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Homes for Sale Near Winter Springs High in Winter Springs - 120 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, Winter Springs nearby homes.

Location: Winter Springs

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  • 335 KIRKCALDY DR, WINTER SPRINGS, FL 32708

    $329,90047 Days on yellowkey   MLS ID: O6400818

    REDUCED by $10,000 (2.9%) on 06/18/2026

    For Sale O6400818 - 335 KIRKCALDY DR, WINTER SPRINGS, FL 32708 50 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1178
       Built: 1984
    Monthly Fee: $36
       Tax: $3,693 (2025)
    Community: Highland Village 1
    Single Family


    Estimated Monthly Payment: $2,151 (change assumption)
    Mortgage ($1,808) + Fees ($36) + Taxes in 2025 ($308)


    Taxes:$3,693

    Elementary School: Highlands Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: South Seminole Middle


  • 577 WALDEN CT, WINTER SPRINGS, FL 32708

    $405,00013 Days on yellowkey   MLS ID: V4949540

    2 Days Off yellowkey (back on 6/18/2026)

    For Sale V4949540 - 577 WALDEN CT, WINTER SPRINGS, FL 32708 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1560
       Built: 1974   Tax: $3,414 (2025)
    Community: Walden Terrace
    Single Family


    Estimated Monthly Payment: $2,504 (change assumption)
    Mortgage ($2,219) + Taxes in 2025 ($284)


    Taxes:$3,414

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1055 CHESTERFIELD CIR, WINTER SPRINGS, FL 32708

    $510,00017 Days on yellowkey   MLS ID: O6413841

    REDUCED by $5,000 (1.0%) on 06/18/2026

    For Sale O6413841 - 1055 CHESTERFIELD CIR, WINTER SPRINGS, FL 32708 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1665
       Built: 1984
    Monthly Fee: $25
       Tax: $5,048 (2025)
    Community: Amherst
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,240 (change assumption)
    Mortgage ($2,794) + Fees ($25) + Taxes in 2025 ($421)


    Taxes:$5,048

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 877 BENCHWOOD DR, WINTER SPRINGS, FL 32708

    $450,00024 Days on yellowkey   MLS ID: O6410431

    REDUCED by $10,000 (2.2%) on 06/18/2026

    For Sale O6410431 - 877 BENCHWOOD DR, WINTER SPRINGS, FL 32708 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1612
       Built: 1983
    Monthly Fee: $3
       Tax: $3,127 (2024)
    Community: Oak Forest Unit 3
    Single Family


    Estimated Monthly Payment: $2,729 (change assumption)
    Mortgage ($2,466) + Fees ($3) + Taxes in 2024 ($261)


    Taxes:$3,127

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 1357 MILL STREAM LN, WINTER SPRINGS, FL 32708

    $400,0004 Days on yellowkey   MLS ID: O6417015

    For Sale O6417015 - 1357 MILL STREAM LN, WINTER SPRINGS, FL 32708 28 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1606
       Built: 2015
    Monthly Fee: $230
       Tax: $4,811 (2025)
    Community: Jesups Landing
    Townhouse


    Estimated Monthly Payment: $2,823 (change assumption)
    Mortgage ($2,192) + Fees ($230) + Taxes in 2025 ($401)


    Taxes:$4,811

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 724 LAKESIDE DR, WINTER SPRINGS, FL 32708

    $264,90018 Days on yellowkey   MLS ID: O6412679

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

    For Sale O6412679 - 724 LAKESIDE DR, WINTER SPRINGS, FL 32708 40 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1168
       Built: 1985
    Monthly Fee: $95
       Tax: $2,675 (2025)
    Community: Wildwood
    Single Family


    Estimated Monthly Payment: $1,769 (change assumption)
    Mortgage ($1,451) + Fees ($95) + Taxes in 2025 ($223)


    Taxes:$2,675

    Elementary School: Highlands Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 116 PHILADELPHIA WAY, WINTER SPRINGS, FL 32708

    $310,000139 Days on yellowkey   MLS ID: O6379053

    REDUCED by $15,000 (4.6%) on 06/17/2026

    For Sale O6379053 - 116 PHILADELPHIA WAY, WINTER SPRINGS, FL 32708 25 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1468
       Built: 2005
    Monthly Fee: $300
       Tax: $4,182 (2024)
    Community: Heritage Park Twnhms
    Townhouse


