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Winter Haven Homes For Sale & Real Estate - 805 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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  • 306 NE X AVE, WINTER HAVEN, FL 33881

    $255,0007 Days on yellowkey   MLS ID: TB8494382

    0 Days Off yellowkey (back on 4/7/2026)

    For Sale TB8494382 - 306 NE X AVE, WINTER HAVEN, FL 33881 19 photos

    Bed: 0   Bath: 0.0
    Liv Area Sq Ft: 1275
       Built: 1962   Tax: $4,265 (2025)
    Community: Booker Sub-Division
    Apartment


    Estimated Monthly Payment: $1,753 (change assumption)
    Mortgage ($1,397) + Taxes in 2025 ($355)


    Taxes:$4,265

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3863 BEDFORD AVE, WINTER HAVEN, FL 33884

    $355,0007 Days on yellowkey   MLS ID: O6396509

    For Sale O6396509 - 3863 BEDFORD AVE, WINTER HAVEN, FL 33884 33 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1797
       Built: 2017
    Monthly Fee: $485
       Tax: $4,293 (2025)
    Community: Traditions Ph 02
    Single Family


    Estimated Monthly Payment: $2,788 (change assumption)
    Mortgage ($1,945) + Fees ($485) + Taxes in 2025 ($358)


    Taxes:$4,293

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 220 RUBY LAKE LN, WINTER HAVEN, FL 33884

    $799,9007 Days on yellowkey   MLS ID: P4938358

    For Sale P4938358 - 220 RUBY LAKE LN, WINTER HAVEN, FL 33884 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2705
       Built: 2001
    Monthly Fee: $71
       Tax: $7,665 (2025)
    Community: Ruby Lake Ph 04
    Single Family


    Estimated Monthly Payment: $5,093 (change assumption)
    Mortgage ($4,383) + Fees ($71) + Taxes in 2025 ($639)


    Taxes:$7,665

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4 CASARENA CT, WINTER HAVEN, FL 33881

    $529,0007 Days on yellowkey   MLS ID: P4938356

    For Sale P4938356 - 4 CASARENA CT, WINTER HAVEN, FL 33881 51 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3911
       Built: 1984
    Monthly Fee: $320
       Tax: $4,267 (2025)
    Community: Casarena On The Lakes
    Single Family


    Estimated Monthly Payment: $3,574 (change assumption)
    Mortgage ($2,899) + Fees ($320) + Taxes in 2025 ($356)


    Taxes:$4,267

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5457 HOGAN LN, WINTER HAVEN, FL 33884

    $589,0007 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


  • 1607 2ND STREET SE, WINTER HAVEN, FL 33880

    $185,000124 Days on yellowkey   MLS ID: P4937275

    0 Days Off yellowkey (back on 4/8/2026)

    For Sale P4937275 - 1607 2ND STREET SE, WINTER HAVEN, FL 33880 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 576
       Built: 1930   Tax: $1,198 (2024)
    Community: Bryson R H Subdivision
    Single Family


    Estimated Monthly Payment: $1,113 (change assumption)
    Mortgage ($1,014) + Taxes in 2024 ($100)


    Taxes:$1,198

    Elementary School: Frank E. Brigham Academy

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Denison Middle


  • 1109 BRIMSTONE CIR, WINTER HAVEN, FL 33884

    $330,000120 Days on yellowkey   MLS ID: L4957925

    For Sale L4957925 - 1109 BRIMSTONE CIR, WINTER HAVEN, FL 33884 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1697
       Built: 2023
    Monthly Fee: $30
       Tax: $3,769 (2025)
    Community: Harmony/Lk Eloise Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,152 (change assumption)
    Mortgage ($1,808) + Fees ($30) + Taxes in 2025 ($314)


    Taxes:$3,769

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1059 MICHELANGELO LN, WINTER HAVEN, FL 33884

