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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Price: $300,000 to $399,000

Winter Haven - 287 properties found

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  • 3815 POMELO, WINTER HAVEN, FL 33884

    $307,900122 Days on yellowkey   MLS ID: O6384844

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

    SHORT SALE O6384844 - 3815 POMELO, WINTER HAVEN, FL 33884 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1672
       Built: 2026
    Monthly Fee: $30
       Tax: $155 (2025)
    Community: Harmony On Lake Eloise
    Single Family


    Estimated Monthly Payment: $1,730 (change assumption)
    Mortgage ($1,687) + Fees ($30) + Taxes in 2025 ($13)


    Taxes:$155

    Elementary School: John Snively Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 146 LAKE RING DR, WINTER HAVEN, FL 33884

    $382,99916 Days on yellowkey   MLS ID: TB8517445

    For Sale TB8517445 - 146 LAKE RING DR, WINTER HAVEN, FL 33884 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1638
       Built: 1976   Tax: $4,154 (2025)
    Community: Lake Ring
    Single Family


    Estimated Monthly Payment: $2,445 (change assumption)
    Mortgage ($2,099) + Taxes in 2025 ($346)


    Taxes:$4,154

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 245 16TH ST NE, WINTER HAVEN, FL 33881

    $309,80063 Days on yellowkey   MLS ID: S5148499

    For Sale S5148499 - 245 16TH ST NE, WINTER HAVEN, FL 33881 7 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1232
       Built: 1960   Tax: $2,300 (2025)
    Community: South Lake Elbert Heights
    Single Family


    Estimated Monthly Payment: $1,889 (change assumption)
    Mortgage ($1,697) + Taxes in 2025 ($192)


    Taxes:$2,300

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3408 COSTELLO CIR, WINTER HAVEN, FL 33884

    $315,00027 Days on yellowkey   MLS ID: O6411460

    INCREASED by $10,000 (3.3%) on 06/01/2026

    For Sale O6411460 - 3408 COSTELLO CIR, WINTER HAVEN, FL 33884 15 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1713
       Built: 2025
    Monthly Fee: $18
       Tax: $3,036 (2025)
    Community: Villamar Ph 6 & Ph 6D
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,997 (change assumption)
    Mortgage ($1,726) + Fees ($18) + Taxes in 2025 ($253)


    Taxes:$3,036

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5456 SAN PIETRO DR, WINTER HAVEN, FL 33884

    $349,49953 Days on yellowkey   MLS ID: TB8504505

    0 Days Off yellowkey (back on 6/9/2026)

    REDUCED by $500 (0.1%) on 05/19/2026

    For Sale TB8504505 - 5456 SAN PIETRO DR, WINTER HAVEN, FL 33884 19 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2471
       Built: 2026
    Monthly Fee: $53
       Tax: $4,690 (2025)
    Community: Villa Mar
    Single Family


    Estimated Monthly Payment: $2,359 (change assumption)
    Mortgage ($1,915) + Fees ($53) + Taxes in 2025 ($391)


    Taxes:$4,690

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 6003 LIVE OAK DR, WINTER HAVEN, FL 33880

    $364,999105 Days on yellowkey   MLS ID: S5145500

    2 Days Off yellowkey (back on 6/9/2026)

    REDUCED by $4,000 (1.1%) on 05/16/2026

    For Sale S5145500 - 6003 LIVE OAK DR, WINTER HAVEN, FL 33880 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1907
       Built: 2006
    Monthly Fee: $20
       Tax: $2,549 (2025)
    Community: Oak Preserve Ph 02
    Single Family


    Estimated Monthly Payment: $2,232 (change assumption)
    Mortgage ($2,000) + Fees ($20) + Taxes in 2025 ($212)


    Taxes:$2,549

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 276 MEREDITH BLVD, WINTER HAVEN, FL 33881

    $329,99017 Days on yellowkey   MLS ID: G5113493

    0 Days Off yellowkey (back on 6/8/2026)

    For Sale G5113493 - 276 MEREDITH BLVD, WINTER HAVEN, FL 33881 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2110
       Built: 2025
    Monthly Fee: $7
       Tax: $500 (2025)
    Community: Willowbrook North
    Single Family


