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Homes for Sale Near Winter Park High in Maitland - 37 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, Maitland nearby homes.

Location: Maitland

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  • 223 QUAYSIDE CIR #C, MAITLAND, FL 32751

    $575,000155 Days on yellowkey   MLS ID: O6362370

    For Sale O6362370 - 223 QUAYSIDE CIR #C, MAITLAND, FL 32751 50 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1734
       Built: 1985
    Monthly Fee: $882
       Tax: $4,185 (2024)
    Community: Moorings On Lake Maitland Condo Bldg 05
    Condo


    Estimated Monthly Payment: $4,381 (change assumption)
    Mortgage ($3,151) + Fees ($882) + Taxes in 2024 ($349)


    Taxes:$4,185

    Elementary School: Lake Sybelia Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 225 QUAYSIDE CIR, MAITLAND, FL 32751

    $560,000205 Days on yellowkey   MLS ID: O6338754

    REDUCED by $35,000 (5.9%) on 04/03/2026

    For Sale O6338754 - 225 QUAYSIDE CIR, MAITLAND, FL 32751 39 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1734
       Built: 1985   Tax: $3,080 (2024)
    Community: Moorings On Lake Maitland Condo Bldg 05
    Condo


    Estimated Monthly Payment: $3,325 (change assumption)
    Mortgage ($3,068) + Taxes in 2024 ($257)


    Taxes:$3,080

    Elementary School: Lake Sybelia Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 101 MARINER WAY, MAITLAND, FL 32751

    $769,00016 Days on yellowkey   MLS ID: O6396663

    0 Days Off yellowkey (back on 4/16/2026)

    For Sale O6396663 - 101 MARINER WAY, MAITLAND, FL 32751 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2413
       Built: 1972
    Monthly Fee: $8
       Tax: $3,528 (2025)
    Community: Maitland Isle
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,516 (change assumption)
    Mortgage ($4,214) + Fees ($8) + Taxes in 2025 ($294)


    Taxes:$3,528

    Elementary School: Lake Sybelia Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2514 TUSCARORA TRL, MAITLAND, FL 32751

    $759,00077 Days on yellowkey   MLS ID: O6380728

    REDUCED by $20,000 (2.6%) on 04/16/2026

    For Sale O6380728 - 2514 TUSCARORA TRL, MAITLAND, FL 32751 37 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 3000
       Built: 1971   Tax: $4,200 (2025)
    Community: Dommerich Hills 2 Nd Add
    Single Family


    Estimated Monthly Payment: $4,509 (change assumption)
    Mortgage ($4,159) + Taxes in 2025 ($350)


    Taxes:$4,200

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1140 S ORLANDO AVE #H-13, MAITLAND, FL 32751

    $449,00050 Days on yellowkey   MLS ID: O6387926

    0 Days Off yellowkey (back on 4/16/2026)

    For Sale O6387926 - 1140 S ORLANDO AVE #H-13, MAITLAND, FL 32751 34 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 816
       Built: 1964
    Monthly Fee: $546
       Tax: $3,419 (2025)
    Community: Lake Maitland Terrace Apts
    Condo


    Estimated Monthly Payment: $3,291 (change assumption)
    Mortgage ($2,460) + Fees ($546) + Taxes in 2025 ($285)


    Taxes:$3,419

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 105 TANGELO CT, MAITLAND, FL 32751

    $1,798,999142 Days on yellowkey   MLS ID: O6364116

    For Sale O6364116 - 105 TANGELO CT, MAITLAND, FL 32751 21 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3203
       Built: 2026   Tax: $6,909 (2024)
    Community: Hollieanna Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,433 (change assumption)
    Mortgage ($9,857) + Taxes in 2024 ($576)


    Taxes:$6,909

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 570 MANOR RD, MAITLAND, FL 32751

    $12,500,000373 Days on yellowkey   MLS ID: O6300040

    For Sale O6300040 - 570 MANOR RD, MAITLAND, FL 32751 99 photos

    Bed: 6   Bath: 8.5   Gar: 6
    Liv Area Sq Ft: 11668
       Built: 1996   Tax: $61,937 (2024)
    Community: Lake Maitland Manor
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $73,653 (change assumption)
    Mortgage ($68,491) + Taxes in 2024 ($5,161)


    Taxes:$61,937

    Elementary School: Lake Sybelia Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 350 NORTHWIND RD, MAITLAND, FL 32751

    $3,100,00085 Days on yellowkey   MLS ID: O6377888

    REDUCED by $199,000 (6.0%) on 04/11/2026

    For Sale O6377888 - 350 NORTHWIND RD, MAITLAND, FL 32751 54 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4819
       Built: 2019   Tax: $18,531 (2025)
    Community: Lake Maitland Owl Preserve
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $18,530 (change assumption)
    Mortgage ($16,986) + Taxes in 2025 ($1,544)


    Taxes:$18,531

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 103 WHITECAPS CIR, MAITLAND, FL 32751

