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Displaying: For Sale

Location: Winter Springs

Property Type(s): Single Family

Price: $400,000 to $499,000

Winter Springs - 29 properties found

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  • 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


  • 568 BUCKHORN DR, WINTER SPRINGS, FL 32708

    $475,00016 Days on yellowkey   MLS ID: O6413584

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

    REDUCED by $10,000 (2.1%) on 06/22/2026

    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: $3,043 (change assumption)
    Mortgage ($2,603) + Fees ($167) + Taxes in 2025 ($273)


    Taxes:$3,280

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 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


  • 122 STONE GABLE CIR, WINTER SPRINGS, FL 32708

    $485,000294 Days on yellowkey   MLS ID: O6340870

    INCREASED by $5,000 (1.0%) on 05/29/2026

    For Sale O6340870 - 122 STONE GABLE CIR, WINTER SPRINGS, FL 32708 42 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2147
       Built: 1999
    Monthly Fee: $58
       Tax: $6,186 (2024)
    Community: Stone Gable
    Single Family


    Estimated Monthly Payment: $3,231 (change assumption)
    Mortgage ($2,657) + Fees ($58) + Taxes in 2024 ($516)


    Taxes:$6,186

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 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


  • 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


  • 203 SWEETGUM, WINTER SPRINGS, FL 32708

    $420,0005 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


  • 1126 TROTWOOD BLVD, WINTER SPRINGS, FL 32708

    $460,000129 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


  • 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


  • 1024 DINERO DR, WINTER SPRINGS, FL 32708

    $419,00054 Days on yellowkey   MLS ID: O6404240

    REDUCED by $5,000 (1.2%) on 06/17/2026

    For Sale O6404240 - 1024 DINERO DR, WINTER SPRINGS, FL 32708 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1463
       Built: 1986
    Monthly Fee: $29
       Tax: $4,882 (2024)
    Community: Sunrise Estates Unit 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,732 (change assumption)
    Mortgage ($2,296) + Fees ($29) + Taxes in 2024 ($407)


    Taxes:$4,882

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 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


  • 1307 ORTEGA ST, WINTER SPRINGS, FL 32708

    $430,00097 Days on yellowkey   MLS ID: O6391915

    REDUCED by $8,000 (1.8%) on 06/09/2026

    For Sale O6391915 - 1307 ORTEGA ST, WINTER SPRINGS, FL 32708 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1881
       Built: 1984
    Monthly Fee: $29
       Tax: $4,874 (2026)
    Community: Sunrise Unit 2-B
    Single Family


    Estimated Monthly Payment: $2,791 (change assumption)
    Mortgage ($2,356) + Fees ($29) + Taxes in 2026 ($406)


    Taxes:$4,874

    Elementary School: Rainbow Elementary

    High School: Oviedo High

    Tax Year: 2026

    Middle School: Indian Trails Middle


  • 1320 ALFONZO CIR, WINTER SPRINGS, FL 32708

    $450,00019 Days on yellowkey   MLS ID: S5151348

    0 Days Off yellowkey (back on 6/11/2026)

    For Sale S5151348 - 1320 ALFONZO CIR, WINTER SPRINGS, FL 32708 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1597
       Built: 1984
    Monthly Fee: $29
       Tax: $1,247 (2025)
    Community: Sunrise Unit 2D
    Single Family


    Estimated Monthly Payment: $2,599 (change assumption)
    Mortgage ($2,466) + Fees ($29) + Taxes in 2025 ($104)


    Taxes:$1,247

    Elementary School: Rainbow Elementary

    High School: None

    Tax Year: 2025

    Middle School: None


12




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