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Homes for Sale Near Winter Park High in Winter Park - 164 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, Winter Park nearby homes.

Location: Winter Park

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  • 781 NORTHWOOD CIR, WINTER PARK, FL 32789

    $775,00024 Days on yellowkey   MLS ID: O6394119

    0 Days Off yellowkey (back on 4/5/2026)

    For Sale O6394119 - 781 NORTHWOOD CIR, WINTER PARK, FL 32789 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1566
       Built: 1971   Tax: $6,931 (2025)
    Community: Winter Park Oasis
    Single Family


    Estimated Monthly Payment: $4,824 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($578)


    Taxes:$6,931

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1134 WASHINGTON AVE #13, WINTER PARK, FL 32789

    $625,000152 Days on yellowkey   MLS ID: O6362206

    For Sale O6362206 - 1134 WASHINGTON AVE #13, WINTER PARK, FL 32789 32 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2083
       Built: 1981   Tax: $7,472 (2025)
    Community: Quarters At Winter Park Condo
    Condo


    Estimated Monthly Payment: $4,047 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($623)


    Taxes:$7,472

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 643 DUNBLANE DR, WINTER PARK, FL 32792

    $699,80057 Days on yellowkey   MLS ID: O6386136

    For Sale O6386136 - 643 DUNBLANE DR, WINTER PARK, FL 32792 62 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1575
       Built: 1962   Tax: $4,598 (2024)
    Community: Kenilworth Shores Section Four Y/71 Lot 21 Blk B
    Single Family


    Estimated Monthly Payment: $4,218 (change assumption)
    Mortgage ($3,834) + Taxes in 2024 ($383)


    Taxes:$4,598

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 7471 CANFORD CT #19, WINTER PARK, FL 32792

    $199,000198 Days on yellowkey   MLS ID: G5103114

    For Sale G5103114 - 7471 CANFORD CT #19, WINTER PARK, FL 32792 15 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1393
       Built: 1974   Tax: $2,750 (2024)
    Community: Whisperwood Condo
    Condo


    Estimated Monthly Payment: $1,320 (change assumption)
    Mortgage ($1,090) + Taxes in 2024 ($229)


    Taxes:$2,750

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1340 PLACE PICARDY, WINTER PARK, FL 32789

    $1,599,00072 Days on yellowkey   MLS ID: O6382113

    3 Days Off yellowkey (back on 3/30/2026)

    For Sale O6382113 - 1340 PLACE PICARDY, WINTER PARK, FL 32789 34 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3459
       Built: 1997   Tax: $7,515 (2025)
    Community: Fontainebleau
    Single Family


    Estimated Monthly Payment: $9,388 (change assumption)
    Mortgage ($8,761) + Taxes in 2025 ($626)


    Taxes:$7,515

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 184 SANDLEWOOD TRL ##2, WINTER PARK, FL 32789

    $314,00077 Days on yellowkey   MLS ID: O6380753

    For Sale O6380753 - 184 SANDLEWOOD TRL ##2, WINTER PARK, FL 32789 29 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1133
       Built: 1985
    Monthly Fee: $310
       Tax: $2,915 (2025)
    Community: Sandlewood Creek Condo Ph 10
    Condo


    Estimated Monthly Payment: $2,273 (change assumption)
    Mortgage ($1,721) + Fees ($310) + Taxes in 2025 ($243)


    Taxes:$2,915

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 758 WARRENTON RD, WINTER PARK, FL 32792

    $318,98524 Days on yellowkey   MLS ID: O6395298

    For Sale O6395298 - 758 WARRENTON RD, WINTER PARK, FL 32792 52 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1196
       Built: 1988
    Monthly Fee: $86
       Tax: $3,689 (2025)
    Community: Winter Park Pines Patio Homes
    Half Duplex


    Estimated Monthly Payment: $2,141 (change assumption)
    Mortgage ($1,748) + Fees ($86) + Taxes in 2025 ($307)


    Taxes:$3,689

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 770 W WEBSTER AVE, WINTER PARK, FL 32789

    $725,000296 Days on yellowkey   MLS ID: O6323574

    For Sale O6323574 - 770 W WEBSTER AVE, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1008
       Built: 1967   Tax: $4,856 (2024)
    Community: Capens Add
    Single Family


    Estimated Monthly Payment: $4,377 (change assumption)
    Mortgage ($3,973) + Taxes in 2024 ($405)


    Taxes:$4,856

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1630 ELM AVE, WINTER PARK, FL 32789

    $2,385,00040 Days on yellowkey   MLS ID: O6388606

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

    For Sale O6388606 - 1630 ELM AVE, WINTER PARK, FL 32789 15 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3408
       Built: 2026   Tax: $1,673 (2024)
    Community: Temple Estates
    Single Family


    Estimated Monthly Payment: $13,208 (change assumption)
    Mortgage ($13,068) + Taxes in 2024 ($139)


    Taxes:$1,673

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 837 APPALACHEE AVE, WINTER PARK, FL 32792

    $439,00029 Days on yellowkey   MLS ID: O6393151

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

    For Sale O6393151 - 837 APPALACHEE AVE, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1771
       Built: 1968   Tax: $6,834 (2025)
    Community: Winter Park Forest
    Single Family


    Estimated Monthly Payment: $2,975 (change assumption)
    Mortgage ($2,405) + Taxes in 2025 ($570)


