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Winter Haven Homes For Sale & Real Estate - 1041 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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  • 41 GREENFIELD CT, WINTER HAVEN, FL 33884

    $379,0003 Days on yellowkey   MLS ID: L4963295

    For Sale L4963295 - 41 GREENFIELD CT, WINTER HAVEN, FL 33884 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2054
       Built: 1978
    Monthly Fee: $152
       Tax: $3,172 (2025)
    Community: Cypresswood
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,493 (change assumption)
    Mortgage ($2,077) + Fees ($152) + Taxes in 2025 ($264)


    Taxes:$3,172

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2390 29TH ST NW, WINTER HAVEN, FL 33881

    $231,7003 Days on yellowkey   MLS ID: TB8527635

    For Sale TB8527635 - 2390 29TH ST NW, WINTER HAVEN, FL 33881 8 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1048
       Built: 1965   Tax: $2,778 (2025)
    Community: Biltmore Shores
    Single Family


    Estimated Monthly Payment: $1,501 (change assumption)
    Mortgage ($1,270) + Taxes in 2025 ($231)


    Taxes:$2,778

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2771 GLADIOLA RD, WINTER HAVEN, FL 33884

    $273,9903 Days on yellowkey   MLS ID: O6424150

    For Sale O6424150 - 2771 GLADIOLA RD, WINTER HAVEN, FL 33884 32 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1758
       Built: 2026
    Monthly Fee: $130
       Tax: $1,773 (2025)
    Community: Harmony On Lake Eloise
    Townhouse


    Estimated Monthly Payment: $1,779 (change assumption)
    Mortgage ($1,501) + Fees ($130) + Taxes in 2025 ($148)


    Taxes:$1,773

    Elementary School: John Snively Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 2741 GLADIOLA RD, WINTER HAVEN, FL 33884

    $273,9903 Days on yellowkey   MLS ID: O6424142

    For Sale O6424142 - 2741 GLADIOLA RD, WINTER HAVEN, FL 33884 32 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1758
       Built: 2026
    Monthly Fee: $130
       Tax: $1,773 (2025)
    Community: Harmony On Lake Eloise
    Townhouse


    Estimated Monthly Payment: $1,779 (change assumption)
    Mortgage ($1,501) + Fees ($130) + Taxes in 2025 ($148)


    Taxes:$1,773

    Elementary School: John Snively Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 1404 AXEL CIR, WINTER HAVEN, FL 33880

    $365,0003 Days on yellowkey   MLS ID: S5153455

    For Sale S5153455 - 1404 AXEL CIR, WINTER HAVEN, FL 33880 22 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2523
       Built: 2022
    Monthly Fee: $63
       Tax: $4,584 (2025)
    Community: Pinnacle Point
    Single Family


    Estimated Monthly Payment: $2,445 (change assumption)
    Mortgage ($2,000) + Fees ($63) + Taxes in 2025 ($382)


    Taxes:$4,584

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 207 AVENUE E SE, WINTER HAVEN, FL 33880

    $420,00067 Days on yellowkey   MLS ID: L4961631

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

    For Sale L4961631 - 207 AVENUE E SE, WINTER HAVEN, FL 33880 29 photos

    Bed: 4   Bath: 4.0
    Liv Area Sq Ft: 2093
       Built: 2026   Tax: $3,201 (2025)
    Community: Twin Oaks Add Pb 12 Pg 16
    Single Family


    Estimated Monthly Payment: $2,568 (change assumption)
    Mortgage ($2,301) + Taxes in 2025 ($267)


    Taxes:$3,201

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 507 SHORT LN, WINTER HAVEN, FL 33881

    $340,00068 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


  • 610 GROVE ST, WINTER HAVEN, FL 33881

    $259,900194 Days on yellowkey   MLS ID: L4957731

    0 Days Off yellowkey (back on 5/15/2026)

    REDUCED by $11,100 (4.1%) on 05/04/2026

    For Sale L4957731 - 610 GROVE ST, WINTER HAVEN, FL 33881 39 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1867
       Built: 2022
    Monthly Fee: $50
       Tax: $4,897 (2024)
    Community: Inman Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $1,882 (change assumption)
    Mortgage ($1,424) + Fees ($50) + Taxes in 2024 ($408)


    Taxes:$4,897

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Denison Middle


  • 3331 TWILIGHT RD, WINTER HAVEN, FL 33881

    $335,990231 Days on yellowkey   MLS ID: TB8451210

    5 Days Off yellowkey (back on 3/10/2026)

    For Sale TB8451210 - 3331 TWILIGHT RD, WINTER HAVEN, FL 33881 2 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1802
       Built: 2025
    Monthly Fee: $57
       Tax: $952 (2025)
    Community: Sunset Hills
    Single Family


    Estimated Monthly Payment: $1,977 (change assumption)
    Mortgage ($1,841) + Fees ($57) + Taxes in 2025 ($79)


    Taxes:$952

    Elementary School: Lake Alfred Elem

    High School: Haines City Senior High

    Tax Year: 2025

    Middle School: Boone Middle


  • 912 AVENUE T SE, WINTER HAVEN, FL 33880

    $295,000649 Days on yellowkey   MLS ID: S5113072

    For Sale S5113072 - 912 AVENUE T SE, WINTER HAVEN, FL 33880 51 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2149
       Built: 1960   Tax: $1,575 (2023)
    Community: Woodmere
    Single Family


    Estimated Monthly Payment: $1,748 (change assumption)
    Mortgage ($1,616) + Taxes in 2023 ($131)


    Taxes:$1,575

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 2335 BRASSIE CT, WINTER HAVEN, FL 33884

