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Winter Haven Homes For Sale & Real Estate - 982 homes

Winter Haven homes for sale are located in Polk County, Florida. Find homes in Winter Haven for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Haven houses.

Location: Winter Haven

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  • 4450 RAPALLO AVE, WINTER HAVEN, FL 33884

    $339,00063 Days on yellowkey   MLS ID: O6394240

    REDUCED by $6,000 (1.7%) on 05/18/2026

    For Sale O6394240 - 4450 RAPALLO AVE, WINTER HAVEN, FL 33884 19 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2480
       Built: 2024
    Monthly Fee: $18
       Tax: $6,608 (2025)
    Community: Villamar Ph 5
    Single Family


    Estimated Monthly Payment: $2,426 (change assumption)
    Mortgage ($1,857) + Fees ($18) + Taxes in 2025 ($551)


    Taxes:$6,608

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 232 W TEMPLE CIR, WINTER HAVEN, FL 33880

    $235,000163 Days on yellowkey   MLS ID: L4957991

    REDUCED by $4,000 (1.7%) on 04/29/2026

    For Sale L4957991 - 232 W TEMPLE CIR, WINTER HAVEN, FL 33880 59 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1700
       Built: 1999   Tax: $872 (2025)
    Community: Orange Hill Sub
    Manufactured Home


    Estimated Monthly Payment: $1,360 (change assumption)
    Mortgage ($1,288) + Taxes in 2025 ($73)


    Taxes:$872

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3307 COSTELLO CIR, WINTER HAVEN, FL 33884

    $294,90025 Days on yellowkey   MLS ID: L4961494

    REDUCED by $5,000 (1.7%) on 05/18/2026

    For Sale L4961494 - 3307 COSTELLO CIR, WINTER HAVEN, FL 33884 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1553
       Built: 2023
    Monthly Fee: $17
       Tax: $4,645 (2025)
    Community: Villamar Ph Four
    Single Family


    Estimated Monthly Payment: $2,020 (change assumption)
    Mortgage ($1,616) + Fees ($17) + Taxes in 2025 ($387)


    Taxes:$4,645

    Elementary School: Garden Grove Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 1246 31ST ST NW, WINTER HAVEN, FL 33881

    $165,900113 Days on yellowkey   MLS ID: TB8470610

    4 Days Off yellowkey (back on 5/18/2026)

    REDUCED by $4,000 (2.4%) on 04/02/2026

    For Sale TB8470610 - 1246 31ST ST NW, WINTER HAVEN, FL 33881 16 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 840
       Built: 1961   Tax: $1,157 (2024)
    Community: West Cannon Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,005 (change assumption)
    Mortgage ($909) + Taxes in 2024 ($96)


    Taxes:$1,157

    Elementary School: Inwood Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Westwood Middle


  • 3147 WHISPERING TRAILS ST, WINTER HAVEN, FL 33884

    $215,00032 Days on yellowkey   MLS ID: O6402822

    For Sale O6402822 - 3147 WHISPERING TRAILS ST, WINTER HAVEN, FL 33884 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1303
       Built: 2006
    Monthly Fee: $56
       Tax: $3,584 (2025)
    Community: Whispering Trails Ph 01
    Single Family


    Estimated Monthly Payment: $1,533 (change assumption)
    Mortgage ($1,178) + Fees ($56) + Taxes in 2025 ($299)


    Taxes:$3,584

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1646 TRESSEL CT, WINTER HAVEN, FL 33881

    $290,00043 Days on yellowkey   MLS ID: P4938246

    For Sale P4938246 - 1646 TRESSEL CT, WINTER HAVEN, FL 33881 46 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2020
    Monthly Fee: $50
       Tax: $4,864 (2025)
    Community: Buckeye Trace
    Single Family


    Estimated Monthly Payment: $2,044 (change assumption)
    Mortgage ($1,589) + Fees ($50) + Taxes in 2025 ($405)


    Taxes:$4,864

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4555 REDWOOD ST, WINTER HAVEN, FL 33880

    $125,000430 Days on yellowkey   MLS ID: P4934214

    0 Days Off yellowkey (back on 5/18/2026)

    For Sale P4934214 - 4555 REDWOOD ST, WINTER HAVEN, FL 33880 68 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1035
       Built: 1983
    Monthly Fee: $163
       Tax: $959 (2024)
    Community: Oakwood Estates
    Manufactured Home


