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Homes for Sale Near Winter Park High in Orlando - 108 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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  • 3701 VIRGINIA DR, ORLANDO, FL 32803

    $699,99037 Days on yellowkey   MLS ID: O6416950

    REDUCED by $25,010 (3.4%) on 07/11/2026

    For Sale O6416950 - 3701 VIRGINIA DR, ORLANDO, FL 32803 58 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2044
       Built: 1954   Tax: $7,924 (2025)
    Community: Audubon Park Tanager Sec
    Single Family


    Estimated Monthly Payment: $4,496 (change assumption)
    Mortgage ($3,835) + Taxes in 2025 ($660)


    Taxes:$7,924

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 2843 UPPER PARK RD, ORLANDO, FL 32814

    $660,00032 Days on yellowkey   MLS ID: O6418525

    For Sale O6418525 - 2843 UPPER PARK RD, ORLANDO, FL 32814 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1818
       Built: 2005
    Monthly Fee: $490
       Tax: $4,936 (2025)
    Community: Baldwin Park 6
    Townhouse


    Estimated Monthly Payment: $4,518 (change assumption)
    Mortgage ($3,616) + Fees ($490) + Taxes in 2025 ($411)


    Taxes:$4,936

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2293 OSPREY AVE, ORLANDO, FL 32814

    $1,195,00031 Days on yellowkey   MLS ID: S5152219

    REDUCED by $63,000 (5.0%) on 07/11/2026

    For Sale S5152219 - 2293 OSPREY AVE, ORLANDO, FL 32814 45 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3159
       Built: 2005
    Monthly Fee: $523
       Tax: $10,414 (2025)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $7,939 (change assumption)
    Mortgage ($6,548) + Fees ($523) + Taxes in 2025 ($868)


    Taxes:$10,414

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


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

    $269,900130 Days on yellowkey   MLS ID: O6390840

    REDUCED by $5,000 (1.8%) on 06/11/2026

    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: $2,124 (change assumption)
    Mortgage ($1,479) + 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


  • 9517 DARIEN AVE #9517, ORLANDO, FL 32817

    $185,000216 Days on yellowkey   MLS ID: O6368148

    1 Days Off yellowkey (back on 7/11/2026)

    REDUCED by $5,000 (2.6%) on 07/02/2026

    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: $1,205 (change assumption)
    Mortgage ($1,014) + Taxes in 2024 ($192)


    Taxes:$2,298

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Union Park Middle


  • 2620 CAVANAUGH DR, ORLANDO, FL 32817

    $600,000212 Days on yellowkey   MLS ID: O6369315

    0 Days Off yellowkey (back on 7/10/2026)

    REDUCED by $25,000 (4.0%) on 06/12/2026

    For Sale O6369315 - 2620 CAVANAUGH DR, ORLANDO, FL 32817 13 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: $3,492 (change assumption)
    Mortgage ($3,288) + Fees ($130) + Taxes in 2025 ($74)


    Taxes:$887

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2656 MEETING PL, ORLANDO, FL 32814

    $2,490,00028 Days on yellowkey   MLS ID: O6419004

    For Sale O6419004 - 2656 MEETING PL, ORLANDO, FL 32814 68 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 3982
       Built: 2012
    Monthly Fee: $93
       Tax: $20,735 (2025)
    Community: Baldwin Park 6
    Single Family


    Estimated Monthly Payment: $15,464 (change assumption)
    Mortgage ($13,643) + Fees ($93) + Taxes in 2025 ($1,728)


    Taxes:$20,735

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2639 BETTY ST, ORLANDO, FL 32803

    $470,000126 Days on yellowkey   MLS ID: O6391321

    For Sale O6391321 - 2639 BETTY ST, ORLANDO, FL 32803 21 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1263
       Built: 1953   Tax: $6,785 (2025)
    Community: Colonial Acres
    Single Family


    Estimated Monthly Payment: $3,141 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($565)


    Taxes:$6,785

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 9514 DARIEN AVE #9514, ORLANDO, FL 32817

    $164,90015 Days on yellowkey   MLS ID: O6422933

    For Sale O6422933 - 9514 DARIEN AVE #9514, ORLANDO, FL 32817 25 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 732
       Built: 1987   Tax: $2,171 (2025)
    Community: Colonial Landings Ph 04
    Condo


    Estimated Monthly Payment: $1,084 (change assumption)
    Mortgage ($904) + Taxes in 2025 ($181)


    Taxes:$2,171

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Union Park Middle


  • 803 HASKELL AVE, ORLANDO, FL 32807

    $364,99977 Days on yellowkey   MLS ID: TB8505733

    REDUCED by $5,000 (1.4%) on 07/08/2026

    For Sale TB8505733 - 803 HASKELL AVE, ORLANDO, FL 32807 18 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: $2,205 (change assumption)
    Mortgage ($2,000) + Taxes in 2025 ($205)


    Taxes:$2,461

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3838 HAWS LN, ORLANDO, FL 32814

