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Homes for Sale Near Winter Springs High in Winter Springs - 96 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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  • 276 SAN GABRIEL ST, WINTER SPRINGS, FL 32708

    $290,000Listed 04/17/2026 12:48PM   MLS ID: O6399623

    For Sale O6399623 - 276 SAN GABRIEL ST, WINTER SPRINGS, FL 32708 35 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1089
       Built: 1994
    Monthly Fee: $127
       Tax: $3,719 (2025)
    Community: Deersong 2
    Single Family


    Estimated Monthly Payment: $2,026 (change assumption)
    Mortgage ($1,589) + Fees ($127) + Taxes in 2025 ($310)


    Taxes:$3,719

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 226 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708

    $824,900Listed 04/17/2026 12:59PM   MLS ID: O6398877

    For Sale O6398877 - 226 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708 40 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2902
       Built: 1994
    Monthly Fee: $44
       Tax: $4,461 (2024)
    Community: Chestnut Ridge
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,936 (change assumption)
    Mortgage ($4,520) + Fees ($44) + Taxes in 2024 ($372)


    Taxes:$4,461

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 630 FALCON CT, WINTER SPRINGS, FL 32708

    $425,0001 Day on yellowkey   MLS ID: O6396134

    For Sale O6396134 - 630 FALCON CT, WINTER SPRINGS, FL 32708 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1360
       Built: 1986
    Monthly Fee: $64
       Tax: $1,454 (2024)
    Community: Greenspointe
    Single Family


    Estimated Monthly Payment: $2,514 (change assumption)
    Mortgage ($2,329) + Fees ($64) + Taxes in 2024 ($121)


    Taxes:$1,454

    Elementary School: Highlands Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 118 BROOKSHIRE CT, WINTER SPRINGS, FL 32708

    $599,0001 Day on yellowkey   MLS ID: O6394521

    For Sale O6394521 - 118 BROOKSHIRE CT, WINTER SPRINGS, FL 32708 49 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2100
       Built: 1996
    Monthly Fee: $48
       Tax: $3,067 (2024)
    Community: Winding Hollow Unit 1
    Single Family


    Estimated Monthly Payment: $3,586 (change assumption)
    Mortgage ($3,282) + Fees ($48) + Taxes in 2024 ($256)


    Taxes:$3,067

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 1327 AUGUSTA NATIONAL BLVD, WINTER SPRINGS, FL 32708

    $448,0002 Days on yellowkey   MLS ID: O6399111

    For Sale O6399111 - 1327 AUGUSTA NATIONAL BLVD, WINTER SPRINGS, FL 32708 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2128
       Built: 1994
    Monthly Fee: $117
       Tax: $2,755 (2024)
    Community: Country Club Village Unit 3
    Single Family


    Estimated Monthly Payment: $2,801 (change assumption)
    Mortgage ($2,455) + Fees ($117) + Taxes in 2024 ($230)


    Taxes:$2,755

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 1352 AUGUSTA NATIONAL BLVD, WINTER SPRINGS, FL 32708

    $399,00048 Days on yellowkey   MLS ID: O6386661

    0 Days Off yellowkey (back on 4/17/2026)

    For Sale O6386661 - 1352 AUGUSTA NATIONAL BLVD, WINTER SPRINGS, FL 32708 48 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1831
       Built: 1993
    Monthly Fee: $39
       Tax: $2,158 (2024)
    Community: Country Club Village Unit 3
    Single Family


    Estimated Monthly Payment: $2,405 (change assumption)
    Mortgage ($2,186) + Fees ($39) + Taxes in 2024 ($180)


    Taxes:$2,158

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 702 GOLFPOINT DR, WINTER SPRINGS, FL 32708

    $965,0009 Days on yellowkey   MLS ID: O6397566

    For Sale O6397566 - 702 GOLFPOINT DR, WINTER SPRINGS, FL 32708 67 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3660
       Built: 1994
    Monthly Fee: $48
       Tax: $11,586 (2025)
    Community: Glen Eagle Unit 3
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,301 (change assumption)
    Mortgage ($5,288) + Fees ($48) + Taxes in 2025 ($966)


    Taxes:$11,586

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 161 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708

    $484,99045 Days on yellowkey   MLS ID: O6386458

    For Sale O6386458 - 161 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1704
       Built: 2026
    Monthly Fee: $356
       Tax: $1,457 (2025)
    Community: Hickory Grove
    Townhouse


    Estimated Monthly Payment: $3,135 (change assumption)
    Mortgage ($2,657) + Fees ($356) + Taxes in 2025 ($121)


    Taxes:$1,457

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 173 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708

    $484,99045 Days on yellowkey   MLS ID: O6386437

    For Sale O6386437 - 173 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1704
       Built: 2026
    Monthly Fee: $356
       Tax: $1,457 (2025)
    Community: Hickory Grove
    Townhouse


    Estimated Monthly Payment: $3,135 (change assumption)
    Mortgage ($2,657) + Fees ($356) + Taxes in 2025 ($121)


    Taxes:$1,457

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 165 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708

    $384,99045 Days on yellowkey   MLS ID: O6386473

    For Sale O6386473 - 165 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1476
       Built: 2026
    Monthly Fee: $356
       Tax: $1,457 (2025)
    Community: Hickory Grove
    Townhouse


    Estimated Monthly Payment: $2,587 (change assumption)
    Mortgage ($2,109) + Fees ($356) + Taxes in 2025 ($121)


