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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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  • 2315 UPPER PARK RD #302, ORLANDO, FL 32814

    $599,90065 Days on yellowkey   MLS ID: O6399861

    REDUCED by $10,100 (1.7%) on 06/06/2026

    For Sale O6399861 - 2315 UPPER PARK RD #302, ORLANDO, FL 32814 35 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1307
       Built: 2006   Tax: $8,191 (2025)
    Community: Baldwin Park #4 Condo
    Condo


    Estimated Monthly Payment: $3,970 (change assumption)
    Mortgage ($3,287) + Taxes in 2025 ($683)


    Taxes:$8,191

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2312 MONTANA ST, ORLANDO, FL 32803

    $1,425,00058 Days on yellowkey   MLS ID: TB8502758

    3 Days Off yellowkey (back on 6/26/2026)

    INCREASED by $46,000 (3.3%) on 06/07/2026

    For Sale TB8502758 - 2312 MONTANA ST, ORLANDO, FL 32803 4 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3465
       Built: 2026   Tax: $1,643 (2025)
    Community: Phillips Rep 01 Lakewood
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,945 (change assumption)
    Mortgage ($7,808) + Taxes in 2025 ($137)


    Taxes:$1,643

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 9889 LAKE GEORGIA DR, ORLANDO, FL 32817

    $2,650,00023 Days on yellowkey   MLS ID: O6412657

    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


  • 2103 GALE ST, ORLANDO, FL 32803

    $1,639,000Listed 06/26/2026 10:55AM   MLS ID: O6417061

    For Sale O6417061 - 2103 GALE ST, ORLANDO, FL 32803 57 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3497
       Built: 2026   Tax: $6,406 (2025)
    Community: North Hampton Park
    Single Family


    Estimated Monthly Payment: $9,514 (change assumption)
    Mortgage ($8,981) + Taxes in 2025 ($534)


    Taxes:$6,406

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4334 N LANDMARK DR, ORLANDO, FL 32817

    $710,0009 Days on yellowkey   MLS ID: O6417868

    For Sale O6417868 - 4334 N LANDMARK DR, ORLANDO, FL 32817 50 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2547
       Built: 1980   Tax: $2,687 (2025)
    Community: Lake Pearl Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,114 (change assumption)
    Mortgage ($3,890) + Taxes in 2025 ($224)


    Taxes:$2,687

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1554 CHATFIELD PL, ORLANDO, FL 32814

    $715,00022 Days on yellowkey   MLS ID: O6413905

    0 Days Off yellowkey (back on 6/26/2026)

    For Sale O6413905 - 1554 CHATFIELD PL, ORLANDO, FL 32814 21 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1887
       Built: 2005
    Monthly Fee: $494
       Tax: $9,472 (2025)
    Community: Baldwin Park Unit 3
    Townhouse


    Estimated Monthly Payment: $5,201 (change assumption)
    Mortgage ($3,918) + Fees ($494) + Taxes in 2025 ($789)


    Taxes:$9,472

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1017 JUEL ST, ORLANDO, FL 32814

    $749,0001 Day on yellowkey   MLS ID: O6419963

    For Sale O6419963 - 1017 JUEL ST, ORLANDO, FL 32814 39 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2221
       Built: 2003
    Monthly Fee: $534
       Tax: $11,130 (2026)
    Community: Baldwin Park Unit 1 - Rep 1
    Townhouse


    Estimated Monthly Payment: $5,566 (change assumption)
    Mortgage ($4,104) + Fees ($534) + Taxes in 2026 ($928)


    Taxes:$11,130

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Glenridge Middle


  • 4346 DAUBERT ST, ORLANDO, FL 32803

    $425,0001 Day on yellowkey   MLS ID: O6419932

    For Sale O6419932 - 4346 DAUBERT ST, ORLANDO, FL 32803 25 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1150
       Built: 1974   Tax: $3,833 (2025)
    Community: Jamajo
    Single Family


