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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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  • 214 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708

    $590,000122 Days on yellowkey   MLS ID: O6372400

    0 Days Off yellowkey (back on 6/21/2026)

    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


  • 877 BENCHWOOD DR, WINTER SPRINGS, FL 32708

    $450,00026 Days on yellowkey   MLS ID: O6410431

    REDUCED by $10,000 (2.2%) on 06/18/2026

    For Sale O6410431 - 877 BENCHWOOD DR, WINTER SPRINGS, FL 32708 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1612
       Built: 1983
    Monthly Fee: $3
       Tax: $3,127 (2024)
    Community: Oak Forest Unit 3
    Single Family


    Estimated Monthly Payment: $2,729 (change assumption)
    Mortgage ($2,466) + Fees ($3) + Taxes in 2024 ($261)


    Taxes:$3,127

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 819 DUNDEE DR, WINTER SPRINGS, FL 32708

    $419,00020 Days on yellowkey   MLS ID: O6412585

    REDUCED by $10,000 (2.3%) on 06/16/2026

    For Sale O6412585 - 819 DUNDEE DR, WINTER SPRINGS, FL 32708 47 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1701
       Built: 1978
    Monthly Fee: $40
       Tax: $1,558 (2025)
    Community: Highlands Sec 1
    Single Family


    Estimated Monthly Payment: $2,466 (change assumption)
    Mortgage ($2,296) + Fees ($40) + Taxes in 2025 ($130)


    Taxes:$1,558

    Elementary School: Highlands Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: South Seminole Middle


  • 140 SEVILLE CHASE DR, WINTER SPRINGS, FL 32708

    $769,90082 Days on yellowkey   MLS ID: O6395594

    REDUCED by $10,000 (1.3%) on 06/10/2026

    For Sale O6395594 - 140 SEVILLE CHASE DR, WINTER SPRINGS, FL 32708 46 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3129
       Built: 1999
    Monthly Fee: $184
       Tax: $5,857 (2024)
    Community: Seville Chase
    Single Family


    Estimated Monthly Payment: $4,891 (change assumption)
    Mortgage ($4,219) + Fees ($184) + Taxes in 2024 ($488)


    Taxes:$5,857

    Elementary School: Sterling Park Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 200 BLUE CREEK DR, WINTER SPRINGS, FL 32708

    $625,0006 Days on yellowkey   MLS ID: O6416327

    0 Days Off yellowkey (back on 6/21/2026)

    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


  • 1530 BRAEWICK ST, WINTER SPRINGS, FL 32708

    $449,9008 Days on yellowkey   MLS ID: TB8518340

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

    For Sale TB8518340 - 1530 BRAEWICK ST, WINTER SPRINGS, FL 32708 15 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1889
       Built: 1999
    Monthly Fee: $115
       Tax: $2,255 (2025)
    Community: Fox Glen At Chelsea Parc Tuscawilla
    Single Family


    Estimated Monthly Payment: $2,768 (change assumption)
    Mortgage ($2,465) + Fees ($115) + Taxes in 2025 ($188)


    Taxes:$2,255

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1105 CLINGING VINE PL, WINTER SPRINGS, FL 32708

    $500,0003 Days 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


  • 1107 WINTER SPRINGS BLVD, WINTER SPRINGS, FL 32708

    $570,0006 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


  • 995 DYSON DR, WINTER SPRINGS, FL 32708

    $750,0004 Days on yellowkey   MLS ID: O6418233

    0 Days Off yellowkey (back on 6/20/2026)

    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


  • 1160 CITRUS OAKS RUN, WINTER SPRINGS, FL 32708

    $825,00036 Days on yellowkey   MLS ID: O6408959

    0 Days Off yellowkey (back on 6/12/2026)

    REDUCED by $25,000 (2.9%) on 06/04/2026

    For Sale O6408959 - 1160 CITRUS OAKS RUN, WINTER SPRINGS, FL 32708 40 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3118
       Built: 2001
    Monthly Fee: $127
       Tax: $8,339 (2025)
    Community: Citrus Oaks
    Single Family


    Estimated Monthly Payment: $5,342 (change assumption)
    Mortgage ($4,520) + Fees ($127) + Taxes in 2025 ($695)


    Taxes:$8,339

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 577 WALDEN CT, WINTER SPRINGS, FL 32708

    $399,00015 Days on yellowkey   MLS ID: V4949540

    REDUCED by $6,000 (1.5%) on 06/20/2026

    For Sale V4949540 - 577 WALDEN CT, WINTER SPRINGS, FL 32708 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1560
       Built: 1974   Tax: $3,414 (2025)
    Community: Walden Terrace
    Single Family


    Estimated Monthly Payment: $2,471 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($284)


    Taxes:$3,414

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1385 SAN DIEGO CT, WINTER SPRINGS, FL 32708

    $320,00075 Days on yellowkey   MLS ID: O6397680

    0 Days Off yellowkey (back on 6/20/2026)

    REDUCED by $29,000 (8.3%) on 06/17/2026

    For Sale O6397680 - 1385 SAN DIEGO CT, WINTER SPRINGS, FL 32708 28 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1518
       Built: 1983
    Monthly Fee: $29
       Tax: $1,283 (2025)
    Community: Sunrise Village Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,889 (change assumption)
    Mortgage ($1,753) + Fees ($29) + Taxes in 2025 ($107)


    Taxes:$1,283

    Elementary School: Rainbow Elementary

    High School: Oviedo High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1208 CHEETAH TRL, WINTER SPRINGS, FL 32708

    $669,9004 Days on yellowkey   MLS ID: O6416652

    0 Days Off yellowkey (back on 6/20/2026)

    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


  • 1201 WOLVERINE TRL, WINTER SPRINGS, FL 32708

    $500,000156 Days on yellowkey   MLS ID: O6374676

    For Sale O6374676 - 1201 WOLVERINE TRL, WINTER SPRINGS, FL 32708 40 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1979
       Built: 1977   Tax: $5,709 (2024)
    Community: Winter Spgs Unit 4
    Single Family


    Estimated Monthly Payment: $3,215 (change assumption)
    Mortgage ($2,740) + Taxes in 2024 ($476)


    Taxes:$5,709

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 724 BARRINGTON CIR, WINTER SPRINGS, FL 32708

    $399,900396 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

    $359,90047 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


  • 809 BIG BUCK CIR, WINTER SPRINGS, FL 32708

    $549,0009 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

    $445,0004 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

    $420,0004 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


  • 270 SAN GABRIEL ST, WINTER SPRINGS, FL 32708

    $249,900223 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




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.