    Taxes:$6,834

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 230 STRATHY LN, WINTER PARK, FL 32792

    $499,000108 Days on yellowkey   MLS ID: O6371054

    For Sale O6371054 - 230 STRATHY LN, WINTER PARK, FL 32792 12 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 920
       Built: 1957   Tax: $4,071 (2024)
    Community: Aloma
    Single Family


    Estimated Monthly Payment: $3,073 (change assumption)
    Mortgage ($2,734) + Taxes in 2024 ($339)


    Taxes:$4,071

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2231 NAIRN DR, WINTER PARK, FL 32792

    $499,000108 Days on yellowkey   MLS ID: O6369016

    For Sale O6369016 - 2231 NAIRN DR, WINTER PARK, FL 32792 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1088
       Built: 1956   Tax: $3,793 (2025)
    Community: Aloma
    Single Family


    Estimated Monthly Payment: $3,050 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($316)


    Taxes:$3,793

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 872 GRANVILLE DR, WINTER PARK, FL 32789

    $2,200,00030 Days on yellowkey   MLS ID: O6391464

    0 Days Off yellowkey (back on 3/31/2026)

    For Sale O6391464 - 872 GRANVILLE DR, WINTER PARK, FL 32789 40 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 3195
       Built: 1961   Tax: $12,465 (2025)
    Community: Park Grove W/125 Lot 10 Blk D
    Single Family


    Estimated Monthly Payment: $13,093 (change assumption)
    Mortgage ($12,054) + Taxes in 2025 ($1,039)


    Taxes:$12,465

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1909 EDWIN BLVD, WINTER PARK, FL 32792

    $440,000154 Days on yellowkey   MLS ID: O6362682

    1 Days Off yellowkey (back on 12/2/2025)

    For Sale O6362682 - 1909 EDWIN BLVD, WINTER PARK, FL 32792 11 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1355
       Built: 1955   Tax: $4,703 (2024)
    Community: Eastgate Sub
    Single Family


    Estimated Monthly Payment: $2,803 (change assumption)
    Mortgage ($2,411) + Taxes in 2024 ($392)


    Taxes:$4,703

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 7300 DANIEL WEBSTER DR #M7, WINTER PARK, FL 32792

    $165,00037 Days on yellowkey   MLS ID: O6388668

    For Sale O6388668 - 7300 DANIEL WEBSTER DR #M7, WINTER PARK, FL 32792 34 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1108
       Built: 1974
    Monthly Fee: $471
       Tax: $2,050 (2025)
    Community: Colonies
    Condo


    Estimated Monthly Payment: $1,546 (change assumption)
    Mortgage ($904) + Fees ($471) + Taxes in 2025 ($171)


    Taxes:$2,050

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3027 AARON BURR AVE #L1, WINTER PARK, FL 32792

    $165,00037 Days on yellowkey   MLS ID: O6390662

    For Sale O6390662 - 3027 AARON BURR AVE #L1, WINTER PARK, FL 32792 35 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1090
       Built: 1974
    Monthly Fee: $471
       Tax: $2,050 (2025)
    Community: Colonies
    Condo


    Estimated Monthly Payment: $1,546 (change assumption)
    Mortgage ($904) + Fees ($471) + Taxes in 2025 ($171)


    Taxes:$2,050

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2423 VIA SIENNA, WINTER PARK, FL 32789

    $2,200,00050 Days on yellowkey   MLS ID: O6386867

    For Sale O6386867 - 2423 VIA SIENNA, WINTER PARK, FL 32789 44 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 3472
       Built: 1990   Tax: $18,918 (2026)
    Community: Cinnamon Shores
    Single Family


    Estimated Monthly Payment: $13,631 (change assumption)
    Mortgage ($12,054) + Taxes in 2026 ($1,577)


    Taxes:$18,918

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 1120 PALMER AVE, WINTER PARK, FL 32789

    $3,800,00065 Days on yellowkey   MLS ID: O6376319

    For Sale O6376319 - 1120 PALMER AVE, WINTER PARK, FL 32789 38 photos

    Bed: 3   Bath: 3.5
    Liv Area Sq Ft: 3413
       Built: 1951   Tax: $20,754 (2024)
    Community: 3223171-3223171
    Single Family


    Estimated Monthly Payment: $22,551 (change assumption)
    Mortgage ($20,821) + Taxes in 2024 ($1,730)


    Taxes:$20,754

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 512 N LAKEMONT AVE, WINTER PARK, FL 32792

    $500,00036 Days on yellowkey   MLS ID: O6392353

    For Sale O6392353 - 512 N LAKEMONT AVE, WINTER PARK, FL 32792 43 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1413
       Built: 1955   Tax: $2,136 (2025)
    Community: Eastgate Sub
    Single Family


    Estimated Monthly Payment: $2,918 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($178)


    Taxes:$2,136

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1836 GRINNELL TER, WINTER PARK, FL 32789

    $1,050,00078 Days on yellowkey   MLS ID: O6380457

    For Sale O6380457 - 1836 GRINNELL TER, WINTER PARK, FL 32789 24 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1907
       Built: 1995   Tax: $11,979 (2025)
    Community: Lake Virginia
    Single Family


    Estimated Monthly Payment: $6,752 (change assumption)
    Mortgage ($5,753) + Taxes in 2025 ($998)


    Taxes:$11,979

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    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, Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park 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.