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Winter Springs Single Family Homes For Sale - 145 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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  • 1107 WINTER SPRINGS BLVD, WINTER SPRINGS, FL 32708

    $570,0004 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

    $399,900394 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


  • 221 SHERRY AVE, WINTER SPRINGS, FL 32708

    $359,90045 Days on yellowkey   MLS ID: O6404854

    REDUCED by $7,000 (1.9%) on 06/17/2026

    For Sale O6404854 - 221 SHERRY AVE, WINTER SPRINGS, FL 32708 18 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1700
       Built: 1971   Tax: $523 (2025)
    Community: North Orlando Townsite Fourth Add Replat
    Single Family


    Estimated Monthly Payment: $2,016 (change assumption)
    Mortgage ($1,972) + Taxes in 2025 ($44)


    Taxes:$523

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 214 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708

    $590,000120 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


  • 809 BIG BUCK CIR, WINTER SPRINGS, FL 32708

    $549,0007 Days on yellowkey   MLS ID: O6416554

    For Sale O6416554 - 809 BIG BUCK CIR, WINTER SPRINGS, FL 32708 52 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2250
       Built: 1984
    Monthly Fee: $3
       Tax: $6,018 (2025)
    Community: Oak Forest Unit 3
    Single Family


    Estimated Monthly Payment: $3,513 (change assumption)
    Mortgage ($3,008) + Fees ($3) + Taxes in 2025 ($502)


    Taxes:$6,018

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 717 ADIDAS RD, WINTER SPRINGS, FL 32708

    $445,0002 Days on yellowkey   MLS ID: V4949727

    For Sale V4949727 - 717 ADIDAS RD, WINTER SPRINGS, FL 32708 31 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1812
       Built: 1986
    Monthly Fee: $95
       Tax: $5,844 (2025)
    Community: Wedgewood Tennis Villas
    Single Family


    Estimated Monthly Payment: $3,020 (change assumption)
    Mortgage ($2,438) + Fees ($95) + Taxes in 2025 ($487)


    Taxes:$5,844

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 203 SWEETGUM, WINTER SPRINGS, FL 32708

    $420,0002 Days on yellowkey   MLS ID: O6417974

    For Sale O6417974 - 203 SWEETGUM, WINTER SPRINGS, FL 32708 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1218
       Built: 1973   Tax: $925 (2025)
    Community: North Orlando Terrace Unit 2 Sec 8
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,378 (change assumption)
    Mortgage ($2,301) + Taxes in 2025 ($77)


    Taxes:$925

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 200 BLUE CREEK DR, WINTER SPRINGS, FL 32708

    $625,0004 Days on yellowkey   MLS ID: O6416327

    For Sale O6416327 - 200 BLUE CREEK DR, WINTER SPRINGS, FL 32708 73 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2344
       Built: 1997
    Monthly Fee: $70
       Tax: $3,467 (2025)
    Community: Chestnut Estates Ph 2
    Single Family


    Estimated Monthly Payment: $3,783 (change assumption)
    Mortgage ($3,425) + Fees ($70) + Taxes in 2025 ($289)


    Taxes:$3,467

    Elementary School: Lawton Elementary

    High School: Oviedo High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 568 BUCKHORN DR, WINTER SPRINGS, FL 32708

    $485,00013 Days on yellowkey   MLS ID: O6413584

    For Sale O6413584 - 568 BUCKHORN DR, WINTER SPRINGS, FL 32708 35 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2076
       Built: 2012
    Monthly Fee: $167
       Tax: $3,280 (2025)
    Community: Winter Spgs Village Ph 1
    Single Family


    Estimated Monthly Payment: $3,098 (change assumption)
    Mortgage ($2,657) + Fees ($167) + Taxes in 2025 ($273)


    Taxes:$3,280

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1105 CLINGING VINE PL, WINTER SPRINGS, FL 32708

    $500,0001 Day on yellowkey   MLS ID: O6416115

    For Sale O6416115 - 1105 CLINGING VINE PL, WINTER SPRINGS, FL 32708 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2044
       Built: 1993
    Monthly Fee: $53
       Tax: $2,249 (2025)
    Community: Eagles Landing
    Single Family


    Estimated Monthly Payment: $2,980 (change assumption)
    Mortgage ($2,740) + Fees ($53) + Taxes in 2025 ($187)


