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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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  • 498 GREEN SPRING CIR, WINTER SPRINGS, FL 32708

    $249,000Listed 06/19/2026 9:07PM   MLS ID: O6418425

    For Sale O6418425 - 498 GREEN SPRING CIR, WINTER SPRINGS, FL 32708 20 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1363
       Built: 1987
    Monthly Fee: $190
       Tax: $1,639 (2025)
    Community: Mount Greenwood Unit 4 Of
    Townhouse


    Estimated Monthly Payment: $1,691 (change assumption)
    Mortgage ($1,364) + Fees ($190) + Taxes in 2025 ($137)


    Taxes:$1,639

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1107 WINTER SPRINGS BLVD, WINTER SPRINGS, FL 32708

    $570,0003 Days on yellowkey   MLS ID: O6417844

    For Sale O6417844 - 1107 WINTER SPRINGS BLVD, WINTER SPRINGS, FL 32708 28 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2345
       Built: 1973
    Monthly Fee: $3
       Tax: $2,525 (2025)
    Community: Winter Spgs Unit 4
    Single Family


    Estimated Monthly Payment: $3,337 (change assumption)
    Mortgage ($3,123) + Fees ($3) + Taxes in 2025 ($210)


    Taxes:$2,525

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 724 BARRINGTON CIR, WINTER SPRINGS, FL 32708

    $399,900393 Days on yellowkey   MLS ID: O6312092

    For Sale O6312092 - 724 BARRINGTON CIR, WINTER SPRINGS, FL 32708 22 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1450
       Built: 1987
    Monthly Fee: $120
       Tax: $1,771 (2024)
    Community: Georgetowne Unit 1
    Single Family


    Estimated Monthly Payment: $2,459 (change assumption)
    Mortgage ($2,191) + Fees ($120) + Taxes in 2024 ($148)


    Taxes:$1,771

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 214 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708

    $590,000119 Days on yellowkey   MLS ID: O6372400

    REDUCED by $10,000 (1.7%) on 06/19/2026

    For Sale O6372400 - 214 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708 68 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2474
       Built: 2001
    Monthly Fee: $42
       Tax: $5,539 (2024)
    Community: Chestnut Ridge In Tuscawilla
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,736 (change assumption)
    Mortgage ($3,233) + Fees ($42) + Taxes in 2024 ($462)


    Taxes:$5,539

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 1406 BLUMBERG BLVD, WINTER SPRINGS, FL 32708

    $420,00033 Days on yellowkey   MLS ID: O6408695

    REDUCED by $5,000 (1.2%) on 06/19/2026

    For Sale O6408695 - 1406 BLUMBERG BLVD, WINTER SPRINGS, FL 32708 62 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1476
       Built: 2024
    Monthly Fee: $356
       Tax: $6,076 (2025)
    Community: Hickory Grove Twnhms
    Townhouse


    Estimated Monthly Payment: $3,164 (change assumption)
    Mortgage ($2,301) + Fees ($356) + Taxes in 2025 ($506)


    Taxes:$6,076

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1208 CHEETAH TRL, WINTER SPRINGS, FL 32708

    $669,9001 Day on yellowkey   MLS ID: O6416652

    For Sale O6416652 - 1208 CHEETAH TRL, WINTER SPRINGS, FL 32708 51 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2837
       Built: 1979   Tax: $3,887 (2025)
    Community: Tuscawilla Unit 06
    Single Family


    Estimated Monthly Payment: $3,995 (change assumption)
    Mortgage ($3,671) + Taxes in 2025 ($324)


    Taxes:$3,887

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 270 SAN GABRIEL ST, WINTER SPRINGS, FL 32708

    $249,900220 Days on yellowkey   MLS ID: O6359666

    REDUCED by $9,100 (3.5%) on 06/16/2026

    For Sale O6359666 - 270 SAN GABRIEL ST, WINTER SPRINGS, FL 32708 35 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1089
       Built: 1994
    Monthly Fee: $121
       Tax: $327 (2024)
    Community: Deersong 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,518 (change assumption)
    Mortgage ($1,369) + Fees ($121) + Taxes in 2024 ($27)


    Taxes:$327

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 995 DYSON DR, WINTER SPRINGS, FL 32708

    $750,000Listed 06/19/2026 9:03PM   MLS ID: O6418233

    For Sale O6418233 - 995 DYSON DR, WINTER SPRINGS, FL 32708 26 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2855
       Built: 1979   Tax: $9,147 (2025)
    Community: Winter Spgs Unit 3
    Single Family


    Estimated Monthly Payment: $4,872 (change assumption)
    Mortgage ($4,109) + Taxes in 2025 ($762)


    Taxes:$9,147

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 498 CLUB DR, WINTER SPRINGS, FL 32708

    $235,000316 Days on yellowkey   MLS ID: O6332792

    For Sale O6332792 - 498 CLUB DR, WINTER SPRINGS, FL 32708 27 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1224
       Built: 1987
    Monthly Fee: $360
       Tax: $2,970 (2024)
    Community: Cypress Club
    Townhouse


    Estimated Monthly Payment: $1,895 (change assumption)
    Mortgage ($1,288) + Fees ($360) + Taxes in 2024 ($248)


    Taxes:$2,970

    Elementary School: Highlands Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 170 WOODED VINE DR, WINTER SPRINGS, FL 32708

    $649,9002 Days on yellowkey   MLS ID: O6418077

    For Sale O6418077 - 170 WOODED VINE DR, WINTER SPRINGS, FL 32708 44 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2470
       Built: 2019
    Monthly Fee: $137
       Tax: $8,571 (2025)
    Community: Tuskawilla Crossings Ph 1
    Single Family


