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Winter Haven Homes For Sale & Real Estate - 971 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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  • 3831 GAINES DR, WINTER HAVEN, FL 33884

    $775,000Listed 06/01/2026 3:40PM   MLS ID: L4962328

    For Sale L4962328 - 3831 GAINES DR, WINTER HAVEN, FL 33884 59 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2678
       Built: 2005
    Monthly Fee: $27
       Tax: $3,522 (2025)
    Community: Gaines Cove
    Single Family


    Estimated Monthly Payment: $4,567 (change assumption)
    Mortgage ($4,246) + Fees ($27) + Taxes in 2025 ($294)


    Taxes:$3,522

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4 CASARENA CT, WINTER HAVEN, FL 33881

    $524,00056 Days on yellowkey   MLS ID: P4938356

    REDUCED by $5,000 (0.9%) on 05/29/2026

    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: $3,547 (change assumption)
    Mortgage ($2,871) + Fees ($320) + Taxes in 2025 ($356)


    Taxes:$4,267

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 725 HERITAGE DR NE, WINTER HAVEN, FL 33881

    $559,00026 Days on yellowkey   MLS ID: L4961718

    For Sale L4961718 - 725 HERITAGE DR NE, WINTER HAVEN, FL 33881 61 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3114
       Built: 1992
    Monthly Fee: $27
       Tax: $7,254 (2025)
    Community: Hamilton Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,694 (change assumption)
    Mortgage ($3,063) + Fees ($27) + Taxes in 2025 ($604)


    Taxes:$7,254

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2117 HIGH POINT AVE SW, WINTER HAVEN, FL 33880

    $389,90029 Days on yellowkey   MLS ID: L4960940

    2 Days Off yellowkey (back on 6/1/2026)

    For Sale L4960940 - 2117 HIGH POINT AVE SW, WINTER HAVEN, FL 33880 34 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2485
       Built: 1977   Tax: $6,491 (2025)
    Community: High Point
    Single Family


    Estimated Monthly Payment: $2,677 (change assumption)
    Mortgage ($2,136) + Taxes in 2025 ($541)


    Taxes:$6,491

    Elementary School: Lake Shipp Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: None


  • 896 EAGLE ROCK TER, WINTER HAVEN, FL 33880

    $404,900Listed 06/01/2026 7:45PM   MLS ID: L4962338

    For Sale L4962338 - 896 EAGLE ROCK TER, WINTER HAVEN, FL 33880 39 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1632
       Built: 2022
    Monthly Fee: $38
       Tax: $3,355 (2025)
    Community: Eagle Lndg Ph Ib
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,536 (change assumption)
    Mortgage ($2,219) + Fees ($38) + Taxes in 2025 ($280)


    Taxes:$3,355

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5041 KAIA AVE, WINTER HAVEN, FL 33884

    $260,00021 Days on yellowkey   MLS ID: TB8502452

    REDUCED by $32,870 (11.2%) on 06/01/2026

    For Sale TB8502452 - 5041 KAIA AVE, WINTER HAVEN, FL 33884 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1269
       Built: 2026
    Monthly Fee: $15
       Tax: $5,000 (2025)
    Community: Villamar
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,856 (change assumption)
    Mortgage ($1,425) + Fees ($15) + Taxes in 2025 ($417)


    Taxes:$5,000

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 144 BEVERLY DR, WINTER HAVEN, FL 33884

    $399,50053 Days on yellowkey   MLS ID: O6397768

    REDUCED by $400 (0.1%) on 06/01/2026

    For Sale O6397768 - 144 BEVERLY DR, WINTER HAVEN, FL 33884 63 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: $2,504 (change assumption)
    Mortgage ($2,189) + Taxes in 2025 ($315)


    Taxes:$3,785

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2953 WHISPERING TRAILS DR, WINTER HAVEN, FL 33884

    $240,00019 Days on yellowkey   MLS ID: O6407939

    For Sale O6407939 - 2953 WHISPERING TRAILS DR, WINTER HAVEN, FL 33884 17 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1274
       Built: 2018
    Monthly Fee: $96
       Tax: $3,757 (2025)
    Community: Whispering Trails Ph 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,724 (change assumption)
    Mortgage ($1,315) + Fees ($96) + Taxes in 2025 ($313)


    Taxes:$3,757

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1100 CAREFREE COVE DR, WINTER HAVEN, FL 33881

    $217,00021 Days on yellowkey   MLS ID: O6407265

    For Sale O6407265 - 1100 CAREFREE COVE DR, WINTER HAVEN, FL 33881 18 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1019
       Built: 1969   Tax: $1,264 (2025)
    Community: Carefree Cove
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,294 (change assumption)
    Mortgage ($1,189) + Taxes in 2025 ($105)


    Taxes:$1,264

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 153 STEVENSON RD, WINTER HAVEN, FL 33884

    $339,90063 Days on yellowkey   MLS ID: L4960685

    For Sale L4960685 - 153 STEVENSON RD, WINTER HAVEN, FL 33884 61 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1867
       Built: 1961   Tax: $4,041 (2025)
    Community: Garden Grove
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,199 (change assumption)
    Mortgage ($1,862) + Taxes in 2025 ($337)


    Taxes:$4,041

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3097 BUCKEYE POINTE DR, WINTER HAVEN, FL 33881

    $449,000Listed 06/01/2026 1:15PM   MLS ID: S5150948

    For Sale S5150948 - 3097 BUCKEYE POINTE DR, WINTER HAVEN, FL 33881 59 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2577
       Built: 2004
    Monthly Fee: $33
       Tax: $4,587 (2025)
    Community: Buckeye Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,875 (change assumption)
    Mortgage ($2,460) + Fees ($33) + Taxes in 2025 ($382)


