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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Living Area Square Feet: 1500 to 1999

Winter Haven - 311 properties found

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  • 1059 MICHELANGELO LN, WINTER HAVEN, FL 33884

    $364,500147 Days on yellowkey   MLS ID: S5142551

    REDUCED by $500 (0.1%) on 06/23/2026

    For Sale S5142551 - 1059 MICHELANGELO LN, WINTER HAVEN, FL 33884 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1844
       Built: 2024
    Monthly Fee: $55
       Tax: $3,878 (2025)
    Community: Estates/Lk Florence
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,375 (change assumption)
    Mortgage ($1,997) + Fees ($55) + Taxes in 2025 ($323)


    Taxes:$3,878

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 4948 KAIA, WINTER HAVEN, FL 33884

    $281,900168 Days on yellowkey   MLS ID: O6370131

    REDUCED by $2,000 (0.7%) on 06/10/2026

    For Sale O6370131 - 4948 KAIA, WINTER HAVEN, FL 33884 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1665
       Built: 2025
    Monthly Fee: $203
       Tax: $3,396 (2025)
    Community: Villamar Phase 6 Pb 203 Pg 7-17 Lot 225
    Single Family


    Estimated Monthly Payment: $2,031 (change assumption)
    Mortgage ($1,545) + Fees ($203) + Taxes in 2025 ($283)


    Taxes:$3,396

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 221 GOLF AIRE BLVD, WINTER HAVEN, FL 33884

    $299,999108 Days on yellowkey   MLS ID: L4959992

    REDUCED by $15,001 (4.8%) on 06/24/2026

    For Sale L4959992 - 221 GOLF AIRE BLVD, WINTER HAVEN, FL 33884 71 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1645
       Built: 1999
    Monthly Fee: $500
       Tax: $2,554 (2025)
    Community: Lake Bess Country Club
    Single Family


    Estimated Monthly Payment: $2,357 (change assumption)
    Mortgage ($1,644) + Fees ($500) + Taxes in 2025 ($213)


    Taxes:$2,554

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4463 RAPALLO AVE, WINTER HAVEN, FL 33884

    $294,900187 Days on yellowkey   MLS ID: L4958024

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

    For Sale L4958024 - 4463 RAPALLO AVE, WINTER HAVEN, FL 33884 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1744
       Built: 2025
    Monthly Fee: $19

    Community: Villamar
    Single Family


    Estimated Monthly Payment: $1,635 (change assumption)
    Mortgage ($1,616) + Fees ($19) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3136 COUNTRY CLUB CIR, WINTER HAVEN, FL 33881

    $290,00020 Days on yellowkey   MLS ID: L4961900

    REDUCED by $10,000 (3.3%) on 06/22/2026

    For Sale L4961900 - 3136 COUNTRY CLUB CIR, WINTER HAVEN, FL 33881 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1690
       Built: 2018
    Monthly Fee: $30
       Tax: $3,839 (2025)
    Community: Country Walk/Winter Haven
    Single Family


    Estimated Monthly Payment: $1,939 (change assumption)
    Mortgage ($1,589) + Fees ($30) + Taxes in 2025 ($320)


    Taxes:$3,839

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3986 JACLYNS JETTY, WINTER HAVEN, FL 33884

    $300,000Listed 06/24/2026 9:57AM   MLS ID: L4962993

    For Sale L4962993 - 3986 JACLYNS JETTY, WINTER HAVEN, FL 33884 58 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1526
       Built: 2001
    Monthly Fee: $440
       Tax: $1,767 (2025)
    Community: Cypress Landing Ph 02
    Single Family


    Estimated Monthly Payment: $2,231 (change assumption)
    Mortgage ($1,644) + Fees ($440) + Taxes in 2025 ($147)


    Taxes:$1,767

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1034 SUMMER GLEN DR, WINTER HAVEN, FL 33880

