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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Price: $300,000 to $399,000

Winter Haven - 287 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


  • 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


  • 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


  • 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


  • 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


  • 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


  • 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


  • 961 DREXEL AVE NE, WINTER HAVEN, FL 33881

    $305,000121 Days on yellowkey   MLS ID: L4959592

    REDUCED by $10,000 (3.2%) on 06/08/2026

    For Sale L4959592 - 961 DREXEL AVE NE, WINTER HAVEN, FL 33881 57 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1856
       Built: 1948   Tax: $3,409 (2025)
    Community: Anna Mar
    Single Family


    Estimated Monthly Payment: $1,955 (change assumption)
    Mortgage ($1,671) + Taxes in 2025 ($284)


    Taxes:$3,409

    Elementary School: Inwood Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Westwood Middle


  • 1328 DAISY FIELD DR, WINTER HAVEN, FL 33884

    $380,00075 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 37 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


  • 681 LAKE DEXTER CIR, WINTER HAVEN, FL 33884

    $349,000Listed 06/24/2026 10:10AM   MLS ID: P4939095

    For Sale P4939095 - 681 LAKE DEXTER CIR, WINTER HAVEN, FL 33884 47 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1320
       Built: 1990
    Monthly Fee: $41
       Tax: $1,397 (2025)
    Community: Lake Dexter Woods Ph 02
    Single Family


    Estimated Monthly Payment: $2,070 (change assumption)
    Mortgage ($1,912) + Fees ($41) + Taxes in 2025 ($116)


    Taxes:$1,397

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 58 LAKE LINK CIR SE, WINTER HAVEN, FL 33884

    $398,50047 Days on yellowkey   MLS ID: P4938677

    0 Days Off yellowkey (back on 5/15/2026)

    For Sale P4938677 - 58 LAKE LINK CIR SE, WINTER HAVEN, FL 33884 42 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2000
       Built: 1971   Tax: $5,997 (2025)
    Community: Lake Link Estates
    Single Family


    Estimated Monthly Payment: $2,683 (change assumption)
    Mortgage ($2,184) + Taxes in 2025 ($500)


    Taxes:$5,997

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884

    $340,000191 Days on yellowkey   MLS ID: P4937220

    For Sale P4937220 - 5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884 54 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1677
       Built: 2016
    Monthly Fee: $5
       Tax: $2,785 (2024)
    Community: Lake Ashton West Ph 01
    Single Family


    Estimated Monthly Payment: $2,100 (change assumption)
    Mortgage ($1,863) + Fees ($5) + Taxes in 2024 ($232)


    Taxes:$2,785

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 443 ITUNA CIR, WINTER HAVEN, FL 33881

    $308,90063 Days on yellowkey   MLS ID: L4961315

    REDUCED by $10,220 (3.2%) on 06/24/2026

    For Sale L4961315 - 443 ITUNA CIR, WINTER HAVEN, FL 33881 4 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1644
       Built: 2026
    Monthly Fee: $50

    Community: Harbor At Lake Henry
    Single Family


    Estimated Monthly Payment: $1,743 (change assumption)
    Mortgage ($1,693) + Fees ($50) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4099 ISLAND LAKES DR, WINTER HAVEN, FL 33881

    $389,000449 Days on yellowkey   MLS ID: P4934266

    REDUCED by $5,000 (1.3%) on 05/28/2026

    For Sale P4934266 - 4099 ISLAND LAKES DR, WINTER HAVEN, FL 33881 37 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1603
       Built: 2006
    Monthly Fee: $17
       Tax: $5,194 (2024)
    Community: Island Lakes
    Single Family


    Estimated Monthly Payment: $2,581 (change assumption)
    Mortgage ($2,131) + Fees ($17) + Taxes in 2024 ($433)


    Taxes:$5,194

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4045 GIORGIO DR, WINTER HAVEN, FL 33884

    $300,9901 Day on yellowkey   MLS ID: O6419297

    For Sale O6419297 - 4045 GIORGIO DR, WINTER HAVEN, FL 33884 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1665
       Built: 2026
    Monthly Fee: $18
       Tax: $3,147 (2025)
    Community: Villamar Phase 6 And Phase 6D
    Single Family


    Estimated Monthly Payment: $1,929 (change assumption)
    Mortgage ($1,649) + Fees ($18) + Taxes in 2025 ($262)


    Taxes:$3,147

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 516 REGGIE RD, WINTER HAVEN, FL 33884

    $325,0001 Day on yellowkey   MLS ID: O6418177

    For Sale O6418177 - 516 REGGIE RD, WINTER HAVEN, FL 33884 56 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2109
       Built: 2024
    Monthly Fee: $16
       Tax: $7,811 (2025)
    Community: Peace Crk Reserve
    Single Family


    Estimated Monthly Payment: $2,448 (change assumption)
    Mortgage ($1,781) + Fees ($16) + Taxes in 2025 ($651)


    Taxes:$7,811

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 3600 JULIUS ESTATES BLVD, WINTER HAVEN, FL 33881

    $340,000299 Days on yellowkey   MLS ID: O6339978

    For Sale O6339978 - 3600 JULIUS ESTATES BLVD, WINTER HAVEN, FL 33881 26 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2526
       Built: 2014
    Monthly Fee: $105
       Tax: $3,256 (2024)
    Community: Lake Smart Estates
    Single Family


    Estimated Monthly Payment: $2,239 (change assumption)
    Mortgage ($1,863) + Fees ($105) + Taxes in 2024 ($271)


    Taxes:$3,256

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1138 MICHELANGELO LN, WINTER HAVEN, FL 33884

    $394,90075 Days on yellowkey   MLS ID: S5147440

    0 Days Off yellowkey (back on 6/23/2026)

    REDUCED by $5,000 (1.3%) on 05/29/2026

    For Sale S5147440 - 1138 MICHELANGELO LN, WINTER HAVEN, FL 33884 72 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2386
       Built: 2023
    Monthly Fee: $55
       Tax: $4,275 (2025)
    Community: Estates/Lk Florence
    Single Family


    Estimated Monthly Payment: $2,575 (change assumption)
    Mortgage ($2,164) + Fees ($55) + Taxes in 2025 ($356)


    Taxes:$4,275

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None






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.