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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Price: $400,000 to $499,000

Winter Haven - 67 properties found

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  • 2118 EDGEWATER CIR, WINTER HAVEN, FL 33880

    $411,000116 Days on yellowkey   MLS ID: TB8480830

    INCREASED by $12,000 (3.0%) on 06/15/2026

    For Sale TB8480830 - 2118 EDGEWATER CIR, WINTER HAVEN, FL 33880 29 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2763
       Built: 2017
    Monthly Fee: $14
       Tax: $4,291 (2025)
    Community: Edgewater Manor
    Single Family


    Estimated Monthly Payment: $2,624 (change assumption)
    Mortgage ($2,252) + Fees ($14) + Taxes in 2025 ($358)


    Taxes:$4,291

    Elementary School: Chain O Lakes Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 355 RUBY LAKE LOOP, WINTER HAVEN, FL 33884

    $474,99941 Days on yellowkey   MLS ID: K4903491

    2 Days Off yellowkey (back on 6/14/2026)

    For Sale K4903491 - 355 RUBY LAKE LOOP, WINTER HAVEN, FL 33884 40 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2648
       Built: 1998
    Monthly Fee: $71
       Tax: $4,848 (2025)
    Community: Ruby Lake Sub Ph Ii
    Single Family


    Estimated Monthly Payment: $3,078 (change assumption)
    Mortgage ($2,603) + Fees ($71) + Taxes in 2025 ($404)


    Taxes:$4,848

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1280 DENALI DR, WINTER HAVEN, FL 33881

    $409,000146 Days on yellowkey   MLS ID: G5107453

    INCREASED by $10,000 (2.5%) on 04/05/2026

    For Sale G5107453 - 1280 DENALI DR, WINTER HAVEN, FL 33881 32 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2566
       Built: 2024
    Monthly Fee: $92
       Tax: $6,203 (2025)
    Community: Lake Lucerne Ii
    Single Family


    Estimated Monthly Payment: $2,850 (change assumption)
    Mortgage ($2,241) + Fees ($92) + Taxes in 2025 ($517)


    Taxes:$6,203

    Elementary School: Bethune Academy

    High School: None

    Tax Year: 2025

    Middle School: Daniel Jenkins Academy of Technology Middle


  • 357 RUBY LAKE LOOP, WINTER HAVEN, FL 33884

    $415,00096 Days on yellowkey   MLS ID: L4960449

    For Sale L4960449 - 357 RUBY LAKE LOOP, WINTER HAVEN, FL 33884 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2107
       Built: 1998
    Monthly Fee: $71
       Tax: $2,731 (2025)
    Community: Ruby Lake Ph 01
    Single Family


    Estimated Monthly Payment: $2,573 (change assumption)
    Mortgage ($2,274) + Fees ($71) + Taxes in 2025 ($228)


    Taxes:$2,731

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 2968 PLANTATION RD, WINTER HAVEN, FL 33884

    $442,00096 Days on yellowkey   MLS ID: P4938120

    0 Days Off yellowkey (back on 5/30/2026)

    REDUCED by $23,000 (4.9%) on 04/23/2026

    For Sale P4938120 - 2968 PLANTATION RD, WINTER HAVEN, FL 33884 83 photos

    Bed: 3   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2433
       Built: 1997
    Monthly Fee: $149
       Tax: $3,191 (2025)
    Community: Cypresswood Plantations
    Single Family


    Estimated Monthly Payment: $2,837 (change assumption)
    Mortgage ($2,422) + Fees ($149) + Taxes in 2025 ($266)


    Taxes:$3,191

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 335 RUBY LAKE LOOP, WINTER HAVEN, FL 33884

    $484,90019 Days on yellowkey   MLS ID: L4962358

    0 Days Off yellowkey (back on 6/12/2026)

    For Sale L4962358 - 335 RUBY LAKE LOOP, WINTER HAVEN, FL 33884 66 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2406
       Built: 1999
    Monthly Fee: $71
       Tax: $3,154 (2025)
    Community: Ruby Lake Ph 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,991 (change assumption)
    Mortgage ($2,657) + Fees ($71) + Taxes in 2025 ($263)


    Taxes:$3,154

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 4 GROVE CT SE, WINTER HAVEN, FL 33884

