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Homes for Sale Near Winter Park High in Orlando - 93 homes

Winter Park High is an High School in Orange County. Find homes for sale close to Winter Park High. Our REALTORS® can assist you in your search for Winter Park High, Orlando nearby homes.

Location: Orlando

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  • 5218 DEXTER ST, ORLANDO, FL 32807

    $450,00033 Days on yellowkey   MLS ID: O6392244

    1 Days Off yellowkey (back on 4/16/2026)

    For Sale O6392244 - 5218 DEXTER ST, ORLANDO, FL 32807 31 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1391
       Built: 1959   Tax: $5,256 (2025)
    Community: Lake Barton Park
    Single Family


    Estimated Monthly Payment: $2,904 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($438)


    Taxes:$5,256

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1500 ASBURY AVE, ORLANDO, FL 32803

    $445,0007 Days on yellowkey   MLS ID: O6398502

    0 Days Off yellowkey (back on 4/16/2026)

    For Sale O6398502 - 1500 ASBURY AVE, ORLANDO, FL 32803 32 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1190
       Built: 1952   Tax: $6,107 (2025)
    Community: Phillips Rep 01 Lakewood
    Single Family


    Estimated Monthly Payment: $2,947 (change assumption)
    Mortgage ($2,438) + Taxes in 2025 ($509)


    Taxes:$6,107

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2680 CAVANAUGH DR, ORLANDO, FL 32817

    $648,990116 Days on yellowkey   MLS ID: O6369656

    For Sale O6369656 - 2680 CAVANAUGH DR, ORLANDO, FL 32817 2 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3198
       Built: 2026
    Monthly Fee: $130
       Tax: $887 (2025)
    Community: Harrell Oaks
    Single Family


    Estimated Monthly Payment: $3,760 (change assumption)
    Mortgage ($3,556) + Fees ($130) + Taxes in 2025 ($74)


    Taxes:$887

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4392 WARDELL PL #102, ORLANDO, FL 32814

    $615,00042 Days on yellowkey   MLS ID: O6389678

    3 Days Off yellowkey (back on 4/16/2026)

    For Sale O6389678 - 4392 WARDELL PL #102, ORLANDO, FL 32814 34 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1410
       Built: 2006
    Monthly Fee: $102
       Tax: $9,557 (2025)
    Community: Baldwin Park
    Condo


    Estimated Monthly Payment: $4,268 (change assumption)
    Mortgage ($3,370) + Fees ($102) + Taxes in 2025 ($796)


    Taxes:$9,557

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2321 ARBOR CT, ORLANDO, FL 32817

    $250,000156 Days on yellowkey   MLS ID: O6360679

    1 Days Off yellowkey (back on 4/16/2026)

    For Sale O6360679 - 2321 ARBOR CT, ORLANDO, FL 32817 42 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 988
       Built: 1985   Tax: $1,277 (2025)
    Community: Arbor Ridge West
    Single Family


    Estimated Monthly Payment: $1,476 (change assumption)
    Mortgage ($1,370) + Taxes in 2025 ($106)


    Taxes:$1,277

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2721 E MARKS ST, ORLANDO, FL 32803

    $677,50096 Days on yellowkey   MLS ID: O6374453

    For Sale O6374453 - 2721 E MARKS ST, ORLANDO, FL 32803 21 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1569
       Built: 1955   Tax: $9,249 (2025)
    Community: Primrose Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,483 (change assumption)
    Mortgage ($3,712) + Taxes in 2025 ($771)


    Taxes:$9,249

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 9717 LAKE DOUGLAS PL, ORLANDO, FL 32817

    $599,99927 Days on yellowkey   MLS ID: O6391068

    For Sale O6391068 - 9717 LAKE DOUGLAS PL, ORLANDO, FL 32817 49 photos

    Bed: 6   Bath: 6.0   Gar: 2
    Liv Area Sq Ft: 2855
       Built: 1987   Tax: $4,727 (2025)
    Community: Arbor Club
    Single Family


    Estimated Monthly Payment: $3,682 (change assumption)
    Mortgage ($3,288) + Taxes in 2025 ($394)


    Taxes:$4,727

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Union Park Middle


  • 918 SHOREVIEW DR, ORLANDO, FL 32807

    $319,00030 Days on yellowkey   MLS ID: O6392300

    REDUCED by $11,000 (3.3%) on 04/15/2026

    For Sale O6392300 - 918 SHOREVIEW DR, ORLANDO, FL 32807 40 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1286
       Built: 1925   Tax: $4,837 (2025)
    Community: Lake Barton Park
    Single Family


    Estimated Monthly Payment: $2,151 (change assumption)
    Mortgage ($1,748) + Taxes in 2025 ($403)


    Taxes:$4,837

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2839 ANTIOCH WAY, ORLANDO, FL 32807

    $329,90057 Days on yellowkey   MLS ID: O6385337

    0 Days Off yellowkey (back on 3/14/2026)

    For Sale O6385337 - 2839 ANTIOCH WAY, ORLANDO, FL 32807 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1459
       Built: 1970   Tax: $2,230 (2025)
    Community: Belmont Ests
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $1,993 (change assumption)
    Mortgage ($1,808) + Taxes in 2025 ($186)


    Taxes:$2,230

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1954 MEETING PL, ORLANDO, FL 32814

