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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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  • 294 SAN GABRIEL ST, WINTER SPRINGS, FL 32708

    $249,9904 Days on yellowkey   MLS ID: O6409921

    For Sale O6409921 - 294 SAN GABRIEL ST, WINTER SPRINGS, FL 32708 43 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1105
       Built: 1994
    Monthly Fee: $127
       Tax: $3,612 (2025)
    Community: Deersong 2
    Single Family


    Estimated Monthly Payment: $1,798 (change assumption)
    Mortgage ($1,370) + Fees ($127) + Taxes in 2025 ($301)


    Taxes:$3,612

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 314 SAN GABRIEL ST, WINTER SPRINGS, FL 32708

    $279,990230 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


  • 560 PLEASANT GROVE DR, WINTER SPRINGS, FL 32708

    $425,00031 Days on yellowkey   MLS ID: O6401016

    REDUCED by $20,000 (4.5%) on 05/20/2026

    For Sale O6401016 - 560 PLEASANT GROVE DR, WINTER SPRINGS, FL 32708 23 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1654
       Built: 1996
    Monthly Fee: $78
       Tax: $5,669 (2024)
    Community: Tusca Oaks
    Single Family


    Estimated Monthly Payment: $2,879 (change assumption)
    Mortgage ($2,329) + Fees ($78) + Taxes in 2024 ($472)


    Taxes:$5,669

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 1054 WINDING WATERS CIR, WINTER SPRINGS, FL 32708

    $559,90043 Days on yellowkey   MLS ID: O6398229

    0 Days Off yellowkey (back on 5/26/2026)

    REDUCED by $10,000 (1.8%) on 04/29/2026

    For Sale O6398229 - 1054 WINDING WATERS CIR, WINTER SPRINGS, FL 32708 29 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2321
       Built: 1998
    Monthly Fee: $42
       Tax: $4,167 (2025)
    Community: Winding Hollow
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,457 (change assumption)
    Mortgage ($3,068) + Fees ($42) + Taxes in 2025 ($347)


    Taxes:$4,167

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 108 SUNDANCE CT, WINTER SPRINGS, FL 32708

    $349,9006 Days on yellowkey   MLS ID: O6409784

    For Sale O6409784 - 108 SUNDANCE CT, WINTER SPRINGS, FL 32708 33 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1161
       Built: 1997
    Monthly Fee: $140
       Tax: $3,505 (2025)
    Community: The Seasons
    Single Family


    Estimated Monthly Payment: $2,349 (change assumption)
    Mortgage ($1,917) + Fees ($140) + Taxes in 2025 ($292)


    Taxes:$3,505

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1018 WEATHERED WOOD CIR, WINTER SPRINGS, FL 32708

    $369,0008 Days on yellowkey   MLS ID: O6408847

    For Sale O6408847 - 1018 WEATHERED WOOD CIR, WINTER SPRINGS, FL 32708 34 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1718
       Built: 1978
    Monthly Fee: $107
       Tax: $1,316 (2025)
    Community: Wedgewood Unit 2
    Single Family


    Estimated Monthly Payment: $2,238 (change assumption)
    Mortgage ($2,022) + Fees ($107) + Taxes in 2025 ($110)


    Taxes:$1,316

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 363 TWELVE OAKS DR, WINTER SPRINGS, FL 32708

    $599,00061 Days on yellowkey   MLS ID: O6394390

    REDUCED by $9,000 (1.5%) on 05/25/2026

    For Sale O6394390 - 363 TWELVE OAKS DR, WINTER SPRINGS, FL 32708 20 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3408
       Built: 2000
    Monthly Fee: $48
       Tax: $4,927 (2025)
    Community: Winding Hollow
    Single Family


    Estimated Monthly Payment: $3,741 (change assumption)
    Mortgage ($3,282) + Fees ($48) + Taxes in 2025 ($411)


    Taxes:$4,927

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 758 N GRETNA CT, WINTER SPRINGS, FL 32708

    $430,00023 Days on yellowkey   MLS ID: O6404912

    REDUCED by $20,000 (4.4%) on 05/25/2026

    For Sale O6404912 - 758 N GRETNA CT, WINTER SPRINGS, FL 32708 58 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2150
       Built: 1977
    Monthly Fee: $33
       Tax: $4,783 (2024)
    Community: Highlands Sec 4
    Single Family


    Estimated Monthly Payment: $2,788 (change assumption)
    Mortgage ($2,356) + Fees ($33) + Taxes in 2024 ($399)


    Taxes:$4,783

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 431 S ALDERWOOD ST, WINTER SPRINGS, FL 32708

    $390,00014 Days on yellowkey   MLS ID: O6407052

    For Sale O6407052 - 431 S ALDERWOOD ST, WINTER SPRINGS, FL 32708 52 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1558
       Built: 1973   Tax: $4,580 (2024)
    Community: North Orlando Terrace Unit 1 Sec 5
    Single Family


    Estimated Monthly Payment: $2,519 (change assumption)
    Mortgage ($2,137) + Taxes in 2024 ($382)


    Taxes:$4,580

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 330 HAYES RD, WINTER SPRINGS, FL 32708

