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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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  • 953 CAMBRIDGE DR, WINTER HAVEN, FL 33881

    $395,000110 Days on yellowkey   MLS ID: O6386825

    For Sale O6386825 - 953 CAMBRIDGE DR, WINTER HAVEN, FL 33881 62 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2364
       Built: 2022
    Monthly Fee: $17
       Tax: $6,877 (2025)
    Community: Lucerne Park Reserve
    Single Family


    Estimated Monthly Payment: $2,754 (change assumption)
    Mortgage ($2,164) + Fees ($17) + Taxes in 2025 ($573)


    Taxes:$6,877

    Elementary School: Fred G. Garnier Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 356 STERLING DR, WINTER HAVEN, FL 33884

    $332,000117 Days on yellowkey   MLS ID: L4959652

    0 Days Off yellowkey (back on 4/6/2026)

    REDUCED by $3,000 (0.9%) on 04/03/2026

    For Sale L4959652 - 356 STERLING DR, WINTER HAVEN, FL 33884 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1535
       Built: 2001
    Monthly Fee: $24
       Tax: $3,462 (2025)
    Community: Berryhill
    Single Family


    Estimated Monthly Payment: $2,132 (change assumption)
    Mortgage ($1,819) + Fees ($24) + Taxes in 2025 ($289)


    Taxes:$3,462

    Elementary School: Garden Grove Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 1533 LEAMINGTON LN, WINTER HAVEN, FL 33884

    $304,366345 Days on yellowkey   MLS ID: L4954446

    REDUCED by $5,000 (1.6%) on 05/01/2026

    For Sale L4954446 - 1533 LEAMINGTON LN, WINTER HAVEN, FL 33884 5 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2200
       Built: 2025
    Monthly Fee: $17
       Tax: $3,122 (2024)
    Community: Villa Mar Phase 3
    Single Family


    Estimated Monthly Payment: $1,945 (change assumption)
    Mortgage ($1,668) + Fees ($17) + Taxes in 2024 ($260)


    Taxes:$3,122

    Elementary School: Chain O Lakes Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Berkley Accelerated Middle


  • 717 BAYSIDE BLVD, WINTER HAVEN, FL 33881

    $334,76563 Days on yellowkey   MLS ID: L4961317

    0 Days Off yellowkey (back on 5/11/2026)

    For Sale L4961317 - 717 BAYSIDE BLVD, WINTER HAVEN, FL 33881 4 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1819
       Built: 2026
    Monthly Fee: $50

    Community: Harbor At Lake Henry
    Single Family


    Estimated Monthly Payment: $1,884 (change assumption)
    Mortgage ($1,834) + Fees ($50) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 528 CODY CALEB DR, WINTER HAVEN, FL 33884

    $304,50065 Days on yellowkey   MLS ID: L4961233

    0 Days Off yellowkey (back on 5/8/2026)

    For Sale L4961233 - 528 CODY CALEB DR, WINTER HAVEN, FL 33884 60 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2250
       Built: 2005
    Monthly Fee: $23
       Tax: $4,538 (2025)
    Community: Savannah Estates
    Single Family


    Estimated Monthly Payment: $2,070 (change assumption)
    Mortgage ($1,668) + Fees ($23) + Taxes in 2025 ($378)


    Taxes:$4,538

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 605 HONEY BELL RD, WINTER HAVEN, FL 33880

    $349,000243 Days on yellowkey   MLS ID: L4956825

    REDUCED by $10,000 (2.8%) on 05/07/2026

    For Sale L4956825 - 605 HONEY BELL RD, WINTER HAVEN, FL 33880 73 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2616
       Built: 2022
    Monthly Fee: $56
       Tax: $5,154 (2024)
    Community: Squires Grove Ph 2
    Single Family


    Estimated Monthly Payment: $2,398 (change assumption)
    Mortgage ($1,912) + Fees ($56) + Taxes in 2024 ($430)


    Taxes:$5,154

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 305 MEADOWBROOK BLVD, WINTER HAVEN, FL 33881

