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Winter Springs Homes For Sale & Real Estate - 198 homes

Winter Springs homes for sale are located in Seminole County, Florida. Find homes in Winter Springs for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Springs houses.

Location: Winter Springs

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  • 1281 NATURES WAY, WINTER SPRINGS, FL 32708

    $1,200,00027 Days on yellowkey   MLS ID: O6404018

    For Sale O6404018 - 1281 NATURES WAY, WINTER SPRINGS, FL 32708 43 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3212
       Built: 1972   Tax: $2,240 (2024)
    Community: Tuscawilla
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,762 (change assumption)
    Mortgage ($6,575) + Taxes in 2024 ($187)


    Taxes:$2,240

    Elementary School: Keeth Elementary

    High School: Oviedo High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 4910 E LAKE DR, WINTER SPRINGS, FL 32708

    $2,399,00027 Days on yellowkey   MLS ID: O6398929

    For Sale O6398929 - 4910 E LAKE DR, WINTER SPRINGS, FL 32708 73 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3657
       Built: 1964   Tax: $6,256 (2024)
    Community: Na
    Single Family


    Estimated Monthly Payment: $13,666 (change assumption)
    Mortgage ($13,145) + Taxes in 2024 ($521)


    Taxes:$6,256

    Elementary School: Sterling Park Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 439 OLD FARM LN, WINTER SPRINGS, FL 32708

    $339,90029 Days on yellowkey   MLS ID: O6403125

    For Sale O6403125 - 439 OLD FARM LN, WINTER SPRINGS, FL 32708 68 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2007
    Monthly Fee: $300
       Tax: $5,063 (2025)
    Community: Jesups Reserve Twnhms Rep
    Townhouse


    Estimated Monthly Payment: $2,584 (change assumption)
    Mortgage ($1,862) + Fees ($300) + Taxes in 2025 ($422)


    Taxes:$5,063

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 600 NORTHERN WAY #1608, WINTER SPRINGS, FL 32708

    $274,90097 Days on yellowkey   MLS ID: G5108558

    REDUCED by $5,100 (1.8%) on 05/01/2026

    For Sale G5108558 - 600 NORTHERN WAY #1608, WINTER SPRINGS, FL 32708 24 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1425
       Built: 1981
    Monthly Fee: $373
       Tax: $2,582 (2025)
    Community: Tuscany Place
    Condo


    Estimated Monthly Payment: $2,094 (change assumption)
    Mortgage ($1,506) + Fees ($373) + Taxes in 2025 ($215)


    Taxes:$2,582

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 421 RINGWOOD CIR, WINTER SPRINGS, FL 32708

    $500,00056 Days on yellowkey   MLS ID: V4948285

    0 Days Off yellowkey (back on 5/1/2026)

    REDUCED by $7,000 (1.4%) on 04/25/2026

    For Sale V4948285 - 421 RINGWOOD CIR, WINTER SPRINGS, FL 32708 38 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2029
       Built: 1984
    Monthly Fee: $23
       Tax: $5,298 (2024)
    Community: Deer Run Unit 21B
    Single Family


    Estimated Monthly Payment: $3,204 (change assumption)
    Mortgage ($2,740) + Fees ($23) + Taxes in 2024 ($441)


    Taxes:$5,298

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 709 SAILFISH RD, WINTER SPRINGS, FL 32708

    $407,500175 Days on yellowkey   MLS ID: O6364715

    REDUCED by $5,000 (1.2%) on 05/01/2026

    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
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,688 (change assumption)
    Mortgage ($2,233) + Taxes in 2024 ($455)


    Taxes:$5,463

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


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

    $269,000441 Days on yellowkey   MLS ID: O6286935

    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: $1,935 (change assumption)
    Mortgage ($1,474) + 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


  • 502 CLUB DR, WINTER SPRINGS, FL 32708

    $219,50069 Days on yellowkey   MLS ID: O6390697

    REDUCED by $10,000 (4.4%) on 05/01/2026

    For Sale O6390697 - 502 CLUB DR, WINTER SPRINGS, FL 32708 32 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1224
       Built: 1987
    Monthly Fee: $520
       Tax: $3,355 (2025)
    Community: Cypress Club
    Townhouse


    Estimated Monthly Payment: $2,002 (change assumption)
    Mortgage ($1,203) + Fees ($520) + Taxes in 2025 ($280)


    Taxes:$3,355

    Elementary School: Highlands Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: South Seminole Middle


  • 632 TUSKAWILLA POINT LN, WINTER SPRINGS, FL 32708

    $450,00055 Days on yellowkey   MLS ID: O6394544

    0 Days Off yellowkey (back on 5/1/2026)

    REDUCED by $20,000 (4.3%) on 04/19/2026

    For Sale O6394544 - 632 TUSKAWILLA POINT LN, WINTER SPRINGS, FL 32708 41 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1917
       Built: 1980
    Monthly Fee: $44
       Tax: $1,888 (2025)
    Community: Tuskawilla Point
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,667 (change assumption)
    Mortgage ($2,466) + Fees ($44) + Taxes in 2025 ($157)


    Taxes:$1,888

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1254 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708

