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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Living Area Square Feet: 2000 to 2499

Winter Haven - 176 properties found

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  • 5580 STATE ROAD 542 W, WINTER HAVEN, FL 33880

    $235,000225 Days on yellowkey   MLS ID: A4671922

    For Sale A4671922 - 5580 STATE ROAD 542 W, WINTER HAVEN, FL 33880 32 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2174
       Built: 1952   Tax: $1,740 (2024)
    Community: Jan Phyl Village
    Single Family


    Estimated Monthly Payment: $1,433 (change assumption)
    Mortgage ($1,288) + Taxes in 2024 ($145)


    Taxes:$1,740

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 204 AVENUE D NE, WINTER HAVEN, FL 33881

    $265,00019 Days on yellowkey   MLS ID: O6413665

    For Sale O6413665 - 204 AVENUE D NE, WINTER HAVEN, FL 33881 36 photos

    Bed: 6   Bath: 3.0
    Liv Area Sq Ft: 2102
       Built: 1915   Tax: $1,902 (2025)
    Community: Winter Haven Heights
    Single Family


    Estimated Monthly Payment: $1,610 (change assumption)
    Mortgage ($1,452) + Taxes in 2025 ($158)


    Taxes:$1,902

    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


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

    $425,000204 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


  • 7 LAKE ARROWHEAD DR, WINTER HAVEN, FL 33880

    $750,00020 Days on yellowkey   MLS ID: P4938946

    For Sale P4938946 - 7 LAKE ARROWHEAD DR, WINTER HAVEN, FL 33880 86 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2056
       Built: 1982   Tax: $2,510 (2025)
    Community: None
    Single Family


    Estimated Monthly Payment: $4,319 (change assumption)
    Mortgage ($4,109) + Taxes in 2025 ($209)


    Taxes:$2,510

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1580 LEAMINGTON LN, WINTER HAVEN, FL 33884

    $294,366593 Days on yellowkey   MLS ID: L4948737

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

    REDUCED by $5,000 (1.7%) on 05/01/2026

    For Sale L4948737 - 1580 LEAMINGTON LN, WINTER HAVEN, FL 33884 29 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2200
       Built: 2025
    Monthly Fee: $15
       Tax: $813 (2025)
    Community: Villamar
    Single Family


    Estimated Monthly Payment: $1,696 (change assumption)
    Mortgage ($1,613) + Fees ($15) + Taxes in 2025 ($68)


    Taxes:$813

    Elementary School: Chain O Lakes Elem

    High School: Lake Gibson High

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 5128 SYLAS JAX AVE E, WINTER HAVEN, FL 33884

    $335,90052 Days on yellowkey   MLS ID: L4961608

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

    REDUCED by $16,355 (4.6%) on 05/27/2026

    For Sale L4961608 - 5128 SYLAS JAX AVE 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: $1,859 (change assumption)
    Mortgage ($1,841) + Fees ($18) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 111 SUNSET DR E, WINTER HAVEN, FL 33881

    $200,000120 Days on yellowkey   MLS ID: P4937961

    REDUCED by $15,000 (7.0%) on 06/04/2026

    For Sale P4937961 - 111 SUNSET DR E, WINTER HAVEN, FL 33881 44 photos

    Bed: 4   Bath: 1.0
    Liv Area Sq Ft: 2078
       Built: 1964   Tax: $1,193 (2025)
    Community: Chris Brown Cemetery Replat
    Single Family


    Estimated Monthly Payment: $1,195 (change assumption)
    Mortgage ($1,096) + Taxes in 2025 ($99)


    Taxes:$1,193

    Elementary School: Jewett School of the Arts

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 6004 KALEY DR, WINTER HAVEN, FL 33880

    $274,99062 Days on yellowkey   MLS ID: S5148589

    For Sale S5148589 - 6004 KALEY DR, WINTER HAVEN, FL 33880 27 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2128
       Built: 2004
    Monthly Fee: $14
       Tax: $4,038 (2025)
    Community: Sunridge Village East
    Single Family


    Estimated Monthly Payment: $1,857 (change assumption)
    Mortgage ($1,507) + Fees ($14) + Taxes in 2025 ($336)


    Taxes:$4,038

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 126 LAKE REGION CIRCLE, WINTER HAVEN, FL 33881

