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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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  • 8825 BUTTERNUT BLVD, ORLANDO, FL 32817

    $455,900Listed 06/01/2026 8:51AM   MLS ID: O6404329

    For Sale O6404329 - 8825 BUTTERNUT BLVD, ORLANDO, FL 32817 50 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1722
       Built: 1979
    Monthly Fee: $67
       Tax: $2,346 (2025)
    Community: Woodside Village
    Single Family


    Estimated Monthly Payment: $2,761 (change assumption)
    Mortgage ($2,498) + Fees ($67) + Taxes in 2025 ($196)


    Taxes:$2,346

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1563 COMMON WAY RD, ORLANDO, FL 32814

    $609,000143 Days on yellowkey   MLS ID: O6371726

    REDUCED by $10,000 (1.6%) on 06/01/2026

    For Sale O6371726 - 1563 COMMON WAY RD, ORLANDO, FL 32814 43 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1871
       Built: 2005
    Monthly Fee: $620
       Tax: $10,738 (2024)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $4,852 (change assumption)
    Mortgage ($3,337) + Fees ($620) + Taxes in 2024 ($895)


    Taxes:$10,738

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 9915 KONA ISLE CT, ORLANDO, FL 32817

    $449,90010 Days on yellowkey   MLS ID: O6409497

    For Sale O6409497 - 9915 KONA ISLE CT, ORLANDO, FL 32817 28 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1965
       Built: 1998
    Monthly Fee: $35
       Tax: $2,442 (2025)
    Community: Deans Reserve
    Single Family


    Estimated Monthly Payment: $2,704 (change assumption)
    Mortgage ($2,465) + Fees ($35) + Taxes in 2025 ($204)


    Taxes:$2,442

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4341 ROUSH AVE, ORLANDO, FL 32803

    $632,43023 Days on yellowkey   MLS ID: TB8506998

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

    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


  • 2839 ANTIOCH WAY, ORLANDO, FL 32807

    $349,90097 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

    $675,000136 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

    $370,00013 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

    $684,90059 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

    $465,00047 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


  • 3916 VALENCIA GROVE LN, ORLANDO, FL 32817

    $365,00077 Days on yellowkey   MLS ID: O6390980

    1 Days Off yellowkey (back on 4/18/2026)

    For Sale O6390980 - 3916 VALENCIA GROVE LN, ORLANDO, FL 32817 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1188
       Built: 1986   Tax: $4,848 (2025)
    Community: Valencia Grove
    Single Family


    Estimated Monthly Payment: $2,404 (change assumption)
    Mortgage ($2,000) + Taxes in 2025 ($404)


    Taxes:$4,848

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2674 CAVANAUGH DR, ORLANDO, FL 32817

    $674,99067 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


  • 8617 AMBER OAK CT, ORLANDO, FL 32817

    $599,0004 Days on yellowkey   MLS ID: O6411412

    For Sale O6411412 - 8617 AMBER OAK CT, ORLANDO, FL 32817 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2253
       Built: 1986   Tax: $8,889 (2025)
    Community: Forest Lakes Ph 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,023 (change assumption)
    Mortgage ($3,282) + Taxes in 2025 ($741)


    Taxes:$8,889

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 4512 BRIDGEWATER DR, ORLANDO, FL 32817

    $895,000177 Days on yellowkey   MLS ID: O6365659

    REDUCED by $41,000 (4.4%) on 05/20/2026

    For Sale O6365659 - 4512 BRIDGEWATER DR, ORLANDO, FL 32817 46 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2091
       Built: 1983   Tax: $7,214 (2025)
    Community: Watermill Sec 01
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,505 (change assumption)
    Mortgage ($4,904) + Taxes in 2025 ($601)


    Taxes:$7,214

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 4357 ROUSH AVE, ORLANDO, FL 32803

    $633,20223 Days on yellowkey   MLS ID: TB8507003

    For Sale TB8507003 - 4357 ROUSH AVE, ORLANDO, FL 32803 35 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: $3,803 (change assumption)
    Mortgage ($3,470) + 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


  • 4475 TWINVIEW LN, ORLANDO, FL 32814

    $949,90031 Days on yellowkey   MLS ID: O6403983

    For Sale O6403983 - 4475 TWINVIEW LN, ORLANDO, FL 32814 28 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2669
       Built: 2004
    Monthly Fee: $523
       Tax: $15,658 (2025)
    Community: Baldwin Park Un #1
    Townhouse


    Estimated Monthly Payment: $7,033 (change assumption)
    Mortgage ($5,205) + Fees ($523) + Taxes in 2025 ($1,305)


    Taxes:$15,658

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 9717 LAKE DOUGLAS PL, ORLANDO, FL 32817

    $679,00067 Days on yellowkey   MLS ID: O6391068

    REDUCED by $70,000 (9.3%) on 05/29/2026

    For Sale O6391068 - 9717 LAKE DOUGLAS PL, ORLANDO, FL 32817 49 photos

    Bed: 6   Bath: 6.0   Gar: 2
    Liv Area Sq Ft: 2855
       Built: 1987   Tax: $4,727 (2025)
    Community: Arbor Club
    Single Family


    Estimated Monthly Payment: $4,114 (change assumption)
    Mortgage ($3,720) + Taxes in 2025 ($394)


    Taxes:$4,727

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Union Park Middle


  • 4333 ROUSH AVE, ORLANDO, FL 32803

    $499,90098 Days on yellowkey   MLS ID: TB8479380

    REDUCED by $17,470 (3.4%) on 05/26/2026

    For Sale TB8479380 - 4333 ROUSH AVE, ORLANDO, FL 32803 36 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1390
       Built: 2026
    Monthly Fee: $290
       Tax: $517 (2025)
    Community: Baldwin Crossing
    Townhouse


    Estimated Monthly Payment: $3,072 (change assumption)
    Mortgage ($2,739) + 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


  • 3884 LOWER PARK RD, ORLANDO, FL 32814

    $1,895,00069 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


  • 3861 BENTFORD CT, ORLANDO, FL 32817

    $399,90080 Days on yellowkey   MLS ID: O6388156

    REDUCED by $10,100 (2.5%) on 04/17/2026

    For Sale O6388156 - 3861 BENTFORD CT, ORLANDO, FL 32817 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1571
       Built: 1990
    Monthly Fee: $28
       Tax: $5,492 (2024)
    Community: Bradford Cove Ph 01
    Single Family


    Estimated Monthly Payment: $2,677 (change assumption)
    Mortgage ($2,191) + Fees ($28) + Taxes in 2024 ($458)


    Taxes:$5,492

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 771 LAKE BALDWIN LN, ORLANDO, FL 32803

    $619,00018 Days on yellowkey   MLS ID: O6407201

    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: $4,143 (change assumption)
    Mortgage ($3,392) + 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




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.