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Homes for Sale Near Tuskawilla Middle in Winter Park - 70 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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  • 2676 BARBADOS DR, WINTER PARK, FL 32792

    $340,0004 Days on yellowkey   MLS ID: O6411958

    For Sale O6411958 - 2676 BARBADOS DR, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1743
       Built: 1978
    Monthly Fee: $98
       Tax: $4,131 (2025)
    Community: Windward Square Sec 2
    Townhouse


    Estimated Monthly Payment: $2,305 (change assumption)
    Mortgage ($1,863) + Fees ($98) + Taxes in 2025 ($344)


    Taxes:$4,131

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 4571 KAWILLA CREST PL, WINTER PARK, FL 32792

    $890,00032 Days on yellowkey   MLS ID: O6400672

    REDUCED by $9,999 (1.1%) on 05/18/2026

    For Sale O6400672 - 4571 KAWILLA CREST PL, WINTER PARK, FL 32792 35 photos

    Bed: 6   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3715
       Built: 1989
    Monthly Fee: $40
       Tax: $9,671 (2024)
    Community: Kawilla Crest
    Single Family


    Estimated Monthly Payment: $5,722 (change assumption)
    Mortgage ($4,877) + Fees ($40) + Taxes in 2024 ($806)


    Taxes:$9,671

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3159 GREENWOOD ST, WINTER PARK, FL 32792

    $290,00013 Days on yellowkey   MLS ID: G5112192

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

    For Sale G5112192 - 3159 GREENWOOD ST, WINTER PARK, FL 32792 43 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1241
       Built: 1984
    Monthly Fee: $57
       Tax: $1,085 (2024)
    Community: Villas Of Casselberry Ph 2
    Townhouse


    Estimated Monthly Payment: $1,736 (change assumption)
    Mortgage ($1,589) + Fees ($57) + Taxes in 2024 ($90)


    Taxes:$1,085

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1832 E CHERYL DR, WINTER PARK, FL 32792

    $439,99539 Days on yellowkey   MLS ID: O6402209

    0 Days Off yellowkey (back on 4/30/2026)

    INCREASED by $10,000 (2.3%) on 04/27/2026

    For Sale O6402209 - 1832 E CHERYL DR, WINTER PARK, FL 32792 22 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1808
       Built: 1983
    Monthly Fee: $8
       Tax: $1,847 (2024)
    Community: Carolyn Estates
    Single Family


    Estimated Monthly Payment: $2,573 (change assumption)
    Mortgage ($2,411) + Fees ($8) + Taxes in 2024 ($154)


    Taxes:$1,847

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 7120 BROOKSIDE TRL, WINTER PARK, FL 32792

    $510,00040 Days on yellowkey   MLS ID: O6398534

    0 Days Off yellowkey (back on 4/30/2026)

    For Sale O6398534 - 7120 BROOKSIDE TRL, WINTER PARK, FL 32792 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1753
       Built: 1976   Tax: $3,098 (2025)
    Community: Replat Of Lts 1 2 & 3 Brookside Sub
    Single Family


    Estimated Monthly Payment: $3,053 (change assumption)
    Mortgage ($2,794) + Taxes in 2025 ($258)


    Taxes:$3,098

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 4190 BEAR GULLY RD, WINTER PARK, FL 32792

    $499,900147 Days on yellowkey   MLS ID: O6371014

    REDUCED by $25,000 (4.8%) on 05/29/2026

    For Sale O6371014 - 4190 BEAR GULLY RD, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2058
       Built: 2003
    Monthly Fee: $52
       Tax: $5,630 (2024)
    Community: Bear Gully Forest
    Single Family


    Estimated Monthly Payment: $3,260 (change assumption)
    Mortgage ($2,739) + Fees ($52) + Taxes in 2024 ($469)


    Taxes:$5,630

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1052 MANCHESTER CIR, WINTER PARK, FL 32792

    $460,000129 Days on yellowkey   MLS ID: O6376260

    REDUCED by $10,000 (2.1%) on 05/28/2026

    For Sale O6376260 - 1052 MANCHESTER CIR, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1703
       Built: 1983   Tax: $5,216 (2025)
    Community: Howell Estates 1St Add
    Single Family


    Estimated Monthly Payment: $2,955 (change assumption)
    Mortgage ($2,520) + Taxes in 2025 ($435)


    Taxes:$5,216

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 3440 ALLSTON LN, WINTER PARK, FL 32792

    $405,00037 Days on yellowkey   MLS ID: O6401731

    REDUCED by $15,000 (3.6%) on 05/26/2026

    For Sale O6401731 - 3440 ALLSTON LN, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1533
       Built: 1993
    Monthly Fee: $65
       Tax: $1,364 (2024)
    Community: Villas Of Casselberry Ph 4
    Single Family


    Estimated Monthly Payment: $2,398 (change assumption)
    Mortgage ($2,219) + Fees ($65) + Taxes in 2024 ($114)


    Taxes:$1,364

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1593 LAWNDALE CIR, WINTER PARK, FL 32792

    $480,00018 Days on yellowkey   MLS ID: O6402014

    REDUCED by $10,000 (2.0%) on 05/27/2026

    For Sale O6402014 - 1593 LAWNDALE CIR, WINTER PARK, FL 32792 47 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1808
       Built: 1984
    Monthly Fee: $49
       Tax: $5,010 (2025)
    Community: Country Lane
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,097 (change assumption)
    Mortgage ($2,630) + Fees ($49) + Taxes in 2025 ($418)


    Taxes:$5,010

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 4348 STEED TER, WINTER PARK, FL 32792

