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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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  • 220 ADAMS DR, MAITLAND, FL 32751

    $1,995,00038 Days on yellowkey   MLS ID: O6413737

    For Sale O6413737 - 220 ADAMS DR, MAITLAND, FL 32751 47 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3005
       Built: 1977   Tax: $15,563 (2025)
    Community: Kings Row
    Spa: No

    Single Family


    Estimated Monthly Payment: $12,228 (change assumption)
    Mortgage ($10,931) + Taxes in 2025 ($1,297)


    Taxes:$15,563

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2112 CHIPPEWA TRL, MAITLAND, FL 32751

    $949,000101 Days on yellowkey   MLS ID: O6394702

    REDUCED by $16,000 (1.7%) on 06/29/2026

    For Sale O6394702 - 2112 CHIPPEWA TRL, MAITLAND, FL 32751 63 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2407
       Built: 1961   Tax: $2,725 (2025)
    Community: Dommerich Hills
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,427 (change assumption)
    Mortgage ($5,200) + Taxes in 2025 ($227)


    Taxes:$2,725

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 791 SEQUOIA TRL, MAITLAND, FL 32751

    $939,000312 Days on yellowkey   MLS ID: O6340919

    REDUCED by $56,000 (5.6%) on 06/28/2026

    For Sale O6340919 - 791 SEQUOIA TRL, MAITLAND, FL 32751 50 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4144
       Built: 1961   Tax: $4,128 (2024)
    Community: Dommerich Woods
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,489 (change assumption)
    Mortgage ($5,145) + Taxes in 2024 ($344)


    Taxes:$4,128

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 204 QUAYSIDE CIR #504, MAITLAND, FL 32751

    $458,500141 Days on yellowkey   MLS ID: O6383019

    0 Days Off yellowkey (back on 6/24/2026)

    REDUCED by $500 (0.1%) on 05/02/2026

    For Sale O6383019 - 204 QUAYSIDE CIR #504, MAITLAND, FL 32751 33 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1270
       Built: 1984
    Monthly Fee: $590
       Tax: $6,851 (2024)
    Community: Moorings On Lake Maitland Condo
    Condo


    Estimated Monthly Payment: $3,673 (change assumption)
    Mortgage ($2,512) + Fees ($590) + Taxes in 2024 ($571)


    Taxes:$6,851

    Elementary School: Lake Sybelia Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1511 E HORATIO AVE, MAITLAND, FL 32751

    $719,00082 Days on yellowkey   MLS ID: O6401235

    For Sale O6401235 - 1511 E HORATIO AVE, MAITLAND, FL 32751 31 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2676
       Built: 1957   Tax: $6,013 (2025)
    Community: Minnehaha Shores
    Single Family


    Estimated Monthly Payment: $4,441 (change assumption)
    Mortgage ($3,940) + Taxes in 2025 ($501)


    Taxes:$6,013

    Elementary School: Lake Sybelia Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 766 TERRA PL, MAITLAND, FL 32751

    $1,149,90041 Days on yellowkey   MLS ID: O6411881

    2 Days Off yellowkey (back on 6/19/2026)

    For Sale O6411881 - 766 TERRA PL, MAITLAND, FL 32751 37 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3040
       Built: 1986   Tax: $8,473 (2025)
    Community: Terra Place
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,007 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($706)


    Taxes:$8,473

    Elementary School: Lake Sybelia Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 570 DOMMERICH DR, MAITLAND, FL 32751

    $795,000136 Days on yellowkey   MLS ID: O6377363

    0 Days Off yellowkey (back on 6/17/2026)

    REDUCED by $80,000 (9.1%) on 06/13/2026

    For Sale O6377363 - 570 DOMMERICH DR, MAITLAND, FL 32751 65 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2956
       Built: 1963   Tax: $5,529 (2024)
    Community: Dommerich Estates 2Nd Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,817 (change assumption)
    Mortgage ($4,356) + Taxes in 2024 ($461)


    Taxes:$5,529

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 908 VERSAILLES CIR, MAITLAND, FL 32751

