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Displaying: For Sale

Location: Winter Springs

Property Type(s): Single Family

Price: $300,000 to $399,000

Winter Springs - 29 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


  • 448 MACGREGOR RD, WINTER SPRINGS, FL 32708

    $350,00077 Days on yellowkey   MLS ID: O6397231

    0 Days Off yellowkey (back on 6/17/2026)

    REDUCED by $10,000 (2.8%) on 05/27/2026

    For Sale O6397231 - 448 MACGREGOR RD, WINTER SPRINGS, FL 32708 26 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1477
       Built: 1993
    Monthly Fee: $6
       Tax: $1,141 (2024)
    Community: Highland Village 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,019 (change assumption)
    Mortgage ($1,918) + Fees ($6) + Taxes in 2024 ($95)


    Taxes:$1,141

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 339 INGLENOOK CIR, WINTER SPRINGS, FL 32708

    $359,90026 Days on yellowkey   MLS ID: O6411718

    1 Days Off yellowkey (back on 6/5/2026)

    For Sale O6411718 - 339 INGLENOOK CIR, WINTER SPRINGS, FL 32708 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1437
       Built: 1992
    Monthly Fee: $22
       Tax: $4,816 (2025)
    Community: Mount Greenwood Unit 1
    Single Family


    Estimated Monthly Payment: $2,395 (change assumption)
    Mortgage ($1,972) + Fees ($22) + Taxes in 2025 ($401)


    Taxes:$4,816

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 240 N DEVON AVE, WINTER SPRINGS, FL 32708

    $375,00012 Days on yellowkey   MLS ID: O6416300

    REDUCED by $9,900 (2.6%) on 06/23/2026

    For Sale O6416300 - 240 N DEVON AVE, WINTER SPRINGS, FL 32708 30 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1238
       Built: 1958   Tax: $476 (2025)
    Community: North Orlando
    Single Family


    Estimated Monthly Payment: $2,094 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($40)


    Taxes:$476

    Elementary School: Highlands Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails 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


  • 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


  • 335 KIRKCALDY DR, WINTER SPRINGS, FL 32708

    $329,90050 Days on yellowkey   MLS ID: O6400818

    REDUCED by $10,000 (2.9%) on 06/18/2026

    For Sale O6400818 - 335 KIRKCALDY DR, WINTER SPRINGS, FL 32708 50 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1178
       Built: 1984
    Monthly Fee: $36
       Tax: $3,693 (2025)
    Community: Highland Village 1
    Single Family


    Estimated Monthly Payment: $2,151 (change assumption)
    Mortgage ($1,808) + Fees ($36) + Taxes in 2025 ($308)


    Taxes:$3,693

    Elementary School: Highlands Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: South Seminole Middle


  • 1411 BORG LN, WINTER SPRINGS, FL 32708

    $385,000144 Days on yellowkey   MLS ID: O6378665

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

    REDUCED by $14,000 (3.5%) on 06/10/2026

    For Sale O6378665 - 1411 BORG LN, WINTER SPRINGS, FL 32708 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1368
       Built: 1981
    Monthly Fee: $90
       Tax: $1,871 (2024)
    Community: Wedgewood Tennis Villas
    Single Family


    Estimated Monthly Payment: $2,355 (change assumption)
    Mortgage ($2,110) + Fees ($90) + Taxes in 2024 ($156)


    Taxes:$1,871

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 65 S DEVON AVE, WINTER SPRINGS, FL 32708

    $314,90044 Days on yellowkey   MLS ID: O6404319

    For Sale O6404319 - 65 S DEVON AVE, WINTER SPRINGS, FL 32708 33 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1075
       Built: 1960   Tax: $2,218 (2024)
    Community: North Orlando 2Nd Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,910 (change assumption)
    Mortgage ($1,725) + Taxes in 2024 ($185)


    Taxes:$2,218

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 239 PANORAMA DR, WINTER SPRINGS, FL 32708

    $340,00075 Days on yellowkey   MLS ID: O6397776

    REDUCED by $10,000 (2.9%) on 04/24/2026

    For Sale O6397776 - 239 PANORAMA DR, WINTER SPRINGS, FL 32708 28 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1349
       Built: 1996
    Monthly Fee: $139
       Tax: $4,336 (2025)
    Community: Seasons The
    Single Family


    Estimated Monthly Payment: $2,363 (change assumption)
    Mortgage ($1,863) + Fees ($139) + Taxes in 2025 ($361)


    Taxes:$4,336

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 807 BUCKIE DR, WINTER SPRINGS, FL 32708