    Estimated Monthly Payment: $2,648 (change assumption)
    Mortgage ($2,329) + Taxes in 2025 ($319)


    Taxes:$3,833

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1420 LAKE BALDWIN LN, ORLANDO, FL 32814

    $1,199,0001 Day on yellowkey   MLS ID: O6419759

    For Sale O6419759 - 1420 LAKE BALDWIN LN, ORLANDO, FL 32814 47 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3150
       Built: 2007
    Monthly Fee: $102
       Tax: $14,105 (2025)
    Community: Baldwin Park Unit 3 - Replat 1 58/76 Lot 559
    Townhouse


    Estimated Monthly Payment: $7,847 (change assumption)
    Mortgage ($6,570) + Fees ($102) + Taxes in 2025 ($1,175)


    Taxes:$14,105

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 7510 STRATFORD BLVD, ORLANDO, FL 32807

    $310,0001 Day on yellowkey   MLS ID: O6419864

    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


  • 1659 COMMON WAY RD, ORLANDO, FL 32814

    $605,0003 Days on yellowkey   MLS ID: O6417414

    For Sale O6417414 - 1659 COMMON WAY RD, ORLANDO, FL 32814 31 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 2005
    Monthly Fee: $102
       Tax: $10,269 (2025)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $4,273 (change assumption)
    Mortgage ($3,315) + Fees ($102) + Taxes in 2025 ($856)


    Taxes:$10,269

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3701 VIRGINIA DR, ORLANDO, FL 32803

    $725,00010 Days on yellowkey   MLS ID: O6417195

    For Sale O6417195 - 3701 VIRGINIA DR, ORLANDO, FL 32803 58 photos

    Bed: 4   Bath: 0.0
    Liv Area Sq Ft: 2044
       Built: 1954   Tax: $7,924 (2025)
    Community: Audubon Park Tanager Sec
    Apartment


    Estimated Monthly Payment: $4,633 (change assumption)
    Mortgage ($3,973) + Taxes in 2025 ($660)


    Taxes:$7,924

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 3701 VIRGINIA DR, ORLANDO, FL 32803

    $725,00010 Days on yellowkey   MLS ID: O6416950

    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: $4,633 (change assumption)
    Mortgage ($3,973) + Taxes in 2025 ($660)


    Taxes:$7,924

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 1735 FOSS AVE, ORLANDO, FL 32814

    $3,195,00086 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 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: $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


  • 2721 E MARKS ST, ORLANDO, FL 32803

    $675,000161 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


  • 771 LAKE BALDWIN LN, ORLANDO, FL 32803

    $599,00043 Days on yellowkey   MLS ID: O6407201

    REDUCED by $20,000 (3.2%) on 06/03/2026

    For Sale O6407201 - 771 LAKE BALDWIN LN, ORLANDO, FL 32803 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2001
       Built: 2020
    Monthly Fee: $80
       Tax: $8,054 (2025)
    Community: Lake Baldwin 5
    Townhouse


    Estimated Monthly Payment: $4,033 (change assumption)
    Mortgage ($3,282) + 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


  • 1451 COMMON WAY RD, ORLANDO, FL 32814

    $715,0008 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


  • 2293 OSPREY AVE, ORLANDO, FL 32814

    $1,258,0004 Days on yellowkey   MLS ID: S5152219

    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: $8,284 (change assumption)
    Mortgage ($6,893) + 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


  • 4063 LAKE MIRA DR, ORLANDO, FL 32817

    $575,0003 Days on yellowkey   MLS ID: G5114144

    For Sale G5114144 - 4063 LAKE MIRA DR, ORLANDO, FL 32817 24 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: $3,738 (change assumption)
    Mortgage ($3,151) + 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


  • 4353 ROUSH AVE, ORLANDO, FL 32803

    $517,48548 Days on yellowkey   MLS ID: TB8507013

    REDUCED by $15 (0.0%) on 06/24/2026

    For Sale TB8507013 - 4353 ROUSH AVE, ORLANDO, FL 32803 34 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: $3,168 (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




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.