    Estimated Monthly Payment: $2,347 (change assumption)
    Mortgage ($1,699) + Fees ($300) + Taxes in 2024 ($349)


    Taxes:$4,182

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 1421 HAPPY BIRD LN, WINTER SPRINGS, FL 32708

    $543,888221 Days on yellowkey   MLS ID: O6359884

    REDUCED by $19,520 (3.5%) on 06/17/2026

    For Sale O6359884 - 1421 HAPPY BIRD LN, WINTER SPRINGS, FL 32708 16 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2502
       Built: 2019
    Monthly Fee: $130
       Tax: $4,781 (2024)
    Community: Tuskawilla Crossings 34'S
    Single Family


    Estimated Monthly Payment: $3,509 (change assumption)
    Mortgage ($2,980) + Fees ($130) + Taxes in 2024 ($398)


    Taxes:$4,781

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 1254 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708

    $485,00096 Days on yellowkey   MLS ID: O6390820

    REDUCED by $10,000 (2.0%) on 04/30/2026

    For Sale O6390820 - 1254 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708 39 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2359
       Built: 2023
    Monthly Fee: $236
       Tax: $6,591 (2024)
    Community: Seminole Crossing Twnhms
    Townhouse


    Estimated Monthly Payment: $3,443 (change assumption)
    Mortgage ($2,657) + Fees ($236) + Taxes in 2024 ($549)


    Taxes:$6,591

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 214 PERTH CT, WINTER SPRINGS, FL 32708

    $589,90039 Days on yellowkey   MLS ID: O6407533

    1 Days Off yellowkey (back on 6/3/2026)

    For Sale O6407533 - 214 PERTH CT, WINTER SPRINGS, FL 32708 80 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2247
       Built: 1980
    Monthly Fee: $67
       Tax: $5,200 (2024)
    Community: Highlands Sec 6
    Single Family


    Estimated Monthly Payment: $3,733 (change assumption)
    Mortgage ($3,232) + Fees ($67) + Taxes in 2024 ($433)


    Taxes:$5,200

    Elementary School: Woodlands Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 214 PERTH CT #A, WINTER SPRINGS, FL 32708

    $589,90040 Days on yellowkey   MLS ID: O6407330

    1 Days Off yellowkey (back on 6/3/2026)

    For Sale O6407330 - 214 PERTH CT #A, WINTER SPRINGS, FL 32708 85 photos

    Bed: 6   Bath: 0.0   Gar: 2
    Liv Area Sq Ft: 2247
       Built: 1980
    Monthly Fee: $67
       Tax: $5,200 (2024)
    Community: Highlands Sec 6
    Apartment


    Estimated Monthly Payment: $3,733 (change assumption)
    Mortgage ($3,232) + Fees ($67) + Taxes in 2024 ($433)


    Taxes:$5,200

    Elementary School: Highlands Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 114 STONE GABLE CIR, WINTER SPRINGS, FL 32708

    $485,9005 Days on yellowkey   MLS ID: O6417280

    For Sale O6417280 - 114 STONE GABLE CIR, WINTER SPRINGS, FL 32708 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1814
       Built: 1998
    Monthly Fee: $50
       Tax: $4,263 (2025)
    Community: Stone Gable
    Single Family


    Estimated Monthly Payment: $3,068 (change assumption)
    Mortgage ($2,662) + Fees ($50) + Taxes in 2025 ($355)


    Taxes:$4,263

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1233 STONE HARBOUR RD, WINTER SPRINGS, FL 32708

    $729,900117 Days on yellowkey   MLS ID: O6384753

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

    For Sale O6384753 - 1233 STONE HARBOUR RD, WINTER SPRINGS, FL 32708 46 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2908
       Built: 2003
    Monthly Fee: $150
       Tax: $2,062 (2025)
    Community: Parkstone Unit 3
    Single Family


    Estimated Monthly Payment: $4,321 (change assumption)
    Mortgage ($3,999) + Fees ($150) + Taxes in 2025 ($172)


    Taxes:$2,062

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1204 SWAN ST, WINTER SPRINGS, FL 32708

    $624,0005 Days on yellowkey   MLS ID: O6417440

    For Sale O6417440 - 1204 SWAN ST, WINTER SPRINGS, FL 32708 26 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3334
       Built: 1973   Tax: $3,677 (2024)
    Community: Winter Spgs Unit 4
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,726 (change assumption)
    Mortgage ($3,419) + Taxes in 2024 ($306)