    $2,000,00040 Days on yellowkey   MLS ID: O6382220

    0 Days Off yellowkey (back on 3/16/2026)

    For Sale O6382220 - 103 WHITECAPS CIR, MAITLAND, FL 32751 10 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3695
       Built: 2026   Tax: $3,439 (2024)
    Community: Hollieanna Shores 1St Add
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,245 (change assumption)
    Mortgage ($10,959) + Taxes in 2024 ($287)


    Taxes:$3,439

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 101 WHITECAPS CIR, MAITLAND, FL 32751

    $2,150,00074 Days on yellowkey   MLS ID: O6375435

    1 Days Off yellowkey (back on 2/16/2026)

    For Sale O6375435 - 101 WHITECAPS CIR, MAITLAND, FL 32751 15 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4004
       Built: 2026   Tax: $3,987 (2024)
    Community: Hollieanna Shores 1St Add
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,113 (change assumption)
    Mortgage ($11,781) + Taxes in 2024 ($332)


    Taxes:$3,987

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1695 E HORATIO AVE, MAITLAND, FL 32751

    $529,000345 Days on yellowkey   MLS ID: O6309191

    0 Days Off yellowkey (back on 4/6/2026)

    For Sale O6309191 - 1695 E HORATIO AVE, MAITLAND, FL 32751 19 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1939
       Built: 1959   Tax: $6,513 (2024)
    Community: Dommerich Estates 1St Add
    Single Family


    Estimated Monthly Payment: $3,441 (change assumption)
    Mortgage ($2,899) + Taxes in 2024 ($543)


    Taxes:$6,513

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1000 S ORLANDO AVE #B25, MAITLAND, FL 32751

    $335,00037 Days on yellowkey   MLS ID: O6391679

    For Sale O6391679 - 1000 S ORLANDO AVE #B25, MAITLAND, FL 32751 55 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 952
       Built: 1964   Tax: $2,559 (2025)
    Community: Maitland Harbour Apts
    Condo


    Estimated Monthly Payment: $2,049 (change assumption)
    Mortgage ($1,836) + Taxes in 2025 ($213)


    Taxes:$2,559

    Elementary School: Lake Sybelia Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1732 RIDGEWOOD AVE #S, MAITLAND, FL 32751

    $749,00081 Days on yellowkey   MLS ID: O6378854

    For Sale O6378854 - 1732 RIDGEWOOD AVE #S, MAITLAND, FL 32751 31 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2407
       Built: 2016
    Monthly Fee: $425
       Tax: $6,155 (2024)
    Community: Ridgewood Villas Condo
    Townhouse


    Estimated Monthly Payment: $5,042 (change assumption)
    Mortgage ($4,104) + Fees ($425) + Taxes in 2024 ($513)


    Taxes:$6,155

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 150 SENECA TRL, MAITLAND, FL 32751

    $745,00037 Days on yellowkey   MLS ID: O6389696

    1 Days Off yellowkey (back on 3/27/2026)

    For Sale O6389696 - 150 SENECA TRL, MAITLAND, FL 32751 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2221
       Built: 1957
    Monthly Fee: $8
       Tax: $10,543 (2025)
    Community: Dommerich Estates 1St Add
    Single Family


    Estimated Monthly Payment: $4,969 (change assumption)
    Mortgage ($4,082) + Fees ($8) + Taxes in 2025 ($879)


    Taxes:$10,543

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 109 MINNEHAHA CIR, MAITLAND, FL 32751

    $770,00094 Days on yellowkey   MLS ID: O6374874

    1 Days Off yellowkey (back on 4/2/2026)

    For Sale O6374874 - 109 MINNEHAHA CIR, MAITLAND, FL 32751 52 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2249
       Built: 1976
    Monthly Fee: $13
       Tax: $3,547 (2025)
    Community: Minnehaha Shores
    Single Family


    Estimated Monthly Payment: $4,528 (change assumption)
    Mortgage ($4,219) + Fees ($13) + Taxes in 2025 ($296)


    Taxes:$3,547

    Elementary School: Lake Sybelia Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1024 KEWANNEE TRL, MAITLAND, FL 32751

    $549,750270 Days on yellowkey   MLS ID: O6331331

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

    For Sale O6331331 - 1024 KEWANNEE TRL, MAITLAND, FL 32751 51 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 1845
       Built: 1965
    Monthly Fee: $8
       Tax: $8,403 (2024)
    Community: Dommerich Hills 3Rd Add
    Single Family


    Estimated Monthly Payment: $3,721 (change assumption)
    Mortgage ($3,012) + Fees ($8) + Taxes in 2024 ($700)


    Taxes:$8,403

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 535 PAWNEE TRL, MAITLAND, FL 32751

    $965,00045 Days on yellowkey   MLS ID: O6389344

    For Sale O6389344 - 535 PAWNEE TRL, MAITLAND, FL 32751 60 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2500
       Built: 1957   Tax: $10,356 (2024)
    Community: Dommerich Estates 1St Add
    Single Family


    Estimated Monthly Payment: $6,151 (change assumption)
    Mortgage ($5,288) + Taxes in 2024 ($863)


    Taxes:$10,356

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


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