    Estimated Monthly Payment: $928 (change assumption)
    Mortgage ($685) + Fees ($163) + Taxes in 2024 ($80)


    Taxes:$959

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3098 LAUREL OAK LN, WINTER HAVEN, FL 33884

    $275,00057 Days on yellowkey   MLS ID: O6390090

    REDUCED by $5,000 (1.8%) on 05/18/2026

    SHORT SALE O6390090 - 3098 LAUREL OAK LN, WINTER HAVEN, FL 33884 13 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1978
       Built: 2023
    Monthly Fee: $18
       Tax: $6,208 (2025)
    Community: Villamar Ph 5
    Single Family


    Estimated Monthly Payment: $2,042 (change assumption)
    Mortgage ($1,507) + Fees ($18) + Taxes in 2025 ($517)


    Taxes:$6,208

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6775 BRENTWOOD DR NE, WINTER HAVEN, FL 33881

    $132,50062 Days on yellowkey   MLS ID: S5146696

    REDUCED by $4,400 (3.2%) on 05/18/2026

    For Sale S5146696 - 6775 BRENTWOOD DR NE, WINTER HAVEN, FL 33881 44 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1320
       Built: 1985
    Monthly Fee: $46
       Tax: $147 (2025)
    Community: Lake N Golf Estates
    Spa: No

    Manufactured Home


    Estimated Monthly Payment: $784 (change assumption)
    Mortgage ($726) + Fees ($46) + Taxes in 2025 ($12)


    Taxes:$147

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3732 GIORGIO DR, WINTER HAVEN, FL 33884

    $260,00037 Days on yellowkey   MLS ID: S5147116

    REDUCED by $10,500 (3.9%) on 05/18/2026

    SHORT SALE S5147116 - 3732 GIORGIO DR, WINTER HAVEN, FL 33884 20 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1713
       Built: 2024
    Monthly Fee: $15
       Tax: $6,432 (2025)
    Community: Villamar Ph 6 & Ph 6D
    Single Family


    Estimated Monthly Payment: $1,976 (change assumption)
    Mortgage ($1,425) + Fees ($15) + Taxes in 2025 ($536)


    Taxes:$6,432

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 419 BIGSTAFF CT, WINTER HAVEN, FL 33884

    $269,90015 Days on yellowkey   MLS ID: L4961921

    0 Days Off yellowkey (back on 5/18/2026)

    For Sale L4961921 - 419 BIGSTAFF CT, WINTER HAVEN, FL 33884 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1405
       Built: 1998
    Monthly Fee: $24
       Tax: $1,562 (2025)
    Community: Berryhill
    Single Family


    Estimated Monthly Payment: $1,633 (change assumption)
    Mortgage ($1,479) + Fees ($24) + Taxes in 2025 ($130)


    Taxes:$1,562

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1228 DENALI DR, WINTER HAVEN, FL 33881

    $315,000268 Days on yellowkey   MLS ID: P4936142

    For Sale P4936142 - 1228 DENALI DR, WINTER HAVEN, FL 33881 24 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1707
       Built: 2023
    Monthly Fee: $73
       Tax: $4,208 (2024)
    Community: Lake Lucerne Ii
    Single Family


    Estimated Monthly Payment: $2,150 (change assumption)
    Mortgage ($1,726) + Fees ($73) + Taxes in 2024 ($351)


    Taxes:$4,208

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3180 COUNTRY CLUB CIR, WINTER HAVEN, FL 33881

    $260,000127 Days on yellowkey   MLS ID: W7882124

    INCREASED by $10,000 (4.0%) on 05/18/2026

    SHORT SALE W7882124 - 3180 COUNTRY CLUB CIR, WINTER HAVEN, FL 33881 15 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1732
       Built: 2019
    Monthly Fee: $30
       Tax: $4,663 (2025)
    Community: Country Walk/Winter Haven
    Single Family


    Estimated Monthly Payment: $1,843 (change assumption)
    Mortgage ($1,425) + Fees ($30) + Taxes in 2025 ($389)


    Taxes:$4,663

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 5457 HOGAN LN, WINTER HAVEN, FL 33884

