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Displaying: For Sale

Location: Winter Springs

Property Type(s): Single Family

Living Area Square Feet: 1500 to 1999

Winter Springs - 39 properties found

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  • 830 DUNBAR TER, WINTER SPRINGS, FL 32708

    $361,0005 Days 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


  • 1441 FOREST HILLS DR, WINTER SPRINGS, FL 32708

    $420,0008 Days on yellowkey   MLS ID: O6413957

    1 Days Off yellowkey (back on 6/24/2026)

    For Sale O6413957 - 1441 FOREST HILLS DR, WINTER SPRINGS, FL 32708 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1731
       Built: 1985
    Monthly Fee: $90
       Tax: $2,546 (2025)
    Community: Wedgewood Tennis Villas
    Single Family


    Estimated Monthly Payment: $2,603 (change assumption)
    Mortgage ($2,301) + Fees ($90) + Taxes in 2025 ($212)


    Taxes:$2,546

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 717 ADIDAS RD, WINTER SPRINGS, FL 32708

    $439,9005 Days on yellowkey   MLS ID: V4949727

    REDUCED by $5,100 (1.1%) on 06/24/2026

    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: $2,992 (change assumption)
    Mortgage ($2,410) + Fees ($95) + Taxes in 2025 ($487)


    Taxes:$5,844

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 440 BUCKSKIN CT, WINTER SPRINGS, FL 32708

    $525,00089 Days on yellowkey   MLS ID: O6394274

    REDUCED by $9,900 (1.9%) on 06/24/2026

    For Sale O6394274 - 440 BUCKSKIN CT, WINTER SPRINGS, FL 32708 52 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: $3,384 (change assumption)
    Mortgage ($2,877) + 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


  • 986 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708

    $494,000159 Days on yellowkey   MLS ID: O6374288

    REDUCED by $4,900 (1.0%) on 06/24/2026

    For Sale O6374288 - 986 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708 54 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1864
       Built: 1985
    Monthly Fee: $3
       Tax: $3,119 (2024)
    Community: Oak Forest Unit 4
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,970 (change assumption)
    Mortgage ($2,707) + Fees ($3) + Taxes in 2024 ($260)


    Taxes:$3,119

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 1530 BRAEWICK ST, WINTER SPRINGS, FL 32708

    $449,9009 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


  • 1055 CHESTERFIELD CIR, WINTER SPRINGS, FL 32708

    $499,90020 Days on yellowkey   MLS ID: O6413841

    REDUCED by $10,100 (2.0%) on 06/23/2026

    For Sale O6413841 - 1055 CHESTERFIELD CIR, WINTER SPRINGS, FL 32708 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1665
       Built: 1984
    Monthly Fee: $25
       Tax: $5,048 (2025)
    Community: Amherst
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,185 (change assumption)
    Mortgage ($2,739) + Fees ($25) + Taxes in 2025 ($421)


    Taxes:$5,048

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1335 SAN FELIPE CT, WINTER SPRINGS, FL 32708

    $450,0007 Days on yellowkey   MLS ID: O6417601

    1 Days Off yellowkey (back on 6/23/2026)

    For Sale O6417601 - 1335 SAN FELIPE CT, WINTER SPRINGS, FL 32708 65 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1571
       Built: 1987   Tax: $5,051 (2025)
    Community: Sunrise Village Unit 6
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,887 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($421)


    Taxes:$5,051

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 629 RYAN CT, WINTER SPRINGS, FL 32708

    $475,00047 Days on yellowkey   MLS ID: O6396980

    REDUCED by $4,000 (0.8%) on 06/23/2026

    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: $2,796 (change assumption)
    Mortgage ($2,603) + Fees ($35) + Taxes in 2024 ($158)


    Taxes:$1,899

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 143 HAYES RD, WINTER SPRINGS, FL 32708

    $479,00040 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


  • 934 TORREY PINE DR, WINTER SPRINGS, FL 32708

    $499,000262 Days on yellowkey   MLS ID: O6349893

    REDUCED by $15,000 (2.9%) on 06/10/2026

    For Sale O6349893 - 934 TORREY PINE DR, WINTER SPRINGS, FL 32708 54 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1678
       Built: 2000
    Monthly Fee: $126
       Tax: $2,280 (2024)
    Community: Greenbriar Sub Ph 2
    Single Family


    Estimated Monthly Payment: $3,050 (change assumption)
    Mortgage ($2,734) + Fees ($126) + Taxes in 2024 ($190)


    Taxes:$2,280

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 984 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708

    $410,00028 Days on yellowkey   MLS ID: O6410083

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

    For Sale O6410083 - 984 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708 44 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1821
       Built: 1985
    Monthly Fee: $3
       Tax: $3,100 (2025)
    Community: Oak Forest Unit 4
    Single Family


    Estimated Monthly Payment: $2,508 (change assumption)
    Mortgage ($2,247) + Fees ($3) + Taxes in 2025 ($258)


    Taxes:$3,100

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 877 BENCHWOOD DR, WINTER SPRINGS, FL 32708

    $450,00027 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

    $419,00021 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


  • 577 WALDEN CT, WINTER SPRINGS, FL 32708

    $399,00016 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

    $320,00076 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


  • 1201 WOLVERINE TRL, WINTER SPRINGS, FL 32708

    $500,000157 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


  • 221 SHERRY AVE, WINTER SPRINGS, FL 32708

    $359,90048 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


  • 114 STONE GABLE CIR, WINTER SPRINGS, FL 32708

    $485,9008 Days on yellowkey   MLS ID: O6417280

    For Sale O6417280 - 114 STONE GABLE CIR, WINTER SPRINGS, FL 32708 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1814
       Built: 1998
    Monthly Fee: $50
       Tax: $4,263 (2025)
    Community: Stone Gable
    Single Family


    Estimated Monthly Payment: $3,068 (change assumption)
    Mortgage ($2,662) + Fees ($50) + Taxes in 2025 ($355)


    Taxes:$4,263

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 907 GLEN ABBEY CIR, WINTER SPRINGS, FL 32708

    $420,00028 Days on yellowkey   MLS ID: O6411321

    For Sale O6411321 - 907 GLEN ABBEY CIR, WINTER SPRINGS, FL 32708 48 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1791
       Built: 1997
    Monthly Fee: $126
       Tax: $2,093 (2025)
    Community: Greenbriar Sub Ph 2
    Single Family


    Estimated Monthly Payment: $2,602 (change assumption)
    Mortgage ($2,301) + Fees ($126) + Taxes in 2025 ($174)


    Taxes:$2,093

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


12




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