    $485,00072 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


  • 807 BUCKIE DR, WINTER SPRINGS, FL 32708

    $375,00029 Days on yellowkey   MLS ID: O6386108

    For Sale O6386108 - 807 BUCKIE DR, WINTER SPRINGS, FL 32708 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1574
       Built: 1978
    Monthly Fee: $35
       Tax: $4,487 (2025)
    Community: Highlands Sec 1
    Single Family


    Estimated Monthly Payment: $2,464 (change assumption)
    Mortgage ($2,055) + Fees ($35) + Taxes in 2025 ($374)


    Taxes:$4,487

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 165 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708

    $384,99085 Days on yellowkey   MLS ID: O6386473

    1 Days Off yellowkey (back on 4/22/2026)

    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


  • 270 SAN GABRIEL ST, WINTER SPRINGS, FL 32708

    $259,000197 Days on yellowkey   MLS ID: O6359666

    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: $1,567 (change assumption)
    Mortgage ($1,419) + 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


  • 337 KIRKCALDY DR, WINTER SPRINGS, FL 32708

    $284,900117 Days on yellowkey   MLS ID: O6375532

    For Sale O6375532 - 337 KIRKCALDY DR, WINTER SPRINGS, FL 32708 28 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 974
       Built: 1984
    Monthly Fee: $6
       Tax: $1,428 (2024)
    Community: Highland Village 1
    Single Family


    Estimated Monthly Payment: $1,686 (change assumption)
    Mortgage ($1,561) + Fees ($6) + Taxes in 2024 ($119)


    Taxes:$1,428

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 30 MOREE LOOP #37, WINTER SPRINGS, FL 32708

    $189,99556 Days on yellowkey   MLS ID: O6395945

    REDUCED by $5,005 (2.6%) on 04/20/2026

    For Sale O6395945 - 30 MOREE LOOP #37, WINTER SPRINGS, FL 32708 25 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1400
       Built: 1973
    Monthly Fee: $424
       Tax: $2,882 (2025)
    Community: Bay Tree
    Condo


    Estimated Monthly Payment: $1,705 (change assumption)
    Mortgage ($1,041) + Fees ($424) + Taxes in 2025 ($240)


    Taxes:$2,882

    Elementary School: Highlands Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: South Seminole Middle


  • 1444 BIRD RD, WINTER SPRINGS, FL 32708

    $838,500254 Days on yellowkey   MLS ID: O6344113

    For Sale O6344113 - 1444 BIRD RD, WINTER SPRINGS, FL 32708 48 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


  • 104 REDTAIL PL, WINTER SPRINGS, FL 32708

    $469,900116 Days on yellowkey   MLS ID: O6378697

    0 Days Off yellowkey (back on 4/24/2026)

    For Sale O6378697 - 104 REDTAIL PL, WINTER SPRINGS, FL 32708 45 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1766
       Built: 1995
    Monthly Fee: $170
       Tax: $2,250 (2024)
    Community: Eagles Watch Ph 1
    Single Family


    Estimated Monthly Payment: $2,932 (change assumption)
    Mortgage ($2,575) + Fees ($170) + Taxes in 2024 ($187)


    Taxes:$2,250

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4431 BROOK HOLLOW CIR, WINTER SPRINGS, FL 32708

    $230,000133 Days on yellowkey   MLS ID: O6374194

    For Sale O6374194 - 4431 BROOK HOLLOW CIR, WINTER SPRINGS, FL 32708 18 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1367
       Built: 1989
    Monthly Fee: $275
       Tax: $2,878 (2024)
    Community: Deer Run Unit 19A
    Townhouse


    Estimated Monthly Payment: $1,775 (change assumption)
    Mortgage ($1,260) + Fees ($275) + Taxes in 2024 ($240)


    Taxes:$2,878

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 455 OLD FARM LN, WINTER SPRINGS, FL 32708

    $356,00084 Days on yellowkey   MLS ID: O6387357

    For Sale O6387357 - 455 OLD FARM LN, WINTER SPRINGS, FL 32708 38 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1085
       Built: 2012
    Monthly Fee: $190
       Tax: $4,528 (2025)
    Community: Jesups Reserves Replat
    Townhouse


    Estimated Monthly Payment: $2,518 (change assumption)
    Mortgage ($1,951) + Fees ($190) + Taxes in 2025 ($377)


    Taxes:$4,528

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 130 DEER SONG DR, WINTER SPRINGS, FL 32708

    $310,00055 Days on yellowkey   MLS ID: O6395309

    For Sale O6395309 - 130 DEER SONG DR, WINTER SPRINGS, FL 32708 27 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1105
       Built: 1994
    Monthly Fee: $127
       Tax: $3,102 (2025)
    Community: Deersong 2
    Single Family


    Estimated Monthly Payment: $2,084 (change assumption)
    Mortgage ($1,699) + Fees ($127) + Taxes in 2025 ($259)


    Taxes:$3,102

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle




Why Bother Searching Elsewhere for Winter Springs Homes for Sale and Other Real Estate?

Winter Springs home, townhome, condo, villa, and other listing sales data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in Winter Springs . You can use our website to view Multiple Listing Service (MLS) data on Winter Springs Real Estate. 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 Winter Springs listings.



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.