    $267,00075 Days on yellowkey   MLS ID: O6398045

    REDUCED by $5,000 (1.8%) on 06/18/2026

    For Sale O6398045 - 1034 SUMMER GLEN DR, WINTER HAVEN, FL 33880 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1847
       Built: 2006
    Monthly Fee: $28
       Tax: $1,607 (2025)
    Community: Coventry Cove
    Single Family


    Estimated Monthly Payment: $1,625 (change assumption)
    Mortgage ($1,463) + Fees ($28) + Taxes in 2025 ($134)


    Taxes:$1,607

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 961 DREXEL AVE NE, WINTER HAVEN, FL 33881

    $305,000121 Days on yellowkey   MLS ID: L4959592

    REDUCED by $10,000 (3.2%) on 06/08/2026

    For Sale L4959592 - 961 DREXEL AVE NE, WINTER HAVEN, FL 33881 57 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1856
       Built: 1948   Tax: $3,409 (2025)
    Community: Anna Mar
    Single Family


    Estimated Monthly Payment: $1,955 (change assumption)
    Mortgage ($1,671) + Taxes in 2025 ($284)


    Taxes:$3,409

    Elementary School: Inwood Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Westwood Middle


  • 3875 OSPREY POINTE CIR, WINTER HAVEN, FL 33884

    $285,00024 Days on yellowkey   MLS ID: O6411657

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

    For Sale O6411657 - 3875 OSPREY POINTE CIR, WINTER HAVEN, FL 33884 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1729
       Built: 2006
    Monthly Fee: $210
       Tax: $3,700 (2026)
    Community: Osprey Pointe
    Single Family


    Estimated Monthly Payment: $2,080 (change assumption)
    Mortgage ($1,562) + Fees ($210) + Taxes in 2026 ($308)


    Taxes:$3,700

    Elementary School: Garden Grove Elem

    High School: Winter Haven Senior

    Tax Year: 2026

    Middle School: Denison Middle


  • 5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884

    $340,000191 Days on yellowkey   MLS ID: P4937220

    For Sale P4937220 - 5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884 54 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1677
       Built: 2016
    Monthly Fee: $5
       Tax: $2,785 (2024)
    Community: Lake Ashton West Ph 01
    Single Family


    Estimated Monthly Payment: $2,100 (change assumption)
    Mortgage ($1,863) + Fees ($5) + Taxes in 2024 ($232)


    Taxes:$2,785

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 443 ITUNA CIR, WINTER HAVEN, FL 33881

    $308,90063 Days on yellowkey   MLS ID: L4961315

    REDUCED by $10,220 (3.2%) on 06/24/2026

    For Sale L4961315 - 443 ITUNA CIR, WINTER HAVEN, FL 33881 4 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1644
       Built: 2026
    Monthly Fee: $50

    Community: Harbor At Lake Henry
    Single Family


    Estimated Monthly Payment: $1,743 (change assumption)
    Mortgage ($1,693) + Fees ($50) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4099 ISLAND LAKES DR, WINTER HAVEN, FL 33881

    $389,000449 Days on yellowkey   MLS ID: P4934266

    REDUCED by $5,000 (1.3%) on 05/28/2026

    For Sale P4934266 - 4099 ISLAND LAKES DR, WINTER HAVEN, FL 33881 37 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1603
       Built: 2006
    Monthly Fee: $17
       Tax: $5,194 (2024)
    Community: Island Lakes
    Single Family


    Estimated Monthly Payment: $2,581 (change assumption)
    Mortgage ($2,131) + Fees ($17) + Taxes in 2024 ($433)


    Taxes:$5,194

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4049 GIORGIO DR, WINTER HAVEN, FL 33884

    $287,9901 Day on yellowkey   MLS ID: O6419242

    For Sale O6419242 - 4049 GIORGIO DR, WINTER HAVEN, FL 33884 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2026
    Monthly Fee: $18
       Tax: $3,147 (2025)
    Community: Villamar Phase 6 And Phase 6D
    Single Family


    Estimated Monthly Payment: $1,858 (change assumption)
    Mortgage ($1,578) + Fees ($18) + Taxes in 2025 ($262)


