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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Price: $300,000 to $399,000

Winter Haven - 286 properties found

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  • 961 DREXEL AVE NE, WINTER HAVEN, FL 33881

    $305,000122 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


  • 58 LAKE LINK CIR SE, WINTER HAVEN, FL 33884

    $398,50048 Days on yellowkey   MLS ID: P4938677

    0 Days Off yellowkey (back on 5/15/2026)

    For Sale P4938677 - 58 LAKE LINK CIR SE, WINTER HAVEN, FL 33884 42 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2000
       Built: 1971   Tax: $5,997 (2025)
    Community: Lake Link Estates
    Single Family


    Estimated Monthly Payment: $2,683 (change assumption)
    Mortgage ($2,184) + Taxes in 2025 ($500)


    Taxes:$5,997

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884

    $340,000192 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

    $308,90064 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

    $389,000450 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


  • 4045 GIORGIO DR, WINTER HAVEN, FL 33884

    $300,9902 Days 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


  • 516 REGGIE RD, WINTER HAVEN, FL 33884

    $325,0002 Days on yellowkey   MLS ID: O6418177

    For Sale O6418177 - 516 REGGIE RD, WINTER HAVEN, FL 33884 56 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2109
       Built: 2024
    Monthly Fee: $16
       Tax: $7,811 (2025)
    Community: Peace Crk Reserve
    Single Family


    Estimated Monthly Payment: $2,448 (change assumption)
    Mortgage ($1,781) + Fees ($16) + Taxes in 2025 ($651)


    Taxes:$7,811

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 1138 MICHELANGELO LN, WINTER HAVEN, FL 33884

    $394,90076 Days on yellowkey   MLS ID: S5147440

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

    REDUCED by $5,000 (1.3%) on 05/29/2026

    For Sale S5147440 - 1138 MICHELANGELO LN, WINTER HAVEN, FL 33884 72 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2386
       Built: 2023
    Monthly Fee: $55
       Tax: $4,275 (2025)
    Community: Estates/Lk Florence
    Single Family


    Estimated Monthly Payment: $2,575 (change assumption)
    Mortgage ($2,164) + Fees ($55) + Taxes in 2025 ($356)


    Taxes:$4,275

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 605 SW SARNER PASS WAY W, WINTER HAVEN, FL 33881

    $399,000116 Days on yellowkey   MLS ID: G5108932

    REDUCED by $14,000 (3.4%) on 04/20/2026

    For Sale G5108932 - 605 SW SARNER PASS WAY W, WINTER HAVEN, FL 33881 53 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2676
       Built: 2022
    Monthly Fee: $76
       Tax: $4,782 (2025)
    Community: Lake Lucerne Ph 5
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,661 (change assumption)
    Mortgage ($2,186) + Fees ($76) + Taxes in 2025 ($399)


    Taxes:$4,782

    Elementary School: Lake Alfred Elem

    High School: Haines City Senior High

    Tax Year: 2025

    Middle School: Boone Middle


  • 528 MCKENNA DR, WINTER HAVEN, FL 33881

    $375,00051 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


  • 423 MAJESTIC GARDENS BLVD, WINTER HAVEN, FL 33880

    $312,90042 Days on yellowkey   MLS ID: TB8508845

    REDUCED by $4,000 (1.3%) on 06/23/2026

    For Sale TB8508845 - 423 MAJESTIC GARDENS BLVD, WINTER HAVEN, FL 33880 26 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1941
       Built: 2006
    Monthly Fee: $29
       Tax: $2,729 (2025)
    Community: Gardens Ph 01
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,971 (change assumption)
    Mortgage ($1,714) + Fees ($29) + Taxes in 2025 ($227)


    Taxes:$2,729

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 5025 KAIA AVE, WINTER HAVEN, FL 33884

    $349,99044 Days on yellowkey   MLS ID: TB8502447

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

    REDUCED by $40 (0.0%) on 06/15/2026

    For Sale TB8502447 - 5025 KAIA AVE, WINTER HAVEN, FL 33884 8 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2631
       Built: 2026
    Monthly Fee: $15
       Tax: $5,000 (2025)
    Community: Villamar
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,349 (change assumption)
    Mortgage ($1,918) + Fees ($15) + Taxes in 2025 ($417)


    Taxes:$5,000

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 757 REGGIE RD, WINTER HAVEN, FL 33884

