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Winter Haven Homes For Sale & Real Estate - 1023 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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  • 1533 MAJESTIC LN, WINTER HAVEN, FL 33880

    $250,000103 Days on yellowkey   MLS ID: L4960031

    REDUCED by $15,000 (5.7%) on 06/05/2026

    For Sale L4960031 - 1533 MAJESTIC LN, WINTER HAVEN, FL 33880 32 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1957
       Built: 2023
    Monthly Fee: $38
       Tax: $4,059 (2025)
    Community: Eagle Lndg Ph Ii
    Single Family


    Estimated Monthly Payment: $1,746 (change assumption)
    Mortgage ($1,370) + Fees ($38) + Taxes in 2025 ($338)


    Taxes:$4,059

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 2500 21ST ST NW #47, WINTER HAVEN, FL 33881

    $177,0004 Days on yellowkey   MLS ID: L4962052

    For Sale L4962052 - 2500 21ST ST NW #47, WINTER HAVEN, FL 33881 41 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1229
       Built: 1975
    Monthly Fee: $412
       Tax: $2,939 (2025)
    Community: Casa Del Sol Condo Village Ph 01
    Condo


    Estimated Monthly Payment: $1,627 (change assumption)
    Mortgage ($970) + Fees ($412) + Taxes in 2025 ($245)


    Taxes:$2,939

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 144 BEVERLY DR, WINTER HAVEN, FL 33884

    $389,90068 Days on yellowkey   MLS ID: O6397768

    REDUCED by $9,600 (2.4%) on 06/03/2026

    For Sale O6397768 - 144 BEVERLY DR, WINTER HAVEN, FL 33884 20 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2492
       Built: 1963   Tax: $3,785 (2025)
    Community: Eloise Woods Lake Roy Unit
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,452 (change assumption)
    Mortgage ($2,136) + Taxes in 2025 ($315)


    Taxes:$3,785

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5872 ROYAL HILLS CIR, WINTER HAVEN, FL 33881

    $310,0008 Days on yellowkey   MLS ID: P4938974

    For Sale P4938974 - 5872 ROYAL HILLS CIR, WINTER HAVEN, FL 33881 24 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1730
       Built: 2006
    Monthly Fee: $25
       Tax: $3,749 (2025)
    Community: Royal Hills
    Single Family


    Estimated Monthly Payment: $2,036 (change assumption)
    Mortgage ($1,699) + Fees ($25) + Taxes in 2025 ($312)


    Taxes:$3,749

    Elementary School: Lake Alfred Elem

    High School: Haines City Senior High

    Tax Year: 2025

    Middle School: Daniel Jenkins Academy of Technology Middle


  • 265 LAKE THOMAS DR, WINTER HAVEN, FL 33880

    $319,950113 Days on yellowkey   MLS ID: L4959685

    REDUCED by $20,000 (5.9%) on 06/16/2026

    For Sale L4959685 - 265 LAKE THOMAS DR, WINTER HAVEN, FL 33880 45 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1517
       Built: 1985   Tax: $1,169 (2025)
    Community: Timber Wood
    Single Family


    Estimated Monthly Payment: $1,851 (change assumption)
    Mortgage ($1,753) + Taxes in 2025 ($97)


    Taxes:$1,169

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 704 EAGLE POND DR #704, WINTER HAVEN, FL 33884

    $179,90019 Days on yellowkey   MLS ID: P4938866

    For Sale P4938866 - 704 EAGLE POND DR #704, WINTER HAVEN, FL 33884 37 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1017
       Built: 2000
    Monthly Fee: $375
       Tax: $2,057 (2025)
    Community: Eagle Pond Condo
    Condo


    Estimated Monthly Payment: $1,532 (change assumption)
    Mortgage ($986) + Fees ($375) + Taxes in 2025 ($171)


    Taxes:$2,057

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 3027 RICHMOND DR, WINTER HAVEN, FL 33884

    $289,00054 Days on yellowkey   MLS ID: L4961338

    REDUCED by $6,000 (2.0%) on 06/16/2026

    For Sale L4961338 - 3027 RICHMOND DR, WINTER HAVEN, FL 33884 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1994
       Built: 2006
    Monthly Fee: $236
       Tax: $3,832 (2025)
    Community: Richmond Square Ph 02
    Single Family