    Taxes:$2,249

    Elementary School: Rainbow Elementary

    High School: Oviedo High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1208 CHEETAH TRL, WINTER SPRINGS, FL 32708

    $669,9002 Days 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


  • 314 SAN GABRIEL ST, WINTER SPRINGS, FL 32708

    $279,990254 Days on yellowkey   MLS ID: O6350799

    For Sale O6350799 - 314 SAN GABRIEL ST, WINTER SPRINGS, FL 32708 30 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1091
       Built: 1992
    Monthly Fee: $127
       Tax: $2,209 (2024)
    Community: Deersong
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,845 (change assumption)
    Mortgage ($1,534) + Fees ($127) + Taxes in 2024 ($184)


    Taxes:$2,209

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4209 LORI LOOP, WINTER SPRINGS, FL 32708

    $625,00043 Days on yellowkey   MLS ID: O6406486

    For Sale O6406486 - 4209 LORI LOOP, WINTER SPRINGS, FL 32708 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2428
       Built: 1986
    Monthly Fee: $17
       Tax: $6,046 (2024)
    Community: Willow Run
    Single Family


    Estimated Monthly Payment: $3,945 (change assumption)
    Mortgage ($3,425) + Fees ($17) + Taxes in 2024 ($504)


    Taxes:$6,046

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 270 SAN GABRIEL ST, WINTER SPRINGS, FL 32708

    $249,900221 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


  • 1126 TROTWOOD BLVD, WINTER SPRINGS, FL 32708

    $460,000126 Days on yellowkey   MLS ID: O6382859

    REDUCED by $10,000 (2.1%) on 06/20/2026

    For Sale O6382859 - 1126 TROTWOOD BLVD, WINTER SPRINGS, FL 32708 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2066
       Built: 1991
    Monthly Fee: $11
       Tax: $5,998 (2024)
    Community: Oak Forest Unit 8
    Single Family


    Estimated Monthly Payment: $3,031 (change assumption)
    Mortgage ($2,520) + Fees ($11) + Taxes in 2024 ($500)


    Taxes:$5,998

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 995 DYSON DR, WINTER SPRINGS, FL 32708

    $750,0001 Day on yellowkey   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


  • 662 SARANAC DR, WINTER SPRINGS, FL 32708

    $643,10016 Days on yellowkey   MLS ID: O6413437

    For Sale O6413437 - 662 SARANAC DR, WINTER SPRINGS, FL 32708 44 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2180
       Built: 1986
    Monthly Fee: $6
       Tax: $3,686 (2025)
    Community: Tuscawilla Unit 14A
    Single Family


    Estimated Monthly Payment: $3,837 (change assumption)
    Mortgage ($3,524) + Fees ($6) + Taxes in 2025 ($307)


    Taxes:$3,686

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 830 DUNBAR TER, WINTER SPRINGS, FL 32708

    $361,0001 Day on yellowkey   MLS ID: O6418603

    For Sale O6418603 - 830 DUNBAR TER, WINTER SPRINGS, FL 32708 26 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1792
       Built: 1978
    Monthly Fee: $35
       Tax: $2,088 (2025)
    Community: Highlands Sec 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,187 (change assumption)
    Mortgage ($1,978) + Fees ($35) + Taxes in 2025 ($174)


    Taxes:$2,088

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 749 WILLOW RUN LN, WINTER SPRINGS, FL 32708

    $620,00038 Days on yellowkey   MLS ID: O6407791

    For Sale O6407791 - 749 WILLOW RUN LN, WINTER SPRINGS, FL 32708 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2456
       Built: 1986
    Monthly Fee: $17
       Tax: $5,752 (2025)
    Community: Willow Run
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,893 (change assumption)
    Mortgage ($3,397) + Fees ($17) + Taxes in 2025 ($479)


    Taxes:$5,752

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 143 HAYES RD, WINTER SPRINGS, FL 32708

    $479,00037 Days on yellowkey   MLS ID: O6407546

    REDUCED by $10,000 (2.0%) on 05/27/2026

    For Sale O6407546 - 143 HAYES RD, WINTER SPRINGS, FL 32708 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1649
       Built: 1983   Tax: $1,782 (2024)
    Community: North Orlando Ranches Sec 02A
    Single Family


    Estimated Monthly Payment: $2,773 (change assumption)
    Mortgage ($2,625) + Taxes in 2024 ($149)


    Taxes:$1,782

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




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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.