    $303,000251 Days on yellowkey   MLS ID: S5136830

    For Sale S5136830 - 757 REGGIE RD, WINTER HAVEN, FL 33884 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1432
       Built: 2023
    Monthly Fee: $14
       Tax: $6,977 (2024)
    Community: Peace Creek Reserve
    Single Family


    Estimated Monthly Payment: $2,256 (change assumption)
    Mortgage ($1,660) + Fees ($14) + Taxes in 2024 ($581)


    Taxes:$6,977

    Elementary School: Wahneta Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Westwood Middle


  • 3827 POMELO DR, WINTER HAVEN, FL 33881

    $317,90079 Days on yellowkey   MLS ID: O6396937

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

    REDUCED by $2,000 (0.6%) on 06/10/2026

    For Sale O6396937 - 3827 POMELO DR, WINTER HAVEN, FL 33881 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1828
       Built: 2026
    Monthly Fee: $69
       Tax: $2,606 (2025)
    Community: Harmony On Lake Eloise Phase 4
    Single Family


    Estimated Monthly Payment: $2,028 (change assumption)
    Mortgage ($1,742) + Fees ($69) + Taxes in 2025 ($217)


    Taxes:$2,606

    Elementary School: John Snively Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 3036 THORNHILL RD, WINTER HAVEN, FL 33880

    $389,95021 Days on yellowkey   MLS ID: L4962365

    For Sale L4962365 - 3036 THORNHILL RD, WINTER HAVEN, FL 33880 6 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1778
       Built: 2026   Tax: $523 (2025)
    Community: Orange Hill Sub
    Single Family


    Estimated Monthly Payment: $2,180 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($44)


    Taxes:$523

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3038 THORNHILL RD, WINTER HAVEN, FL 33880

    $369,95021 Days on yellowkey   MLS ID: L4962366

    For Sale L4962366 - 3038 THORNHILL RD, WINTER HAVEN, FL 33880 6 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1467
       Built: 2026   Tax: $403 (2025)
    Community: Orange Hill Sub
    Single Family


    Estimated Monthly Payment: $2,061 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($34)


    Taxes:$403

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3614 PLYMOUTH DR, WINTER HAVEN, FL 33884

    $320,0003 Days on yellowkey   MLS ID: TB8522011

    For Sale TB8522011 - 3614 PLYMOUTH DR, WINTER HAVEN, FL 33884 57 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2109
       Built: 2006
    Monthly Fee: $504
       Tax: $2,165 (2025)
    Community: Traditions Ph 01
    Single Family


    Estimated Monthly Payment: $2,438 (change assumption)
    Mortgage ($1,753) + Fees ($504) + Taxes in 2025 ($180)


    Taxes:$2,165

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: None


  • 2095 W HARTRIDGE TER, WINTER HAVEN, FL 33881

    $305,0003 Days on yellowkey   MLS ID: P4939103

    For Sale P4939103 - 2095 W HARTRIDGE TER, WINTER HAVEN, FL 33881 17 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1816
       Built: 1964   Tax: $2,677 (2025)
    Community: Not In Subdivision
    Single Family


    Estimated Monthly Payment: $1,894 (change assumption)
    Mortgage ($1,671) + Taxes in 2025 ($223)


    Taxes:$2,677

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2820 SAM MARCY WAY E, WINTER HAVEN, FL 33884

    $351,3703 Days on yellowkey   MLS ID: L4962977

    0 Days Off yellowkey (back on 6/22/2026)

    For Sale L4962977 - 2820 SAM MARCY WAY E, WINTER HAVEN, FL 33884 5 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2227
       Built: 2026
    Monthly Fee: $18

    Community: Villamar
    Single Family


    Estimated Monthly Payment: $1,943 (change assumption)
    Mortgage ($1,925) + Fees ($18) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2610 SAN MARCO WAY, WINTER HAVEN, FL 33884

    $329,90012 Days on yellowkey   MLS ID: L4962574

    For Sale L4962574 - 2610 SAN MARCO WAY, WINTER HAVEN, FL 33884 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1819
       Built: 2023
    Monthly Fee: $13
       Tax: $3,953 (2024)
    Community: Villamar
    Single Family


    Estimated Monthly Payment: $2,150 (change assumption)
    Mortgage ($1,808) + Fees ($13) + Taxes in 2024 ($329)


    Taxes:$3,953

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: McLaughlin Academy Of Excellence






Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.