  • 2700 CADY WAY, WINTER PARK, FL 32792

    $649,000268 Days on yellowkey   MLS ID: O6347690

    For Sale O6347690 - 2700 CADY WAY, WINTER PARK, FL 32792 49 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1876
       Built: 1965   Tax: $8,335 (2024)
    Community: Winter Park Pines Unit 4
    Single Family


    Estimated Monthly Payment: $4,251 (change assumption)
    Mortgage ($3,556) + Taxes in 2024 ($695)


    Taxes:$8,335

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2501 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,795,0008 Days on yellowkey   MLS ID: O6416565

    For Sale O6416565 - 2501 LAFAYETTE AVE, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2819
       Built: 2026   Tax: $4,608 (2026)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $10,219 (change assumption)
    Mortgage ($9,835) + Taxes in 2026 ($384)


    Taxes:$4,608

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 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


  • 1220 WOODMERE DR, WINTER PARK, FL 32789

    $1,700,00013 Days on yellowkey   MLS ID: O6415611

    0 Days Off yellowkey (back on 6/17/2026)

    For Sale O6415611 - 1220 WOODMERE DR, WINTER PARK, FL 32789 44 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2815
       Built: 1996   Tax: $7,845 (2025)
    Community: Woodmere Terrace Rep
    Single Family


    Estimated Monthly Payment: $9,969 (change assumption)
    Mortgage ($9,315) + Taxes in 2025 ($654)


    Taxes:$7,845

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1849 VIBURNUM LN, WINTER PARK, FL 32792

    $408,000322 Days on yellowkey   MLS ID: O6333863

    2 Days Off yellowkey (back on 6/17/2026)

    REDUCED by $17,000 (4.0%) on 06/10/2026

    For Sale O6333863 - 1849 VIBURNUM LN, WINTER PARK, FL 32792 27 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1627
       Built: 1961   Tax: $3,645 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,539 (change assumption)
    Mortgage ($2,236) + Taxes in 2024 ($304)


    Taxes:$3,645

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 313 SYLVAN DR, WINTER PARK, FL 32789

    $5,500,00010 Days on yellowkey   MLS ID: O6407606

    For Sale O6407606 - 313 SYLVAN DR, WINTER PARK, FL 32789 10 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4775
       Built: 2027   Tax: $11,409 (2025)
    Community: Sylvan Park
    Single Family


    Estimated Monthly Payment: $31,087 (change assumption)
    Mortgage ($30,136) + Taxes in 2025 ($951)


    Taxes:$11,409

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1900 WINTER PARK RD, WINTER PARK, FL 32789

    $799,00059 Days on yellowkey   MLS ID: O6402566

    REDUCED by $50,900 (6.0%) on 06/16/2026

    For Sale O6402566 - 1900 WINTER PARK RD, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1511
       Built: 1947   Tax: $2,803 (2025)
    Community: Charmont
    Single Family


    Estimated Monthly Payment: $4,612 (change assumption)
    Mortgage ($4,378) + Taxes in 2025 ($234)


    Taxes:$2,803

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1529 HOLTS GROVE CIR, WINTER PARK, FL 32789

    $2,699,00085 Days on yellowkey   MLS ID: O6395062

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

    REDUCED by $96,000 (3.4%) on 05/20/2026

    For Sale O6395062 - 1529 HOLTS GROVE CIR, WINTER PARK, FL 32789 77 photos

    Bed: 4   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4356
       Built: 2005
    Monthly Fee: $262
       Tax: $21,342 (2025)
    Community: Windsong Lakeside Sec 02 43/71
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,829 (change assumption)
    Mortgage ($14,789) + Fees ($262) + Taxes in 2025 ($1,779)


    Taxes:$21,342

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1981 BLUE RIDGE RD, WINTER PARK, FL 32789

    $1,150,00055 Days on yellowkey   MLS ID: O6402961

    For Sale O6402961 - 1981 BLUE RIDGE RD, WINTER PARK, FL 32789 52 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2750
       Built: 1963   Tax: $11,270 (2025)
    Community: Timberlane Shores
    Single Family


    Estimated Monthly Payment: $7,240 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($939)


    Taxes:$11,270

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 1404 BORDER DR, WINTER PARK, FL 32789

    $1,175,00027 Days on yellowkey   MLS ID: O6412140

    REDUCED by $25,000 (2.1%) on 06/16/2026

    For Sale O6412140 - 1404 BORDER DR, WINTER PARK, FL 32789 38 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2469
       Built: 2023   Tax: $16,220 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $7,790 (change assumption)
    Mortgage ($6,438) + Taxes in 2025 ($1,352)


    Taxes:$16,220

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle






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