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Homes for Sale Near Winter Park High in Orlando - 113 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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  • 4512 BRIDGEWATER DR, ORLANDO, FL 32817

    $895,000186 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


  • 2936 MOORCROFT CT, ORLANDO, FL 32817

    $485,0005 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


  • 9889 LAKE GEORGIA DR, ORLANDO, FL 32817

    $2,790,0007 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

    $449,90019 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

    $449,00012 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

    $589,0006 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


  • 2806 MOSS GROVE BLVD, ORLANDO, FL 32807

    $349,9906 Days on yellowkey   MLS ID: S5151206

    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


  • 9517 DARIEN AVE #9517, ORLANDO, FL 32817

    $190,000173 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


  • 1310 COLETTA DR, ORLANDO, FL 32807

    $319,99985 Days on yellowkey   MLS ID: O6386157

    REDUCED by $10,000 (3.0%) on 06/04/2026

    For Sale O6386157 - 1310 COLETTA DR, ORLANDO, FL 32807 34 photos

    Bed: 3   Bath: 1.5
    Liv Area Sq Ft: 1513
       Built: 1952   Tax: $5,177 (2025)
    Community: J J Kates Sub
    Single Family


    Estimated Monthly Payment: $2,185 (change assumption)
    Mortgage ($1,753) + Taxes in 2025 ($431)


    Taxes:$5,177

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4337 ROUSH AVE, ORLANDO, FL 32803

    $632,43048 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


  • 4357 ROUSH AVE, ORLANDO, FL 32803

    $633,20232 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


  • 4333 ROUSH AVE, ORLANDO, FL 32803

    $499,900107 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

    $499,000174 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

    $3,195,00070 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

    $1,149,00015 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


  • 8617 AMBER OAK CT, ORLANDO, FL 32817

    $599,00013 Days on yellowkey   MLS ID: O6411412

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

    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


  • 2726 & 2740 N DEAN RD, ORLANDO, FL 32817

    $2,600,0001149 Days on yellowkey   MLS ID: O6104701

    12 Days Off yellowkey (back on 8/2/2023)

    For Sale O6104701 - 2726 & 2740 N DEAN RD, ORLANDO, FL 32817 9 photos

    Bed: 6   Bath: 4.0
    Liv Area Sq Ft: 4304
       Built: 1947   Tax: $2,320 (2022)
    Community: Orlando
    Single Family


    Estimated Monthly Payment: $14,440 (change assumption)
    Mortgage ($14,246) + Taxes in 2022 ($193)


    Taxes:$2,320

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2022

    Middle School: Union Park Middle


  • 2916 PLAZA TERRACE DRIVE #2916, ORLANDO, FL 32803

    $299,90048 Days on yellowkey   MLS ID: O6401067

    2 Days Off yellowkey (back on 6/2/2026)

    REDUCED by $5,100 (1.7%) on 05/22/2026

    For Sale O6401067 - 2916 PLAZA TERRACE DRIVE #2916, ORLANDO, FL 32803 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 890
       Built: 1972
    Monthly Fee: $281
       Tax: $3,594 (2025)
    Community: Audubon Place City Condo
    Condo


    Estimated Monthly Payment: $2,224 (change assumption)
    Mortgage ($1,643) + Fees ($281) + Taxes in 2025 ($300)


    Taxes:$3,594

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4475 TWINVIEW LN, ORLANDO, FL 32814

    $949,90040 Days on yellowkey   MLS ID: O6403983

    1 Days Off yellowkey (back on 6/2/2026)

    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


  • 1563 COMMON WAY RD, ORLANDO, FL 32814

    $609,000152 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




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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.