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Homes for Sale Near Winter Park High in Orlando - 109 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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  • 1563 COMMON WAY RD, ORLANDO, FL 32814

    $599,990156 Days on yellowkey   MLS ID: O6371726

    REDUCED by $9,010 (1.5%) on 06/11/2026

    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: $4,802 (change assumption)
    Mortgage ($3,288) + 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


  • 2806 MOSS GROVE BLVD, ORLANDO, FL 32807

    $349,99010 Days on yellowkey   MLS ID: S5151206

    0 Days Off yellowkey (back on 6/11/2026)

    For Sale S5151206 - 2806 MOSS GROVE BLVD, ORLANDO, FL 32807 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1272
       Built: 1975   Tax: $1,398 (2025)
    Community: Hanging Moss Estates
    Single Family


    Estimated Monthly Payment: $2,034 (change assumption)
    Mortgage ($1,918) + Taxes in 2025 ($117)


    Taxes:$1,398

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2066 BRINK ALY, ORLANDO, FL 32814

    $680,000131 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


  • 2936 MOORCROFT CT, ORLANDO, FL 32817

    $485,0009 Days on yellowkey   MLS ID: O6413385

    For Sale O6413385 - 2936 MOORCROFT CT, ORLANDO, FL 32817 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1670
       Built: 1994   Tax: $2,294 (2025)
    Community: Arbor Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,849 (change assumption)
    Mortgage ($2,657) + Taxes in 2025 ($191)


    Taxes:$2,294

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 803 HASKELL AVE, ORLANDO, FL 32807

    $369,99938 Days on yellowkey   MLS ID: TB8505733

    REDUCED by $5,001 (1.3%) on 06/10/2026

    For Sale TB8505733 - 803 HASKELL AVE, ORLANDO, FL 32807 18 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1197
       Built: 1957   Tax: $2,461 (2025)
    Community: Lake Barton Park
    Single Family


    Estimated Monthly Payment: $2,232 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($205)


    Taxes:$2,461

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5416 PENWAY DR, ORLANDO, FL 32814

    $939,000219 Days on yellowkey   MLS ID: O6357821

    REDUCED by $10,999 (1.2%) on 06/09/2026

    For Sale O6357821 - 5416 PENWAY DR, ORLANDO, FL 32814 79 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: $5,898 (change assumption)
    Mortgage ($5,145) + 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


  • 224 CAPE SABLE DR, ORLANDO, FL 32825

    $459,0006 Days on yellowkey   MLS ID: O6414734

    For Sale O6414734 - 224 CAPE SABLE DR, ORLANDO, FL 32825 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1832
       Built: 2004
    Monthly Fee: $100
       Tax: $6,143 (2025)
    Community: Woodland Lakes
    Single Family


    Estimated Monthly Payment: $3,127 (change assumption)
    Mortgage ($2,515) + Fees ($100) + Taxes in 2025 ($512)


    Taxes:$6,143

    Elementary School: Cypress Springs Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Legacy Middle


  • 8825 BUTTERNUT BLVD, ORLANDO, FL 32817

    $455,90013 Days on yellowkey   MLS ID: O6404329

    0 Days Off yellowkey (back on 6/8/2026)

    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


  • 1604 COLE RD, ORLANDO, FL 32803

    $1,399,0007 Days on yellowkey   MLS ID: TB8516648

    For Sale TB8516648 - 1604 COLE RD, ORLANDO, FL 32803 4 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


  • 4029 TAMARISK WAY, ORLANDO, FL 32817

    $475,00025 Days on yellowkey   MLS ID: O6409365

    0 Days Off yellowkey (back on 5/22/2026)

    For Sale O6409365 - 4029 TAMARISK WAY, ORLANDO, FL 32817 49 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1992
       Built: 1979
    Monthly Fee: $67
       Tax: $2,650 (2025)
    Community: Woodside Village
    Single Family


    Estimated Monthly Payment: $2,891 (change assumption)
    Mortgage ($2,603) + Fees ($67) + Taxes in 2025 ($221)


    Taxes:$2,650

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2506 WOODSIDE AVE, ORLANDO, FL 32803

    $1,149,00011 Days on yellowkey   MLS ID: O6413252

    For Sale O6413252 - 2506 WOODSIDE AVE, ORLANDO, FL 32803 21 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2642
       Built: 2017   Tax: $14,777 (2025)
    Community: Beeman Park
    Single Family


    Estimated Monthly Payment: $7,527 (change assumption)
    Mortgage ($6,296) + Taxes in 2025 ($1,231)


    Taxes:$14,777

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1554 CHATFIELD PL, ORLANDO, FL 32814

    $715,00010 Days on yellowkey   MLS ID: O6413905

    For Sale O6413905 - 1554 CHATFIELD PL, ORLANDO, FL 32814 41 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


  • 2312 MONTANA ST, ORLANDO, FL 32803

    $1,425,00046 Days on yellowkey   MLS ID: TB8502758

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

    For Sale TB8502758 - 2312 MONTANA ST, ORLANDO, FL 32803 2 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


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

    $599,90053 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


  • 4512 BRIDGEWATER DR, ORLANDO, FL 32817

    $895,000190 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


  • 9889 LAKE GEORGIA DR, ORLANDO, FL 32817

    $2,790,00011 Days on yellowkey   MLS ID: O6412657

    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: $17,130 (change assumption)
    Mortgage ($15,287) + 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


  • 9915 KONA ISLE CT, ORLANDO, FL 32817

    $449,90023 Days on yellowkey   MLS ID: O6409497

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

    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


  • 9909 EARLSTON ST, ORLANDO, FL 32817

    $449,00016 Days on yellowkey   MLS ID: O6411569

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

    For Sale O6411569 - 9909 EARLSTON ST, ORLANDO, FL 32817 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2140
       Built: 1985
    Monthly Fee: $15
       Tax: $4,619 (2025)
    Community: Hunters Trace
    Single Family


    Estimated Monthly Payment: $2,860 (change assumption)
    Mortgage ($2,460) + Fees ($15) + Taxes in 2025 ($385)


    Taxes:$4,619

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Union Park Middle


  • 2959 UPPER PARK RD, ORLANDO, FL 32814

    $589,00010 Days on yellowkey   MLS ID: O6412043

    For Sale O6412043 - 2959 UPPER PARK RD, ORLANDO, FL 32814 63 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1897
       Built: 2005
    Monthly Fee: $534
       Tax: $9,857 (2025)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $4,583 (change assumption)
    Mortgage ($3,227) + Fees ($534) + Taxes in 2025 ($821)


    Taxes:$9,857

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 9517 DARIEN AVE #9517, ORLANDO, FL 32817

    $190,000177 Days on yellowkey   MLS ID: O6368148

    REDUCED by $2,000 (1.0%) on 06/04/2026

    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: $1,233 (change assumption)
    Mortgage ($1,041) + Taxes in 2024 ($192)


    Taxes:$2,298

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Union Park Middle




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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.