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Displaying: For Sale

Location: Winter Springs

Property Type(s): Single Family

Price: $500,000 to $599,000

Winter Springs - 23 properties found

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  • 1389 PONCE DE LEON BLVD, WINTER SPRINGS, FL 32708

    $535,0001 Day on yellowkey   MLS ID: O6413725

    For Sale O6413725 - 1389 PONCE DE LEON BLVD, WINTER SPRINGS, FL 32708 54 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2056
       Built: 1980
    Monthly Fee: $32
       Tax: $2,474 (2025)
    Community: Sunrise Unit 2-A
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,170 (change assumption)
    Mortgage ($2,931) + Fees ($32) + Taxes in 2025 ($206)


    Taxes:$2,474

    Elementary School: Rainbow Elementary

    High School: Oviedo High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 947 GLEN ABBEY CIR, WINTER SPRINGS, FL 32708

    $525,0002 Days on yellowkey   MLS ID: O6418792

    For Sale O6418792 - 947 GLEN ABBEY CIR, WINTER SPRINGS, FL 32708 37 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2416
       Built: 1997
    Monthly Fee: $126
       Tax: $2,980 (2025)
    Community: Greenbriar Sub Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,251 (change assumption)
    Mortgage ($2,877) + Fees ($126) + Taxes in 2025 ($248)


    Taxes:$2,980

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 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


  • 363 TWELVE OAKS DR, WINTER SPRINGS, FL 32708

    $537,00088 Days on yellowkey   MLS ID: O6394390

    REDUCED by $42,000 (7.3%) on 06/23/2026

    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: $3,401 (change assumption)
    Mortgage ($2,942) + Fees ($48) + Taxes in 2025 ($411)


    Taxes:$4,927

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 71 TARPON CIR, WINTER SPRINGS, FL 32708

    $525,0004 Days on yellowkey   MLS ID: O6418735

    For Sale O6418735 - 71 TARPON CIR, WINTER SPRINGS, FL 32708 24 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2637
       Built: 1973
    Monthly Fee: $3
       Tax: $2,415 (2025)
    Community: Winter Spgs Unit 4
    Single Family


    Estimated Monthly Payment: $3,081 (change assumption)
    Mortgage ($2,877) + Fees ($3) + Taxes in 2025 ($201)


    Taxes:$2,415

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 268 TAVESTOCK LOOP, WINTER SPRINGS, FL 32708

    $557,90041 Days on yellowkey   MLS ID: O6407307

    REDUCED by $12,000 (2.1%) on 06/22/2026

    For Sale O6407307 - 268 TAVESTOCK LOOP, WINTER SPRINGS, FL 32708 45 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2415
       Built: 2001
    Monthly Fee: $150
       Tax: $4,293 (2025)
    Community: Parkstone
    Single Family


    Estimated Monthly Payment: $3,565 (change assumption)
    Mortgage ($3,057) + Fees ($150) + Taxes in 2025 ($358)


    Taxes:$4,293

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 214 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708

    $590,000123 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


  • 1105 CLINGING VINE PL, WINTER SPRINGS, FL 32708

    $500,0004 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

    $570,0007 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


  • 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


  • 809 BIG BUCK CIR, WINTER SPRINGS, FL 32708

    $549,00010 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


  • 424 FLATWOOD DR, WINTER SPRINGS, FL 32708

    $525,00043 Days on yellowkey   MLS ID: S5149589

    For Sale S5149589 - 424 FLATWOOD DR, WINTER SPRINGS, FL 32708 1 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2164
       Built: 1997
    Monthly Fee: $82
       Tax: $3,052 (2024)
    Community: Tusca Oaks
    Single Family


    Estimated Monthly Payment: $3,213 (change assumption)
    Mortgage ($2,877) + Fees ($82) + Taxes in 2024 ($254)


    Taxes:$3,052

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1016 WALNUT CREEK CV, WINTER SPRINGS, FL 32708

    $539,9008 Days on yellowkey   MLS ID: O6414948

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

    For Sale O6414948 - 1016 WALNUT CREEK CV, WINTER SPRINGS, FL 32708 39 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2375
       Built: 2003
    Monthly Fee: $150
       Tax: $3,482 (2025)
    Community: Parkstone Unit 4
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,398 (change assumption)
    Mortgage ($2,958) + Fees ($150) + Taxes in 2025 ($290)