    $369,00076 Days on yellowkey   MLS ID: S5142551

    For Sale S5142551 - 1059 MICHELANGELO LN, WINTER HAVEN, FL 33884 21 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1844
       Built: 2024
    Monthly Fee: $55
       Tax: $3,878 (2025)
    Community: Estates/Lk Florence
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,400 (change assumption)
    Mortgage ($2,022) + Fees ($55) + Taxes in 2025 ($323)


    Taxes:$3,878

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 2500 21ST ST NW #15, WINTER HAVEN, FL 33881

    $194,00011 Days on yellowkey   MLS ID: S5147117

    REDUCED by $4,000 (2.0%) on 04/07/2026

    For Sale S5147117 - 2500 21ST ST NW #15, WINTER HAVEN, FL 33881 21 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1184
       Built: 1976   Tax: $2,616 (2025)
    Community: Casa Del Sol Condo Village Ph 02
    Condo


    Estimated Monthly Payment: $1,281 (change assumption)
    Mortgage ($1,063) + Taxes in 2025 ($218)


    Taxes:$2,616

    Elementary School: Fred G. Garnier Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Westwood Middle


  • 3306 OAK HILL PL, WINTER HAVEN, FL 33884

    $297,50060 Days on yellowkey   MLS ID: L4959302

    0 Days Off yellowkey (back on 3/12/2026)

    For Sale L4959302 - 3306 OAK HILL PL, WINTER HAVEN, FL 33884 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1722
       Built: 2004
    Monthly Fee: $148
       Tax: $4,783 (2025)
    Community: Oakgrove Sub
    Single Family


    Estimated Monthly Payment: $2,177 (change assumption)
    Mortgage ($1,630) + Fees ($148) + Taxes in 2025 ($399)


    Taxes:$4,783

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1799 CARNOSTIE RD, WINTER HAVEN, FL 33884

    $309,00036 Days on yellowkey   MLS ID: P4938087

    For Sale P4938087 - 1799 CARNOSTIE RD, WINTER HAVEN, FL 33884 39 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1680
       Built: 2022
    Monthly Fee: $18
       Tax: $5,703 (2025)
    Community: Villamar Ph 3
    Single Family


    Estimated Monthly Payment: $2,186 (change assumption)
    Mortgage ($1,693) + Fees ($18) + Taxes in 2025 ($475)


    Taxes:$5,703

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Mclaughlin Middle


  • 1051 LENA RUN CT, WINTER HAVEN, FL 33880

    $477,55562 Days on yellowkey   MLS ID: L4959294

    For Sale L4959294 - 1051 LENA RUN CT, WINTER HAVEN, FL 33880 43 photos

    Bed: 4   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2428
       Built: 2016
    Monthly Fee: $123
       Tax: $3,613 (2025)
    Community: Hidden Creek
    Single Family


    Estimated Monthly Payment: $3,041 (change assumption)
    Mortgage ($2,617) + Fees ($123) + Taxes in 2025 ($301)


    Taxes:$3,613

    Elementary School: Eagle Lake Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 112 PAINE DR, WINTER HAVEN, FL 33884

    $350,000128 Days on yellowkey   MLS ID: L4957763

    For Sale L4957763 - 112 PAINE DR, WINTER HAVEN, FL 33884 36 photos

    Bed: 5   Bath: 2.0
    Liv Area Sq Ft: 2078
       Built: 1965   Tax: $3,343 (2024)
    Community: Fla Highlands Co Sub
    Single Family


    Estimated Monthly Payment: $2,196 (change assumption)
    Mortgage ($1,918) + Taxes in 2024 ($279)


    Taxes:$3,343

    Elementary School: Garden Grove Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Denison Middle


  • 906 LAKE JESSIE DR, WINTER HAVEN, FL 33881

    $880,000129 Days on yellowkey   MLS ID: L4957757

    For Sale L4957757 - 906 LAKE JESSIE DR, WINTER HAVEN, FL 33881 46 photos

    Bed: 9   Bath: 6.5   Gar: 2
    Liv Area Sq Ft: 5700
       Built: 1954   Tax: $5,237 (2024)
    Community: East View Pkwy
    Single Family


