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Homes for Sale Near Winter Park High in Orlando - 105 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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  • 1408 VILLA MARIE DR, ORLANDO, FL 32807

    $339,00037 Days on yellowkey   MLS ID: O6407157

    0 Days Off yellowkey (back on 6/14/2026)

    For Sale O6407157 - 1408 VILLA MARIE DR, ORLANDO, FL 32807 41 photos

    Bed: 3   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 1152
       Built: 1959   Tax: $2,320 (2025)
    Community: Corrine Terrace
    Single Family


    Estimated Monthly Payment: $2,051 (change assumption)
    Mortgage ($1,857) + Taxes in 2025 ($193)


    Taxes:$2,320

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4512 BRIDGEWATER DR, ORLANDO, FL 32817

    $890,000194 Days on yellowkey   MLS ID: O6365659

    REDUCED by $5,000 (0.6%) on 06/14/2026

    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: $5,478 (change assumption)
    Mortgage ($4,877) + Taxes in 2025 ($601)


    Taxes:$7,214

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 4392 WARDELL PL #201, ORLANDO, FL 32814

    $615,0008 Days on yellowkey   MLS ID: O6411195

    For Sale O6411195 - 4392 WARDELL PL #201, ORLANDO, FL 32814 34 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1434
       Built: 2006
    Monthly Fee: $838
       Tax: $4,311 (2025)
    Community: Baldwin Park #5
    Condo


    Estimated Monthly Payment: $4,567 (change assumption)
    Mortgage ($3,370) + Fees ($838) + Taxes in 2025 ($359)


    Taxes:$4,311

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 771 LAKE BALDWIN LN, ORLANDO, FL 32803

    $599,00035 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


  • 4033 IBIS DR, ORLANDO, FL 32803

    $525,00014 Days on yellowkey   MLS ID: O6413734

    For Sale O6413734 - 4033 IBIS DR, ORLANDO, FL 32803 29 photos

    Bed: 3   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 1190
       Built: 1956   Tax: $7,091 (2025)
    Community: Audubon Park Card Heights Sec
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,468 (change assumption)
    Mortgage ($2,877) + Taxes in 2025 ($591)


    Taxes:$7,091

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 3004 PLAZA TERRACE DR #3004, ORLANDO, FL 32803

    $269,90095 Days on yellowkey   MLS ID: O6390840

    REDUCED by $5,000 (1.8%) on 06/11/2026

    For Sale O6390840 - 3004 PLAZA TERRACE DR #3004, ORLANDO, FL 32803 30 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 890
       Built: 1972
    Monthly Fee: $289
       Tax: $4,271 (2025)
    Community: Audubon Place City Condo
    Condo


    Estimated Monthly Payment: $2,124 (change assumption)
    Mortgage ($1,479) + Fees ($289) + Taxes in 2025 ($356)


    Taxes:$4,271

    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

    $299,0006 Days on yellowkey   MLS ID: O6415787

    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: $1,988 (change assumption)
    Mortgage ($1,638) + 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


  • 2620 CAVANAUGH DR, ORLANDO, FL 32817

    $600,000177 Days on yellowkey   MLS ID: O6369315

    REDUCED by $25,000 (4.0%) on 06/12/2026

    For Sale O6369315 - 2620 CAVANAUGH DR, ORLANDO, FL 32817 2 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2560
       Built: 2025
    Monthly Fee: $130
       Tax: $887 (2025)
    Community: Harrell Oaks
    Single Family


    Estimated Monthly Payment: $3,492 (change assumption)
    Mortgage ($3,288) + Fees ($130) + Taxes in 2025 ($74)


    Taxes:$887

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 918 SHOREVIEW DR, ORLANDO, FL 32807

    $309,00087 Days on yellowkey   MLS ID: O6392300

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

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

    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: $2,096 (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


  • 2806 MOSS GROVE BLVD, ORLANDO, FL 32807

    $349,99014 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


  • 2936 MOORCROFT CT, ORLANDO, FL 32817

    $485,00013 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

    $369,99942 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


  • 4029 TAMARISK WAY, ORLANDO, FL 32817

    $475,00029 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

    $1,149,00015 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


  • 9909 EARLSTON ST, ORLANDO, FL 32817

    $449,00020 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


  • 4337 ROUSH AVE, ORLANDO, FL 32803

    $632,43056 Days on yellowkey   MLS ID: TB8501100

    2 Days Off yellowkey (back on 5/13/2026)

    For Sale TB8501100 - 4337 ROUSH AVE, ORLANDO, FL 32803 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1932
       Built: 2025
    Monthly Fee: $299
       Tax: $517 (2025)
    Community: Baldwin Crossing
    Townhouse


    Estimated Monthly Payment: $3,807 (change assumption)
    Mortgage ($3,465) + Fees ($299) + Taxes in 2025 ($43)


    Taxes:$517

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4333 ROUSH AVE, ORLANDO, FL 32803

    $499,900115 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


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

    $499,000182 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


  • 1735 FOSS AVE, ORLANDO, FL 32814

    $3,195,00078 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 44 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


  • 3838 HAWS LN, ORLANDO, FL 32814

    $1,149,00023 Days on yellowkey   MLS ID: O6410550

    For Sale O6410550 - 3838 HAWS LN, ORLANDO, FL 32814 52 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2731
       Built: 2005
    Monthly Fee: $92
       Tax: $17,789 (2025)
    Community: Baldwin Park
    Single Family


    Estimated Monthly Payment: $7,870 (change assumption)
    Mortgage ($6,296) + Fees ($92) + Taxes in 2025 ($1,482)


    Taxes:$17,789

    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.