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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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  • 4341 ROUSH AVE, ORLANDO, FL 32803

    $632,43017 Days on yellowkey   MLS ID: TB8506998

    For Sale TB8506998 - 4341 ROUSH AVE, ORLANDO, FL 32803 36 photos

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


    Estimated Monthly Payment: $3,798 (change assumption)
    Mortgage ($3,465) + 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


  • 1203 SASOON AVE, ORLANDO, FL 32803

    $395,00017 Days on yellowkey   MLS ID: O6405655

    For Sale O6405655 - 1203 SASOON AVE, ORLANDO, FL 32803 42 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 816
       Built: 1940   Tax: $3,369 (2025)
    Community: Ponce De Leon
    Single Family


    Estimated Monthly Payment: $2,445 (change assumption)
    Mortgage ($2,164) + Taxes in 2025 ($281)


    Taxes:$3,369

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3613 STONEHAVEN CT, ORLANDO, FL 32817

    $399,99020 Days on yellowkey   MLS ID: O6404992

    0 Days Off yellowkey (back on 5/9/2026)

    For Sale O6404992 - 3613 STONEHAVEN CT, ORLANDO, FL 32817 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1684
       Built: 1985
    Monthly Fee: $15
       Tax: $1,806 (2025)
    Community: Hunters Trace
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,357 (change assumption)
    Mortgage ($2,192) + Fees ($15) + Taxes in 2025 ($151)


    Taxes:$1,806

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Union Park Middle


  • 4345 ROUSH AVE, ORLANDO, FL 32803

    $517,37020 Days on yellowkey   MLS ID: TB8505792

    For Sale TB8505792 - 4345 ROUSH AVE, ORLANDO, FL 32803 5 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1390
       Built: 2025
    Monthly Fee: $289
       Tax: $517 (2025)
    Community: Baldwin Crossing
    Townhouse


    Estimated Monthly Payment: $3,167 (change assumption)
    Mortgage ($2,835) + Fees ($289) + Taxes in 2025 ($43)


    Taxes:$517

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1751 FIREHOUSE LN #25102, ORLANDO, FL 32814

    $525,00060 Days on yellowkey   MLS ID: O6394284

    1 Days Off yellowkey (back on 5/9/2026)

    For Sale O6394284 - 1751 FIREHOUSE LN #25102, ORLANDO, FL 32814 48 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1392
       Built: 2010
    Monthly Fee: $108
       Tax: $6,787 (2025)
    Community: Baldwin Park 07
    Condo


    Estimated Monthly Payment: $3,550 (change assumption)
    Mortgage ($2,877) + Fees ($108) + Taxes in 2025 ($566)


    Taxes:$6,787

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2847 T C U BLVD, ORLANDO, FL 32817

    $500,00025 Days on yellowkey   MLS ID: O6403587

    0 Days Off yellowkey (back on 5/8/2026)

    For Sale O6403587 - 2847 T C U BLVD, ORLANDO, FL 32817 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1708
       Built: 1973   Tax: $7,883 (2025)
    Community: University Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,397 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($657)


    Taxes:$7,883

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 9517 DARIEN AVE #9517, ORLANDO, FL 32817

    $192,000158 Days on yellowkey   MLS ID: O6368148

    REDUCED by $1,000 (0.5%) on 05/08/2026

    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: $1,244 (change assumption)
    Mortgage ($1,052) + Taxes in 2024 ($192)


    Taxes:$2,298

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Union Park Middle


  • 9502 DARIEN AVE #9502, ORLANDO, FL 32817

    $200,000316 Days on yellowkey   MLS ID: O6326912

    For Sale O6326912 - 9502 DARIEN AVE #9502, ORLANDO, FL 32817 34 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 992
       Built: 1987   Tax: $2,555 (2024)
    Community: Colonial Landings Ph 04
    Condo


    Estimated Monthly Payment: $1,309 (change assumption)
    Mortgage ($1,096) + Taxes in 2024 ($213)


    Taxes:$2,555

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Union Park Middle


  • 2501 COLE RD, ORLANDO, FL 32803

    $1,875,00021 Days on yellowkey   MLS ID: O6403103

    For Sale O6403103 - 2501 COLE RD, ORLANDO, FL 32803 14 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3750
       Built: 2026   Tax: $846 (2025)
    Community: Phillips Rep 01 Lakewood
    Single Family


    Estimated Monthly Payment: $10,344 (change assumption)
    Mortgage ($10,274) + Taxes in 2025 ($71)