    $424,90055 Days on yellowkey   MLS ID: O6401108

    REDUCED by $5,000 (1.2%) on 06/10/2026

    For Sale O6401108 - 4 GROVE CT SE, WINTER HAVEN, FL 33884 49 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 1983
       Built: 1977   Tax: $2,779 (2025)
    Community: Lake Winterset Acres
    Single Family


    Estimated Monthly Payment: $2,560 (change assumption)
    Mortgage ($2,328) + Taxes in 2025 ($232)


    Taxes:$2,779

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 900 LAKE JESSIE DR, WINTER HAVEN, FL 33881

    $450,00088 Days on yellowkey   MLS ID: S5146723

    REDUCED by $19,900 (4.2%) on 06/06/2026

    For Sale S5146723 - 900 LAKE JESSIE DR, WINTER HAVEN, FL 33881 50 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1828
       Built: 1948   Tax: $4,023 (2025)
    Community: East View Pkwy
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,801 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($335)


    Taxes:$4,023

    Elementary School: Auburndale Central Elem

    High School: Auburndale High School

    Tax Year: 2025

    Middle School: Westwood Middle


  • 106 JARDIN LN, WINTER HAVEN, FL 33884

    $419,900163 Days on yellowkey   MLS ID: L4958336

    For Sale L4958336 - 106 JARDIN LN, WINTER HAVEN, FL 33884 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2319
       Built: 2001
    Monthly Fee: $308
       Tax: $5,361 (2025)
    Community: Gardens Interlochen
    Single Family


    Estimated Monthly Payment: $3,056 (change assumption)
    Mortgage ($2,301) + Fees ($308) + Taxes in 2025 ($447)


    Taxes:$5,361

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 1217 MICHELANGELO LN, WINTER HAVEN, FL 33884

    $450,00025 Days on yellowkey   MLS ID: P4938819

    REDUCED by $15,000 (3.2%) on 06/11/2026

    For Sale P4938819 - 1217 MICHELANGELO LN, WINTER HAVEN, FL 33884 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2960
       Built: 2023
    Monthly Fee: $57
       Tax: $5,498 (2025)
    Community: Estates/Lk Florence
    Single Family


    Estimated Monthly Payment: $2,981 (change assumption)
    Mortgage ($2,466) + Fees ($57) + Taxes in 2025 ($458)


    Taxes:$5,498

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1797 HUMMINGBIRD RD, WINTER HAVEN, FL 33884

    $476,99014 Days on yellowkey   MLS ID: O6415738

    For Sale O6415738 - 1797 HUMMINGBIRD RD, WINTER HAVEN, FL 33884 53 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2787
       Built: 2026
    Monthly Fee: $30
       Tax: $2,606 (2025)
    Community: Harmony On Lake Eloise Phase 4
    Single Family


    Estimated Monthly Payment: $2,861 (change assumption)
    Mortgage ($2,614) + Fees ($30) + Taxes in 2025 ($217)


    Taxes:$2,606

    Elementary School: John Snively Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 301 TERRANOVA BLVD, WINTER HAVEN, FL 33884

    $415,00018 Days on yellowkey   MLS ID: S5151390

    For Sale S5151390 - 301 TERRANOVA BLVD, WINTER HAVEN, FL 33884 23 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1960
       Built: 2005
    Monthly Fee: $50
       Tax: $4,429 (2025)
    Community: Terranova Ph 04
    Single Family


    Estimated Monthly Payment: $2,693 (change assumption)
    Mortgage ($2,274) + Fees ($50) + Taxes in 2025 ($369)


    Taxes:$4,429

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 108 LAKE REGION BLVD N, WINTER HAVEN, FL 33881

    $425,000203 Days on yellowkey   MLS ID: L4957549

    REDUCED by $14,000 (3.2%) on 04/13/2026

    For Sale L4957549 - 108 LAKE REGION BLVD N, WINTER HAVEN, FL 33881 52 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2495
       Built: 1996
    Monthly Fee: $85
       Tax: $3,479 (2025)
    Community: Gates Of Lake Region
    Single Family


    Estimated Monthly Payment: $2,704 (change assumption)
    Mortgage ($2,329) + Fees ($85) + Taxes in 2025 ($290)


