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Winter Springs Single Family Homes For Sale - 130 homes

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

Location: Winter Springs

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  • 1452 CONNORS LN, WINTER SPRINGS, FL 32708

    $475,00024 Days on yellowkey   MLS ID: O6404505

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

    For Sale O6404505 - 1452 CONNORS LN, WINTER SPRINGS, FL 32708 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1766
       Built: 1986
    Monthly Fee: $90
       Tax: $4,752 (2024)
    Community: Wedgewood Tennis Villas
    Single Family


    Estimated Monthly Payment: $3,089 (change assumption)
    Mortgage ($2,603) + Fees ($90) + Taxes in 2024 ($396)


    Taxes:$4,752

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 4951 COURTLAND LOOP, WINTER SPRINGS, FL 32708

    $690,000133 Days on yellowkey   MLS ID: O6374007

    REDUCED by $10,000 (1.4%) on 05/05/2026

    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: $4,471 (change assumption)
    Mortgage ($3,781) + 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


  • 1029 E PEBBLE BEACH CIR, WINTER SPRINGS, FL 32708

    $395,00027 Days on yellowkey   MLS ID: O6404082

    0 Days Off yellowkey (back on 5/4/2026)

    For Sale O6404082 - 1029 E PEBBLE BEACH CIR, WINTER SPRINGS, FL 32708 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1314
       Built: 1993
    Monthly Fee: $117
       Tax: $1,736 (2025)
    Community: Country Club Village Unit 3
    Single Family


    Estimated Monthly Payment: $2,426 (change assumption)
    Mortgage ($2,164) + Fees ($117) + Taxes in 2025 ($145)


    Taxes:$1,736

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 903 TORREY PINE DR, WINTER SPRINGS, FL 32708

    $469,900111 Days on yellowkey   MLS ID: O6377459

    1 Days Off yellowkey (back on 5/4/2026)

    For Sale O6377459 - 903 TORREY PINE DR, WINTER SPRINGS, FL 32708 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1501
       Built: 1998
    Monthly Fee: $126
       Tax: $2,155 (2024)
    Community: Greenbriar Sub Ph 2
    Single Family


    Estimated Monthly Payment: $2,880 (change assumption)
    Mortgage ($2,575) + Fees ($126) + Taxes in 2024 ($180)


    Taxes:$2,155

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 421 HORIZON DR, WINTER SPRINGS, FL 32708

    $299,90090 Days on yellowkey   MLS ID: O6384932

    REDUCED by $15,100 (4.8%) on 04/29/2026

    For Sale O6384932 - 421 HORIZON DR, WINTER SPRINGS, FL 32708 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1069
       Built: 1998
    Monthly Fee: $142
       Tax: $3,681 (2025)
    Community: Seasons The
    Single Family


    Estimated Monthly Payment: $2,092 (change assumption)
    Mortgage ($1,643) + Fees ($142) + Taxes in 2025 ($307)


    Taxes:$3,681

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 649 DAVID ST, WINTER SPRINGS, FL 32708

    $265,00056 Days on yellowkey   MLS ID: O6395999

    0 Days Off yellowkey (back on 5/2/2026)

    For Sale O6395999 - 649 DAVID ST, WINTER SPRINGS, FL 32708 27 photos

    Bed: 3   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 1077
       Built: 1971   Tax: $3,074 (2025)
    Community: North Orlando Townsite 4Th Add Rep
    Single Family


    Estimated Monthly Payment: $1,708 (change assumption)
    Mortgage ($1,452) + Taxes in 2025 ($256)


    Taxes:$3,074

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 936 TORREY PINE DR, WINTER SPRINGS, FL 32708

    $420,00057 Days on yellowkey   MLS ID: O6386843

    0 Days Off yellowkey (back on 5/2/2026)

    For Sale O6386843 - 936 TORREY PINE DR, WINTER SPRINGS, FL 32708 26 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1678
       Built: 2000
    Monthly Fee: $126
       Tax: $2,652 (2024)
    Community: Greenbriar Sub Ph 2
    Single Family


    Estimated Monthly Payment: $2,648 (change assumption)
    Mortgage ($2,301) + Fees ($126) + Taxes in 2024 ($221)


    Taxes:$2,652

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 684 OLEAN CT, WINTER SPRINGS, FL 32708

    $849,90041 Days on yellowkey   MLS ID: O6399510

    0 Days Off yellowkey (back on 5/2/2026)

    For Sale O6399510 - 684 OLEAN CT, WINTER SPRINGS, FL 32708 62 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 2832
       Built: 1988
    Monthly Fee: $8
       Tax: $8,448 (2025)
    Community: Chelsea Woods
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,369 (change assumption)
    Mortgage ($4,657) + Fees ($8) + Taxes in 2025 ($704)


    Taxes:$8,448

    Elementary School: Lawton Elementary

    High School: Oviedo High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 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


  • 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


  • 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


  • 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


  • 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


  • 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


  • 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


  • 1421 HAPPY BIRD LN, WINTER SPRINGS, FL 32708

    $573,448197 Days on yellowkey   MLS ID: O6359884

    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: $3,671 (change assumption)
    Mortgage ($3,142) + 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




Why Bother Searching Elsewhere for Winter Springs Single Family Homes for Sale?

Winter Springs home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Springs . You can use our website to view Multiple Listing Service (MLS) data on Winter Springs single family homes. 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 single family home 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.