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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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  • 7923 THURMOND CT, ORLANDO, FL 32817

    $475,0007 Days on yellowkey   MLS ID: O6399360

    For Sale O6399360 - 7923 THURMOND CT, ORLANDO, FL 32817 60 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1820
       Built: 1984
    Monthly Fee: $7
       Tax: $2,979 (2025)
    Community: Aloma Estates
    Single Family


    Estimated Monthly Payment: $2,858 (change assumption)
    Mortgage ($2,603) + Fees ($7) + Taxes in 2025 ($248)


    Taxes:$2,979

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3838 HAWS LN, ORLANDO, FL 32814

    $1,190,000210 Days on yellowkey   MLS ID: O6344126

    REDUCED by $10,000 (0.8%) on 04/17/2026

    For Sale O6344126 - 3838 HAWS LN, ORLANDO, FL 32814 67 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2731
       Built: 2005
    Monthly Fee: $92
       Tax: $16,584 (2024)
    Community: Baldwin Park
    Single Family


    Estimated Monthly Payment: $7,994 (change assumption)
    Mortgage ($6,520) + Fees ($92) + Taxes in 2024 ($1,382)


    Taxes:$16,584

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 817 ALTALOMA AVE, ORLANDO, FL 32803

    $399,00096 Days on yellowkey   MLS ID: O6374066

    For Sale O6374066 - 817 ALTALOMA AVE, ORLANDO, FL 32803 26 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 723
       Built: 1930   Tax: $4,527 (2024)
    Community: Weidows Rep
    Single Family


    Estimated Monthly Payment: $2,564 (change assumption)
    Mortgage ($2,186) + Taxes in 2024 ($377)


    Taxes:$4,527

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 3504 FINCH ST, ORLANDO, FL 32803

    $799,00096 Days on yellowkey   MLS ID: O6371554

    2 Days Off yellowkey (back on 4/7/2026)

    For Sale O6371554 - 3504 FINCH ST, ORLANDO, FL 32803 34 photos

    Bed: 3   Bath: 1.5   Gar: 2
    Liv Area Sq Ft: 1332
       Built: 1955   Tax: $5,038 (2024)
    Community: Audubon Park
    Single Family


    Estimated Monthly Payment: $4,798 (change assumption)
    Mortgage ($4,378) + Taxes in 2024 ($420)


    Taxes:$5,038

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 4512 BRIDGEWATER DR, ORLANDO, FL 32817

    $956,000137 Days on yellowkey   MLS ID: O6365659

    For Sale O6365659 - 4512 BRIDGEWATER DR, ORLANDO, FL 32817 46 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2091
       Built: 1983   Tax: $7,214 (2025)
    Community: Watermill Sec 01
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,839 (change assumption)
    Mortgage ($5,238) + Taxes in 2025 ($601)


    Taxes:$7,214

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 9504 CANNON DR, ORLANDO, FL 32817

    $420,0004 Days on yellowkey   MLS ID: O6400350

    For Sale O6400350 - 9504 CANNON DR, ORLANDO, FL 32817 27 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1521
       Built: 1985   Tax: $3,518 (2025)
    Community: Watermill Sec 03
    Single Family


    Estimated Monthly Payment: $2,594 (change assumption)
    Mortgage ($2,301) + Taxes in 2025 ($293)


    Taxes:$3,518

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 9516 CULLOWHEE CT, ORLANDO, FL 32817

    $460,0009 Days on yellowkey   MLS ID: O6398497

    For Sale O6398497 - 9516 CULLOWHEE CT, ORLANDO, FL 32817 45 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2130
       Built: 1988   Tax: $1,967 (2025)
    Community: Arbor Club
    Single Family


    Estimated Monthly Payment: $2,684 (change assumption)
    Mortgage ($2,520) + Taxes in 2025 ($164)


    Taxes:$1,967

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Union Park Middle


  • 1302 MOSELLE AVE, ORLANDO, FL 32807

    $495,00026 Days on yellowkey   MLS ID: O6393827

    For Sale O6393827 - 1302 MOSELLE AVE, ORLANDO, FL 32807 29 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


  • 3884 LOWER PARK RD, ORLANDO, FL 32814

    $2,090,00029 Days on yellowkey   MLS ID: O6393290

    For Sale O6393290 - 3884 LOWER PARK RD, ORLANDO, FL 32814 53 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4315
       Built: 2004
    Monthly Fee: $93
       Tax: $17,622 (2025)
    Community: Baldwin Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,013 (change assumption)
    Mortgage ($11,452) + Fees ($93) + Taxes in 2025 ($1,469)


    Taxes:$17,622

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2268 OSPREY AVE, ORLANDO, FL 32814

    $789,00028 Days on yellowkey   MLS ID: O6393457

    For Sale O6393457 - 2268 OSPREY AVE, ORLANDO, FL 32814 65 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2019
       Built: 2005
    Monthly Fee: $490
       Tax: $6,986 (2025)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $5,395 (change assumption)
    Mortgage ($4,323) + Fees ($490) + Taxes in 2025 ($582)


    Taxes:$6,986

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2409 GARBELIA AVE, ORLANDO, FL 32817

    $340,000149 Days on yellowkey   MLS ID: O6362011

    For Sale O6362011 - 2409 GARBELIA AVE, ORLANDO, FL 32817 83 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1010
       Built: 1970   Tax: $2,597 (2024)
    Community: Harrell Heights Rep
    Single Family