    Taxes:$3,479

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 592 LAKE SMART BLVD, WINTER HAVEN, FL 33881

    $415,00054 Days on yellowkey   MLS ID: S5148989

    For Sale S5148989 - 592 LAKE SMART BLVD, WINTER HAVEN, FL 33881 72 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2944
       Built: 2021
    Monthly Fee: $55
       Tax: $4,862 (2025)
    Community: Lake Smart Pointe
    Single Family


    Estimated Monthly Payment: $2,734 (change assumption)
    Mortgage ($2,274) + Fees ($55) + Taxes in 2025 ($405)


    Taxes:$4,862

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 126 LAKE REGION CIRCLE, WINTER HAVEN, FL 33881

    $400,000251 Days on yellowkey   MLS ID: P4936583

    For Sale P4936583 - 126 LAKE REGION CIRCLE, WINTER HAVEN, FL 33881 53 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2142
       Built: 2003
    Monthly Fee: $95
       Tax: $3,169 (2025)
    Community: Gates Of Lake Region
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,551 (change assumption)
    Mortgage ($2,192) + Fees ($95) + Taxes in 2025 ($264)


    Taxes:$3,169

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 980 WEDGEWOOD DR SE, WINTER HAVEN, FL 33880

    $450,00021 Days on yellowkey   MLS ID: P4938917

    For Sale P4938917 - 980 WEDGEWOOD DR SE, WINTER HAVEN, FL 33880 66 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2363
       Built: 2023   Tax: $6,039 (2025)
    Community: Wedgewood Terrace
    Single Family


    Estimated Monthly Payment: $2,969 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($503)


    Taxes:$6,039

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 240 SANTA ROSA DR, WINTER HAVEN, FL 33884

    $439,000182 Days on yellowkey   MLS ID: L4958092

    1 Days Off yellowkey (back on 5/29/2026)

    INCREASED by $4,100 (0.9%) on 05/17/2026

    For Sale L4958092 - 240 SANTA ROSA DR, WINTER HAVEN, FL 33884 25 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2850
       Built: 1988
    Monthly Fee: $46
       Tax: $2,790 (2023)
    Community: Overlook Ests Ph 3
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,684 (change assumption)
    Mortgage ($2,405) + Fees ($46) + Taxes in 2023 ($233)


    Taxes:$2,790

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2023

    Middle School: Denison Middle


  • 247 S LAKE PANSY DR, WINTER HAVEN, FL 33881

    $469,90072 Days on yellowkey   MLS ID: TB8496517

    REDUCED by $10,000 (2.1%) on 05/10/2026

    For Sale TB8496517 - 247 S LAKE PANSY DR, WINTER HAVEN, FL 33881 56 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2247
       Built: 1986
    Monthly Fee: $136
       Tax: $2,948 (2025)
    Community: Hartridge Hills
    Single Family


    Estimated Monthly Payment: $2,956 (change assumption)
    Mortgage ($2,575) + Fees ($136) + Taxes in 2025 ($246)


    Taxes:$2,948

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 148 LAKE OTIS RD, WINTER HAVEN, FL 33884

    $459,000156 Days on yellowkey   MLS ID: L4958667

    For Sale L4958667 - 148 LAKE OTIS RD, WINTER HAVEN, FL 33884 45 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2663
       Built: 1974
    Monthly Fee: $100
       Tax: $6,141 (2025)
    Community: Lakewood
    Single Family


    Estimated Monthly Payment: $3,127 (change assumption)
    Mortgage ($2,515) + Fees ($100) + Taxes in 2025 ($512)


    Taxes:$6,141

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4020 CARTERET DR, WINTER HAVEN, FL 33884

    $405,900106 Days on yellowkey   MLS ID: O6389154

    REDUCED by $14,000 (3.3%) on 05/22/2026

    For Sale O6389154 - 4020 CARTERET DR, WINTER HAVEN, FL 33884 28 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2282
       Built: 2015
    Monthly Fee: $484
       Tax: $3,537 (2025)
    Community: Traditions
    Single Family


    Estimated Monthly Payment: $3,003 (change assumption)
    Mortgage ($2,224) + Fees ($484) + Taxes in 2025 ($295)


    Taxes:$3,537

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    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.