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Homes for Sale Near Winter Park High in Orlando - 113 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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  • 2839 ANTIOCH WAY, ORLANDO, FL 32807

    $349,900106 Days on yellowkey   MLS ID: O6385337

    0 Days Off yellowkey (back on 6/1/2026)

    INCREASED by $20,000 (6.1%) on 05/26/2026

    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: $2,103 (change assumption)
    Mortgage ($1,917) + Taxes in 2025 ($186)


    Taxes:$2,230

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2721 E MARKS ST, ORLANDO, FL 32803

    $675,000145 Days on yellowkey   MLS ID: O6374453

    REDUCED by $2,500 (0.4%) on 04/29/2026

    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: $4,469 (change assumption)
    Mortgage ($3,699) + 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


  • 4238 WATERMILL AVE, ORLANDO, FL 32817

    $370,00022 Days on yellowkey   MLS ID: O6409100

    INCREASED by $30,000 (8.8%) on 06/01/2026

    For Sale O6409100 - 4238 WATERMILL AVE, ORLANDO, FL 32817 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1798
       Built: 1983
    Monthly Fee: $6
       Tax: $5,416 (2025)
    Community: Watermill Sec 1
    Single Family


    Estimated Monthly Payment: $2,485 (change assumption)
    Mortgage ($2,027) + Fees ($6) + Taxes in 2025 ($451)


    Taxes:$5,416

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2001 GALE ST, ORLANDO, FL 32803

    $684,90068 Days on yellowkey   MLS ID: O6396150

    0 Days Off yellowkey (back on 6/1/2026)

    REDUCED by $5,000 (0.7%) on 05/21/2026

    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: $4,305 (change assumption)
    Mortgage ($3,753) + 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


  • 7923 THURMOND CT, ORLANDO, FL 32817

    $465,00056 Days on yellowkey   MLS ID: O6399360

    REDUCED by $10,000 (2.1%) on 06/01/2026

    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: $2,803 (change assumption)
    Mortgage ($2,548) + 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


  • 2674 CAVANAUGH DR, ORLANDO, FL 32817

    $674,99076 Days on yellowkey   MLS ID: O6393964

    0 Days Off yellowkey (back on 5/31/2026)

    For Sale O6393964 - 2674 CAVANAUGH DR, ORLANDO, FL 32817 2 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2903
       Built: 2026
    Monthly Fee: $130
       Tax: $887 (2025)
    Community: Harrell Oaks
    Single Family


    Estimated Monthly Payment: $3,902 (change assumption)
    Mortgage ($3,698) + Fees ($130) + Taxes in 2025 ($74)


    Taxes:$887

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3884 LOWER PARK RD, ORLANDO, FL 32814

    $1,895,00078 Days on yellowkey   MLS ID: O6393290

    REDUCED by $195,000 (9.3%) on 05/28/2026

    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: $11,945 (change assumption)
    Mortgage ($10,383) + 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


  • 3915 PELICAN LN, ORLANDO, FL 32803

    $485,000134 Days on yellowkey   MLS ID: O6377362

    0 Days Off yellowkey (back on 5/30/2026)

    For Sale O6377362 - 3915 PELICAN LN, ORLANDO, FL 32803 28 photos

    Bed: 3   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 1154
       Built: 1956   Tax: $6,546 (2024)
    Community: Audubon Park Card Heights Sec
    Single Family


    Estimated Monthly Payment: $3,203 (change assumption)
    Mortgage ($2,657) + Taxes in 2024 ($546)


    Taxes:$6,546

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 3803 ETHAN LN, ORLANDO, FL 32814

    $889,00040 Days on yellowkey   MLS ID: O6402987

    2 Days Off yellowkey (back on 5/30/2026)

    For Sale O6402987 - 3803 ETHAN LN, ORLANDO, FL 32814 47 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2178
       Built: 2005
    Monthly Fee: $534
       Tax: $12,183 (2025)
    Community: Baldwin Park
    Spa: No

    Townhouse


    Estimated Monthly Payment: $6,420 (change assumption)
    Mortgage ($4,871) + Fees ($534) + Taxes in 2025 ($1,015)


    Taxes:$12,183

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4649 NEW BROAD ST, ORLANDO, FL 32814

    $3,650,00041 Days on yellowkey   MLS ID: O6402857

    REDUCED by $50,000 (1.4%) on 05/29/2026

    For Sale O6402857 - 4649 NEW BROAD ST, ORLANDO, FL 32814 70 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5411
       Built: 2008
    Monthly Fee: $93
       Tax: $40,937 (2025)
    Community: Baldwin Park Ut 01 50 121
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $23,504 (change assumption)
    Mortgage ($20,000) + Fees ($93) + Taxes in 2025 ($3,411)


