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Homes for Sale Near Winter Springs High in Winter Springs - 99 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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  • 859 BENCHWOOD DR, WINTER SPRINGS, FL 32708

    $454,90018 Days on yellowkey   MLS ID: O6397781

    For Sale O6397781 - 859 BENCHWOOD DR, WINTER SPRINGS, FL 32708 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1632
       Built: 1984   Tax: $1,787 (2025)
    Community: Oak Forest Unit 3
    Single Family


    Estimated Monthly Payment: $2,641 (change assumption)
    Mortgage ($2,493) + Taxes in 2025 ($149)


    Taxes:$1,787

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 171 CONSTITUTION WAY, WINTER SPRINGS, FL 32708

    $325,00018 Days on yellowkey   MLS ID: O6396871

    For Sale O6396871 - 171 CONSTITUTION WAY, WINTER SPRINGS, FL 32708 46 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1468
       Built: 2005
    Monthly Fee: $300
       Tax: $2,346 (2024)
    Community: Heritage Park Twnhms
    Townhouse


    Estimated Monthly Payment: $2,276 (change assumption)
    Mortgage ($1,781) + Fees ($300) + Taxes in 2024 ($195)


    Taxes:$2,346

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 120 E BAHAMA RD, WINTER SPRINGS, FL 32708

    $1,299,90083 Days on yellowkey   MLS ID: O6379165

    REDUCED by $100,000 (7.1%) on 04/09/2026

    For Sale O6379165 - 120 E BAHAMA RD, WINTER SPRINGS, FL 32708 47 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 4464
       Built: 1989   Tax: $12,488 (2025)
    Community: Bahama Ranches
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,163 (change assumption)
    Mortgage ($7,123) + Taxes in 2025 ($1,041)


    Taxes:$12,488

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 202 ARROWHEAD CT, WINTER SPRINGS, FL 32708

    $1,250,000248 Days on yellowkey   MLS ID: O6337777

    0 Days Off yellowkey (back on 4/8/2026)

    For Sale O6337777 - 202 ARROWHEAD CT, WINTER SPRINGS, FL 32708 46 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4078
       Built: 1996
    Monthly Fee: $96
       Tax: $14,910 (2024)
    Community: Arrowhead At Tuscawilla Unit 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,188 (change assumption)
    Mortgage ($6,849) + Fees ($96) + Taxes in 2024 ($1,243)


    Taxes:$14,910

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 689 SEVEN OAKS BLVD, WINTER SPRINGS, FL 32708

    $600,00033 Days on yellowkey   MLS ID: O6393344

    1 Days Off yellowkey (back on 3/30/2026)

    For Sale O6393344 - 689 SEVEN OAKS BLVD, WINTER SPRINGS, FL 32708 42 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2541
       Built: 2017
    Monthly Fee: $100
       Tax: $3,845 (2024)
    Community: Seven Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,708 (change assumption)
    Mortgage ($3,288) + Fees ($100) + Taxes in 2024 ($320)


    Taxes:$3,845

    Elementary School: Highlands Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 449 GEE HAMMOCK LN, WINTER SPRINGS, FL 32708

    $355,000115 Days on yellowkey   MLS ID: O6370606

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

    REDUCED by $4,000 (1.1%) on 04/02/2026

    For Sale O6370606 - 449 GEE HAMMOCK LN, WINTER SPRINGS, FL 32708 59 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1435
       Built: 2016
    Monthly Fee: $226
       Tax: $5,182 (2025)
    Community: Jesups Landing
    Townhouse


    Estimated Monthly Payment: $2,603 (change assumption)
    Mortgage ($1,945) + Fees ($226) + Taxes in 2025 ($432)


    Taxes:$5,182

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 986 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708

    $498,900101 Days on yellowkey   MLS ID: O6374288

    For Sale O6374288 - 986 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708 56 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1864
       Built: 1985
    Monthly Fee: $3
       Tax: $3,119 (2024)
    Community: Oak Forest Unit 4
    Single Family


    Estimated Monthly Payment: $2,997 (change assumption)
    Mortgage ($2,734) + Fees ($3) + Taxes in 2024 ($260)


    Taxes:$3,119

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 620 STALLION CT, WINTER SPRINGS, FL 32708

    $650,00026 Days on yellowkey   MLS ID: O6395164

    0 Days Off yellowkey (back on 4/3/2026)

    For Sale O6395164 - 620 STALLION CT, WINTER SPRINGS, FL 32708 15 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2856
       Built: 1979   Tax: $3,831 (2024)
    Community: Winter Spgs Unit 3
    Single Family


    Estimated Monthly Payment: $3,881 (change assumption)
    Mortgage ($3,562) + Taxes in 2024 ($319)


    Taxes:$3,831

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 1233 STONE HARBOUR RD, WINTER SPRINGS, FL 32708

    $729,90062 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


  • 203 HERRELL RD, WINTER SPRINGS, FL 32708

    $573,000167 Days on yellowkey   MLS ID: O6358036

    For Sale O6358036 - 203 HERRELL RD, WINTER SPRINGS, FL 32708 45 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3566
       Built: 1987   Tax: $5,127 (2024)
    Community: North Orlando Ranches Sec 06
    Single Family