    $295,529364 Days on yellowkey   MLS ID: L4954447

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

    For Sale L4954447 - 2335 BRASSIE CT, WINTER HAVEN, FL 33884 5 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2202
       Built: 2025
    Monthly Fee: $17
       Tax: $3,079 (2024)
    Community: Villa Mar Phase 3
    Single Family


    Estimated Monthly Payment: $1,893 (change assumption)
    Mortgage ($1,619) + Fees ($17) + Taxes in 2024 ($257)


    Taxes:$3,079

    Elementary School: Chain O Lakes Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Berkley Accelerated Middle


  • 1533 LEAMINGTON LN, WINTER HAVEN, FL 33884

    $304,366364 Days on yellowkey   MLS ID: L4954446

    2 Days Off yellowkey (back on 6/27/2026)

    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


  • 1525 LEAMINGTON LN, WINTER HAVEN, FL 33884

    $299,366409 Days on yellowkey   MLS ID: L4952865

    1 Days Off yellowkey (back on 5/21/2026)

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

    For Sale L4952865 - 1525 LEAMINGTON LN, WINTER HAVEN, FL 33884 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2200
       Built: 2025
    Monthly Fee: $67
       Tax: $7,400 (2025)
    Community: Villa Mar Phase 3
    Single Family


    Estimated Monthly Payment: $2,324 (change assumption)
    Mortgage ($1,640) + Fees ($67) + Taxes in 2025 ($617)


    Taxes:$7,400

    Elementary School: Chain O Lakes Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Berkley Accelerated Middle


  • 23 CASARENA CT, WINTER HAVEN, FL 33881

    $219,90081 Days on yellowkey   MLS ID: S5148554

    0 Days Off yellowkey (back on 7/10/2026)

    REDUCED by $10,100 (4.4%) on 06/19/2026

    For Sale S5148554 - 23 CASARENA CT, WINTER HAVEN, FL 33881 50 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2045
       Built: 1984
    Monthly Fee: $310
       Tax: $3,909 (2025)
    Community: Casarena/Lks
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,841 (change assumption)
    Mortgage ($1,205) + Fees ($310) + Taxes in 2025 ($326)


    Taxes:$3,909

    Elementary School: Inwood Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Westwood Middle


  • 961 HAROLD PASS, WINTER HAVEN, FL 33884

    $249,99096 Days on yellowkey   MLS ID: O6397178

    REDUCED by $9,910 (3.8%) on 07/10/2026

    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: $1,944 (change assumption)
    Mortgage ($1,370) + Fees ($16) + Taxes in 2025 ($559)


    Taxes:$6,703

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 400 EL CAMINO DR #210, WINTER HAVEN, FL 33884

    $120,000168 Days on yellowkey   MLS ID: S5142500

    REDUCED by $10,000 (7.7%) on 07/10/2026

    SHORT SALE S5142500 - 400 EL CAMINO DR #210, WINTER HAVEN, FL 33884 33 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1666
       Built: 1974
    Monthly Fee: $448
       Tax: $1,368 (2025)
    Community: Orchid Spgs Vill 400 San Miguel
    Spa: No

    Condo


    Estimated Monthly Payment: $1,220 (change assumption)
    Mortgage ($658) + Fees ($448) + Taxes in 2025 ($114)


    Taxes:$1,368

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 404 COUNTRY LN NE #404, WINTER HAVEN, FL 33881

    $80,000102 Days on yellowkey   MLS ID: L4960788

    REDUCED by $25,000 (23.8%) on 07/10/2026

    SHORT SALE L4960788 - 404 COUNTRY LN NE #404, WINTER HAVEN, FL 33881 21 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1252
       Built: 1985
    Monthly Fee: $325
       Tax: $1,415 (2025)
    Community: Country Lake Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $881 (change assumption)
    Mortgage ($438) + Fees ($325) + Taxes in 2025 ($118)


    Taxes:$1,415

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 3865 OSPREY POINTE CIR, WINTER HAVEN, FL 33884

    $255,000189 Days on yellowkey   MLS ID: S5141071

    REDUCED by $10,000 (3.8%) on 04/29/2026

    For Sale S5141071 - 3865 OSPREY POINTE CIR, WINTER HAVEN, FL 33884 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1603
       Built: 2006
    Monthly Fee: $210
       Tax: $3,716 (2025)
    Community: Osprey Pointe
    Single Family


    Estimated Monthly Payment: $1,917 (change assumption)
    Mortgage ($1,397) + Fees ($210) + Taxes in 2025 ($310)


    Taxes:$3,716

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1034 SUMMER GLEN DR, WINTER HAVEN, FL 33880

    $267,00094 Days on yellowkey   MLS ID: O6398045

    2 Days Off yellowkey (back on 7/10/2026)

    REDUCED by $5,000 (1.8%) on 06/18/2026

    For Sale O6398045 - 1034 SUMMER GLEN DR, WINTER HAVEN, FL 33880 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1847
       Built: 2006
    Monthly Fee: $28
       Tax: $1,607 (2025)
    Community: Coventry Cove
    Single Family


    Estimated Monthly Payment: $1,625 (change assumption)
    Mortgage ($1,463) + Fees ($28) + Taxes in 2025 ($134)


    Taxes:$1,607

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 732 7TH ST NE, WINTER HAVEN, FL 33881

    $79,900155 Days on yellowkey   MLS ID: L4958841

    0 Days Off yellowkey (back on 2/12/2026)

    For Sale L4958841 - 732 7TH ST NE, WINTER HAVEN, FL 33881 18 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1528
       Built: 1925   Tax: $417 (2025)
    Community: Martha Heights
    Single Family


    Estimated Monthly Payment: $473 (change assumption)
    Mortgage ($438) + Taxes in 2025 ($35)


    Taxes:$417

    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.