    Taxes:$846

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4649 NEW BROAD ST, ORLANDO, FL 32814

    $3,700,00026 Days on yellowkey   MLS ID: O6402857

    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: $23,778 (change assumption)
    Mortgage ($20,273) + 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


  • 2839 ANTIOCH WAY, ORLANDO, FL 32807

    $329,90091 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


  • 5416 PENWAY DR, ORLANDO, FL 32814

    $949,999200 Days on yellowkey   MLS ID: O6357821

    REDUCED by $17,001 (1.8%) on 04/30/2026

    For Sale O6357821 - 5416 PENWAY DR, ORLANDO, FL 32814 78 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2518
       Built: 2006
    Monthly Fee: $93
       Tax: $7,918 (2024)
    Community: Baldwin Park Poa
    Single Family


    Estimated Monthly Payment: $5,958 (change assumption)
    Mortgage ($5,205) + Fees ($93) + Taxes in 2024 ($660)


    Taxes:$7,918

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 995 JUEL ST, ORLANDO, FL 32814

    $660,000192 Days on yellowkey   MLS ID: O6360876

    38 Days Off yellowkey (back on 5/6/2026)

    For Sale O6360876 - 995 JUEL ST, ORLANDO, FL 32814 46 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2070
       Built: 2003
    Monthly Fee: $606
       Tax: $6,882 (2024)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $4,796 (change assumption)
    Mortgage ($3,616) + Fees ($606) + Taxes in 2024 ($573)


    Taxes:$6,882

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1902 MERRITT PARK DR, ORLANDO, FL 32803

    $685,00057 Days on yellowkey   MLS ID: O6394769

    0 Days Off yellowkey (back on 3/30/2026)

    For Sale O6394769 - 1902 MERRITT PARK DR, ORLANDO, FL 32803 1 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 2000
       Built: 1958   Tax: $10,273 (2025)
    Community: Merritt Park
    Single Family


    Estimated Monthly Payment: $4,609 (change assumption)
    Mortgage ($3,753) + Taxes in 2025 ($856)


    Taxes:$10,273

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1735 FOSS AVE, ORLANDO, FL 32814

    $3,195,00055 Days on yellowkey   MLS ID: O6394768

    REDUCED by $100,000 (3.0%) on 04/15/2026

    For Sale O6394768 - 1735 FOSS AVE, ORLANDO, FL 32814 45 photos

    Bed: 5   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 5358
       Built: 2014
    Monthly Fee: $93
       Tax: $26,052 (2025)
    Community: Baldwin Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,770 (change assumption)
    Mortgage ($17,506) + Fees ($93) + Taxes in 2025 ($2,171)


    Taxes:$26,052

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1894 PROSPECT AVE, ORLANDO, FL 32814

    $650,00041 Days on yellowkey   MLS ID: O6393158

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

    For Sale O6393158 - 1894 PROSPECT AVE, ORLANDO, FL 32814 38 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2420
       Built: 2008
    Monthly Fee: $592
       Tax: $12,484 (2025)
    Community: Baldwin Park Rep 01
    Townhouse


    Estimated Monthly Payment: $5,194 (change assumption)
    Mortgage ($3,562) + Fees ($592) + Taxes in 2025 ($1,040)


    Taxes:$12,484

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 918 SHOREVIEW DR, ORLANDO, FL 32807

    $319,00064 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


  • 1657 LAKE BALDWIN LN, ORLANDO, FL 32814

    $2,100,00022 Days on yellowkey   MLS ID: O6404530

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

    For Sale O6404530 - 1657 LAKE BALDWIN LN, ORLANDO, FL 32814 1 photos

    Bed: 6   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 5016
       Built: 2006
    Monthly Fee: $102
       Tax: $30,187 (2025)
    Community: Baldwin Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,124 (change assumption)
    Mortgage ($11,507) + Fees ($102) + Taxes in 2025 ($2,516)


    Taxes:$30,187

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2613 JAMIE CIR, ORLANDO, FL 32803

    $400,00055 Days on yellowkey   MLS ID: O6395373

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

    For Sale O6395373 - 2613 JAMIE CIR, ORLANDO, FL 32803 7 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 840
       Built: 1954   Tax: $1,312 (2025)
    Community: Colonial Acres
    Single Family


    Estimated Monthly Payment: $2,301 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($109)


    Taxes:$1,312

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1027 JUEL ST, ORLANDO, FL 32814

    $2,225,000139 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




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.