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Homes for Sale Near Tuskawilla Middle in Winter Park - 59 homes

Tuskawilla Middle is an Middle School in Seminole County. Find homes for sale close to Tuskawilla Middle. Our REALTORS® can assist you in your search for Tuskawilla Middle, Winter Park nearby homes.

Location: Winter Park

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  • 1605 PURITAN AVE, WINTER PARK, FL 32792

    $399,00028 Days on yellowkey   MLS ID: O6417098

    For Sale O6417098 - 1605 PURITAN AVE, WINTER PARK, FL 32792 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1285
       Built: 1963   Tax: $3,605 (2025)
    Community: Eastbrook Sub Unit 06 2Nd Rep
    Single Family


    Estimated Monthly Payment: $2,487 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($300)


    Taxes:$3,605

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 5340 N LAKE BURKETT LN, WINTER PARK, FL 32792

    $469,90040 Days on yellowkey   MLS ID: O6413717

    REDUCED by $5,100 (1.1%) on 07/14/2026

    For Sale O6413717 - 5340 N LAKE BURKETT LN, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1746
       Built: 1994
    Monthly Fee: $76
       Tax: $1,591 (2025)
    Community: Trinity Bay Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,783 (change assumption)
    Mortgage ($2,575) + Fees ($76) + Taxes in 2025 ($133)


    Taxes:$1,591

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1914 BONANZA CT, WINTER PARK, FL 32792

    $429,99961 Days on yellowkey   MLS ID: O6408461

    For Sale O6408461 - 1914 BONANZA CT, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1727
       Built: 1968   Tax: $4,497 (2025)
    Community: Eastbrook Sub Unit 13
    Single Family


    Estimated Monthly Payment: $2,731 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($375)


    Taxes:$4,497

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1564 LAWNDALE CIR, WINTER PARK, FL 32792

    $450,00022 Days on yellowkey   MLS ID: O6418817

    For Sale O6418817 - 1564 LAWNDALE CIR, WINTER PARK, FL 32792 45 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1980
       Built: 1985
    Monthly Fee: $46
       Tax: $3,124 (2025)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $2,772 (change assumption)
    Mortgage ($2,466) + Fees ($46) + Taxes in 2025 ($260)


    Taxes:$3,124

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1418 LONE FEATHER TRL, WINTER PARK, FL 32792

    $750,00029 Days on yellowkey   MLS ID: O6417341

    For Sale O6417341 - 1418 LONE FEATHER TRL, WINTER PARK, FL 32792 46 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2197
       Built: 2022
    Monthly Fee: $244
       Tax: $6,224 (2025)
    Community: Landings At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,872 (change assumption)
    Mortgage ($4,109) + Fees ($244) + Taxes in 2025 ($519)


    Taxes:$6,224

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 4469 OLD BEAR RUN, WINTER PARK, FL 32792

    $1,799,999156 Days on yellowkey   MLS ID: O6375415

    0 Days Off yellowkey (back on 7/14/2026)

    REDUCED by $50,001 (2.7%) on 05/22/2026

    For Sale O6375415 - 4469 OLD BEAR RUN, WINTER PARK, FL 32792 77 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4288
       Built: 1978   Tax: $10,710 (2024)
    Community: Pervis Survey For R E
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,755 (change assumption)
    Mortgage ($9,863) + Taxes in 2024 ($893)


    Taxes:$10,710

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1320 GLADIOLAS DR, WINTER PARK, FL 32792

    $475,00047 Days on yellowkey   MLS ID: O6412139

    REDUCED by $5,000 (1.0%) on 06/15/2026

    For Sale O6412139 - 1320 GLADIOLAS DR, WINTER PARK, FL 32792 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1624
       Built: 1983   Tax: $1,380 (2025)
    Community: Garden Lake Estates Unit 3
    Single Family


    Estimated Monthly Payment: $2,718 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($115)


    Taxes:$1,380

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2087 LAURELWOOD WAY, WINTER PARK, FL 32792

    $625,00034 Days on yellowkey   MLS ID: O6415387

    For Sale O6415387 - 2087 LAURELWOOD WAY, WINTER PARK, FL 32792 48 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1920
       Built: 2019
    Monthly Fee: $244
       Tax: $4,970 (2025)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,083 (change assumption)
    Mortgage ($3,425) + Fees ($244) + Taxes in 2025 ($414)


    Taxes:$4,970

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1840 ASTER DR, WINTER PARK, FL 32792

    $419,90044 Days on yellowkey   MLS ID: O6412364

    REDUCED by $10,090 (2.3%) on 07/09/2026

    For Sale O6412364 - 1840 ASTER DR, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1667
       Built: 1978   Tax: $864 (2025)
    Community: Garden Lake Estates Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,373 (change assumption)
    Mortgage ($2,301) + Taxes in 2025 ($72)


    Taxes:$864

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2651 CAYMAN WAY, WINTER PARK, FL 32792

    $255,000176 Days on yellowkey   MLS ID: O6375086

    For Sale O6375086 - 2651 CAYMAN WAY, WINTER PARK, FL 32792 28 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1020
       Built: 1978
    Monthly Fee: $99
       Tax: $3,553 (2024)
    Community: Windward Square Sec 2
    Townhouse