    $400,000252 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


  • 1290 N LAKE SHIPP DR N, WINTER HAVEN, FL 33880

    $795,00069 Days on yellowkey   MLS ID: L4961193

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

    For Sale L4961193 - 1290 N LAKE SHIPP DR N, WINTER HAVEN, FL 33880 57 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2001
       Built: 2021   Tax: $7,094 (2025)
    Community: N/A
    Single Family


    Estimated Monthly Payment: $4,947 (change assumption)
    Mortgage ($4,356) + Taxes in 2025 ($591)


    Taxes:$7,094

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 980 WEDGEWOOD DR SE, WINTER HAVEN, FL 33880

    $450,00022 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


  • 1818 6TH ST SE, WINTER HAVEN, FL 33880

    $500,000294 Days on yellowkey   MLS ID: O6341480

    For Sale O6341480 - 1818 6TH ST SE, WINTER HAVEN, FL 33880 63 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 2006
       Built: 1963   Tax: $3,632 (2023)
    Community: Southeast Terrace
    Single Family


    Estimated Monthly Payment: $3,042 (change assumption)
    Mortgage ($2,740) + Taxes in 2023 ($303)


    Taxes:$3,632

    Elementary School: John Snively Elem

    High School: Winter Haven Senior

    Tax Year: 2023

    Middle School: Denison Middle


  • 3134 LAUREL OAK LN, WINTER HAVEN, FL 33884

    $330,925177 Days on yellowkey   MLS ID: L4958155

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

    For Sale L4958155 - 3134 LAUREL OAK LN, WINTER HAVEN, FL 33884 1 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2005
       Built: 2026
    Monthly Fee: $19

    Community: Villamar
    Single Family


    Estimated Monthly Payment: $1,832 (change assumption)
    Mortgage ($1,813) + Fees ($19) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $469,90073 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


  • 35 S LAKE FOX RD, WINTER HAVEN, FL 33884

    $399,999309 Days on yellowkey   MLS ID: O6337767

    For Sale O6337767 - 35 S LAKE FOX RD, WINTER HAVEN, FL 33884 43 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2149
       Built: 1981   Tax: $2,600 (2023)
    Community: N/A
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,408 (change assumption)
    Mortgage ($2,192) + Taxes in 2023 ($217)


    Taxes:$2,600

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 333 MEREDITH BLVD, WINTER HAVEN, FL 33881

    $356,94030 Days on yellowkey   MLS ID: O6410465

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

    INCREASED by $15,000 (4.4%) on 05/26/2026

    For Sale O6410465 - 333 MEREDITH BLVD, WINTER HAVEN, FL 33881 3 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2371
       Built: 2026
    Monthly Fee: $6
       Tax: $2,808 (2025)
    Community: Willowbrook North
    Single Family


    Estimated Monthly Payment: $2,196 (change assumption)
    Mortgage ($1,956) + Fees ($6) + Taxes in 2025 ($234)


    Taxes:$2,808

    Elementary School: Fred G. Garnier Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 352 VAIL DR, WINTER HAVEN, FL 33884

    $274,90024 Days on yellowkey   MLS ID: L4962337

    For Sale L4962337 - 352 VAIL DR, WINTER HAVEN, FL 33884 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2040
       Built: 1990
    Monthly Fee: $17
       Tax: $1,538 (2025)
    Community: Cedar Cove Ph 02
    Single Family


    Estimated Monthly Payment: $1,651 (change assumption)
    Mortgage ($1,506) + Fees ($17) + Taxes in 2025 ($128)


    Taxes:$1,538

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2117 HIGH POINT AVE SW, WINTER HAVEN, FL 33880

    $389,90052 Days on yellowkey   MLS ID: L4960940

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

    For Sale L4960940 - 2117 HIGH POINT AVE SW, WINTER HAVEN, FL 33880 34 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2485
       Built: 1977   Tax: $6,491 (2025)
    Community: High Point
    Single Family


    Estimated Monthly Payment: $2,677 (change assumption)
    Mortgage ($2,136) + Taxes in 2025 ($541)


    Taxes:$6,491

    Elementary School: Lake Shipp Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: None


  • 4020 CARTERET DR, WINTER HAVEN, FL 33884

    $405,900107 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.