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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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  • 5492 PENWAY DR, ORLANDO, FL 32814

    $905,00037 Days on yellowkey   MLS ID: O6417286

    For Sale O6417286 - 5492 PENWAY DR, ORLANDO, FL 32814 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1970
       Built: 2006
    Monthly Fee: $75
       Tax: $13,068 (2025)
    Community: Baldwin Parka
    Single Family


    Estimated Monthly Payment: $6,123 (change assumption)
    Mortgage ($4,959) + Fees ($75) + Taxes in 2025 ($1,089)


    Taxes:$13,068

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3069 STANFIELD AVE, ORLANDO, FL 32814

    $1,350,00030 Days on yellowkey   MLS ID: O6419066

    For Sale O6419066 - 3069 STANFIELD AVE, ORLANDO, FL 32814 34 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2607
       Built: 2009
    Monthly Fee: $102
       Tax: $13,890 (2025)
    Community: Baldwin Park
    Single Family


    Estimated Monthly Payment: $8,657 (change assumption)
    Mortgage ($7,397) + Fees ($102) + Taxes in 2025 ($1,157)


    Taxes:$13,890

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4365 ROUSH AVE, ORLANDO, FL 32803

    $516,57075 Days on yellowkey   MLS ID: TB8505940

    1 Days Off yellowkey (back on 7/22/2026)

    For Sale TB8505940 - 4365 ROUSH AVE, ORLANDO, FL 32803 22 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: $3,163 (change assumption)
    Mortgage ($2,830) + 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


  • 1615 COLE RD, ORLANDO, FL 32803

    $1,582,00026 Days on yellowkey   MLS ID: O6420285

    REDUCED by $8,000 (0.5%) on 07/16/2026

    For Sale O6420285 - 1615 COLE RD, ORLANDO, FL 32803 32 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2895
       Built: 2026   Tax: $1,945 (2025)
    Community: Phillips Rep 01 Lakewood
    Single Family


    Estimated Monthly Payment: $8,830 (change assumption)
    Mortgage ($8,668) + Taxes in 2025 ($162)


    Taxes:$1,945

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4063 LAKE MIRA DR, ORLANDO, FL 32817

    $565,00030 Days on yellowkey   MLS ID: G5114144

    REDUCED by $10,000 (1.7%) on 07/13/2026

    For Sale G5114144 - 4063 LAKE MIRA DR, ORLANDO, FL 32817 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 1981
    Monthly Fee: $17
       Tax: $6,844 (2025)
    Community: Cove At Lake Mira
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,683 (change assumption)
    Mortgage ($3,096) + Fees ($17) + Taxes in 2025 ($570)


    Taxes:$6,844

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 8243 PAMLICO ST, ORLANDO, FL 32817

    $525,00014 Days on yellowkey   MLS ID: O6423802

    For Sale O6423802 - 8243 PAMLICO ST, ORLANDO, FL 32817 55 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2084
       Built: 1977   Tax: $6,791 (2025)
    Community: Harbor East
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,443 (change assumption)
    Mortgage ($2,877) + Taxes in 2025 ($566)


    Taxes:$6,791

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 9889 LAKE GEORGIA DR, ORLANDO, FL 32817

    $2,650,00050 Days on yellowkey   MLS ID: O6412657

    4 Days Off yellowkey (back on 7/21/2026)

    REDUCED by $140,000 (5.0%) on 06/26/2026

    For Sale O6412657 - 9889 LAKE GEORGIA DR, ORLANDO, FL 32817 82 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 5638
       Built: 2022   Tax: $22,108 (2025)
    Community: Lake Georgia Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,363 (change assumption)
    Mortgage ($14,520) + Taxes in 2025 ($1,842)


    Taxes:$22,108

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1604 COLE RD, ORLANDO, FL 32803

    $1,399,00046 Days on yellowkey   MLS ID: TB8516648

    For Sale TB8516648 - 1604 COLE RD, ORLANDO, FL 32803 10 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3465
       Built: 2026   Tax: $3,458 (2025)
    Community: Phillips Rep 01 Lakewood
    Single Family


    Estimated Monthly Payment: $7,954 (change assumption)
    Mortgage ($7,666) + Taxes in 2025 ($288)


    Taxes:$3,458

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2410 LAKE SHORE DR, ORLANDO, FL 32803

    $1,975,00010 Days on yellowkey   MLS ID: O6424495

    For Sale O6424495 - 2410 LAKE SHORE DR, ORLANDO, FL 32803 35 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3815
       Built: 1959   Tax: $11,707 (2025)
    Community: Rose Isle Sec 09
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,797 (change assumption)
    Mortgage ($10,822) + Taxes in 2025 ($976)


    Taxes:$11,707

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2501 LONG MEADOW WAY, ORLANDO, FL 32817

    $284,00041 Days on yellowkey   MLS ID: O6415787

    REDUCED by $6,000 (2.1%) on 07/21/2026

    For Sale O6415787 - 2501 LONG MEADOW WAY, ORLANDO, FL 32817 20 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1079
       Built: 1986
    Monthly Fee: $13
       Tax: $4,044 (2025)
    Community: Carmel Park
    Spa: No

    Half Duplex


    Estimated Monthly Payment: $1,906 (change assumption)
    Mortgage ($1,556) + Fees ($13) + Taxes in 2025 ($337)


