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Homes for Sale Near Winter Springs High in Casselberry - 23 homes

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

Location: Casselberry

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  • 725 LEGACY PARK DR, CASSELBERRY, FL 32707

    $545,000Listed 06/12/2026 11:38AM   MLS ID: O6415376

    For Sale O6415376 - 725 LEGACY PARK DR, CASSELBERRY, FL 32707 40 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2548
       Built: 2006
    Monthly Fee: $231
       Tax: $3,667 (2025)
    Community: Legacy Park Residential Ph 1 & 2 A Rep
    Single Family


    Estimated Monthly Payment: $3,523 (change assumption)
    Mortgage ($2,986) + Fees ($231) + Taxes in 2025 ($306)


    Taxes:$3,667

    Elementary School: Sterling Park Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: South Seminole Middle


  • 1637 ORRINGTON PAYNE PL, CASSELBERRY, FL 32707

    $284,90078 Days on yellowkey   MLS ID: O6393548

    REDUCED by $10,000 (3.4%) on 04/25/2026

    For Sale O6393548 - 1637 ORRINGTON PAYNE PL, CASSELBERRY, FL 32707 32 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1409
       Built: 2010
    Monthly Fee: $184
       Tax: $3,618 (2025)
    Community: The Parke At Hanover Place
    Townhouse


    Estimated Monthly Payment: $2,047 (change assumption)
    Mortgage ($1,561) + Fees ($184) + Taxes in 2025 ($302)


    Taxes:$3,618

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Milwee Middle


  • 1054 CRYSTAL BOWL CIR, CASSELBERRY, FL 32707

    $650,00040 Days on yellowkey   MLS ID: O6404542

    For Sale O6404542 - 1054 CRYSTAL BOWL CIR, CASSELBERRY, FL 32707 61 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3014
       Built: 2003   Tax: $6,187 (2025)
    Community: Crystal Bowl Add
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,077 (change assumption)
    Mortgage ($3,562) + Taxes in 2025 ($516)


    Taxes:$6,187

    Elementary School: Casselberry Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: South Seminole Middle


  • 421 BRIDLE PATH, CASSELBERRY, FL 32707

    $474,9009 Days on yellowkey   MLS ID: O6412740

    0 Days Off yellowkey (back on 6/10/2026)

    For Sale O6412740 - 421 BRIDLE PATH, CASSELBERRY, FL 32707 42 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1873
       Built: 1980   Tax: $5,077 (2025)
    Community: Wyndham Woods Ph 1 Rep
    Single Family


    Estimated Monthly Payment: $3,025 (change assumption)
    Mortgage ($2,602) + Taxes in 2025 ($423)


    Taxes:$5,077

    Elementary School: Casselberry Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: South Seminole Middle


  • 956 OSCEOLA TRL, CASSELBERRY, FL 32707

    $253,90024 Days on yellowkey   MLS ID: O6407211

    REDUCED by $7,000 (2.7%) on 06/10/2026

    For Sale O6407211 - 956 OSCEOLA TRL, CASSELBERRY, FL 32707 32 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1012
       Built: 1972   Tax: $3,631 (2024)
    Community: Colonnades 3Rd Sec
    Single Family


    Estimated Monthly Payment: $1,694 (change assumption)
    Mortgage ($1,391) + Taxes in 2024 ($303)


    Taxes:$3,631

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Milwee Middle


  • 2353 GRATIA PL, CASSELBERRY, FL 32707

    $525,00027 Days on yellowkey   MLS ID: O6406654

    0 Days Off yellowkey (back on 6/10/2026)

    For Sale O6406654 - 2353 GRATIA PL, CASSELBERRY, FL 32707 56 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2110
       Built: 2017
    Monthly Fee: $150
       Tax: $7,233 (2025)
    Community: Reserve At Legacy Park
    Single Family


    Estimated Monthly Payment: $3,629 (change assumption)
    Mortgage ($2,877) + Fees ($150) + Taxes in 2025 ($603)


    Taxes:$7,233

    Elementary School: Sterling Park Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: South Seminole Middle


  • 1289 ASH TREE CV, CASSELBERRY, FL 32707

    $539,000206 Days on yellowkey   MLS ID: S5138860

    For Sale S5138860 - 1289 ASH TREE CV, CASSELBERRY, FL 32707 34 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2412
       Built: 2025
    Monthly Fee: $140
       Tax: $1,510 (2024)
    Community: Greenville Commons
    Single Family