    $1,149,00058 Days on yellowkey   MLS ID: O6410550

    1 Days Off yellowkey (back on 7/8/2026)

    For Sale O6410550 - 3838 HAWS LN, ORLANDO, FL 32814 52 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2731
       Built: 2005
    Monthly Fee: $92
       Tax: $17,789 (2025)
    Community: Baldwin Park
    Single Family


    Estimated Monthly Payment: $7,870 (change assumption)
    Mortgage ($6,296) + Fees ($92) + Taxes in 2025 ($1,482)


    Taxes:$17,789

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 9509 HANDLEY CT, ORLANDO, FL 32817

    $399,00041 Days on yellowkey   MLS ID: O6416400

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

    For Sale O6416400 - 9509 HANDLEY CT, ORLANDO, FL 32817 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1142
       Built: 1987   Tax: $5,163 (2025)
    Community: Arbor Ridge North
    Single Family


    Estimated Monthly Payment: $2,617 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($430)


    Taxes:$5,163

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Arbor Ridge Middle


  • 2216 STONINGTON AVE #2216, ORLANDO, FL 32817

    $229,90017 Days on yellowkey   MLS ID: O6422846

    For Sale O6422846 - 2216 STONINGTON AVE #2216, ORLANDO, FL 32817 35 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1228
       Built: 1986   Tax: $3,235 (2025)
    Community: Colonial Landings Ph 24
    Condo


    Estimated Monthly Payment: $1,529 (change assumption)
    Mortgage ($1,260) + Taxes in 2025 ($270)


    Taxes:$3,235

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Union Park Middle


  • 1631 LAKEMONT AVE, ORLANDO, FL 32814

    $600,00056 Days on yellowkey   MLS ID: O6410319

    REDUCED by $15,000 (2.4%) on 07/06/2026

    For Sale O6410319 - 1631 LAKEMONT AVE, ORLANDO, FL 32814 47 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 2005
    Monthly Fee: $715
       Tax: $11,321 (2024)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $4,946 (change assumption)
    Mortgage ($3,288) + Fees ($715) + Taxes in 2024 ($943)


    Taxes:$11,321

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1218 KINGSTON AVE, ORLANDO, FL 32807

    $289,90020 Days on yellowkey   MLS ID: O6422169

    For Sale O6422169 - 1218 KINGSTON AVE, ORLANDO, FL 32807 21 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 544
       Built: 1964   Tax: $3,138 (2025)
    Community: J J Kates Sub
    Single Family


    Estimated Monthly Payment: $1,850 (change assumption)
    Mortgage ($1,588) + Taxes in 2025 ($262)


    Taxes:$3,138

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2260 GRENWICH AVE #2260, ORLANDO, FL 32817

    $215,000118 Days on yellowkey   MLS ID: O6392730

    0 Days Off yellowkey (back on 7/3/2026)

    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


  • 817 ALTALOMA AVE, ORLANDO, FL 32803

    $380,000188 Days on yellowkey   MLS ID: O6374066

    REDUCED by $10,000 (2.6%) on 07/03/2026

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

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 723
       Built: 1930   Tax: $4,527 (2024)
    Community: Weidows Rep
    Single Family


    Estimated Monthly Payment: $2,459 (change assumption)
    Mortgage ($2,082) + 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


  • 2458 LONG MEADOW WAY, ORLANDO, FL 32817

    $294,90021 Days on yellowkey   MLS ID: O6420840

    For Sale O6420840 - 2458 LONG MEADOW WAY, ORLANDO, FL 32817 30 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 981
       Built: 1989
    Monthly Fee: $17
       Tax: $3,535 (2025)
    Community: Carmel Park
    Half Duplex


    Estimated Monthly Payment: $1,927 (change assumption)
    Mortgage ($1,616) + Fees ($17) + Taxes in 2025 ($295)


    Taxes:$3,535

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Union Park Middle


  • 7510 STRATFORD BLVD, ORLANDO, FL 32807

    $310,00028 Days on yellowkey   MLS ID: O6419864

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

    For Sale O6419864 - 7510 STRATFORD BLVD, ORLANDO, FL 32807 16 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1025
       Built: 1971   Tax: $893 (2025)
    Community: Ivanhoe Estates
    Single Family


    Estimated Monthly Payment: $1,773 (change assumption)
    Mortgage ($1,699) + Taxes in 2025 ($74)


    Taxes:$893

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1205 FALCON DR, ORLANDO, FL 32803

    $2,150,00022 Days on yellowkey   MLS ID: O6421432

    For Sale O6421432 - 1205 FALCON DR, ORLANDO, FL 32803 84 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4017
       Built: 1955   Tax: $7,830 (2025)
    Community: Audubon Park Tanager Sec
    Single Family


    Estimated Monthly Payment: $12,433 (change assumption)
    Mortgage ($11,781) + Taxes in 2025 ($653)


    Taxes:$7,830

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8




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.