    $340,000133 Days on yellowkey   MLS ID: O6381073

    REDUCED by $10,000 (2.9%) on 04/25/2026

    For Sale O6381073 - 305 MEADOWBROOK BLVD, WINTER HAVEN, FL 33881 49 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2696
       Built: 2020
    Monthly Fee: $17
       Tax: $6,152 (2025)
    Community: Lucerne Park Reserve
    Single Family


    Estimated Monthly Payment: $2,393 (change assumption)
    Mortgage ($1,863) + Fees ($17) + Taxes in 2025 ($513)


    Taxes:$6,152

    Elementary School: Lake Alfred Elem

    High School: Haines City Senior High

    Tax Year: 2025

    Middle School: Daniel Jenkins Academy of Technology Middle


  • 4856 SUMMERFIELD CIR, WINTER HAVEN, FL 33881

    $309,90049 Days on yellowkey   MLS ID: O6405577

    For Sale O6405577 - 4856 SUMMERFIELD CIR, WINTER HAVEN, FL 33881 39 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1688
       Built: 2016
    Monthly Fee: $36
       Tax: $4,268 (2025)
    Community: Country Club Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,090 (change assumption)
    Mortgage ($1,698) + Fees ($36) + Taxes in 2025 ($356)


    Taxes:$4,268

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 507 SHORT LN, WINTER HAVEN, FL 33881

    $340,00049 Days on yellowkey   MLS ID: O6404950

    For Sale O6404950 - 507 SHORT LN, WINTER HAVEN, FL 33881 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1867
       Built: 2022
    Monthly Fee: $54
       Tax: $5,124 (2025)
    Community: Inman Grvs Ph 1
    Single Family


    Estimated Monthly Payment: $2,344 (change assumption)
    Mortgage ($1,863) + Fees ($54) + Taxes in 2025 ($427)


    Taxes:$5,124

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 604 SARNER PASS WAY, WINTER HAVEN, FL 33881

    $340,00050 Days on yellowkey   MLS ID: O6404949

    For Sale O6404949 - 604 SARNER PASS WAY, WINTER HAVEN, FL 33881 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2004
       Built: 2022
    Monthly Fee: $76
       Tax: $4,998 (2025)
    Community: Lake Lucerne Ph 5
    Single Family


    Estimated Monthly Payment: $2,355 (change assumption)
    Mortgage ($1,863) + Fees ($76) + Taxes in 2025 ($417)


    Taxes:$4,998

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5389 SAN PIETRO DR, WINTER HAVEN, FL 33884

    $354,999112 Days on yellowkey   MLS ID: TB8482823

    0 Days Off yellowkey (back on 3/23/2026)

    For Sale TB8482823 - 5389 SAN PIETRO DR, WINTER HAVEN, FL 33884 25 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2470
       Built: 2025
    Monthly Fee: $53
       Tax: $2,688 (2025)
    Community: Villa Mar
    Single Family


    Estimated Monthly Payment: $2,222 (change assumption)
    Mortgage ($1,945) + Fees ($53) + Taxes in 2025 ($224)


    Taxes:$2,688

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 6036 NAVONA WAY, WINTER HAVEN, FL 33884

    $304,999272 Days on yellowkey   MLS ID: TB8431493

    1 Days Off yellowkey (back on 3/19/2026)

    For Sale TB8431493 - 6036 NAVONA WAY, WINTER HAVEN, FL 33884 29 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2039
       Built: 2025
    Monthly Fee: $18
       Tax: $8,495 (2025)
    Community: Villa Mar
    Single Family


    Estimated Monthly Payment: $2,397 (change assumption)
    Mortgage ($1,671) + Fees ($18) + Taxes in 2025 ($708)


    Taxes:$8,495

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 5171 KINSLEY DR, WINTER HAVEN, FL 33884

    $336,899303 Days on yellowkey   MLS ID: S5133352

    REDUCED by $3,100 (0.9%) on 05/05/2026

    For Sale S5133352 - 5171 KINSLEY DR, WINTER HAVEN, FL 33884 20 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2050
       Built: 2025
    Monthly Fee: $38