    $899,00037 Days on yellowkey   MLS ID: O6413200

    2 Days Off yellowkey (back on 6/17/2026)

    For Sale O6413200 - 908 VERSAILLES CIR, MAITLAND, FL 32751 53 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2151
       Built: 1979   Tax: $11,362 (2025)
    Community: Versailles
    Single Family


    Estimated Monthly Payment: $5,873 (change assumption)
    Mortgage ($4,926) + Taxes in 2025 ($947)


    Taxes:$11,362

    Elementary School: Lake Sybelia Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1781 TONTO TRL, MAITLAND, FL 32751

    $600,00030 Days on yellowkey   MLS ID: O6414036

    1 Days Off yellowkey (back on 6/17/2026)

    For Sale O6414036 - 1781 TONTO TRL, MAITLAND, FL 32751 45 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1880
       Built: 1968
    Monthly Fee: $17
       Tax: $2,220 (2025)
    Community: Dommerich Estates 1St Add
    Single Family


    Estimated Monthly Payment: $3,490 (change assumption)
    Mortgage ($3,288) + Fees ($17) + Taxes in 2025 ($185)


    Taxes:$2,220

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 204 QUAYSIDE CIR #201, MAITLAND, FL 32751

    $467,00086 Days on yellowkey   MLS ID: O6394791

    REDUCED by $15,000 (3.1%) on 06/16/2026

    For Sale O6394791 - 204 QUAYSIDE CIR #201, MAITLAND, FL 32751 33 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1270
       Built: 1984   Tax: $6,566 (2025)
    Community: Moorings On Lake Maitland Condo
    Condo


    Estimated Monthly Payment: $3,106 (change assumption)
    Mortgage ($2,559) + Taxes in 2025 ($547)


    Taxes:$6,566

    Elementary School: Lake Sybelia Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1140 S ORLANDO AVE #I14, MAITLAND, FL 32751

    $325,00049 Days on yellowkey   MLS ID: O6410595

    For Sale O6410595 - 1140 S ORLANDO AVE #I14, MAITLAND, FL 32751 37 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 816
       Built: 1971
    Monthly Fee: $535
       Tax: $2,086 (2026)
    Community: Lake Maitland Terr
    Condo


    Estimated Monthly Payment: $2,490 (change assumption)
    Mortgage ($1,781) + Fees ($535) + Taxes in 2026 ($174)


    Taxes:$2,086

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 204 QUAYSIDE CIR #304, MAITLAND, FL 32751

    $395,000295 Days on yellowkey   MLS ID: O6345967

    REDUCED by $20,000 (4.8%) on 06/03/2026

    For Sale O6345967 - 204 QUAYSIDE CIR #304, MAITLAND, FL 32751 21 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1270
       Built: 1984   Tax: $1,928 (2024)
    Community: Moorings On Lake Maitland Condo
    Condo


    Estimated Monthly Payment: $2,325 (change assumption)
    Mortgage ($2,164) + Taxes in 2024 ($161)


    Taxes:$1,928

    Elementary School: Lake Sybelia Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 105 TANGELO CT, MAITLAND, FL 32751

    $1,798,999220 Days on yellowkey   MLS ID: O6364116

    2 Days Off yellowkey (back on 5/25/2026)

    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: No

    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


  • 1100 S ORLANDO AVE #306, MAITLAND, FL 32751

    $649,000113 Days on yellowkey   MLS ID: O6392583

    For Sale O6392583 - 1100 S ORLANDO AVE #306, MAITLAND, FL 32751 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1125
       Built: 1973
    Monthly Fee: $618
       Tax: $4,561 (2025)
    Community: West Cove Condo
    Condo


    Estimated Monthly Payment: $4,554 (change assumption)
    Mortgage ($3,556) + Fees ($618) + Taxes in 2025 ($380)


    Taxes:$4,561

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 570 MANOR RD, MAITLAND, FL 32751

    $12,500,000451 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


  • 103 WHITECAPS CIR, MAITLAND, FL 32751

    $2,000,000118 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

    $2,150,000152 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


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