    Estimated Monthly Payment: $1,857 (change assumption)
    Mortgage ($1,808) + Fees ($7) + Taxes in 2025 ($42)


    Taxes:$500

    Elementary School: Fred G. Garnier Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 3322 OAK HILL PL, WINTER HAVEN, FL 33884

    $333,00055 Days on yellowkey   MLS ID: O6404080

    0 Days Off yellowkey (back on 6/8/2026)

    REDUCED by $4,000 (1.2%) on 05/21/2026

    For Sale O6404080 - 3322 OAK HILL PL, WINTER HAVEN, FL 33884 37 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2109
       Built: 2006
    Monthly Fee: $155

    Community: Oakgrove Sub
    Single Family


    Estimated Monthly Payment: $1,980 (change assumption)
    Mortgage ($1,825) + Fees ($155) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1522 ECKART DR, WINTER HAVEN, FL 33881

    $359,99985 Days on yellowkey   MLS ID: L4959745

    REDUCED by $19,901 (5.2%) on 06/08/2026

    For Sale L4959745 - 1522 ECKART DR, WINTER HAVEN, FL 33881 60 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1524
       Built: 1982   Tax: $3,192 (2025)
    Community: Rochelle Gardens
    Single Family


    Estimated Monthly Payment: $2,239 (change assumption)
    Mortgage ($1,973) + Taxes in 2025 ($266)


    Taxes:$3,192

    Elementary School: Lake Alfred Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 441 MCKENNA DR, WINTER HAVEN, FL 33881

    $335,00076 Days on yellowkey   MLS ID: O6398240

    REDUCED by $18,000 (5.1%) on 05/26/2026

    For Sale O6398240 - 441 MCKENNA DR, WINTER HAVEN, FL 33881 36 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2360
       Built: 2021
    Monthly Fee: $17
       Tax: $6,548 (2025)
    Community: Lucerne Park Reserve
    Single Family


    Estimated Monthly Payment: $2,398 (change assumption)
    Mortgage ($1,836) + Fees ($17) + Taxes in 2025 ($546)


    Taxes:$6,548

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1215 26TH ST NW, WINTER HAVEN, FL 33881

    $374,000106 Days on yellowkey   MLS ID: S5145609

    REDUCED by $5,000 (1.3%) on 05/08/2026

    For Sale S5145609 - 1215 26TH ST NW, WINTER HAVEN, FL 33881 40 photos

    Bed: 4   Bath: 4.0
    Liv Area Sq Ft: 2083
       Built: 1940   Tax: $4,946 (2025)
    Community: Inwood #1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,461 (change assumption)
    Mortgage ($2,049) + Taxes in 2025 ($412)


    Taxes:$4,946

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5444 SAN PIETRO DR, WINTER HAVEN, FL 33884

    $324,99990 Days on yellowkey   MLS ID: TB8491382

    0 Days Off yellowkey (back on 6/8/2026)

    REDUCED by $5,000 (1.5%) on 06/04/2026

    For Sale TB8491382 - 5444 SAN PIETRO DR, WINTER HAVEN, FL 33884 33 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2226
       Built: 2025
    Monthly Fee: $53
       Tax: $2,689 (2025)
    Community: Villa Mar
    Single Family


    Estimated Monthly Payment: $2,058 (change assumption)
    Mortgage ($1,781) + Fees ($53) + Taxes in 2025 ($224)


    Taxes:$2,689

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 3686 PLYMOUTH DR, WINTER HAVEN, FL 33884

    $369,900240 Days on yellowkey   MLS ID: P4936787

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

    For Sale P4936787 - 3686 PLYMOUTH DR, WINTER HAVEN, FL 33884 52 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2404
       Built: 2015
    Monthly Fee: $485
       Tax: $3,398 (2025)
    Community: Traditions Ph 02
    Single Family


    Estimated Monthly Payment: $2,795 (change assumption)
    Mortgage ($2,027) + Fees ($485) + Taxes in 2025 ($283)


    Taxes:$3,398

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3337 COSTELLO CIR, WINTER HAVEN, FL 33884