    Estimated Monthly Payment: $4,412 (change assumption)
    Mortgage ($3,561) + Fees ($137) + Taxes in 2025 ($714)


    Taxes:$8,571

    Elementary School: None

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1200 ROYAL OAK DR, WINTER SPRINGS, FL 32708

    $499,99952 Days on yellowkey   MLS ID: O6401888

    REDUCED by $10,001 (2.0%) on 05/26/2026

    For Sale O6401888 - 1200 ROYAL OAK DR, WINTER SPRINGS, FL 32708 40 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2378
       Built: 1981
    Monthly Fee: $118
       Tax: $4,618 (2025)
    Community: Fairway Oaks Unit 1
    Single Family


    Estimated Monthly Payment: $3,242 (change assumption)
    Mortgage ($2,740) + Fees ($118) + Taxes in 2025 ($385)


    Taxes:$4,618

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 975 DYSON DR, WINTER SPRINGS, FL 32708

    $879,0003 Days on yellowkey   MLS ID: O6417467

    0 Days Off yellowkey (back on 6/19/2026)

    For Sale O6417467 - 975 DYSON DR, WINTER SPRINGS, FL 32708 76 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2191
       Built: 1980   Tax: $6,089 (2025)
    Community: Winter Spgs Unit 3
    Single Family


    Estimated Monthly Payment: $5,324 (change assumption)
    Mortgage ($4,816) + Taxes in 2025 ($507)


    Taxes:$6,089

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 600 NORTHERN WAY #302, WINTER SPRINGS, FL 32708

    $269,90073 Days on yellowkey   MLS ID: O6396912

    1 Days Off yellowkey (back on 6/19/2026)

    REDUCED by $5,100 (1.9%) on 06/03/2026

    For Sale O6396912 - 600 NORTHERN WAY #302, WINTER SPRINGS, FL 32708 39 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1425
       Built: 1981   Tax: $4,268 (2025)
    Community: Tuscany Place Ph 1
    Condo


    Estimated Monthly Payment: $1,835 (change assumption)
    Mortgage ($1,479) + Taxes in 2025 ($356)


    Taxes:$4,268

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 472 DEWARS CT, WINTER SPRINGS, FL 32708

    $499,90016 Days on yellowkey   MLS ID: O6413206

    0 Days Off yellowkey (back on 6/19/2026)

    For Sale O6413206 - 472 DEWARS CT, WINTER SPRINGS, FL 32708 45 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2222
       Built: 1995
    Monthly Fee: $13
       Tax: $2,066 (2025)
    Community: Highland Lake Ph 2
    Single Family


    Estimated Monthly Payment: $2,924 (change assumption)
    Mortgage ($2,739) + Fees ($13) + Taxes in 2025 ($172)


    Taxes:$2,066

    Elementary School: Highlands Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: South Seminole Middle


  • 1016 WALNUT CREEK CV, WINTER SPRINGS, FL 32708

    $539,9004 Days on yellowkey   MLS ID: O6414948

    1 Days Off yellowkey (back on 6/19/2026)

    For Sale O6414948 - 1016 WALNUT CREEK CV, WINTER SPRINGS, FL 32708 39 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2375
       Built: 2003
    Monthly Fee: $150
       Tax: $3,482 (2025)
    Community: Parkstone Unit 4
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,398 (change assumption)
    Mortgage ($2,958) + Fees ($150) + Taxes in 2025 ($290)


    Taxes:$3,482

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1326 TARFLOWER DR, WINTER SPRINGS, FL 32708

    $435,0002 Days on yellowkey   MLS ID: O6416617

    For Sale O6416617 - 1326 TARFLOWER DR, WINTER SPRINGS, FL 32708 30 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1678
       Built: 2025
    Monthly Fee: $356
       Tax: $1,457 (2025)
    Community: Hickory Grove Twnhms
    Townhouse


    Estimated Monthly Payment: $2,861 (change assumption)
    Mortgage ($2,384) + 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

    $439,990108 Days on yellowkey   MLS ID: O6386437

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

    REDUCED by $45,000 (9.3%) on 06/01/2026

    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: $2,888 (change assumption)
    Mortgage ($2,411) + 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


  • 161 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708

    $444,990108 Days on yellowkey   MLS ID: O6386458

    REDUCED by $40,000 (8.2%) on 06/01/2026

    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: $2,916 (change assumption)
    Mortgage ($2,438) + 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


  • 600 NORTHERN WAY #502, WINTER SPRINGS, FL 32708

    $249,900464 Days on yellowkey   MLS ID: O6286935

    REDUCED by $15,100 (5.7%) on 06/18/2026

    For Sale O6286935 - 600 NORTHERN WAY #502, WINTER SPRINGS, FL 32708 47 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1425
       Built: 1985
    Monthly Fee: $397
       Tax: $766 (2024)
    Community: Tuscany Place Ph 1
    Spa: No

    Condo


    Estimated Monthly Payment: $1,830 (change assumption)
    Mortgage ($1,369) + Fees ($397) + Taxes in 2024 ($64)


    Taxes:$766

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 805 LEOPARD TRL, WINTER SPRINGS, FL 32708

    $565,00044 Days on yellowkey   MLS ID: O6405925

    REDUCED by $10,000 (1.7%) on 05/25/2026

    For Sale O6405925 - 805 LEOPARD TRL, WINTER SPRINGS, FL 32708 28 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2608
       Built: 1978   Tax: $2,946 (2024)
    Community: Winter Spgs Unit 4
    Single Family


    Estimated Monthly Payment: $3,341 (change assumption)
    Mortgage ($3,096) + Taxes in 2024 ($245)


    Taxes:$2,946

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    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.