    Taxes:$3,677

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 1441 FOREST HILLS DR, WINTER SPRINGS, FL 32708

    $420,0005 Days on yellowkey   MLS ID: O6413957

    For Sale O6413957 - 1441 FOREST HILLS DR, WINTER SPRINGS, FL 32708 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1731
       Built: 1985
    Monthly Fee: $90
       Tax: $2,546 (2025)
    Community: Wedgewood Tennis Villas
    Single Family


    Estimated Monthly Payment: $2,603 (change assumption)
    Mortgage ($2,301) + Fees ($90) + Taxes in 2025 ($212)


    Taxes:$2,546

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 600 NORTHERN WAY #906, WINTER SPRINGS, FL 32708

    $290,000143 Days on yellowkey   MLS ID: O6375918

    REDUCED by $20,000 (6.5%) on 06/01/2026

    For Sale O6375918 - 600 NORTHERN WAY #906, WINTER SPRINGS, FL 32708 29 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1609
       Built: 2016   Tax: $4,259 (2024)
    Community: Tuscany Place Ph 1
    Condo


    Estimated Monthly Payment: $1,944 (change assumption)
    Mortgage ($1,589) + Taxes in 2024 ($355)


    Taxes:$4,259

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 1112 ORANGE AVE, WINTER SPRINGS, FL 32708

    $3,998,000437 Days on yellowkey   MLS ID: O6298615

    For Sale O6298615 - 1112 ORANGE AVE, WINTER SPRINGS, FL 32708 82 photos

    Bed: 5   Bath: 6.5   Gar: 6
    Liv Area Sq Ft: 8685
       Built: 2008   Tax: $14,976 (2024)
    Community: Lake Jessup
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $23,154 (change assumption)
    Mortgage ($21,906) + Taxes in 2024 ($1,248)


    Taxes:$14,976

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 819 DUNDEE DR, WINTER SPRINGS, FL 32708

    $419,00018 Days on yellowkey   MLS ID: O6412585

    REDUCED by $10,000 (2.3%) on 06/16/2026

    For Sale O6412585 - 819 DUNDEE DR, WINTER SPRINGS, FL 32708 47 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1701
       Built: 1978
    Monthly Fee: $40
       Tax: $1,558 (2025)
    Community: Highlands Sec 1
    Single Family


    Estimated Monthly Payment: $2,466 (change assumption)
    Mortgage ($2,296) + Fees ($40) + Taxes in 2025 ($130)


    Taxes:$1,558

    Elementary School: Highlands Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: South Seminole Middle


  • 140 SEVILLE CHASE DR, WINTER SPRINGS, FL 32708

    $769,90080 Days on yellowkey   MLS ID: O6395594

    REDUCED by $10,000 (1.3%) on 06/10/2026

    For Sale O6395594 - 140 SEVILLE CHASE DR, WINTER SPRINGS, FL 32708 46 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3129
       Built: 1999
    Monthly Fee: $184
       Tax: $5,857 (2024)
    Community: Seville Chase
    Single Family


    Estimated Monthly Payment: $4,891 (change assumption)
    Mortgage ($4,219) + Fees ($184) + Taxes in 2024 ($488)


    Taxes:$5,857

    Elementary School: Sterling Park Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 1110 SHADOWBROOK TRL, WINTER SPRINGS, FL 32708

    $575,00017 Days on yellowkey   MLS ID: O6413323

    0 Days Off yellowkey (back on 6/15/2026)

    For Sale O6413323 - 1110 SHADOWBROOK TRL, WINTER SPRINGS, FL 32708 35 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2214
       Built: 1998
    Monthly Fee: $50
       Tax: $3,542 (2025)
    Community: Winding Hollow Unit 4
    Single Family


    Estimated Monthly Payment: $3,496 (change assumption)
    Mortgage ($3,151) + Fees ($50) + Taxes in 2025 ($295)


    Taxes:$3,542

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle




Why Bother Searching Elsewhere for Homes For Sale and Real Estate nearby Winter Springs High?

Home, townhome, condo, villa, and other listing sales data closeby Winter Springs High is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on homes for sale nearby Winter Springs High, Winter Springs . You can use our website to view Multiple Listing Service (MLS) data on Winter Springs homes near Winter Springs High. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our listings that are close to Winter Springs High.



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.