    Taxes:$4,044

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7909 WALDORF CT, ORLANDO, FL 32817

    $440,0007 Days on yellowkey   MLS ID: O6425425

    For Sale O6425425 - 7909 WALDORF CT, ORLANDO, FL 32817 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1628
       Built: 1992   Tax: $5,492 (2025)
    Community: Bradford Cove Ph 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,869 (change assumption)
    Mortgage ($2,411) + Taxes in 2025 ($458)


    Taxes:$5,492

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1735 FOSS AVE, ORLANDO, FL 32814

    $2,995,000113 Days on yellowkey   MLS ID: O6394768

    REDUCED by $200,000 (6.3%) on 07/08/2026

    For Sale O6394768 - 1735 FOSS AVE, ORLANDO, FL 32814 48 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: $18,675 (change assumption)
    Mortgage ($16,411) + 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


  • 771 LAKE BALDWIN LN, ORLANDO, FL 32803

    $549,90070 Days on yellowkey   MLS ID: O6407201

    REDUCED by $25,100 (4.4%) on 07/11/2026

    For Sale O6407201 - 771 LAKE BALDWIN LN, ORLANDO, FL 32803 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1868
       Built: 2020
    Monthly Fee: $80
       Tax: $8,054 (2025)
    Community: Lake Baldwin 5
    Townhouse


    Estimated Monthly Payment: $3,764 (change assumption)
    Mortgage ($3,013) + Fees ($80) + Taxes in 2025 ($671)


    Taxes:$8,054

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4445 BEACH BLVD, ORLANDO, FL 32803

    $900,0003 Days on yellowkey   MLS ID: O6425971

    0 Days Off yellowkey (back on 7/20/2026)

    For Sale O6425971 - 4445 BEACH BLVD, ORLANDO, FL 32803 9 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2387
       Built: 1955   Tax: $2,419 (2025)
    Community: Jamajo
    Single Family


    Estimated Monthly Payment: $5,133 (change assumption)
    Mortgage ($4,931) + Taxes in 2025 ($202)


    Taxes:$2,419

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 8736 LARWIN LN, ORLANDO, FL 32817

    $575,00012 Days on yellowkey   MLS ID: O6424408

    For Sale O6424408 - 8736 LARWIN LN, ORLANDO, FL 32817 41 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2064
       Built: 1980
    Monthly Fee: $60
       Tax: $4,541 (2025)
    Community: Woodside Village
    Single Family


    Estimated Monthly Payment: $3,589 (change assumption)
    Mortgage ($3,151) + Fees ($60) + Taxes in 2025 ($378)


    Taxes:$4,541

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1819 COMMON WAY RD #203, ORLANDO, FL 32814

    $499,000217 Days on yellowkey   MLS ID: O6367794

    REDUCED by $8,000 (1.6%) on 05/28/2026

    For Sale O6367794 - 1819 COMMON WAY RD #203, ORLANDO, FL 32814 23 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1429
       Built: 2010   Tax: $4,266 (2024)
    Community: Baldwin Park 07
    Condo


    Estimated Monthly Payment: $3,090 (change assumption)
    Mortgage ($2,734) + Taxes in 2024 ($356)


    Taxes:$4,266

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 9241 TOBY LN, ORLANDO, FL 32817

    $335,00026 Days on yellowkey   MLS ID: O6420573

    REDUCED by $4,900 (1.4%) on 07/11/2026

    For Sale O6420573 - 9241 TOBY LN, ORLANDO, FL 32817 8 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1399
       Built: 1983   Tax: $4,477 (2025)
    Community: Woodsong
    Single Family


    Estimated Monthly Payment: $2,209 (change assumption)
    Mortgage ($1,836) + Taxes in 2025 ($373)


    Taxes:$4,477

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 759 LAKE BALDWIN LN, ORLANDO, FL 32803

    $555,0005 Days on yellowkey   MLS ID: R4911663

    For Sale R4911663 - 759 LAKE BALDWIN LN, ORLANDO, FL 32803 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1842
       Built: 2020
    Monthly Fee: $80
       Tax: $7,967 (2025)
    Community: Lake Baldwin 5
    Spa: Yes

    Townhouse


    Estimated Monthly Payment: $3,785 (change assumption)
    Mortgage ($3,041) + Fees ($80) + Taxes in 2025 ($664)


    Taxes:$7,967

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 918 SHOREVIEW DR, ORLANDO, FL 32807

    $309,000122 Days on yellowkey   MLS ID: O6392300

    REDUCED by $10,000 (3.1%) on 05/28/2026

    For Sale O6392300 - 918 SHOREVIEW DR, ORLANDO, FL 32807 41 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: $2,096 (change assumption)
    Mortgage ($1,693) + Taxes in 2025 ($403)


    Taxes:$4,837

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1451 COMMON WAY RD, ORLANDO, FL 32814

    $715,00035 Days on yellowkey   MLS ID: O6417956

    For Sale O6417956 - 1451 COMMON WAY RD, ORLANDO, FL 32814 39 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2539
       Built: 2004
    Monthly Fee: $658
       Tax: $8,809 (2025)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $5,310 (change assumption)
    Mortgage ($3,918) + Fees ($658) + Taxes in 2025 ($734)


    Taxes:$8,809

    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.