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Homes for Sale Near Winter Park High in Orlando - 111 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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  • 4029 TAMARISK WAY, ORLANDO, FL 32817

    $475,00016 Days on yellowkey   MLS ID: O6409365

    0 Days Off yellowkey (back on 5/22/2026)

    For Sale O6409365 - 4029 TAMARISK WAY, ORLANDO, FL 32817 49 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1992
       Built: 1979
    Monthly Fee: $67
       Tax: $2,650 (2025)
    Community: Woodside Village
    Single Family


    Estimated Monthly Payment: $2,891 (change assumption)
    Mortgage ($2,603) + Fees ($67) + Taxes in 2025 ($221)


    Taxes:$2,650

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3709 MOCKINGBIRD LN, ORLANDO, FL 32803

    $575,00092 Days on yellowkey   MLS ID: O6387642

    0 Days Off yellowkey (back on 5/22/2026)

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

    For Sale O6387642 - 3709 MOCKINGBIRD LN, ORLANDO, FL 32803 35 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: $3,705 (change assumption)
    Mortgage ($3,151) + 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


  • 3715 WREN LANE, ORLANDO, FL 32803

    $699,00021 Days on yellowkey   MLS ID: O6404996

    0 Days Off yellowkey (back on 5/22/2026)

    For Sale O6404996 - 3715 WREN LANE, ORLANDO, FL 32803 36 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1425
       Built: 1956   Tax: $6,730 (2025)
    Community: Audubon Park Tanager Sec
    Single Family


    Estimated Monthly Payment: $4,391 (change assumption)
    Mortgage ($3,830) + Taxes in 2025 ($561)


    Taxes:$6,730

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 9504 CANNON DR, ORLANDO, FL 32817

    $420,00048 Days on yellowkey   MLS ID: O6400350

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

    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


  • 2268 OSPREY AVE, ORLANDO, FL 32814

    $789,00072 Days on yellowkey   MLS ID: O6393457

    0 Days Off yellowkey (back on 5/21/2026)

    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


  • 2326 VIVADA ST, ORLANDO, FL 32803

    $1,365,000106 Days on yellowkey   MLS ID: TB8478263

    4 Days Off yellowkey (back on 5/21/2026)

    For Sale TB8478263 - 2326 VIVADA ST, ORLANDO, FL 32803 22 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3497
       Built: 2026   Tax: $5,937 (2025)
    Community: Colonialtown North
    Single Family


    Estimated Monthly Payment: $7,974 (change assumption)
    Mortgage ($7,479) + Taxes in 2025 ($495)


    Taxes:$5,937

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4201 PARK LAKE ST, ORLANDO, FL 32803

    $409,99942 Days on yellowkey   MLS ID: O6402149

    REDUCED by $50,001 (10.9%) on 05/21/2026

    For Sale O6402149 - 4201 PARK LAKE ST, ORLANDO, FL 32803 21 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1601
       Built: 1958   Tax: $5,467 (2025)
    Community: Tinker Heights
    Single Family


    Estimated Monthly Payment: $2,702 (change assumption)
    Mortgage ($2,247) + Taxes in 2025 ($456)


    Taxes:$5,467

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 925 HANLEY ALY, ORLANDO, FL 32814

    $1,100,00049 Days on yellowkey   MLS ID: O6398590

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

    For Sale O6398590 - 925 HANLEY ALY, ORLANDO, FL 32814 59 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2160
       Built: 2003
    Monthly Fee: $102
       Tax: $10,144 (2025)
    Community: Baldwin Park Ut 01 50 121
    Single Family


    Estimated Monthly Payment: $6,975 (change assumption)
    Mortgage ($6,027) + Fees ($102) + Taxes in 2025 ($845)


    Taxes:$10,144

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1302 MOSELLE AVE, ORLANDO, FL 32807

    $485,00070 Days on yellowkey   MLS ID: O6393827

    4 Days Off yellowkey (back on 5/19/2026)

    REDUCED by $10,000 (2.0%) on 05/01/2026

    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: $2,713 (change assumption)
    Mortgage ($2,657) + Taxes in 2025 ($56)


    Taxes:$671

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1296 MOSELLE AVE, ORLANDO, FL 32807

    $485,00070 Days on yellowkey   MLS ID: O6393720

    4 Days Off yellowkey (back on 5/19/2026)

    REDUCED by $10,000 (2.0%) on 05/01/2026

    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: $2,713 (change assumption)
    Mortgage ($2,657) + Taxes in 2025 ($56)


    Taxes:$671

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 803 HASKELL AVE, ORLANDO, FL 32807

    $375,00029 Days on yellowkey   MLS ID: TB8505733

    For Sale TB8505733 - 803 HASKELL AVE, ORLANDO, FL 32807 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1197
       Built: 1957   Tax: $2,461 (2025)
    Community: Lake Barton Park
    Single Family


    Estimated Monthly Payment: $2,260 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($205)


    Taxes:$2,461

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 916 FERN AVE, ORLANDO, FL 32814