    $820,00024 Days on yellowkey   MLS ID: O6404598

    REDUCED by $20,000 (2.4%) on 05/25/2026

    For Sale O6404598 - 330 HAYES RD, WINTER SPRINGS, FL 32708 58 photos

    Bed: 4   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2252
       Built: 1977   Tax: $2,738 (2024)
    Community: North Orlando Ranches Sec 04
    Single Family


    Estimated Monthly Payment: $4,721 (change assumption)
    Mortgage ($4,493) + Taxes in 2024 ($228)


    Taxes:$2,738

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: None


  • 629 RYAN CT, WINTER SPRINGS, FL 32708

    $479,00020 Days on yellowkey   MLS ID: O6396980

    For Sale O6396980 - 629 RYAN CT, WINTER SPRINGS, FL 32708 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1857
       Built: 2004
    Monthly Fee: $35
       Tax: $1,899 (2024)
    Community: The Highlands Sections Seven & Eight
    Single Family


    Estimated Monthly Payment: $2,818 (change assumption)
    Mortgage ($2,625) + Fees ($35) + Taxes in 2024 ($158)


    Taxes:$1,899

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 140 SEVILLE CHASE DR, WINTER SPRINGS, FL 32708

    $779,90056 Days on yellowkey   MLS ID: O6395594

    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: $4,945 (change assumption)
    Mortgage ($4,273) + 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


  • 30 SABLE CT, WINTER SPRINGS, FL 32708

    $569,000104 Days on yellowkey   MLS ID: O6382648

    REDUCED by $10,000 (1.7%) on 04/12/2026

    For Sale O6382648 - 30 SABLE CT, WINTER SPRINGS, FL 32708 11 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2674
       Built: 1976   Tax: $3,043 (2024)
    Community: Tuscawilla
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,371 (change assumption)
    Mortgage ($3,118) + Taxes in 2024 ($254)


    Taxes:$3,043

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 724 BARRINGTON CIR, WINTER SPRINGS, FL 32708

    $399,900370 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

    $366,90021 Days on yellowkey   MLS ID: O6404854

    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: $2,054 (change assumption)
    Mortgage ($2,010) + Taxes in 2025 ($44)


    Taxes:$523

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 276 SAN GABRIEL ST, WINTER SPRINGS, FL 32708

    $285,00041 Days on yellowkey   MLS ID: O6399623

    REDUCED by $5,000 (1.7%) on 05/20/2026

    For Sale O6399623 - 276 SAN GABRIEL ST, WINTER SPRINGS, FL 32708 35 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1089
       Built: 1994
    Monthly Fee: $127
       Tax: $3,719 (2025)
    Community: Deersong 2
    Single Family


    Estimated Monthly Payment: $1,999 (change assumption)
    Mortgage ($1,562) + Fees ($127) + Taxes in 2025 ($310)


    Taxes:$3,719

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 440 BUCKSKIN CT, WINTER SPRINGS, FL 32708

    $534,90062 Days on yellowkey   MLS ID: O6394274

    REDUCED by $14,100 (2.6%) on 05/22/2026

    For Sale O6394274 - 440 BUCKSKIN CT, WINTER SPRINGS, FL 32708 62 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1922
       Built: 1986
    Monthly Fee: $30
       Tax: $5,731 (2025)
    Community: Deer Run Unit 20
    Single Family


    Estimated Monthly Payment: $3,438 (change assumption)
    Mortgage ($2,931) + Fees ($30) + Taxes in 2025 ($478)


    Taxes:$5,731

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 4991 COURTLAND LOOP, WINTER SPRINGS, FL 32708

    $750,0007 Days on yellowkey   MLS ID: O6409511

    1 Days Off yellowkey (back on 5/24/2026)

    For Sale O6409511 - 4991 COURTLAND LOOP, WINTER SPRINGS, FL 32708 53 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3217
       Built: 1983
    Monthly Fee: $40
       Tax: $6,752 (2025)
    Community: Tuskabay
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,712 (change assumption)
    Mortgage ($4,109) + Fees ($40) + Taxes in 2025 ($563)


    Taxes:$6,752

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 736 SUMMERLAND DR, WINTER SPRINGS, FL 32708

    $298,90034 Days on yellowkey   MLS ID: O6402028

    REDUCED by $1,100 (0.4%) on 05/05/2026

    For Sale O6402028 - 736 SUMMERLAND DR, WINTER SPRINGS, FL 32708 67 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1298
       Built: 1983
    Monthly Fee: $95
       Tax: $2,905 (2025)
    Community: Wildwood
    Single Family


    Estimated Monthly Payment: $1,975 (change assumption)
    Mortgage ($1,638) + Fees ($95) + Taxes in 2025 ($242)


    Taxes:$2,905

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1020 TAPROOT DR, WINTER SPRINGS, FL 32708

    $509,9008 Days on yellowkey   MLS ID: O6409011

    For Sale O6409011 - 1020 TAPROOT DR, WINTER SPRINGS, FL 32708 41 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1905
       Built: 2021   Tax: $4,953 (2024)
    Community: Oak Forest Unit 1
    Single Family


    Estimated Monthly Payment: $3,207 (change assumption)
    Mortgage ($2,794) + Taxes in 2024 ($413)


    Taxes:$4,953

    Elementary School: Keeth 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.