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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Winter Haven - 804 properties found

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  • 1059 MICHELANGELO LN, WINTER HAVEN, FL 33884

    $364,500147 Days on yellowkey   MLS ID: S5142551

    REDUCED by $500 (0.1%) on 06/23/2026

    For Sale S5142551 - 1059 MICHELANGELO LN, WINTER HAVEN, FL 33884 33 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: $2,375 (change assumption)
    Mortgage ($1,997) + 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


  • 4948 KAIA, WINTER HAVEN, FL 33884

    $281,900168 Days on yellowkey   MLS ID: O6370131

    REDUCED by $2,000 (0.7%) on 06/10/2026

    For Sale O6370131 - 4948 KAIA, WINTER HAVEN, FL 33884 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1665
       Built: 2025
    Monthly Fee: $203
       Tax: $3,396 (2025)
    Community: Villamar Phase 6 Pb 203 Pg 7-17 Lot 225
    Single Family


    Estimated Monthly Payment: $2,031 (change assumption)
    Mortgage ($1,545) + Fees ($203) + Taxes in 2025 ($283)


    Taxes:$3,396

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 302 STERLING DR, WINTER HAVEN, FL 33884

    $365,000Listed 06/24/2026 3:50PM   MLS ID: O6419370

    SHORT SALE O6419370 - 302 STERLING DR, WINTER HAVEN, FL 33884 0 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2460
       Built: 1994
    Monthly Fee: $24
       Tax: $2,764 (2025)
    Community: Berryhill
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,254 (change assumption)
    Mortgage ($2,000) + Fees ($24) + Taxes in 2025 ($230)


    Taxes:$2,764

    Elementary School: Garden Grove Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 306 TERRANOVA BLVD, WINTER HAVEN, FL 33884

    $390,0001 Day on yellowkey   MLS ID: TB8522219

    For Sale TB8522219 - 306 TERRANOVA BLVD, WINTER HAVEN, FL 33884 54 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2413
       Built: 2006
    Monthly Fee: $55
       Tax: $6,079 (2025)
    Community: Terranova Ph 04
    Single Family


    Estimated Monthly Payment: $2,699 (change assumption)
    Mortgage ($2,137) + Fees ($55) + Taxes in 2025 ($507)


    Taxes:$6,079

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 221 GOLF AIRE BLVD, WINTER HAVEN, FL 33884

    $299,999108 Days on yellowkey   MLS ID: L4959992

    REDUCED by $15,001 (4.8%) on 06/24/2026

    For Sale L4959992 - 221 GOLF AIRE BLVD, WINTER HAVEN, FL 33884 71 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1645
       Built: 1999
    Monthly Fee: $500
       Tax: $2,554 (2025)
    Community: Lake Bess Country Club
    Single Family


    Estimated Monthly Payment: $2,357 (change assumption)
    Mortgage ($1,644) + Fees ($500) + Taxes in 2025 ($213)


    Taxes:$2,554

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4463 RAPALLO AVE, WINTER HAVEN, FL 33884

    $294,900187 Days on yellowkey   MLS ID: L4958024

    0 Days Off yellowkey (back on 6/24/2026)

    For Sale L4958024 - 4463 RAPALLO AVE, WINTER HAVEN, FL 33884 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1744
       Built: 2025
    Monthly Fee: $19

    Community: Villamar
    Single Family


    Estimated Monthly Payment: $1,635 (change assumption)
    Mortgage ($1,616) + Fees ($19) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 506 15TH CT NE, WINTER HAVEN, FL 33881

    $265,00015 Days on yellowkey   MLS ID: L4962442

    4 Days Off yellowkey (back on 6/22/2026)

    For Sale L4962442 - 506 15TH CT NE, WINTER HAVEN, FL 33881 35 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1320
       Built: 1964   Tax: $2,989 (2025)
    Community: Hills Lake Elbert
    Single Family


    Estimated Monthly Payment: $1,701 (change assumption)
    Mortgage ($1,452) + Taxes in 2025 ($249)


    Taxes:$2,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6457 DOMIZIO DR, WINTER HAVEN, FL 33884