    Taxes:$1,457

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1276 CRAB APPLE LN, WINTER SPRINGS, FL 32708

    $381,99088 Days on yellowkey   MLS ID: O6375116

    For Sale O6375116 - 1276 CRAB APPLE LN, WINTER SPRINGS, FL 32708 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1476
       Built: 2025
    Monthly Fee: $356
       Tax: $1,457 (2025)
    Community: Hickory Grove
    Townhouse


    Estimated Monthly Payment: $2,570 (change assumption)
    Mortgage ($2,093) + Fees ($356) + Taxes in 2025 ($121)


    Taxes:$1,457

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 189 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708

    $491,99099 Days on yellowkey   MLS ID: O6372546

    For Sale O6372546 - 189 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1704
       Built: 2025
    Monthly Fee: $356
       Tax: $1,457 (2025)
    Community: Hickory Grove
    Townhouse


    Estimated Monthly Payment: $3,173 (change assumption)
    Mortgage ($2,696) + Fees ($356) + Taxes in 2025 ($121)


    Taxes:$1,457

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1272 CRAB APPLE LN, WINTER SPRINGS, FL 32708

    $397,99099 Days on yellowkey   MLS ID: O6371853

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale O6371853 - 1272 CRAB APPLE LN, WINTER SPRINGS, FL 32708 27 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1678
       Built: 2025
    Monthly Fee: $356
       Tax: $1,457 (2025)
    Community: Hickory Grove
    Townhouse


    Estimated Monthly Payment: $2,658 (change assumption)
    Mortgage ($2,181) + Fees ($356) + Taxes in 2025 ($121)


    Taxes:$1,457

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1444 BIRD RD, WINTER SPRINGS, FL 32708

    $838,500214 Days on yellowkey   MLS ID: O6344113

    For Sale O6344113 - 1444 BIRD RD, WINTER SPRINGS, FL 32708 62 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2350
       Built: 1977   Tax: $2,076 (2024)
    Community: Watts Farms
    Single Family


    Estimated Monthly Payment: $4,767 (change assumption)
    Mortgage ($4,594) + Taxes in 2024 ($173)


    Taxes:$2,076

    Elementary School: Sterling Park Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 1447 BIRD RD, WINTER SPRINGS, FL 32708

    $2,900,00043 Days on yellowkey   MLS ID: O6388126

    For Sale O6388126 - 1447 BIRD RD, WINTER SPRINGS, FL 32708 68 photos

    Bed: 6   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 6132
       Built: 2026   Tax: $2,989 (2024)
    Community: Talis Crossing
    Single Family


    Estimated Monthly Payment: $16,139 (change assumption)
    Mortgage ($15,890) + Taxes in 2024 ($249)


    Taxes:$2,989

    Elementary School: Sterling Park Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 1011 W PEBBLE BEACH CIR, WINTER SPRINGS, FL 32708

    $439,00030 Days on yellowkey   MLS ID: O6391562

    0 Days Off yellowkey (back on 4/10/2026)

    For Sale O6391562 - 1011 W PEBBLE BEACH CIR, WINTER SPRINGS, FL 32708 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1804
       Built: 1980
    Monthly Fee: $117
       Tax: $2,390 (2024)
    Community: Country Club Village Unit 1
    Single Family


    Estimated Monthly Payment: $2,722 (change assumption)
    Mortgage ($2,405) + Fees ($117) + Taxes in 2024 ($199)


    Taxes:$2,390

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


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

    $299,99979 Days on yellowkey   MLS ID: O6375918

    REDUCED by $10,001 (3.2%) on 04/01/2026

    For Sale O6375918 - 600 NORTHERN WAY #906, WINTER SPRINGS, FL 32708 27 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: $1,999 (change assumption)
    Mortgage ($1,644) + Taxes in 2024 ($355)


    Taxes:$4,259

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 60 SHEOAH BLVD #38A, WINTER SPRINGS, FL 32708

    $185,00017 Days on yellowkey   MLS ID: O6394692

    0 Days Off yellowkey (back on 4/17/2026)

    For Sale O6394692 - 60 SHEOAH BLVD #38A, WINTER SPRINGS, FL 32708 29 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1080
       Built: 1973   Tax: $1,873 (2025)
    Community: Sheoah Sec 1
    Condo


    Estimated Monthly Payment: $1,170 (change assumption)
    Mortgage ($1,014) + Taxes in 2025 ($156)


    Taxes:$1,873

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1128 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708

    $489,00016 Days on yellowkey   MLS ID: O6395600

    For Sale O6395600 - 1128 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708 34 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2344
       Built: 2021
    Monthly Fee: $236
       Tax: $2,985 (2025)
    Community: Seminole Crossing Twnhms
    Townhouse


    Estimated Monthly Payment: $3,164 (change assumption)
    Mortgage ($2,679) + Fees ($236) + Taxes in 2025 ($249)


    Taxes:$2,985

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1300 SWIFT CREEK WAY, WINTER SPRINGS, FL 32708

    $550,00025 Days on yellowkey   MLS ID: V4948084

    0 Days Off yellowkey (back on 4/7/2026)

    For Sale V4948084 - 1300 SWIFT CREEK WAY, WINTER SPRINGS, FL 32708 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2030
       Built: 2021
    Monthly Fee: $137
       Tax: $6,465 (2025)
    Community: Tuskawilla Crossings Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,689 (change assumption)
    Mortgage ($3,014) + Fees ($137) + Taxes in 2025 ($539)


    Taxes:$6,465

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle




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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.