    Community: Seasons At Annabelle Estates
    Single Family


    Estimated Monthly Payment: $1,884 (change assumption)
    Mortgage ($1,846) + Fees ($38) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3151 LAUREL OAK LN, WINTER HAVEN, FL 33884

    $346,55551 Days on yellowkey   MLS ID: L4961605

    For Sale L4961605 - 3151 LAUREL OAK LN, WINTER HAVEN, FL 33884 4 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2029
       Built: 2026
    Monthly Fee: $18

    Community: Villamar
    Single Family


    Estimated Monthly Payment: $1,917 (change assumption)
    Mortgage ($1,899) + Fees ($18) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5121 SYLAS JAX AVE, WINTER HAVEN, FL 33884

    $308,17051 Days on yellowkey   MLS ID: L4961604

    For Sale L4961604 - 5121 SYLAS JAX AVE, WINTER HAVEN, FL 33884 13 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1568
       Built: 2026
    Monthly Fee: $18

    Community: Villamar
    Single Family


    Estimated Monthly Payment: $1,707 (change assumption)
    Mortgage ($1,689) + Fees ($18) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2 CASARENA CT, WINTER HAVEN, FL 33881

    $320,000148 Days on yellowkey   MLS ID: L4958770

    For Sale L4958770 - 2 CASARENA CT, WINTER HAVEN, FL 33881 44 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2377
       Built: 1983
    Monthly Fee: $310
       Tax: $5,755 (2025)
    Community: Casarena On Lakes
    Single Family


    Estimated Monthly Payment: $2,543 (change assumption)
    Mortgage ($1,753) + Fees ($310) + Taxes in 2025 ($480)


    Taxes:$5,755

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 740 SQUIRES GROVE DR, WINTER HAVEN, FL 33880

    $364,990123 Days on yellowkey   MLS ID: S5144206

    REDUCED by $5,000 (1.4%) on 05/02/2026

    For Sale S5144206 - 740 SQUIRES GROVE DR, WINTER HAVEN, FL 33880 35 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2616
       Built: 2022
    Monthly Fee: $64
       Tax: $5,142 (2025)
    Community: Squires Grove Ph 2
    Single Family


    Estimated Monthly Payment: $2,492 (change assumption)
    Mortgage ($2,000) + Fees ($64) + Taxes in 2025 ($429)


    Taxes:$5,142

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1640 NW PEARCE RD, WINTER HAVEN, FL 33881

    $330,000329 Days on yellowkey   MLS ID: L4954651

    REDUCED by $15,000 (4.3%) on 05/02/2026

    For Sale L4954651 - 1640 NW PEARCE RD, WINTER HAVEN, FL 33881 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1421
       Built: 2025
    Community: Lake View Sub Pb 3 Pg 80
    Single Family


    Estimated Monthly Payment: $1,808 (change assumption)
    Mortgage ($1,808) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • WINTER HAVEN, FL 33880

    $390,000243 Days on yellowkey   MLS ID: TB8441385

    REDUCED by $9,500 (2.4%) on 04/22/2026

    SHORT SALE TB8441385 - WINTER HAVEN, FL 33880 13 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2242
       Built: 2007
    Monthly Fee: $15
       Tax: $3,305 (2024)
    Community: Ridge Acres Ph Ii
    Single Family


    Estimated Monthly Payment: $2,427 (change assumption)
    Mortgage ($2,137) + Fees ($15) + Taxes in 2024 ($275)


    Taxes:$3,305

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2117 RIVER HAWK LOOP, WINTER HAVEN, FL 33880

    $335,00061 Days on yellowkey   MLS ID: S5148367

    0 Days Off yellowkey (back on 4/25/2026)

    For Sale S5148367 - 2117 RIVER HAWK LOOP, WINTER HAVEN, FL 33880 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1605
       Built: 2026
    Monthly Fee: $98
       Tax: $228 (2025)
    Community: Residences At Winter Haven
    Single Family


    Estimated Monthly Payment: $1,953 (change assumption)
    Mortgage ($1,836) + Fees ($98) + Taxes in 2025 ($19)


    Taxes:$228

    Elementary School: Lake Shipp Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood 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.