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Winter Haven Homes For Sale & Real Estate - 929 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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  • 1148 TYLER LOOP, WINTER HAVEN, FL 33884

    $265,00044 Days on yellowkey   MLS ID: L4960292

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

    SHORT SALE L4960292 - 1148 TYLER LOOP, WINTER HAVEN, FL 33884 13 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2093
       Built: 2024
    Monthly Fee: $16
       Tax: $7,039 (2025)
    Community: Peace River Reserve
    Single Family


    Estimated Monthly Payment: $2,055 (change assumption)
    Mortgage ($1,452) + Fees ($16) + Taxes in 2025 ($587)


    Taxes:$7,039

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3927 PALAZZO PL, WINTER HAVEN, FL 33884

    $305,00072 Days on yellowkey   MLS ID: O6383833

    For Sale O6383833 - 3927 PALAZZO PL, WINTER HAVEN, FL 33884 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1597
       Built: 2023
    Monthly Fee: $40
       Tax: $4,716 (2025)
    Community: Villamar Ph 4
    Single Family


    Estimated Monthly Payment: $2,104 (change assumption)
    Mortgage ($1,671) + Fees ($40) + Taxes in 2025 ($393)


    Taxes:$4,716

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2664 COUNTRY CLUB RD N, WINTER HAVEN, FL 33881

    $525,00069 Days on yellowkey   MLS ID: L4959468

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

    For Sale L4959468 - 2664 COUNTRY CLUB RD N, WINTER HAVEN, FL 33881 61 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2696
       Built: 2001   Tax: $6,393 (2025)
    Community: Poinsettia Park
    Single Family


    Estimated Monthly Payment: $3,409 (change assumption)
    Mortgage ($2,877) + Taxes in 2025 ($533)


    Taxes:$6,393

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6309 GROVE POINTE DR SE, WINTER HAVEN, FL 33884

    $159,75028 Days on yellowkey   MLS ID: P4938313

    For Sale P4938313 - 6309 GROVE POINTE DR SE, WINTER HAVEN, FL 33884 53 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1248
       Built: 1986
    Monthly Fee: $65
       Tax: $2,108 (2025)
    Community: Garden Grove Oaks
    Manufactured Home


    Estimated Monthly Payment: $1,116 (change assumption)
    Mortgage ($875) + Fees ($65) + Taxes in 2025 ($176)


    Taxes:$2,108

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4270 ROBERTA DR, WINTER HAVEN, FL 33881

    $315,00080 Days on yellowkey   MLS ID: O6381790

    For Sale O6381790 - 4270 ROBERTA DR, WINTER HAVEN, FL 33881 19 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1851
       Built: 2019
    Monthly Fee: $25
       Tax: $2,961 (2025)
    Community: Buckeye Ridge
    Single Family


    Estimated Monthly Payment: $1,998 (change assumption)
    Mortgage ($1,726) + Fees ($25) + Taxes in 2025 ($247)


    Taxes:$2,961

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2208 LAKE BLVD, WINTER HAVEN, FL 33881

    $215,00090 Days on yellowkey   MLS ID: L4959022

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

    For Sale L4959022 - 2208 LAKE BLVD, WINTER HAVEN, FL 33881 42 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 1044
       Built: 1954   Tax: $2,551 (2025)
    Community: Inwood
    Single Family


    Estimated Monthly Payment: $1,391 (change assumption)
    Mortgage ($1,178) + Taxes in 2025 ($213)


    Taxes:$2,551

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1511 GAINES RD, WINTER HAVEN, FL 33880

    $155,00028 Days on yellowkey   MLS ID: TB8493080

    For Sale TB8493080 - 1511 GAINES RD, WINTER HAVEN, FL 33880 20 photos

    Bed: 3   Bath: 1.5   Gar: 1
    Liv Area Sq Ft: 860
       Built: 1974   Tax: $2,075 (2025)
    Community: Acreage & Unrec
    Mobile Home


    Estimated Monthly Payment: $1,022 (change assumption)
    Mortgage ($849) + Taxes in 2025 ($173)


    Taxes:$2,075

    Elementary School: Eagle Lake Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 1640 NW PEARCE RD, WINTER HAVEN, FL 33881

    $345,000276 Days on yellowkey   MLS ID: L4954651

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

    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: $1,890 (change assumption)
    Mortgage ($1,890) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 953 6TH ST SE, WINTER HAVEN, FL 33880

    $925,00042 Days on yellowkey   MLS ID: L4960452

    For Sale L4960452 - 953 6TH ST SE, WINTER HAVEN, FL 33880 12 photos

    Bed: 10   Bath: 0.0
    Liv Area Sq Ft: 4440
       Built: 1955   Tax: $10,338 (2025)
    Community: Hackles Add
    Apartment


    Estimated Monthly Payment: $5,930 (change assumption)
    Mortgage ($5,068) + Taxes in 2025 ($862)


    Taxes:$10,338

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4576 BACK NINE DR, WINTER HAVEN, FL 33884

    $344,500121 Days on yellowkey   MLS ID: P4937279

    For Sale P4937279 - 4576 BACK NINE DR, WINTER HAVEN, FL 33884 90 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1514
       Built: 2019
    Monthly Fee: $5
       Tax: $1,937 (2025)
    Community: Lake Ashton West Ph 01
    Single Family


    Estimated Monthly Payment: $2,054 (change assumption)
    Mortgage ($1,888) + Fees ($5) + Taxes in 2025 ($161)


    Taxes:$1,937

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2805 WINGFOOT CT, WINTER HAVEN, FL 33884