    Taxes:$3,482

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1702 DAVENPORT CT, WINTER SPRINGS, FL 32708

    $569,90068 Days on yellowkey   MLS ID: O6398359

    0 Days Off yellowkey (back on 6/18/2026)

    REDUCED by $10,000 (1.7%) on 06/12/2026

    For Sale O6398359 - 1702 DAVENPORT CT, WINTER SPRINGS, FL 32708 44 photos

    Bed: 3   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2101
       Built: 1994
    Monthly Fee: $42
       Tax: $7,266 (2024)
    Community: Davenport Glen
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,770 (change assumption)
    Mortgage ($3,123) + Fees ($42) + Taxes in 2024 ($605)


    Taxes:$7,266

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1421 HAPPY BIRD LN, WINTER SPRINGS, FL 32708

    $543,888224 Days on yellowkey   MLS ID: O6359884

    REDUCED by $19,520 (3.5%) on 06/17/2026

    For Sale O6359884 - 1421 HAPPY BIRD LN, WINTER SPRINGS, FL 32708 16 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2502
       Built: 2019
    Monthly Fee: $130
       Tax: $4,781 (2024)
    Community: Tuskawilla Crossings 34'S
    Single Family


    Estimated Monthly Payment: $3,509 (change assumption)
    Mortgage ($2,980) + Fees ($130) + Taxes in 2024 ($398)


    Taxes:$4,781

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 214 PERTH CT, WINTER SPRINGS, FL 32708

    $589,90042 Days on yellowkey   MLS ID: O6407533

    1 Days Off yellowkey (back on 6/3/2026)

    For Sale O6407533 - 214 PERTH CT, WINTER SPRINGS, FL 32708 80 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2247
       Built: 1980
    Monthly Fee: $67
       Tax: $5,200 (2024)
    Community: Highlands Sec 6
    Single Family


    Estimated Monthly Payment: $3,733 (change assumption)
    Mortgage ($3,232) + Fees ($67) + Taxes in 2024 ($433)


    Taxes:$5,200

    Elementary School: Woodlands Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 811 MAPLE LEAF LOOP, WINTER SPRINGS, FL 32708

    $545,00020 Days on yellowkey   MLS ID: O6413927

    0 Days Off yellowkey (back on 6/16/2026)

    For Sale O6413927 - 811 MAPLE LEAF LOOP, WINTER SPRINGS, FL 32708 30 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2852
       Built: 2016
    Monthly Fee: $100
       Tax: $4,089 (2025)
    Community: Seven Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,427 (change assumption)
    Mortgage ($2,986) + Fees ($100) + Taxes in 2025 ($341)


    Taxes:$4,089

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1110 SHADOWBROOK TRL, WINTER SPRINGS, FL 32708

    $575,00020 Days on yellowkey   MLS ID: O6413323

    0 Days Off yellowkey (back on 6/15/2026)

    For Sale O6413323 - 1110 SHADOWBROOK TRL, WINTER SPRINGS, FL 32708 35 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2214
       Built: 1998
    Monthly Fee: $50
       Tax: $3,542 (2025)
    Community: Winding Hollow Unit 4
    Single Family


    Estimated Monthly Payment: $3,496 (change assumption)
    Mortgage ($3,151) + Fees ($50) + Taxes in 2025 ($295)


    Taxes:$3,542

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 30 SABLE CT, WINTER SPRINGS, FL 32708

    $569,000131 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


  • 118 PARTRIDGE CIR, WINTER SPRINGS, FL 32708

    $560,00049 Days on yellowkey   MLS ID: O6405183

    0 Days Off yellowkey (back on 5/9/2026)

    For Sale O6405183 - 118 PARTRIDGE CIR, WINTER SPRINGS, FL 32708 36 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2456
       Built: 1973   Tax: $2,913 (2024)
    Community: Winter Spgs Unit 4
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,311 (change assumption)
    Mortgage ($3,068) + Taxes in 2024 ($243)


    Taxes:$2,913

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


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