    $890,00017 Days on yellowkey   MLS ID: O6394286

    0 Days Off yellowkey (back on 4/14/2026)

    For Sale O6394286 - 1954 MEETING PL, ORLANDO, FL 32814 40 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2410
       Built: 2005
    Monthly Fee: $523
       Tax: $8,022 (2025)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $6,068 (change assumption)
    Mortgage ($4,877) + Fees ($523) + Taxes in 2025 ($668)


    Taxes:$8,022

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3994 IRMA SHORES DR, ORLANDO, FL 32817

    $439,90036 Days on yellowkey   MLS ID: O6391265

    1 Days Off yellowkey (back on 4/14/2026)

    REDUCED by $15,100 (3.3%) on 04/12/2026

    For Sale O6391265 - 3994 IRMA SHORES DR, ORLANDO, FL 32817 41 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1969
       Built: 1974   Tax: $2,132 (2025)
    Community: Irma Shores Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,588 (change assumption)
    Mortgage ($2,410) + Taxes in 2025 ($178)


    Taxes:$2,132

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2260 GRENWICH AVE #2260, ORLANDO, FL 32817

    $215,00026 Days on yellowkey   MLS ID: O6392730

    For Sale O6392730 - 2260 GRENWICH AVE #2260, ORLANDO, FL 32817 47 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 874
       Built: 1991   Tax: $2,591 (2025)
    Community: Colonial Landings Ph 05
    Condo


    Estimated Monthly Payment: $1,394 (change assumption)
    Mortgage ($1,178) + Taxes in 2025 ($216)


    Taxes:$2,591

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Union Park Middle


  • 5441 BALDWIN PARK ST, ORLANDO, FL 32814

    $574,00033 Days on yellowkey   MLS ID: O6391146

    1 Days Off yellowkey (back on 4/13/2026)

    For Sale O6391146 - 5441 BALDWIN PARK ST, ORLANDO, FL 32814 60 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1640
       Built: 2007
    Monthly Fee: $534
       Tax: $6,059 (2025)
    Community: Baldwin Park
    Spa: No

    Townhouse


    Estimated Monthly Payment: $4,184 (change assumption)
    Mortgage ($3,145) + Fees ($534) + Taxes in 2025 ($505)


    Taxes:$6,059

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2612 MARTZ CT, ORLANDO, FL 32817

    $329,90013 Days on yellowkey   MLS ID: O6396617

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale O6396617 - 2612 MARTZ CT, ORLANDO, FL 32817 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1032
       Built: 1981   Tax: $4,428 (2025)
    Community: Arbor Ridge West
    Single Family


    Estimated Monthly Payment: $2,177 (change assumption)
    Mortgage ($1,808) + Taxes in 2025 ($369)


    Taxes:$4,428

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Union Park Middle


  • 3709 MOCKINGBIRD LN, ORLANDO, FL 32803

    $595,00048 Days on yellowkey   MLS ID: O6387642

    For Sale O6387642 - 3709 MOCKINGBIRD LN, ORLANDO, FL 32803 33 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1675
       Built: 1954   Tax: $6,647 (2025)
    Community: Audubon Park Tanager Sec
    Single Family


    Estimated Monthly Payment: $3,814 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($554)


    Taxes:$6,647

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4333 ROUSH AVE, ORLANDO, FL 32803

    $517,37058 Days on yellowkey   MLS ID: TB8479380

    For Sale TB8479380 - 4333 ROUSH AVE, ORLANDO, FL 32803 36 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1390
       Built: 2026
    Monthly Fee: $290
       Tax: $517 (2025)
    Community: Baldwin Crossing
    Townhouse


    Estimated Monthly Payment: $3,168 (change assumption)
    Mortgage ($2,835) + Fees ($290) + Taxes in 2025 ($43)


    Taxes:$517

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2001 GALE ST, ORLANDO, FL 32803

    $698,90019 Days on yellowkey   MLS ID: O6396150

    For Sale O6396150 - 2001 GALE ST, ORLANDO, FL 32803 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1682
       Built: 1954   Tax: $6,632 (2025)
    Community: North Hampton Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,382 (change assumption)
    Mortgage ($3,829) + Taxes in 2025 ($553)


    Taxes:$6,632

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1296 MOSELLE AVE, ORLANDO, FL 32807

    $495,00026 Days on yellowkey   MLS ID: O6393720

    For Sale O6393720 - 1296 MOSELLE AVE, ORLANDO, FL 32807 31 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1768
       Built: 2026   Tax: $671 (2025)
    Community: J J Kates Sub
    Single Family


    Estimated Monthly Payment: $2,768 (change assumption)
    Mortgage ($2,712) + Taxes in 2025 ($56)


    Taxes:$671

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2733 MIDDLE ST, ORLANDO, FL 32807

    $400,00026 Days on yellowkey   MLS ID: O6394410

    For Sale O6394410 - 2733 MIDDLE ST, ORLANDO, FL 32807 23 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1204
       Built: 1975   Tax: $5,667 (2025)
    Community: Hanging Moss Estates
    Single Family


    Estimated Monthly Payment: $2,664 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($472)


    Taxes:$5,667

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1027 JUEL ST, ORLANDO, FL 32814

    $2,225,000105 Days on yellowkey   MLS ID: O6371881

    For Sale O6371881 - 1027 JUEL ST, ORLANDO, FL 32814 78 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4414
       Built: 2005
    Monthly Fee: $93
       Tax: $26,437 (2025)
    Community: Baldwin Park Ut 01 50 121
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,488 (change assumption)
    Mortgage ($12,191) + Fees ($93) + Taxes in 2025 ($2,203)


    Taxes:$26,437

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle




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