    $589,00052 Days on yellowkey   MLS ID: P4938326

    For Sale P4938326 - 5457 HOGAN LN, WINTER HAVEN, FL 33884 80 photos

    Bed: 4   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2676
       Built: 2013
    Monthly Fee: $5
       Tax: $8,313 (2025)
    Community: Lake Ashton West Atlee Add
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,925 (change assumption)
    Mortgage ($3,227) + Fees ($5) + Taxes in 2025 ($693)


    Taxes:$8,313

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4040 CARTERET, WINTER HAVEN, FL 33884

    $254,00055 Days on yellowkey   MLS ID: B4902225

    0 Days Off yellowkey (back on 5/18/2026)

    REDUCED by $5,000 (1.9%) on 05/05/2026

    For Sale B4902225 - 4040 CARTERET, WINTER HAVEN, FL 33884 30 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1599
       Built: 2006
    Monthly Fee: $484
       Tax: $1,588 (2024)
    Community: Traditions Phase 1
    Single Family


    Estimated Monthly Payment: $2,008 (change assumption)
    Mortgage ($1,392) + Fees ($484) + Taxes in 2024 ($132)


    Taxes:$1,588

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 420 ITUNA CIR, WINTER HAVEN, FL 33881

    $324,900178 Days on yellowkey   MLS ID: L4957641

    0 Days Off yellowkey (back on 5/18/2026)

    For Sale L4957641 - 420 ITUNA CIR, WINTER HAVEN, FL 33881 4 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1744
       Built: 2026
    Monthly Fee: $50

    Community: Harbor At Lake Henry
    Single Family


    Estimated Monthly Payment: $1,830 (change assumption)
    Mortgage ($1,780) + Fees ($50) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2327 BRASSIE CT, WINTER HAVEN, FL 33884

    $295,529226 Days on yellowkey   MLS ID: L4956621

    5 Days Off yellowkey (back on 5/18/2026)

    REDUCED by $10,000 (3.3%) on 05/01/2026

    For Sale L4956621 - 2327 BRASSIE CT, WINTER HAVEN, FL 33884 4 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2202
       Built: 2025
    Monthly Fee: $17
       Tax: $3,122 (2024)
    Community: Villa Mar Phase 3
    Single Family


    Estimated Monthly Payment: $1,896 (change assumption)
    Mortgage ($1,619) + 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


  • 1052 MEDINAH DR, WINTER HAVEN, FL 33884

    $190,00045 Days on yellowkey   MLS ID: L4961077

    REDUCED by $20,000 (9.5%) on 05/18/2026

    For Sale L4961077 - 1052 MEDINAH DR, WINTER HAVEN, FL 33884 47 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1422
       Built: 1980
    Monthly Fee: $334
       Tax: $2,847 (2025)
    Community: Cypresswood
    Villa


    Estimated Monthly Payment: $1,612 (change assumption)
    Mortgage ($1,041) + Fees ($334) + Taxes in 2025 ($237)


    Taxes:$2,847

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 961 HAROLD PASS, WINTER HAVEN, FL 33884

    $259,90051 Days on yellowkey   MLS ID: O6397178

    REDUCED by $5,100 (1.9%) on 05/18/2026

    For Sale O6397178 - 961 HAROLD PASS, WINTER HAVEN, FL 33884 14 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1432
       Built: 2024
    Monthly Fee: $16
       Tax: $6,703 (2025)
    Community: Peace Crk Reserve
    Single Family


    Estimated Monthly Payment: $1,999 (change assumption)
    Mortgage ($1,424) + Fees ($16) + Taxes in 2025 ($559)


    Taxes:$6,703

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 73 WINTER RIDGE RD #73, WINTER HAVEN, FL 33881

    $159,90012 Days on yellowkey   MLS ID: S5149842

    0 Days Off yellowkey (back on 5/18/2026)

    For Sale S5149842 - 73 WINTER RIDGE RD #73, WINTER HAVEN, FL 33881 1 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1073
       Built: 1992
    Monthly Fee: $253
       Tax: $2,473 (2025)
    Community: Winter Rdg Condos
    Condo


    Estimated Monthly Payment: $1,335 (change assumption)
    Mortgage ($876) + Fees ($253) + Taxes in 2025 ($206)


    Taxes:$2,473

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




Why Bother Searching Elsewhere for Winter Haven Homes for Sale and Other Real Estate?

Winter Haven home, townhome, condo, villa, and other listing sales data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in Winter Haven. You can use our website to view Multiple Listing Service (MLS) data on Winter Haven Real Estate. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Winter Haven listings.



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.