    Estimated Monthly Payment: $3,219 (change assumption)
    Mortgage ($2,953) + Fees ($140) + Taxes in 2024 ($126)


    Taxes:$1,510

    Elementary School: Sterling Park Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 537 SUNBRANCH LN, CASSELBERRY, FL 32707

    $385,00064 Days on yellowkey   MLS ID: O6397366

    For Sale O6397366 - 537 SUNBRANCH LN, CASSELBERRY, FL 32707 30 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1847
       Built: 2021
    Monthly Fee: $144
       Tax: $4,897 (2025)
    Community: Legacy At Sunbranch
    Single Family


    Estimated Monthly Payment: $2,662 (change assumption)
    Mortgage ($2,110) + Fees ($144) + Taxes in 2025 ($408)


    Taxes:$4,897

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Milwee Middle


  • 509 SUNBRANCH LN, CASSELBERRY, FL 32707

    $399,00064 Days on yellowkey   MLS ID: O6397363

    For Sale O6397363 - 509 SUNBRANCH LN, CASSELBERRY, FL 32707 34 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1996
       Built: 2021
    Monthly Fee: $144
       Tax: $5,677 (2025)
    Community: Legacy At Sunbranch
    Single Family


    Estimated Monthly Payment: $2,803 (change assumption)
    Mortgage ($2,186) + Fees ($144) + Taxes in 2025 ($473)


    Taxes:$5,677

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Milwee Middle


  • 1801 GRAND RUE DR, CASSELBERRY, FL 32707

    $349,90029 Days on yellowkey   MLS ID: O6407878

    REDUCED by $19,100 (5.2%) on 05/26/2026

    For Sale O6407878 - 1801 GRAND RUE DR, CASSELBERRY, FL 32707 52 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1620
       Built: 2011
    Monthly Fee: $295
       Tax: $5,215 (2025)
    Community: Legacy Park Residential Townhome A Rep
    Townhouse


    Estimated Monthly Payment: $2,647 (change assumption)
    Mortgage ($1,917) + Fees ($295) + Taxes in 2025 ($435)


    Taxes:$5,215

    Elementary School: Sterling Park Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: South Seminole Middle


  • 217 COLONY DR, CASSELBERRY, FL 32707

    $245,00061 Days on yellowkey   MLS ID: O6398512

    REDUCED by $5,000 (2.0%) on 06/04/2026

    For Sale O6398512 - 217 COLONY DR, CASSELBERRY, FL 32707 27 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1000
       Built: 1972   Tax: $147 (2024)
    Community: Colonnades 3Rd Sec
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,355 (change assumption)
    Mortgage ($1,342) + Taxes in 2024 ($12)


    Taxes:$147

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Milwee Middle


  • 800 DIANE CIR, CASSELBERRY, FL 32707

    $344,900222 Days on yellowkey   MLS ID: O6357379

    For Sale O6357379 - 800 DIANE CIR, CASSELBERRY, FL 32707 25 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1287
       Built: 1972   Tax: $3,777 (2025)
    Community: Lake Kathryn Woods
    Single Family


    Estimated Monthly Payment: $2,205 (change assumption)
    Mortgage ($1,890) + Taxes in 2025 ($315)


    Taxes:$3,777

    Elementary School: Casselberry Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: South Seminole Middle


  • 1375 LAKE DR, CASSELBERRY, FL 32707

    $379,000100 Days on yellowkey   MLS ID: O6387594

    REDUCED by $1,000 (0.3%) on 04/11/2026

    For Sale O6387594 - 1375 LAKE DR, CASSELBERRY, FL 32707 60 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2083
       Built: 1950   Tax: $3,294 (2024)
    Community: Duck Pond Add To Casselberry
    Single Family


    Estimated Monthly Payment: $2,351 (change assumption)
    Mortgage ($2,077) + Taxes in 2024 ($274)


    Taxes:$3,294

    Elementary School: Sterling Park Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 1262 SEMINOLA BLVD, CASSELBERRY, FL 32707