    Taxes:$4,587

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 3421 HICKORY ST NW, WINTER HAVEN, FL 33881

    $187,000Listed 06/01/2026 6:05PM   MLS ID: O6412571

    For Sale O6412571 - 3421 HICKORY ST NW, WINTER HAVEN, FL 33881 25 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 690
       Built: 1955   Tax: $962 (2025)
    Community: Biltmore Shores
    Single Family


    Estimated Monthly Payment: $1,105 (change assumption)
    Mortgage ($1,025) + Taxes in 2025 ($80)


    Taxes:$962

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3408 COSTELLO CIR, WINTER HAVEN, FL 33884

    $299,0004 Days on yellowkey   MLS ID: O6411460

    REDUCED by $6,000 (2.0%) on 06/01/2026

    For Sale O6411460 - 3408 COSTELLO CIR, WINTER HAVEN, FL 33884 15 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1713
       Built: 2025
    Monthly Fee: $18
       Tax: $3,036 (2025)
    Community: Villamar Ph 6 & Ph 6D
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,909 (change assumption)
    Mortgage ($1,638) + Fees ($18) + Taxes in 2025 ($253)


    Taxes:$3,036

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 622 RIDGE TER, WINTER HAVEN, FL 33881

    $150,0008 Days on yellowkey   MLS ID: L4962178

    For Sale L4962178 - 622 RIDGE TER, WINTER HAVEN, FL 33881 31 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1073
       Built: 1997
    Monthly Fee: $253
       Tax: $1,644 (2025)
    Community: Winter Ridge Condo
    Condo


    Estimated Monthly Payment: $1,212 (change assumption)
    Mortgage ($822) + Fees ($253) + Taxes in 2025 ($137)


    Taxes:$1,644

    Elementary School: Lake Alfred Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 440 KENSINGTON VIEW DR, WINTER HAVEN, FL 33880

    $263,000170 Days on yellowkey   MLS ID: G5105497

    1 Days Off yellowkey (back on 4/15/2026)

    INCREASED by $23,000 (9.6%) on 04/15/2026

    SHORT SALE G5105497 - 440 KENSINGTON VIEW DR, WINTER HAVEN, FL 33880 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1688
       Built: 2020
    Monthly Fee: $53
       Tax: $3,809 (2024)
    Community: Kensington View
    Single Family


    Estimated Monthly Payment: $1,812 (change assumption)
    Mortgage ($1,441) + Fees ($53) + Taxes in 2024 ($317)


    Taxes:$3,809

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1055 30TH ST NW, WINTER HAVEN, FL 33881

    $209,90020 Days on yellowkey   MLS ID: TB8507249

    REDUCED by $10,000 (4.5%) on 06/01/2026

    For Sale TB8507249 - 1055 30TH ST NW, WINTER HAVEN, FL 33881 13 photos

    Bed: 4   Bath: 1.0
    Liv Area Sq Ft: 1020
       Built: 1955   Tax: $1,715 (2025)
    Community: Rosewood Manor
    Single Family


    Estimated Monthly Payment: $1,293 (change assumption)
    Mortgage ($1,150) + Taxes in 2025 ($143)


    Taxes:$1,715

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 504 MANILLA LN, WINTER HAVEN, FL 33880

    $149,9004 Days on yellowkey   MLS ID: W7886152

    For Sale W7886152 - 504 MANILLA LN, WINTER HAVEN, FL 33880 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1350
       Built: 2000   Tax: $1,121 (2025)
    Community: Ridge Acres Ph Iv
    Manufactured Home


    Estimated Monthly Payment: $915 (change assumption)
    Mortgage ($821) + Taxes in 2025 ($93)


    Taxes:$1,121

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2026 KINGS XING SW, WINTER HAVEN, FL 33880

    $235,0004 Days on yellowkey   MLS ID: O6410748

    For Sale O6410748 - 2026 KINGS XING SW, WINTER HAVEN, FL 33880 35 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1131
       Built: 1980
    Monthly Fee: $165
       Tax: $3,604 (2025)
    Community: Stonebridge Ph 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,753 (change assumption)
    Mortgage ($1,288) + Fees ($165) + Taxes in 2025 ($300)


    Taxes:$3,604

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 352 VAIL DR, WINTER HAVEN, FL 33884

    $274,900Listed 06/01/2026 11:12AM   MLS ID: L4962337

    For Sale L4962337 - 352 VAIL DR, WINTER HAVEN, FL 33884 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2040
       Built: 1990
    Monthly Fee: $17
       Tax: $1,538 (2025)
    Community: Cedar Cove Ph 02
    Single Family


    Estimated Monthly Payment: $1,651 (change assumption)
    Mortgage ($1,506) + Fees ($17) + Taxes in 2025 ($128)


    Taxes:$1,538

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2108 RIVER HAWK LOOP, WINTER HAVEN, FL 33880

    $384,90033 Days on yellowkey   MLS ID: S5148855

    For Sale S5148855 - 2108 RIVER HAWK LOOP, WINTER HAVEN, FL 33880 24 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2032
       Built: 2026
    Monthly Fee: $98
       Tax: $228 (2025)
    Community: Residences At Winter Haven
    Single Family


    Estimated Monthly Payment: $2,226 (change assumption)
    Mortgage ($2,109) + Fees ($98) + Taxes in 2025 ($19)


    Taxes:$228

    Elementary School: Lake Shipp Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood 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.