    $245,50061 Days on yellowkey   MLS ID: B4902197

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

    For Sale B4902197 - 2805 WINGFOOT CT, WINTER HAVEN, FL 33884 47 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1602
       Built: 1987
    Monthly Fee: $295
       Tax: $1,543 (2025)
    Community: Cypress Wood
    Villa


    Estimated Monthly Payment: $1,769 (change assumption)
    Mortgage ($1,345) + Fees ($295) + Taxes in 2025 ($129)


    Taxes:$1,543

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1700 6TH ST NW #A38, WINTER HAVEN, FL 33881

    $82,500298 Days on yellowkey   MLS ID: P4935379

    REDUCED by $2,000 (2.4%) on 04/04/2026

    For Sale P4935379 - 1700 6TH ST NW #A38, WINTER HAVEN, FL 33881 21 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 840
       Built: 1964
    Monthly Fee: $350
       Tax: $594 (2024)
    Community: Winter Haven Harbour Apts Condo
    Condo


    Estimated Monthly Payment: $852 (change assumption)
    Mortgage ($452) + Fees ($350) + Taxes in 2024 ($50)


    Taxes:$594

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5132 SYLAS JAX AVE, WINTER HAVEN, FL 33884

    $370,09029 Days on yellowkey   MLS ID: L4960822

    0 Days Off yellowkey (back on 4/3/2026)

    For Sale L4960822 - 5132 SYLAS JAX AVE, WINTER HAVEN, FL 33884 5 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2587
       Built: 2026
    Monthly Fee: $17

    Community: Villamar
    Single Family


    Estimated Monthly Payment: $2,045 (change assumption)
    Mortgage ($2,028) + Fees ($17) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 287 INMAN BLVD, WINTER HAVEN, FL 33881

    $315,00029 Days on yellowkey   MLS ID: S5147134

    For Sale S5147134 - 287 INMAN BLVD, WINTER HAVEN, FL 33881 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1560
       Built: 2023
    Monthly Fee: $49
       Tax: $3,542 (2025)
    Community: Inman Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $2,070 (change assumption)
    Mortgage ($1,726) + Fees ($49) + Taxes in 2025 ($295)


    Taxes:$3,542

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 411 AVENUE A SE, WINTER HAVEN, FL 33880

    $215,000277 Days on yellowkey   MLS ID: L4954810

    0 Days Off yellowkey (back on 4/3/2026)

    For Sale L4954810 - 411 AVENUE A SE, WINTER HAVEN, FL 33880 25 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 1240
       Built: 1958   Tax: $1,474 (2024)
    Community: Denison Heights Estates Rep Pt
    Single Family


    Estimated Monthly Payment: $1,301 (change assumption)
    Mortgage ($1,178) + Taxes in 2024 ($123)


    Taxes:$1,474

    Elementary School: John Snively Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Denison Middle


  • 3826 GAINES CT, WINTER HAVEN, FL 33884

    $1,779,90091 Days on yellowkey   MLS ID: P4937567

    0 Days Off yellowkey (back on 4/3/2026)

    For Sale P4937567 - 3826 GAINES CT, WINTER HAVEN, FL 33884 89 photos

    Bed: 6   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 5400
       Built: 1989
    Monthly Fee: $44
       Tax: $14,471 (2025)
    Community: Gaines Cove
    Single Family


    Estimated Monthly Payment: $11,003 (change assumption)
    Mortgage ($9,753) + Fees ($44) + Taxes in 2025 ($1,206)


    Taxes:$14,471

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 260 GREENFIELD RD, WINTER HAVEN, FL 33884

    $393,00081 Days on yellowkey   MLS ID: P4937787

    For Sale P4937787 - 260 GREENFIELD RD, WINTER HAVEN, FL 33884 52 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1947
       Built: 1978
    Monthly Fee: $152
       Tax: $5,885 (2025)
    Community: Cypresswood Greenfield Village
    Single Family


    Estimated Monthly Payment: $2,796 (change assumption)
    Mortgage ($2,153) + Fees ($152) + Taxes in 2025 ($490)


    Taxes:$5,885

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 688 AUGUSTA RD, WINTER HAVEN, FL 33884

    $337,00066 Days on yellowkey   MLS ID: P4937966

    For Sale P4937966 - 688 AUGUSTA RD, WINTER HAVEN, FL 33884 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1586
       Built: 1980
    Monthly Fee: $137
       Tax: $3,636 (2025)
    Community: Cypresswood Fairway Patio Homes
    Single Family


    Estimated Monthly Payment: $2,287 (change assumption)
    Mortgage ($1,847) + Fees ($137) + Taxes in 2025 ($303)


    Taxes:$3,636

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 2336 W CANNON TER NW, WINTER HAVEN, FL 33881

    $729,000109 Days on yellowkey   MLS ID: L4958323

    For Sale L4958323 - 2336 W CANNON TER NW, WINTER HAVEN, FL 33881 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1856
       Built: 1995   Tax: $6,634 (2025)
    Community: West Cannon Terrace
    Single Family


    Estimated Monthly Payment: $4,547 (change assumption)
    Mortgage ($3,994) + Taxes in 2025 ($553)


    Taxes:$6,634

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 333 LAKE HOWARD DR NW #113D, WINTER HAVEN, FL 33880

    $112,00035 Days on yellowkey   MLS ID: P4938082

    For Sale P4938082 - 333 LAKE HOWARD DR NW #113D, WINTER HAVEN, FL 33880 60 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1030
       Built: 1974   Tax: $1,073 (2025)
    Community: Imperial Harboursphases 01 & 02
    Condo


    Estimated Monthly Payment: $703 (change assumption)
    Mortgage ($614) + Taxes in 2025 ($89)


    Taxes:$1,073

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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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.