    $354,00048 Days on yellowkey   MLS ID: O6400917

    REDUCED by $15,000 (4.1%) on 06/01/2026

    For Sale O6400917 - 1262 SEMINOLA BLVD, CASSELBERRY, FL 32707 20 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 936
       Built: 1958   Tax: $1,951 (2024)
    Community: Sportsmans Paradise
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,102 (change assumption)
    Mortgage ($1,940) + Taxes in 2024 ($163)


    Taxes:$1,951

    Elementary School: Casselberry Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 1828 GRAND RUE DR, CASSELBERRY, FL 32707

    $380,00045 Days on yellowkey   MLS ID: O6403365

    0 Days Off yellowkey (back on 5/28/2026)

    For Sale O6403365 - 1828 GRAND RUE DR, CASSELBERRY, FL 32707 35 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2210
       Built: 2008
    Monthly Fee: $203
       Tax: $6,143 (2025)
    Community: Legacy Park Residential Townhome A Rep
    Townhouse


    Estimated Monthly Payment: $2,797 (change assumption)
    Mortgage ($2,082) + Fees ($203) + Taxes in 2025 ($512)


    Taxes:$6,143

    Elementary School: Sterling Park Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: South Seminole Middle


  • 432 E ST #432, CASSELBERRY, FL 32707

    $142,50015 Days on yellowkey   MLS ID: G5112993

    For Sale G5112993 - 432 E ST #432, CASSELBERRY, FL 32707 32 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 690
       Built: 1966
    Monthly Fee: $370
       Tax: $2,309 (2025)
    Community: Lake Kathryn Village
    Spa: No

    Condo


    Estimated Monthly Payment: $1,343 (change assumption)
    Mortgage ($781) + Fees ($370) + Taxes in 2025 ($192)


    Taxes:$2,309

    Elementary School: Casselberry Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Milwee Middle


  • 406 CAPRON ASH LOOP, CASSELBERRY, FL 32707

    $435,000106 Days on yellowkey   MLS ID: O6384763

    0 Days Off yellowkey (back on 5/27/2026)

    REDUCED by $15,000 (3.3%) on 05/14/2026

    SHORT SALE O6384763 - 406 CAPRON ASH LOOP, CASSELBERRY, FL 32707 15 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2200
       Built: 2013
    Monthly Fee: $90
       Tax: $2,875 (2025)
    Community: Legacy Park Residential Ph Iii A Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,713 (change assumption)
    Mortgage ($2,384) + Fees ($90) + Taxes in 2025 ($240)


    Taxes:$2,875

    Elementary School: Sterling Park Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: South Seminole Middle


  • 474 C ST, CASSELBERRY, FL 32707

    $147,900201 Days on yellowkey   MLS ID: S5139143

    For Sale S5139143 - 474 C ST, CASSELBERRY, FL 32707 21 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 690
       Built: 1966   Tax: $2,035 (2024)
    Community: Lake Kathryn Village
    Condo


    Estimated Monthly Payment: $980 (change assumption)
    Mortgage ($810) + Taxes in 2024 ($170)


    Taxes:$2,035

    Elementary School: Casselberry Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Milwee Middle


  • 1251 ASH TREE CV, CASSELBERRY, FL 32707

    $519,000404 Days on yellowkey   MLS ID: S5126272

    For Sale S5126272 - 1251 ASH TREE CV, CASSELBERRY, FL 32707 37 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2412
       Built: 2025
    Monthly Fee: $140
       Tax: $1,510 (2024)
    Community: Greenville Commons
    Single Family


    Estimated Monthly Payment: $3,110 (change assumption)
    Mortgage ($2,844) + Fees ($140) + Taxes in 2024 ($126)


    Taxes:$1,510

    Elementary School: Sterling Park Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 1252 ASH TREE CV, CASSELBERRY, FL 32707

    $529,000487 Days on yellowkey   MLS ID: S5120542

    For Sale S5120542 - 1252 ASH TREE CV, CASSELBERRY, FL 32707 35 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2412
       Built: 2025
    Monthly Fee: $140
       Tax: $1,510 (2024)
    Community: Greenville Commons
    Single Family


    Estimated Monthly Payment: $3,164 (change assumption)
    Mortgage ($2,899) + Fees ($140) + Taxes in 2024 ($126)


    Taxes:$1,510

    Elementary School: Sterling Park Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole 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.