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Winter Haven Single Family Homes For Sale - 706 homes

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

Location: Winter Haven

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  • 2362 BRASSIE CT, WINTER HAVEN, FL 33884

    $274,90068 Days on yellowkey   MLS ID: O6384404

    For Sale O6384404 - 2362 BRASSIE CT, WINTER HAVEN, FL 33884 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1260
       Built: 2022
    Monthly Fee: $18
       Tax: $5,003 (2025)
    Community: Villmar
    Single Family


    Estimated Monthly Payment: $1,941 (change assumption)
    Mortgage ($1,506) + Fees ($18) + Taxes in 2025 ($417)


    Taxes:$5,003

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 1454 GRAND CAYMAN CIR, WINTER HAVEN, FL 33884

    $272,00024 Days on yellowkey   MLS ID: O6396319

    For Sale O6396319 - 1454 GRAND CAYMAN CIR, WINTER HAVEN, FL 33884 50 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1366
       Built: 1987
    Monthly Fee: $45
       Tax: $2,901 (2025)
    Community: Lake Dexter Moorings
    Single Family


    Estimated Monthly Payment: $1,777 (change assumption)
    Mortgage ($1,490) + Fees ($45) + Taxes in 2025 ($242)


    Taxes:$2,901

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2438 4TH ST NE, WINTER HAVEN, FL 33881

    $239,90050 Days on yellowkey   MLS ID: L4960053

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

    For Sale L4960053 - 2438 4TH ST NE, WINTER HAVEN, FL 33881 26 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1135
       Built: 2026   Tax: $223 (2025)
    Community: Lincoln Sub
    Single Family


    Estimated Monthly Payment: $1,333 (change assumption)
    Mortgage ($1,314) + Taxes in 2025 ($19)


    Taxes:$223

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1280 DENALI DR, WINTER HAVEN, FL 33881

    $409,00090 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 33 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


  • 1148 TYLER LOOP, WINTER HAVEN, FL 33884

    $265,00041 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

    $305,00069 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

    $525,00066 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


  • 228 SPIRIT LANDINGS CIR, WINTER HAVEN, FL 33880

    $330,00027 Days on yellowkey   MLS ID: O6395083

    For Sale O6395083 - 228 SPIRIT LANDINGS CIR, WINTER HAVEN, FL 33880 28 photos

    Bed: 3   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 1941
       Built: 2023
    Monthly Fee: $93
       Tax: $4,592 (2025)
    Community: Spirit Lndgs
    Single Family


    Estimated Monthly Payment: $2,284 (change assumption)
    Mortgage ($1,808) + Fees ($93) + Taxes in 2025 ($383)


    Taxes:$4,592

    Elementary School: Eagle Lake Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 4270 ROBERTA DR, WINTER HAVEN, FL 33881

    $315,00077 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

    $215,00087 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


  • 1640 NW PEARCE RD, WINTER HAVEN, FL 33881

    $345,000273 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


  • 4576 BACK NINE DR, WINTER HAVEN, FL 33884

    $344,500118 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


  • 6625 THORNHILL RD, WINTER HAVEN, FL 33880

    $299,900390 Days on yellowkey   MLS ID: L4951980

    For Sale L4951980 - 6625 THORNHILL RD, WINTER HAVEN, FL 33880 35 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1221
       Built: 2024   Tax: $569 (2024)
    Community: Thornhill Oaks
    Single Family


    Estimated Monthly Payment: $1,691 (change assumption)
    Mortgage ($1,643) + Taxes in 2024 ($47)


    Taxes:$569

    Elementary School: Eagle Lake Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Westwood Middle


  • 5132 SYLAS JAX AVE, WINTER HAVEN, FL 33884

    $370,09026 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

    $315,00026 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


  • 104 11TH ST SE, WINTER HAVEN, FL 33880

    $295,90026 Days on yellowkey   MLS ID: P4938332

    For Sale P4938332 - 104 11TH ST SE, WINTER HAVEN, FL 33880 42 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 1792
       Built: 1953   Tax: $3,956 (2025)
    Community: East El Otis Park Rep
    Single Family


    Estimated Monthly Payment: $1,951 (change assumption)
    Mortgage ($1,621) + Taxes in 2025 ($330)


    Taxes:$3,956

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 1382 SALISBURY DR, WINTER HAVEN, FL 33881

    $329,90026 Days on yellowkey   MLS ID: P4938331

    For Sale P4938331 - 1382 SALISBURY DR, WINTER HAVEN, FL 33881 23 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1764
       Built: 2014
    Monthly Fee: $38
       Tax: $2,866 (2025)
    Community: Dundee Station
    Single Family


    Estimated Monthly Payment: $2,084 (change assumption)
    Mortgage ($1,808) + Fees ($38) + Taxes in 2025 ($239)


    Taxes:$2,866

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 411 AVENUE A SE, WINTER HAVEN, FL 33880

    $215,000274 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

    $1,779,90088 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

    $393,00078 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




Why Bother Searching Elsewhere for Winter Haven Single Family Homes for Sale?

Winter Haven home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Haven . You can use our website to view Multiple Listing Service (MLS) data on Winter Haven single family homes. 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 single family home 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.