    Estimated Monthly Payment: $5,258 (change assumption)
    Mortgage ($4,822) + Taxes in 2024 ($436)


    Taxes:$5,237

    Elementary School: Auburndale Central Elem

    High School: Auburndale High School

    Tax Year: 2024

    Middle School: Westwood Middle


  • 2274 FIRESTONE PL, WINTER HAVEN, FL 33884

    $182,500100 Days on yellowkey   MLS ID: L4957980

    0 Days Off yellowkey (back on 4/7/2026)

    For Sale L4957980 - 2274 FIRESTONE PL, WINTER HAVEN, FL 33884 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1410
       Built: 1984
    Monthly Fee: $285
       Tax: $2,566 (2024)
    Community: Cypresswood Golf Villas Bldg G
    Villa


    Estimated Monthly Payment: $1,499 (change assumption)
    Mortgage ($1,000) + Fees ($285) + Taxes in 2024 ($214)


    Taxes:$2,566

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 634 WEXFORD CT, WINTER HAVEN, FL 33884

    $244,90081 Days on yellowkey   MLS ID: L4958804

    For Sale L4958804 - 634 WEXFORD CT, WINTER HAVEN, FL 33884 30 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1328
       Built: 1980
    Monthly Fee: $130
       Tax: $1,723 (2025)
    Community: Cypresswood Patio Homes
    Single Family


    Estimated Monthly Payment: $1,615 (change assumption)
    Mortgage ($1,342) + Fees ($130) + Taxes in 2025 ($144)


    Taxes:$1,723

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 20 LAKE IDYLWILD DR N, WINTER HAVEN, FL 33881

    $739,00091 Days on yellowkey   MLS ID: L4958394

    1 Days Off yellowkey (back on 2/18/2026)

    For Sale L4958394 - 20 LAKE IDYLWILD DR N, WINTER HAVEN, FL 33881 74 photos

    Bed: 6   Bath: 4.0
    Liv Area Sq Ft: 3911
       Built: 1961   Tax: $8,364 (2025)
    Community: Not In Subdivision
    Single Family


    Estimated Monthly Payment: $4,746 (change assumption)
    Mortgage ($4,049) + Taxes in 2025 ($697)


    Taxes:$8,364

    Elementary School: Frank E. Brigham Academy

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Westwood Middle


  • 3396 AVENUE U NW, WINTER HAVEN, FL 33881

    $289,9908 Days on yellowkey   MLS ID: L4960885

    For Sale L4960885 - 3396 AVENUE U NW, WINTER HAVEN, FL 33881 30 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1592
       Built: 1961   Tax: $2,872 (2025)
    Community: Inwood No 4 Pb 9 Pgs 35A & 35B
    Single Family


    Estimated Monthly Payment: $1,828 (change assumption)
    Mortgage ($1,589) + Taxes in 2025 ($239)


    Taxes:$2,872

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 329 MEREDITH BLVD, WINTER HAVEN, FL 33881

    $299,990210 Days on yellowkey   MLS ID: O6342366

    REDUCED by $20,000 (6.3%) on 04/07/2026

    For Sale O6342366 - 329 MEREDITH BLVD, WINTER HAVEN, FL 33881 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1624
       Built: 2025
    Monthly Fee: $6

    Community: Willowbrook North
    Single Family


    Estimated Monthly Payment: $1,650 (change assumption)
    Mortgage ($1,644) + Fees ($6) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Lake Alfred Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Denison Middle


  • 337 MEREDITH BLVD, WINTER HAVEN, FL 33881

    $294,99067 Days on yellowkey   MLS ID: O6379298

    For Sale O6379298 - 337 MEREDITH BLVD, WINTER HAVEN, FL 33881 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1480
       Built: 2026
    Monthly Fee: $6
       Tax: $2,808 (2025)
    Community: Willowbrook North
    Single Family


    Estimated Monthly Payment: $1,856 (change assumption)
    Mortgage ($1,616) + Fees ($6) + Taxes in 2025 ($234)


    Taxes:$2,808

    Elementary School: Lake Alfred Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle




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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.