    Taxes:$3,147

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 4045 GIORGIO DR, WINTER HAVEN, FL 33884

    $300,9901 Day on yellowkey   MLS ID: O6419297

    For Sale O6419297 - 4045 GIORGIO DR, WINTER HAVEN, FL 33884 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1665
       Built: 2026
    Monthly Fee: $18
       Tax: $3,147 (2025)
    Community: Villamar Phase 6 And Phase 6D
    Single Family


    Estimated Monthly Payment: $1,929 (change assumption)
    Mortgage ($1,649) + Fees ($18) + Taxes in 2025 ($262)


    Taxes:$3,147

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 4663 OSTERO ST, WINTER HAVEN, FL 33884

    $279,9001 Day on yellowkey   MLS ID: O6415737

    For Sale O6415737 - 4663 OSTERO ST, WINTER HAVEN, FL 33884 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1665
       Built: 2026
    Monthly Fee: $18
       Tax: $3,035 (2025)
    Community: Villamar
    Single Family


    Estimated Monthly Payment: $1,805 (change assumption)
    Mortgage ($1,534) + Fees ($18) + Taxes in 2025 ($253)


    Taxes:$3,035

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 374 TROON CT, WINTER HAVEN, FL 33884

    $249,9001 Day on yellowkey   MLS ID: L4962639

    For Sale L4962639 - 374 TROON CT, WINTER HAVEN, FL 33884 23 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1634
       Built: 1978
    Monthly Fee: $129
       Tax: $3,099 (2024)
    Community: Cypresswood Patio Homes
    Single Family


    Estimated Monthly Payment: $1,757 (change assumption)
    Mortgage ($1,369) + Fees ($129) + Taxes in 2024 ($258)


    Taxes:$3,099

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 450 AVENUE B NE, WINTER HAVEN, FL 33881

    $259,000220 Days on yellowkey   MLS ID: TB8448756

    For Sale TB8448756 - 450 AVENUE B NE, WINTER HAVEN, FL 33881 16 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1624
       Built: 1946   Tax: $3,747 (2024)
    Community: Revised Map Of Fernwood Add
    Single Family


    Estimated Monthly Payment: $1,731 (change assumption)
    Mortgage ($1,419) + Taxes in 2024 ($312)


    Taxes:$3,747

    Elementary School: Fred G. Garnier Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Denison Middle


  • 119 ALLEN AVE, WINTER HAVEN, FL 33880

    $250,000367 Days on yellowkey   MLS ID: TB8399712

    SHORT SALE TB8399712 - 119 ALLEN AVE, WINTER HAVEN, FL 33880 9 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1520
       Built: 1961   Tax: $3,776 (2024)
    Community: Jan Phyl Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,684 (change assumption)
    Mortgage ($1,370) + Taxes in 2024 ($315)


    Taxes:$3,776

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 528 MCKENNA DR, WINTER HAVEN, FL 33881

    $375,00050 Days on yellowkey   MLS ID: TB8505250

    For Sale TB8505250 - 528 MCKENNA DR, WINTER HAVEN, FL 33881 16 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1964
       Built: 2021
    Monthly Fee: $17
       Tax: $7,508 (2025)
    Community: Lucerne Park Reserve
    Single Family


    Estimated Monthly Payment: $2,697 (change assumption)
    Mortgage ($2,055) + Fees ($17) + Taxes in 2025 ($626)


    Taxes:$7,508

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 29 GOLF VIEW CIR NE, WINTER HAVEN, FL 33881

    $290,000202 Days on yellowkey   MLS ID: TB8453876

    REDUCED by $10,000 (3.3%) on 06/23/2026

    SHORT SALE TB8453876 - 29 GOLF VIEW CIR NE, WINTER HAVEN, FL 33881 23 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1604
       Built: 1962   Tax: $4,496 (2024)
    Community: North Lake Elbert Heights
    Single Family


    Estimated Monthly Payment: $1,964 (change assumption)
    Mortgage ($1,589) + Taxes in 2024 ($375)


    Taxes:$4,496

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Denison Middle






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