    Taxes:$40,937

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1631 LAKEMONT AVE, ORLANDO, FL 32814

    $615,00013 Days on yellowkey   MLS ID: O6410319

    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: $5,028 (change assumption)
    Mortgage ($3,370) + 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


  • 4317 ROUSH AVE, ORLANDO, FL 32803

    $630,000243 Days on yellowkey   MLS ID: TB8436757

    0 Days Off yellowkey (back on 4/22/2026)

    For Sale TB8436757 - 4317 ROUSH AVE, ORLANDO, FL 32803 39 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1932
       Built: 2025
    Monthly Fee: $290
       Tax: $517 (2024)
    Community: Baldwin Crossing
    Townhouse


    Estimated Monthly Payment: $3,785 (change assumption)
    Mortgage ($3,452) + Fees ($290) + Taxes in 2024 ($43)


    Taxes:$517

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 817 ALTALOMA AVE, ORLANDO, FL 32803

    $399,000145 Days on yellowkey   MLS ID: O6374066

    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: $2,564 (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


  • 2264 GRENWICH AVE #2264, ORLANDO, FL 32817

    $249,00020 Days on yellowkey   MLS ID: O6409470

    0 Days Off yellowkey (back on 5/28/2026)

    For Sale O6409470 - 2264 GRENWICH AVE #2264, ORLANDO, FL 32817 44 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1248
       Built: 1991
    Monthly Fee: $380
       Tax: $3,287 (2025)
    Community: Colonial Landings Ph 05
    Condo


    Estimated Monthly Payment: $2,018 (change assumption)
    Mortgage ($1,364) + Fees ($380) + Taxes in 2025 ($274)


    Taxes:$3,287

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2066 BRINK ALY, ORLANDO, FL 32814

    $680,000127 Days on yellowkey   MLS ID: O6379018

    0 Days Off yellowkey (back on 4/20/2026)

    REDUCED by $15,000 (2.2%) on 04/17/2026

    For Sale O6379018 - 2066 BRINK ALY, ORLANDO, FL 32814 36 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2123
       Built: 2010
    Monthly Fee: $572
       Tax: $11,203 (2025)
    Community: Baldwin Park Rep 01
    Townhouse


    Estimated Monthly Payment: $5,232 (change assumption)
    Mortgage ($3,726) + Fees ($572) + Taxes in 2025 ($934)


    Taxes:$11,203

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2414 ILLINOIS ST, ORLANDO, FL 32803

    $450,000251 Days on yellowkey   MLS ID: NS1086116

    0 Days Off yellowkey (back on 5/27/2026)

    REDUCED by $5,000 (1.1%) on 05/17/2026

    For Sale NS1086116 - 2414 ILLINOIS ST, ORLANDO, FL 32803 33 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 1094
       Built: 1953   Tax: $7,656 (2024)
    Community: Colonial Acres
    Single Family


    Estimated Monthly Payment: $3,104 (change assumption)
    Mortgage ($2,466) + Taxes in 2024 ($638)


    Taxes:$7,656

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 2733 MIDDLE ST, ORLANDO, FL 32807

    $395,00075 Days on yellowkey   MLS ID: O6394410

    REDUCED by $5,000 (1.3%) on 05/26/2026

    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: $2,637 (change assumption)
    Mortgage ($2,164) + Taxes in 2025 ($472)


    Taxes:$5,667

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2614 CAVANAUGH DR, ORLANDO, FL 32817

    $600,00027 Days on yellowkey   MLS ID: O6408051

    0 Days Off yellowkey (back on 5/26/2026)

    REDUCED by $24,990 (4.0%) on 05/15/2026

    For Sale O6408051 - 2614 CAVANAUGH DR, ORLANDO, FL 32817 9 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: $3,492 (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


  • 4036 BIBB LN, ORLANDO, FL 32817

    $440,000124 Days on yellowkey   MLS ID: O6379247

    REDUCED by $10,000 (2.2%) on 05/26/2026

    For Sale O6379247 - 4036 BIBB LN, ORLANDO, FL 32817 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1645
       Built: 1980   Tax: $3,374 (2024)
    Community: Harbor East
    Single Family


    Estimated Monthly Payment: $2,692 (change assumption)
    Mortgage ($2,411) + Taxes in 2024 ($281)


    Taxes:$3,374

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2639 BETTY ST, ORLANDO, FL 32803

    $470,00083 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




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.