    Estimated Monthly Payment: $2,079 (change assumption)
    Mortgage ($1,863) + Taxes in 2024 ($216)


    Taxes:$2,597

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Union Park Middle


  • 2503 JAMIE CIR, ORLANDO, FL 32803

    $560,00075 Days on yellowkey   MLS ID: O6380344

    For Sale O6380344 - 2503 JAMIE CIR, ORLANDO, FL 32803 25 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 1449
       Built: 1954   Tax: $6,700 (2024)
    Community: Colonial Acres
    Single Family


    Estimated Monthly Payment: $3,627 (change assumption)
    Mortgage ($3,068) + Taxes in 2024 ($558)


    Taxes:$6,700

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 3004 PLAZA TERRACE DR #3004, ORLANDO, FL 32803

    $279,90038 Days on yellowkey   MLS ID: O6390840

    REDUCED by $5,100 (1.8%) on 04/02/2026

    For Sale O6390840 - 3004 PLAZA TERRACE DR #3004, ORLANDO, FL 32803 30 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 890
       Built: 1972
    Monthly Fee: $289
       Tax: $4,271 (2025)
    Community: Audubon Place City Condo
    Condo


    Estimated Monthly Payment: $2,179 (change assumption)
    Mortgage ($1,534) + Fees ($289) + Taxes in 2025 ($356)


    Taxes:$4,271

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 825 N PRIMROSE DR #204, ORLANDO, FL 32803

    $150,000125 Days on yellowkey   MLS ID: O6367436

    For Sale O6367436 - 825 N PRIMROSE DR #204, ORLANDO, FL 32803 16 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 618
       Built: 1966   Tax: $1,539 (2025)
    Community: Primrose Plaza
    Condo


    Estimated Monthly Payment: $950 (change assumption)
    Mortgage ($822) + Taxes in 2025 ($128)


    Taxes:$1,539

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 3916 VALENCIA GROVE LN, ORLANDO, FL 32817

    $365,00037 Days on yellowkey   MLS ID: O6390980

    1 Days Off yellowkey (back on 4/18/2026)

    For Sale O6390980 - 3916 VALENCIA GROVE LN, ORLANDO, FL 32817 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1188
       Built: 1986   Tax: $4,848 (2025)
    Community: Valencia Grove
    Single Family


    Estimated Monthly Payment: $2,404 (change assumption)
    Mortgage ($2,000) + Taxes in 2025 ($404)


    Taxes:$4,848

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1353 CHATFIELD PL, ORLANDO, FL 32814

    $595,00040 Days on yellowkey   MLS ID: O6389946

    REDUCED by $15,000 (2.5%) on 04/17/2026

    For Sale O6389946 - 1353 CHATFIELD PL, ORLANDO, FL 32814 30 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1994
       Built: 2004
    Monthly Fee: $93
       Tax: $9,917 (2025)
    Community: Baldwin Park 115
    Townhouse


    Estimated Monthly Payment: $4,180 (change assumption)
    Mortgage ($3,260) + Fees ($93) + Taxes in 2025 ($826)


    Taxes:$9,917

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2415 LAURA PL, ORLANDO, FL 32803

    $1,600,00047 Days on yellowkey   MLS ID: O6386133

    0 Days Off yellowkey (back on 4/17/2026)

    REDUCED by $80,000 (4.8%) on 04/03/2026

    For Sale O6386133 - 2415 LAURA PL, ORLANDO, FL 32803 37 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3500
       Built: 2026   Tax: $5,502 (2025)
    Community: Colonial Acres
    Single Family


    Estimated Monthly Payment: $9,225 (change assumption)
    Mortgage ($8,767) + Taxes in 2025 ($459)


    Taxes:$5,502

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 9517 DARIEN AVE #9517, ORLANDO, FL 32817

    $193,000124 Days on yellowkey   MLS ID: O6368148

    For Sale O6368148 - 9517 DARIEN AVE #9517, ORLANDO, FL 32817 26 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 992
       Built: 1987   Tax: $2,298 (2024)
    Community: Colonial Landings Ph 04
    Condo


    Estimated Monthly Payment: $1,249 (change assumption)
    Mortgage ($1,058) + Taxes in 2024 ($192)


    Taxes:$2,298

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Union Park Middle


  • 4416 TWINVIEW LN, ORLANDO, FL 32814

    $1,695,00065 Days on yellowkey   MLS ID: O6382016

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

    For Sale O6382016 - 4416 TWINVIEW LN, ORLANDO, FL 32814 70 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4026
       Built: 2003
    Monthly Fee: $93
       Tax: $19,932 (2025)
    Community: Baldwin Park Ut 01 50 121
    Single Family


    Estimated Monthly Payment: $11,041 (change assumption)
    Mortgage ($9,287) + Fees ($93) + Taxes in 2025 ($1,661)


    Taxes:$19,932

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3605 CHELSEA ST, ORLANDO, FL 32803

    $725,00011 Days on yellowkey   MLS ID: O6398313

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

    For Sale O6398313 - 3605 CHELSEA ST, ORLANDO, FL 32803 68 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1555
       Built: 1955   Tax: $9,589 (2025)
    Community: Audubon Park Tanager Sec
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,772 (change assumption)
    Mortgage ($3,973) + Taxes in 2025 ($799)


    Taxes:$9,589

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8




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Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.