    $309,49097 Days on yellowkey   MLS ID: O6392165

    2 Days Off yellowkey (back on 6/24/2026)

    INCREASED by $500 (0.2%) on 04/07/2026

    For Sale O6392165 - 6457 DOMIZIO DR, WINTER HAVEN, FL 33884 31 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2326
       Built: 2025
    Monthly Fee: $53
       Tax: $32 (2024)
    Community: Villa Mar 40'S
    Single Family


    Estimated Monthly Payment: $1,751 (change assumption)
    Mortgage ($1,696) + Fees ($53) + Taxes in 2024 ($3)


    Taxes:$32

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Denison Middle


  • 3136 COUNTRY CLUB CIR, WINTER HAVEN, FL 33881

    $290,00020 Days on yellowkey   MLS ID: L4961900

    REDUCED by $10,000 (3.3%) on 06/22/2026

    For Sale L4961900 - 3136 COUNTRY CLUB CIR, WINTER HAVEN, FL 33881 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1690
       Built: 2018
    Monthly Fee: $30
       Tax: $3,839 (2025)
    Community: Country Walk/Winter Haven
    Single Family


    Estimated Monthly Payment: $1,939 (change assumption)
    Mortgage ($1,589) + Fees ($30) + Taxes in 2025 ($320)


    Taxes:$3,839

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2799 ADELINE AVE, WINTER HAVEN, FL 33881

    $305,740183 Days on yellowkey   MLS ID: O6369098

    1 Days Off yellowkey (back on 3/25/2026)

    For Sale O6369098 - 2799 ADELINE AVE, WINTER HAVEN, FL 33881 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1328
       Built: 2026
    Monthly Fee: $8
       Tax: $3,455 (2025)
    Community: Willowbrook South
    Single Family


    Estimated Monthly Payment: $1,971 (change assumption)
    Mortgage ($1,675) + Fees ($8) + Taxes in 2025 ($288)


    Taxes:$3,455

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 1620 17TH ST NW, WINTER HAVEN, FL 33881

    $479,0007 Days on yellowkey   MLS ID: P4938977

    For Sale P4938977 - 1620 17TH ST NW, WINTER HAVEN, FL 33881 23 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 965
       Built: 1939   Tax: $3,581 (2025)
    Community: Hendersons Ext Kenilworth Park
    Single Family


    Estimated Monthly Payment: $2,923 (change assumption)
    Mortgage ($2,625) + Taxes in 2025 ($298)


    Taxes:$3,581

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2323 BRASSIE CT, WINTER HAVEN, FL 33884

    $313,967252 Days on yellowkey   MLS ID: L4956626

    2 Days Off yellowkey (back on 5/21/2026)

    REDUCED by $5,000 (1.6%) on 05/01/2026

    For Sale L4956626 - 2323 BRASSIE CT, WINTER HAVEN, FL 33884 4 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2405
       Built: 2025
    Monthly Fee: $68
       Tax: $7,100 (2025)
    Community: Villa Mar Phase 3
    Single Family


    Estimated Monthly Payment: $2,380 (change assumption)
    Mortgage ($1,720) + Fees ($68) + Taxes in 2025 ($592)


    Taxes:$7,100

    Elementary School: Chain O Lakes Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Berkley Accelerated Middle


  • 1525 LEAMINGTON LN, WINTER HAVEN, FL 33884

    $299,366390 Days on yellowkey   MLS ID: L4952865

    1 Days Off yellowkey (back on 5/21/2026)

    REDUCED by $5,000 (1.6%) on 05/01/2026

    For Sale L4952865 - 1525 LEAMINGTON LN, WINTER HAVEN, FL 33884 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2200
       Built: 2025
    Monthly Fee: $67
       Tax: $7,400 (2025)
    Community: Villa Mar Phase 3
    Single Family


    Estimated Monthly Payment: $2,324 (change assumption)
    Mortgage ($1,640) + Fees ($67) + Taxes in 2025 ($617)


    Taxes:$7,400

    Elementary School: Chain O Lakes Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Berkley Accelerated Middle