    $824,00025 Days on yellowkey   MLS ID: O6406018

    0 Days Off yellowkey (back on 5/26/2026)

    For Sale O6406018 - 4348 STEED TER, WINTER PARK, FL 32792 74 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3040
       Built: 1989
    Monthly Fee: $29
       Tax: $3,652 (2024)
    Community: Kings Cove
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,848 (change assumption)
    Mortgage ($4,515) + Fees ($29) + Taxes in 2024 ($304)


    Taxes:$3,652

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 7706 COUNTRY PL #7706, WINTER PARK, FL 32792

    $225,000456 Days on yellowkey   MLS ID: O6285927

    2 Days Off yellowkey (back on 5/26/2026)

    For Sale O6285927 - 7706 COUNTRY PL #7706, WINTER PARK, FL 32792 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1230
       Built: 1984   Tax: $2,744 (2024)
    Community: Goldenrod Villas Condo
    Condo


    Estimated Monthly Payment: $1,462 (change assumption)
    Mortgage ($1,233) + Taxes in 2024 ($229)


    Taxes:$2,744

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1871 CASSELWOOD ST, WINTER PARK, FL 32792

    $419,90031 Days on yellowkey   MLS ID: O6404306

    0 Days Off yellowkey (back on 5/26/2026)

    REDUCED by $5,000 (1.2%) on 05/12/2026

    For Sale O6404306 - 1871 CASSELWOOD ST, WINTER PARK, FL 32792 37 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1616
       Built: 1988
    Monthly Fee: $39
       Tax: $1,223 (2024)
    Community: Villas Of Casselberry Ph 2
    Townhouse


    Estimated Monthly Payment: $2,442 (change assumption)
    Mortgage ($2,301) + Fees ($39) + Taxes in 2024 ($102)


    Taxes:$1,223

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1174 WILDMEADOW RUN, WINTER PARK, FL 32792

    $625,00063 Days on yellowkey   MLS ID: O6394974

    0 Days Off yellowkey (back on 5/24/2026)

    REDUCED by $24,900 (3.8%) on 05/09/2026

    For Sale O6394974 - 1174 WILDMEADOW RUN, WINTER PARK, FL 32792 54 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2021
    Monthly Fee: $170
       Tax: $6,672 (2025)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,151 (change assumption)
    Mortgage ($3,425) + Fees ($170) + Taxes in 2025 ($556)


    Taxes:$6,672

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1540 FLORENTINO LN, WINTER PARK, FL 32792

    $335,00010 Days on yellowkey   MLS ID: O6408841

    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: $2,456 (change assumption)
    Mortgage ($1,836) + 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


  • 5210 OHIO ST, WINTER PARK, FL 32792

    $445,00018 Days on yellowkey   MLS ID: O6408143

    0 Days Off yellowkey (back on 5/23/2026)

    For Sale O6408143 - 5210 OHIO ST, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1946
       Built: 1973   Tax: $4,869 (2024)
    Community: Suburban Homes Sec 2
    Single Family


    Estimated Monthly Payment: $2,844 (change assumption)
    Mortgage ($2,438) + Taxes in 2024 ($406)


    Taxes:$4,869

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2087 LAURELWOOD WAY, WINTER PARK, FL 32792

    $624,000259 Days on yellowkey   MLS ID: O6344482

    REDUCED by $35,000 (5.3%) on 05/06/2026

    For Sale O6344482 - 2087 LAURELWOOD WAY, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1920
       Built: 2019
    Monthly Fee: $236
       Tax: $4,680 (2024)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,045 (change assumption)
    Mortgage ($3,419) + Fees ($236) + Taxes in 2024 ($390)


    Taxes:$4,680

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1617 CHILEAN LN, WINTER PARK, FL 32792

    $367,500138 Days on yellowkey   MLS ID: O6373026

    1 Days Off yellowkey (back on 5/15/2026)

    REDUCED by $2,400 (0.6%) on 04/30/2026

    For Sale O6373026 - 1617 CHILEAN LN, WINTER PARK, FL 32792 40 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1359
       Built: 1960   Tax: $3,432 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,300 (change assumption)
    Mortgage ($2,014) + Taxes in 2024 ($286)


    Taxes:$3,432

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2707 TIERRA CIR, WINTER PARK, FL 32792

    $495,00034 Days on yellowkey   MLS ID: O6398979

    2 Days Off yellowkey (back on 5/22/2026)

    For Sale O6398979 - 2707 TIERRA CIR, WINTER PARK, FL 32792 42 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1710
       Built: 1970   Tax: $3,237 (2025)
    Community: Casa Aloma
    Single Family


    Estimated Monthly Payment: $2,982 (change assumption)
    Mortgage ($2,712) + Taxes in 2025 ($270)


    Taxes:$3,237

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 4469 OLD BEAR RUN, WINTER PARK, FL 32792

    $1,799,999113 Days on yellowkey   MLS ID: O6375415

    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


  • 7771 COUNTRY PL #7, WINTER PARK, FL 32792

    $219,900182 Days on yellowkey   MLS ID: O6364384

    For Sale O6364384 - 7771 COUNTRY PL #7, WINTER PARK, FL 32792 15 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1230
       Built: 1987
    Monthly Fee: $310
       Tax: $2,950 (2024)
    Community: Goldenrod Villas Condo
    Condo


    Estimated Monthly Payment: $1,761 (change assumption)
    Mortgage ($1,205) + Fees ($310) + Taxes in 2024 ($246)


    Taxes:$2,950

    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.