    Estimated Monthly Payment: $1,792 (change assumption)
    Mortgage ($1,397) + Fees ($99) + Taxes in 2024 ($296)


    Taxes:$3,553

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792

    $245,00086 Days on yellowkey   MLS ID: O6400674

    REDUCED by $5,000 (2.0%) on 07/11/2026

    For Sale O6400674 - 2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792 32 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1295
       Built: 1985
    Monthly Fee: $499
       Tax: $2,560 (2024)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $2,055 (change assumption)
    Mortgage ($1,342) + Fees ($499) + Taxes in 2024 ($213)


    Taxes:$2,560

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3463 ARNEL DR, WINTER PARK, FL 32792

    $414,900120 Days on yellowkey   MLS ID: O6390301

    REDUCED by $5,000 (1.2%) on 07/02/2026

    For Sale O6390301 - 3463 ARNEL DR, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 1967   Tax: $4,648 (2024)
    Community: Eastbrook Sub Unit 11
    Single Family


    Estimated Monthly Payment: $2,661 (change assumption)
    Mortgage ($2,273) + Taxes in 2024 ($387)


    Taxes:$4,648

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1956 JAPONICA RD, WINTER PARK, FL 32792

    $549,00014 Days on yellowkey   MLS ID: O6421731

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6421731 - 1956 JAPONICA RD, WINTER PARK, FL 32792 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1923
       Built: 1972
    Monthly Fee: $2
       Tax: $4,849 (2025)
    Community: Winter Woods
    Single Family


    Estimated Monthly Payment: $3,414 (change assumption)
    Mortgage ($3,008) + Fees ($2) + Taxes in 2025 ($404)


    Taxes:$4,849

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 5781 SHALE CT, WINTER PARK, FL 32792

    $320,0009 Days on yellowkey   MLS ID: O6422583

    For Sale O6422583 - 5781 SHALE CT, WINTER PARK, FL 32792 46 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1086
       Built: 1985
    Monthly Fee: $69
       Tax: $2,096 (2025)
    Community: Aloma Park
    Spa: No

    Half Duplex


    Estimated Monthly Payment: $1,997 (change assumption)
    Mortgage ($1,753) + Fees ($69) + Taxes in 2025 ($175)


    Taxes:$2,096

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1189 LAZY HOLLOW PL, WINTER PARK, FL 32792

    $450,00012 Days on yellowkey   MLS ID: O6422142

    For Sale O6422142 - 1189 LAZY HOLLOW PL, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1525
       Built: 1984   Tax: $2,369 (2025)
    Community: Springview
    Single Family


    Estimated Monthly Payment: $2,663 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($197)


    Taxes:$2,369

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2521 GALLIANO CIR, WINTER PARK, FL 32792

    $360,00021 Days on yellowkey   MLS ID: O6419329

    For Sale O6419329 - 2521 GALLIANO CIR, WINTER PARK, FL 32792 27 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1682
       Built: 2003
    Monthly Fee: $175
       Tax: $4,532 (2025)
    Community: Vistas At Lake Howell
    Townhouse


    Estimated Monthly Payment: $2,525 (change assumption)
    Mortgage ($1,973) + Fees ($175) + Taxes in 2025 ($378)


    Taxes:$4,532

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 283 LEWFIELD CIR #283, WINTER PARK, FL 32792

    $142,50013 Days on yellowkey   MLS ID: O6420915

    1 Days Off yellowkey (back on 7/12/2026)

    For Sale O6420915 - 283 LEWFIELD CIR #283, WINTER PARK, FL 32792 23 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973   Tax: $1,729 (2025)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $925 (change assumption)
    Mortgage ($781) + Taxes in 2025 ($144)


    Taxes:$1,729

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1540 FLORENTINO LN, WINTER PARK, FL 32792

    $315,00053 Days on yellowkey   MLS ID: O6408841

    REDUCED by $20,000 (6.0%) on 07/12/2026

    For Sale O6408841 - 1540 FLORENTINO LN, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1682
       Built: 2004
    Monthly Fee: $175
       Tax: $5,340 (2025)
    Community: Vistas At Lake Howell
    Townhouse


    Estimated Monthly Payment: $2,346 (change assumption)
    Mortgage ($1,726) + Fees ($175) + Taxes in 2025 ($445)


    Taxes:$5,340

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2008 HOUNDSLAKE DR, WINTER PARK, FL 32792

    $515,00030 Days on yellowkey   MLS ID: O6414369

    For Sale O6414369 - 2008 HOUNDSLAKE DR, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2250
       Built: 1980   Tax: $5,253 (2025)
    Community: Cedar Ridge
    Single Family


    Estimated Monthly Payment: $3,260 (change assumption)
    Mortgage ($2,822) + Taxes in 2025 ($438)


    Taxes:$5,253

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1090 WILDMEADOW RUN, WINTER PARK, FL 32792

    $835,000110 Days on yellowkey   MLS ID: O6394208

    REDUCED by $10,000 (1.2%) on 06/02/2026

    For Sale O6394208 - 1090 WILDMEADOW RUN, WINTER PARK, FL 32792 37 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2589
       Built: 2021
    Monthly Fee: $243
       Tax: $6,258 (2024)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,340 (change assumption)
    Mortgage ($4,575) + Fees ($243) + Taxes in 2024 ($521)


    Taxes:$6,258

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


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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.