    $597,50022 Days on yellowkey   MLS ID: O6406702

    1 Days Off yellowkey (back on 5/16/2026)

    For Sale O6406702 - 916 FERN AVE, ORLANDO, FL 32814 51 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1680
       Built: 2003
    Monthly Fee: $534
       Tax: $6,364 (2025)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $4,338 (change assumption)
    Mortgage ($3,274) + Fees ($534) + Taxes in 2025 ($530)


    Taxes:$6,364

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7520 LOIS MARIE CT, ORLANDO, FL 32807

    $344,000150 Days on yellowkey   MLS ID: O6370974

    For Sale O6370974 - 7520 LOIS MARIE CT, ORLANDO, FL 32807 43 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1225
       Built: 1971   Tax: $2,703 (2025)
    Community: Ivanhoe Estates
    Single Family


    Estimated Monthly Payment: $2,110 (change assumption)
    Mortgage ($1,885) + Taxes in 2025 ($225)


    Taxes:$2,703

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 8128 WOODSWORTH DR, ORLANDO, FL 32817

    $450,00098 Days on yellowkey   MLS ID: O6386117

    0 Days Off yellowkey (back on 5/16/2026)

    INCREASED by $8,000 (1.8%) on 05/12/2026

    For Sale O6386117 - 8128 WOODSWORTH DR, ORLANDO, FL 32817 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1681
       Built: 1993
    Monthly Fee: $25
       Tax: $3,958 (2025)
    Community: Bradford Cove Ph 04
    Single Family


    Estimated Monthly Payment: $2,821 (change assumption)
    Mortgage ($2,466) + Fees ($25) + Taxes in 2025 ($330)


    Taxes:$3,958

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 8013 RHEA CIR, ORLANDO, FL 32807

    $320,000142 Days on yellowkey   MLS ID: O6373437

    REDUCED by $10,000 (3.0%) on 05/16/2026

    For Sale O6373437 - 8013 RHEA CIR, ORLANDO, FL 32807 31 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1025
       Built: 1970   Tax: $3,535 (2025)
    Community: Ivanhoe Estates
    Single Family


    Estimated Monthly Payment: $2,048 (change assumption)
    Mortgage ($1,753) + Taxes in 2025 ($295)


    Taxes:$3,535

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2620 CAVANAUGH DR, ORLANDO, FL 32817

    $625,000164 Days on yellowkey   MLS ID: O6369315

    REDUCED by $33,990 (5.2%) on 05/15/2026

    For Sale O6369315 - 2620 CAVANAUGH DR, ORLANDO, FL 32817 2 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2560
       Built: 2025
    Monthly Fee: $130
       Tax: $887 (2025)
    Community: Harrell Oaks
    Single Family


    Estimated Monthly Payment: $3,629 (change assumption)
    Mortgage ($3,425) + Fees ($130) + Taxes in 2025 ($74)


    Taxes:$887

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 8101 DOMINGUIN ST, ORLANDO, FL 32817

    $289,000475 Days on yellowkey   MLS ID: S5120808

    0 Days Off yellowkey (back on 5/15/2026)

    For Sale S5120808 - 8101 DOMINGUIN ST, ORLANDO, FL 32817 22 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1200
       Built: 1960   Tax: $3,558 (2024)
    Community: Sun Haven First Add
    Single Family


    Estimated Monthly Payment: $1,880 (change assumption)
    Mortgage ($1,584) + Taxes in 2024 ($297)


    Taxes:$3,558

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1315 GEORGIA BLVD, ORLANDO, FL 32803

    $1,890,000150 Days on yellowkey   MLS ID: O6371109

    For Sale O6371109 - 1315 GEORGIA BLVD, ORLANDO, FL 32803 10 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3939
       Built: 2026   Tax: $6,159 (2024)
    Community: Colonial Manor
    Single Family


    Estimated Monthly Payment: $10,869 (change assumption)
    Mortgage ($10,356) + Taxes in 2024 ($513)


    Taxes:$6,159

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1864 PROSPECT AVE, ORLANDO, FL 32814

    $644,00099 Days on yellowkey   MLS ID: O6383275

    1 Days Off yellowkey (back on 5/15/2026)

    REDUCED by $5,000 (0.8%) on 05/04/2026

    For Sale O6383275 - 1864 PROSPECT AVE, ORLANDO, FL 32814 100 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2434
       Built: 2009
    Monthly Fee: $592
       Tax: $11,810 (2024)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $5,105 (change assumption)
    Mortgage ($3,529) + Fees ($592) + Taxes in 2024 ($984)


    Taxes:$11,810

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2680 CAVANAUGH DR, ORLANDO, FL 32817

    $648,990160 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




Why Bother Searching Elsewhere for Homes For Sale and Real Estate nearby Winter Park High?

Home, townhome, condo, villa, and other listing sales data closeby Winter Park High is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on homes for sale nearby Winter Park High, Orlando . You can use our website to view Multiple Listing Service (MLS) data on Orlando homes near Winter Park High. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our listings that are close to Winter Park High.



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.