    Estimated Monthly Payment: $2,139 (change assumption)
    Mortgage ($1,584) + Fees ($236) + Taxes in 2025 ($319)


    Taxes:$3,832

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 241 GREENFIELD RD, WINTER HAVEN, FL 33884

    $349,950119 Days on yellowkey   MLS ID: L4959462

    REDUCED by $10,000 (2.8%) on 06/16/2026

    For Sale L4959462 - 241 GREENFIELD RD, WINTER HAVEN, FL 33884 43 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2523
       Built: 1976
    Monthly Fee: $152
       Tax: $4,915 (2025)
    Community: Cypresswood
    Single Family


    Estimated Monthly Payment: $2,479 (change assumption)
    Mortgage ($1,917) + Fees ($152) + Taxes in 2025 ($410)


    Taxes:$4,915

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 276 TERRANOVA BLVD, WINTER HAVEN, FL 33884

    $379,9991 Day on yellowkey   MLS ID: TB8519660

    For Sale TB8519660 - 276 TERRANOVA BLVD, WINTER HAVEN, FL 33884 37 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2262
       Built: 2005
    Monthly Fee: $55
       Tax: $2,996 (2025)
    Community: Terranova Ph 04
    Single Family


    Estimated Monthly Payment: $2,387 (change assumption)
    Mortgage ($2,082) + Fees ($55) + Taxes in 2025 ($250)


    Taxes:$2,996

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 852 CINNAMON DR, WINTER HAVEN, FL 33880

    $235,0001 Day on yellowkey   MLS ID: O6416669

    For Sale O6416669 - 852 CINNAMON DR, WINTER HAVEN, FL 33880 41 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1072
       Built: 1981   Tax: $1,109 (2025)
    Community: Cinnamon Ridge Ph 02
    Single Family


    Estimated Monthly Payment: $1,380 (change assumption)
    Mortgage ($1,288) + Taxes in 2025 ($92)


    Taxes:$1,109

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 321 ORANGE BLOSSOM DR, WINTER HAVEN, FL 33880

    $205,00079 Days on yellowkey   MLS ID: S5146754

    REDUCED by $10,500 (4.9%) on 06/02/2026

    For Sale S5146754 - 321 ORANGE BLOSSOM DR, WINTER HAVEN, FL 33880 31 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1407
       Built: 2001
    Monthly Fee: $408
       Tax: $2,757 (2025)
    Community: Waters Edge Unit 01 A Rep
    Spa: No

    Townhouse


    Estimated Monthly Payment: $1,761 (change assumption)
    Mortgage ($1,123) + Fees ($408) + Taxes in 2025 ($230)


    Taxes:$2,757

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3905 WARBLER DR, WINTER HAVEN, FL 33880

    $282,90025 Days on yellowkey   MLS ID: G5112816

    4 Days Off yellowkey (back on 6/16/2026)

    INCREASED by $3,000 (1.1%) on 06/16/2026

    For Sale G5112816 - 3905 WARBLER DR, WINTER HAVEN, FL 33880 21 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2101
       Built: 2004
    Monthly Fee: $12
       Tax: $3,712 (2025)
    Community: Queens Cove Ph 04
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,871 (change assumption)
    Mortgage ($1,550) + Fees ($12) + Taxes in 2025 ($309)


    Taxes:$3,712

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 316 LAKE SMART CIR, WINTER HAVEN, FL 33881

    $274,90049 Days on yellowkey   MLS ID: L4961472

    REDUCED by $15,000 (5.2%) on 06/16/2026

    FORECLOSURE L4961472 - 316 LAKE SMART CIR, WINTER HAVEN, FL 33881 23 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1500
       Built: 2022
    Monthly Fee: $50
       Tax: $4,224 (2025)
    Community: Lake Smart Pointe
    Single Family


    Estimated Monthly Payment: $1,908 (change assumption)
    Mortgage ($1,506) + Fees ($50) + Taxes in 2025 ($352)


    Taxes:$4,224

    Elementary School: Lake Alfred Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 5429 SAN PIETRO DR, WINTER HAVEN, FL 33884

    $374,999198 Days on yellowkey   MLS ID: TB8452537

    0 Days Off yellowkey (back on 6/16/2026)

    REDUCED by $5,000 (1.3%) on 06/09/2026

    For Sale TB8452537 - 5429 SAN PIETRO DR, WINTER HAVEN, FL 33884 20 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2892
       Built: 2025
    Monthly Fee: $53
       Tax: $2,688 (2025)
    Community: Villa Mar
    Single Family