    $345,000139 Days on yellowkey   MLS ID: L4959241

    For Sale L4959241 - 3337 COSTELLO CIR, WINTER HAVEN, FL 33884 56 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2522
       Built: 2023
    Monthly Fee: $17
       Tax: $7,388 (2025)
    Community: Villamar Phase 5
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,523 (change assumption)
    Mortgage ($1,890) + Fees ($17) + Taxes in 2025 ($616)


    Taxes:$7,388

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 5351 MICKEY AVE, WINTER HAVEN, FL 33884

    $308,950217 Days on yellowkey   MLS ID: S5138935

    INCREASED by $8,951 (3.0%) on 05/05/2026

    For Sale S5138935 - 5351 MICKEY AVE, WINTER HAVEN, FL 33884 16 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1700
       Built: 2025
    Monthly Fee: $38

    Community: Seasons At Annabelle Estates
    Single Family


    Estimated Monthly Payment: $1,731 (change assumption)
    Mortgage ($1,693) + Fees ($38) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4612 REYNOSA DR SW, WINTER HAVEN, FL 33880

    $310,000322 Days on yellowkey   MLS ID: V4944212

    1 Days Off yellowkey (back on 6/7/2026)

    REDUCED by $10,000 (3.1%) on 05/27/2026

    SHORT SALE V4944212 - 4612 REYNOSA DR SW, WINTER HAVEN, FL 33880 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1716
       Built: 1984   Tax: $4,573 (2024)
    Community: Plaza Sub
    Single Family


    Estimated Monthly Payment: $2,080 (change assumption)
    Mortgage ($1,699) + Taxes in 2024 ($381)


    Taxes:$4,573

    Elementary School: Lake Shipp Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Westwood Middle


  • 329 LAKE DAISY LOOP, WINTER HAVEN, FL 33884

    $320,00042 Days on yellowkey   MLS ID: G5112198

    REDUCED by $10,000 (3.0%) on 05/31/2026

    For Sale G5112198 - 329 LAKE DAISY LOOP, WINTER HAVEN, FL 33884 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1563
       Built: 1995   Tax: $3,888 (2025)
    Community: Lake Daisy Estates
    Single Family


    Estimated Monthly Payment: $2,077 (change assumption)
    Mortgage ($1,753) + Taxes in 2025 ($324)


    Taxes:$3,888

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5137 WINGED FOOT LN, WINTER HAVEN, FL 33884

    $380,00076 Days on yellowkey   MLS ID: P4938411

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

    For Sale P4938411 - 5137 WINGED FOOT LN, WINTER HAVEN, FL 33884 97 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2107
       Built: 2006
    Monthly Fee: $5
       Tax: $3,291 (2025)
    Community: Lake Ashton West Ph 01
    Single Family


    Estimated Monthly Payment: $2,361 (change assumption)
    Mortgage ($2,082) + Fees ($5) + Taxes in 2025 ($274)


    Taxes:$3,291

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 326 MEADOWBROOK BLVD, WINTER HAVEN, FL 33881

    $359,000231 Days on yellowkey   MLS ID: S5137744

    For Sale S5137744 - 326 MEADOWBROOK BLVD, WINTER HAVEN, FL 33881 22 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2696
       Built: 2021
    Monthly Fee: $200
       Tax: $8,499 (2024)
    Community: Lucerne Park Reserve
    Single Family


    Estimated Monthly Payment: $2,875 (change assumption)
    Mortgage ($1,967) + Fees ($200) + Taxes in 2024 ($708)


    Taxes:$8,499

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3742 FIELDSTONE CIR, WINTER HAVEN, FL 33881

    $300,00020 Days on yellowkey   MLS ID: L4962401

    For Sale L4962401 - 3742 FIELDSTONE CIR, WINTER HAVEN, FL 33881 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1919
       Built: 2016
    Monthly Fee: $36
       Tax: $4,631 (2025)
    Community: Country Club Estates
    Single Family


    Estimated Monthly Payment: $2,066 (change assumption)
    Mortgage ($1,644) + Fees ($36) + Taxes in 2025 ($386)


    Taxes:$4,631

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle






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.