  • 1871 EMILY DR, WINTER HAVEN, FL 33884

    $312,50043 Days on yellowkey   MLS ID: S5149517

    For Sale S5149517 - 1871 EMILY DR, WINTER HAVEN, FL 33884 66 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2012
       Built: 2005
    Monthly Fee: $38
       Tax: $3,862 (2025)
    Community: Emily Estates
    Single Family


    Estimated Monthly Payment: $2,072 (change assumption)
    Mortgage ($1,712) + Fees ($38) + Taxes in 2025 ($322)


    Taxes:$3,862

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 3986 JACLYNS JETTY, WINTER HAVEN, FL 33884

    $300,000Listed 06/24/2026 9:57AM   MLS ID: L4962993

    For Sale L4962993 - 3986 JACLYNS JETTY, WINTER HAVEN, FL 33884 58 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1526
       Built: 2001
    Monthly Fee: $440
       Tax: $1,767 (2025)
    Community: Cypress Landing Ph 02
    Single Family


    Estimated Monthly Payment: $2,231 (change assumption)
    Mortgage ($1,644) + Fees ($440) + Taxes in 2025 ($147)


    Taxes:$1,767

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 120 HAWTHORNE RD, WINTER HAVEN, FL 33884

    $265,000Listed 06/24/2026 1:43PM   MLS ID: L4963036

    0 Days Off yellowkey (back on 6/24/2026)

    For Sale L4963036 - 120 HAWTHORNE RD, WINTER HAVEN, FL 33884 1 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1439
       Built: 1963   Tax: $3,040 (2025)
    Community: Garden Grove 03
    Single Family


    Estimated Monthly Payment: $1,705 (change assumption)
    Mortgage ($1,452) + Taxes in 2025 ($253)


    Taxes:$3,040

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1558 DREXEL AVE NE, WINTER HAVEN, FL 33881

    $349,50071 Days on yellowkey   MLS ID: L4960971

    3 Days Off yellowkey (back on 6/22/2026)

    REDUCED by $34,500 (9.0%) on 06/20/2026

    For Sale L4960971 - 1558 DREXEL AVE NE, WINTER HAVEN, FL 33881 37 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1160
       Built: 1957   Tax: $2,598 (2025)
    Community: Lake Elbert Heights Unit 01 02 Rep
    Single Family


    Estimated Monthly Payment: $2,131 (change assumption)
    Mortgage ($1,915) + Taxes in 2025 ($216)


    Taxes:$2,598

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6224 BOTTICELLA BLVD, WINTER HAVEN, FL 33884

    $289,4907 Days on yellowkey   MLS ID: O6417853

    1 Days Off yellowkey (back on 6/24/2026)

    REDUCED by $5,000 (1.7%) on 06/19/2026

    For Sale O6417853 - 6224 BOTTICELLA BLVD, WINTER HAVEN, FL 33884 15 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2112
       Built: 2026
    Monthly Fee: $53
       Tax: $32 (2025)
    Community: Villa Mar 40'S
    Single Family


    Estimated Monthly Payment: $1,642 (change assumption)
    Mortgage ($1,586) + Fees ($53) + Taxes in 2025 ($3)


    Taxes:$32

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 1394 OAKMONT DR, WINTER HAVEN, FL 33884

    $549,50039 Days on yellowkey   MLS ID: L4961930

    For Sale L4961930 - 1394 OAKMONT DR, WINTER HAVEN, FL 33884 98 photos

    Bed: 3   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2606
       Built: 2018
    Monthly Fee: $5
       Tax: $10,681 (2025)
    Community: Lake Ashton West Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,906 (change assumption)
    Mortgage ($3,011) + Fees ($5) + Taxes in 2025 ($890)


    Taxes:$10,681

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1733 SANDALWOOD CIR SW, WINTER HAVEN, FL 33880

    $260,000145 Days on yellowkey   MLS ID: L4958444

    For Sale L4958444 - 1733 SANDALWOOD CIR SW, WINTER HAVEN, FL 33880 23 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1075
       Built: 1984   Tax: $1,330 (2025)
    Community: Sandalwood Sub
    Single Family


    Estimated Monthly Payment: $1,535 (change assumption)
    Mortgage ($1,425) + Taxes in 2025 ($111)


    Taxes:$1,330

    Elementary School: Lake Shipp Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Westwood Middle






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.