    $375,00056 Days on yellowkey   MLS ID: O6386108

    For Sale O6386108 - 807 BUCKIE DR, WINTER SPRINGS, FL 32708 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1574
       Built: 1978
    Monthly Fee: $35
       Tax: $4,487 (2025)
    Community: Highlands Sec 1
    Single Family


    Estimated Monthly Payment: $2,464 (change assumption)
    Mortgage ($2,055) + Fees ($35) + Taxes in 2025 ($374)


    Taxes:$4,487

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1018 WEATHERED WOOD CIR, WINTER SPRINGS, FL 32708

    $369,00035 Days on yellowkey   MLS ID: O6408847

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

    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


  • 1328 ANDES DR, WINTER SPRINGS, FL 32708

    $373,00063 Days on yellowkey   MLS ID: O6398729

    REDUCED by $12,000 (3.1%) on 06/08/2026

    For Sale O6398729 - 1328 ANDES DR, WINTER SPRINGS, FL 32708 20 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1582
       Built: 1987
    Monthly Fee: $29
       Tax: $3,128 (2024)
    Community: Sunrise Village Unit 6
    Single Family


    Estimated Monthly Payment: $2,333 (change assumption)
    Mortgage ($2,044) + Fees ($29) + Taxes in 2024 ($261)


    Taxes:$3,128

    Elementary School: Rainbow Elementary

    High School: Oviedo High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 717 WILSON RD, WINTER SPRINGS, FL 32708

    $340,000163 Days on yellowkey   MLS ID: O6372938

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

    REDUCED by $35,000 (9.3%) on 05/29/2026

    For Sale O6372938 - 717 WILSON RD, WINTER SPRINGS, FL 32708 59 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1368
       Built: 1981
    Monthly Fee: $90
       Tax: $164 (2024)
    Community: Wedgewood Tennis Villas
    Single Family


    Estimated Monthly Payment: $1,967 (change assumption)
    Mortgage ($1,863) + Fees ($90) + Taxes in 2024 ($14)


    Taxes:$164

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 114 SUNDANCE CT, WINTER SPRINGS, FL 32708

    $305,500222 Days on yellowkey   MLS ID: O6359275

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

    REDUCED by $10,000 (3.2%) on 04/23/2026

    For Sale O6359275 - 114 SUNDANCE CT, WINTER SPRINGS, FL 32708 40 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1356
       Built: 1997
    Monthly Fee: $120
       Tax: $4,059 (2024)
    Community: Seasons The
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,132 (change assumption)
    Mortgage ($1,674) + Fees ($120) + Taxes in 2024 ($338)


    Taxes:$4,059

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 710 BRIARWOOD DR, WINTER SPRINGS, FL 32708

    $365,00081 Days on yellowkey   MLS ID: O6396343

    REDUCED by $7,500 (2.0%) on 06/01/2026

    For Sale O6396343 - 710 BRIARWOOD DR, WINTER SPRINGS, FL 32708 24 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1769
       Built: 1974
    Monthly Fee: $90
       Tax: $4,070 (2025)
    Community: Wildwood
    Single Family


    Estimated Monthly Payment: $2,429 (change assumption)
    Mortgage ($2,000) + Fees ($90) + Taxes in 2025 ($339)


    Taxes:$4,070

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 622 ANHINGA RD, WINTER SPRINGS, FL 32708

    $384,900182 Days on yellowkey   MLS ID: O6369225

    REDUCED by $13,600 (3.4%) on 05/18/2026

    For Sale O6369225 - 622 ANHINGA RD, WINTER SPRINGS, FL 32708 73 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1721
       Built: 1988
    Monthly Fee: $106
       Tax: $4,083 (2024)
    Community: Greenspointe
    Single Family


    Estimated Monthly Payment: $2,555 (change assumption)
    Mortgage ($2,109) + Fees ($106) + Taxes in 2024 ($340)


    Taxes:$4,083

    Elementary School: Highlands Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 324 DORNOCH CT, WINTER SPRINGS, FL 32708

    $399,00027 Days on yellowkey   MLS ID: O6411464

    0 Days Off yellowkey (back on 5/31/2026)

    For Sale O6411464 - 324 DORNOCH CT, WINTER SPRINGS, FL 32708 59 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1579
       Built: 1989
    Monthly Fee: $35
       Tax: $1,941 (2025)
    Community: Highland Village 2
    Single Family


    Estimated Monthly Payment: $2,383 (change assumption)
    Mortgage ($2,186) + Fees ($35) + Taxes in 2025 ($162)


    Taxes:$1,941

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 431 S ALDERWOOD ST, WINTER SPRINGS, FL 32708

    $390,00041 Days on yellowkey   MLS ID: O6407052

    0 Days Off yellowkey (back on 5/31/2026)

    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


12




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