    Estimated Monthly Payment: $3,567 (change assumption)
    Mortgage ($3,140) + Taxes in 2024 ($427)


    Taxes:$5,127

    Elementary School: Sterling Park Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 4951 COURTLAND LOOP, WINTER SPRINGS, FL 32708

    $700,000102 Days on yellowkey   MLS ID: O6374007

    REDUCED by $14,000 (2.0%) on 04/02/2026

    For Sale O6374007 - 4951 COURTLAND LOOP, WINTER SPRINGS, FL 32708 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2562
       Built: 1984
    Monthly Fee: $40
       Tax: $7,807 (2024)
    Community: Tuskabay Ph 1
    Single Family


    Estimated Monthly Payment: $4,526 (change assumption)
    Mortgage ($3,836) + Fees ($40) + Taxes in 2024 ($651)


    Taxes:$7,807

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 1262 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708

    $489,97580 Days on yellowkey   MLS ID: O6380617

    For Sale O6380617 - 1262 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708 63 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2353
       Built: 2023
    Monthly Fee: $236
       Tax: $5,937 (2024)
    Community: Seminole Crossing Twnhms
    Townhouse


    Estimated Monthly Payment: $3,415 (change assumption)
    Mortgage ($2,685) + Fees ($236) + Taxes in 2024 ($495)


    Taxes:$5,937

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 709 SAILFISH RD, WINTER SPRINGS, FL 32708

    $412,500144 Days on yellowkey   MLS ID: O6364715

    REDUCED by $2,500 (0.6%) on 04/02/2026

    For Sale O6364715 - 709 SAILFISH RD, WINTER SPRINGS, FL 32708 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1737
       Built: 1984   Tax: $5,463 (2024)
    Community: North Orlando Ranches Sec 10
    Single Family


    Estimated Monthly Payment: $2,716 (change assumption)
    Mortgage ($2,260) + Taxes in 2024 ($455)


    Taxes:$5,463

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 498 CLUB DR, WINTER SPRINGS, FL 32708

    $235,000262 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


  • 1254 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708

    $495,00041 Days on yellowkey   MLS ID: O6390820

    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: $3,498 (change assumption)
    Mortgage ($2,712) + 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


  • 203 WISE OWL WAY, WINTER SPRINGS, FL 32708

    $599,90079 Days on yellowkey   MLS ID: O6380678

    REDUCED by $14,600 (2.4%) on 03/31/2026

    For Sale O6380678 - 203 WISE OWL WAY, WINTER SPRINGS, FL 32708 60 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2531
       Built: 2020
    Monthly Fee: $130
       Tax: $6,177 (2024)
    Community: Tuskawilla Crossings
    Single Family


    Estimated Monthly Payment: $3,932 (change assumption)
    Mortgage ($3,287) + Fees ($130) + Taxes in 2024 ($515)


    Taxes:$6,177

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 422 SANDRINGHAM CT, WINTER SPRINGS, FL 32708

    $822,80066 Days on yellowkey   MLS ID: O6384155

    For Sale O6384155 - 422 SANDRINGHAM CT, WINTER SPRINGS, FL 32708 64 photos

    Bed: 5   Bath: 3.5
    Liv Area Sq Ft: 3512
       Built: 2001
    Monthly Fee: $150
       Tax: $12,732 (2025)
    Community: Parkstone
    Single Family


    Estimated Monthly Payment: $5,719 (change assumption)
    Mortgage ($4,508) + Fees ($150) + Taxes in 2025 ($1,061)


    Taxes:$12,732

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 421 WOODCREST ST, WINTER SPRINGS, FL 32708

    $550,00031 Days on yellowkey   MLS ID: O6394375

    1 Days Off yellowkey (back on 3/30/2026)

    For Sale O6394375 - 421 WOODCREST ST, WINTER SPRINGS, FL 32708 55 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2374
       Built: 1996
    Monthly Fee: $42
       Tax: $3,295 (2024)
    Community: Winding Hollow Unit 2
    Single Family


    Estimated Monthly Payment: $3,330 (change assumption)
    Mortgage ($3,014) + Fees ($42) + Taxes in 2024 ($275)


    Taxes:$3,295

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 1132 HOWELL CREEK DR, WINTER SPRINGS, FL 32708

    $625,00045 Days on yellowkey   MLS ID: O6390266

    1 Days Off yellowkey (back on 3/27/2026)

    For Sale O6390266 - 1132 HOWELL CREEK DR, WINTER SPRINGS, FL 32708 33 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2441
       Built: 1991
    Monthly Fee: $6
       Tax: $2,804 (2025)
    Community: Winter Spgs
    Single Family


    Estimated Monthly Payment: $3,664 (change assumption)
    Mortgage ($3,425) + Fees ($6) + Taxes in 2025 ($234)


    Taxes:$2,804

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails 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.