    Estimated Monthly Payment: $2,332 (change assumption)
    Mortgage ($2,055) + Fees ($53) + Taxes in 2025 ($224)


    Taxes:$2,688

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 1568 S LAKE SHIPP DR, WINTER HAVEN, FL 33880

    $259,900121 Days on yellowkey   MLS ID: P4937858

    REDUCED by $5,000 (1.9%) on 06/16/2026

    For Sale P4937858 - 1568 S LAKE SHIPP DR, WINTER HAVEN, FL 33880 35 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1032
       Built: 1955   Tax: $3,517 (2025)
    Community: Lake Shipp Heights
    Single Family


    Estimated Monthly Payment: $1,717 (change assumption)
    Mortgage ($1,424) + Taxes in 2025 ($293)


    Taxes:$3,517

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1864 EMILY DR, WINTER HAVEN, FL 33884

    $291,900217 Days on yellowkey   MLS ID: TB8447490

    REDUCED by $1,000 (0.3%) on 06/12/2026

    For Sale TB8447490 - 1864 EMILY DR, WINTER HAVEN, FL 33884 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1836
       Built: 2005
    Monthly Fee: $25
       Tax: $3,788 (2024)
    Community: Emily Estates
    Single Family


    Estimated Monthly Payment: $1,940 (change assumption)
    Mortgage ($1,599) + Fees ($25) + Taxes in 2024 ($316)


    Taxes:$3,788

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6518 RAINTREE LN NE, WINTER HAVEN, FL 33881

    $165,000242 Days on yellowkey   MLS ID: S5136893

    REDUCED by $5,000 (2.9%) on 04/08/2026

    For Sale S5136893 - 6518 RAINTREE LN NE, WINTER HAVEN, FL 33881 42 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1525
       Built: 1989
    Monthly Fee: $34
       Tax: $1,157 (2025)
    Community: Brookhaven Village First Add
    Manufactured Home


    Estimated Monthly Payment: $1,035 (change assumption)
    Mortgage ($904) + Fees ($34) + Taxes in 2025 ($96)


    Taxes:$1,157

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1985 SARAH ST, WINTER HAVEN, FL 33884

    $298,00049 Days on yellowkey   MLS ID: P4938491

    0 Days Off yellowkey (back on 6/16/2026)

    REDUCED by $8,000 (2.6%) on 06/11/2026

    For Sale P4938491 - 1985 SARAH ST, WINTER HAVEN, FL 33884 40 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1874
       Built: 2025
    Monthly Fee: $14
       Tax: $3,519 (2025)
    Community: Peace Creek Reserve
    Single Family


    Estimated Monthly Payment: $1,940 (change assumption)
    Mortgage ($1,633) + Fees ($14) + Taxes in 2025 ($293)


    Taxes:$3,519

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1328 DAISY FIELD DR, WINTER HAVEN, FL 33884

    $380,00068 Days on yellowkey   MLS ID: L4960820

    REDUCED by $10,000 (2.6%) on 05/19/2026

    For Sale L4960820 - 1328 DAISY FIELD DR, WINTER HAVEN, FL 33884 33 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2696
       Built: 2024
    Monthly Fee: $30
       Tax: $7,633 (2025)
    Community: Harmony/Lk Eloise Ph 1
    Single Family


    Estimated Monthly Payment: $2,748 (change assumption)
    Mortgage ($2,082) + Fees ($30) + Taxes in 2025 ($636)


    Taxes:$7,633

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 248 MEREDITH BLVD, WINTER HAVEN, FL 33881

    $259,99053 Days on yellowkey   MLS ID: G5111557

    0 Days Off yellowkey (back on 6/14/2026)

    REDUCED by $25,000 (8.8%) on 06/04/2026

    For Sale G5111557 - 248 MEREDITH BLVD, WINTER HAVEN, FL 33881 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1598
       Built: 2026
    Monthly Fee: $6
       Tax: $500 (2025)
    Community: Willowbrook North
    Single Family


    Estimated Monthly Payment: $1,472 (change assumption)
    Mortgage ($1,425) + Fees ($6) + Taxes in 2025 ($42)


    Taxes:$500

    Elementary School: Lake Alfred Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle




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.