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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Price: $300,000 to $399,000

Winter Haven - 251 properties found

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  • 4507 RAPALLO AVE, WINTER HAVEN, FL 33884

    $302,90087 Days on yellowkey   MLS ID: L4959233

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

    For Sale L4959233 - 4507 RAPALLO AVE, WINTER HAVEN, FL 33884 20 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1754
       Built: 2025
    Monthly Fee: $18

    Community: Villamar
    Single Family


    Estimated Monthly Payment: $1,678 (change assumption)
    Mortgage ($1,660) + Fees ($18) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 524 HAINES TRL, WINTER HAVEN, FL 33881

    $329,0004 Days on yellowkey   MLS ID: L4961454

    For Sale L4961454 - 524 HAINES TRL, WINTER HAVEN, FL 33881 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1980
       Built: 2016
    Monthly Fee: $48
       Tax: $2,501 (2025)
    Community: Lakes/Lucerne Park Ph 4
    Single Family


    Estimated Monthly Payment: $2,059 (change assumption)
    Mortgage ($1,803) + Fees ($48) + Taxes in 2025 ($208)


    Taxes:$2,501

    Elementary School: Lake Alfred Elem

    High School: None

    Tax Year: 2025

    Middle School: Lake Alfred-Addair Middle


  • 239 SUNFISH DR, WINTER HAVEN, FL 33881

    $325,0004 Days on yellowkey   MLS ID: O6403244

    For Sale O6403244 - 239 SUNFISH DR, WINTER HAVEN, FL 33881 44 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1996
       Built: 2021
    Monthly Fee: $92
       Tax: $5,146 (2025)
    Community: Lake Lucurne
    Single Family


    Estimated Monthly Payment: $2,302 (change assumption)
    Mortgage ($1,781) + Fees ($92) + Taxes in 2025 ($429)


    Taxes:$5,146

    Elementary School: Lake Alfred Elem

    High School: Haines City Senior High

    Tax Year: 2025

    Middle School: Boone Middle


  • 1210 ZAMBRANA CT, WINTER HAVEN, FL 33884

    $375,0004 Days on yellowkey   MLS ID: O6401308

    For Sale O6401308 - 1210 ZAMBRANA CT, WINTER HAVEN, FL 33884 41 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2360
       Built: 2021
    Monthly Fee: $13
       Tax: $6,968 (2024)
    Community: Villamar Ph 2
    Single Family


    Estimated Monthly Payment: $2,648 (change assumption)
    Mortgage ($2,055) + Fees ($13) + Taxes in 2024 ($581)


    Taxes:$6,968

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2117 RIVER HAWK LOOP, WINTER HAVEN, FL 33880

    $335,00010 Days on yellowkey   MLS ID: S5148367

    0 Days Off yellowkey (back on 4/25/2026)

    For Sale S5148367 - 2117 RIVER HAWK LOOP, WINTER HAVEN, FL 33880 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1605
       Built: 2026
    Monthly Fee: $98
       Tax: $228 (2025)
    Community: Residences At Winter Haven
    Single Family


    Estimated Monthly Payment: $1,953 (change assumption)
    Mortgage ($1,836) + 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


  • 814 TURNER LN, WINTER HAVEN, FL 33881

    $369,000241 Days on yellowkey   MLS ID: S5134153

    For Sale S5134153 - 814 TURNER LN, WINTER HAVEN, FL 33881 24 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2696
       Built: 2023
    Monthly Fee: $49
       Tax: $5,461 (2024)
    Community: Inman Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $2,526 (change assumption)
    Mortgage ($2,022) + Fees ($49) + Taxes in 2024 ($455)


    Taxes:$5,461

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5335 MICKEY AVE, WINTER HAVEN, FL 33884

    $364,999182 Days on yellowkey   MLS ID: S5137808

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

    For Sale S5137808 - 5335 MICKEY AVE, WINTER HAVEN, FL 33884 22 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2807
       Built: 2025
    Monthly Fee: $38

    Community: Seasons At Annabelle Estates
    Single Family


    Estimated Monthly Payment: $2,038 (change assumption)
    Mortgage ($2,000) + Fees ($38) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5307 MICKEY AVE, WINTER HAVEN, FL 33884

    $329,99945 Days on yellowkey   MLS ID: S5146225

    2 Days Off yellowkey (back on 3/30/2026)

    For Sale S5146225 - 5307 MICKEY AVE, WINTER HAVEN, FL 33884 19 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2077
       Built: 2026
    Monthly Fee: $38

    Community: Seasons At Annabelle Estates
    Single Family


    Estimated Monthly Payment: $1,846 (change assumption)
    Mortgage ($1,808) + Fees ($38) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 5355 MICKEY AVE, WINTER HAVEN, FL 33884

    $339,950153 Days on yellowkey   MLS ID: S5139501

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

    For Sale S5139501 - 5355 MICKEY AVE, WINTER HAVEN, FL 33884 19 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2077
       Built: 2025
    Monthly Fee: $38

    Community: Seasons At Annabelle Estates
    Single Family


    Estimated Monthly Payment: $1,901 (change assumption)
    Mortgage ($1,863) + Fees ($38) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 780 OVERLOOK GROVE DR, WINTER HAVEN, FL 33884

    $302,5005 Days on yellowkey   MLS ID: L4960255

    For Sale L4960255 - 780 OVERLOOK GROVE DR, WINTER HAVEN, FL 33884 45 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1583
       Built: 2013
    Monthly Fee: $38
       Tax: $4,294 (2025)
    Community: Overlook Rdg
    Single Family


    Estimated Monthly Payment: $2,053 (change assumption)
    Mortgage ($1,657) + Fees ($38) + Taxes in 2025 ($358)


    Taxes:$4,294

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 961 DREXEL AVE NE, WINTER HAVEN, FL 33881

    $315,00070 Days on yellowkey   MLS ID: L4959592

    REDUCED by $5,000 (1.6%) on 04/19/2026

    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: $2,010 (change assumption)
    Mortgage ($1,726) + Taxes in 2025 ($284)


    Taxes:$3,409

    Elementary School: Inwood Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Westwood Middle


  • 116 MANDOLIN DR, WINTER HAVEN, FL 33884

    $370,0005 Days on yellowkey   MLS ID: O6403313

    For Sale O6403313 - 116 MANDOLIN DR, WINTER HAVEN, FL 33884 51 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2248
       Built: 2009
    Monthly Fee: $56
       Tax: $5,678 (2025)
    Community: Mandolin
    Single Family


    Estimated Monthly Payment: $2,557 (change assumption)
    Mortgage ($2,027) + Fees ($56) + Taxes in 2025 ($473)


    Taxes:$5,678

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 643 GROVE ST, WINTER HAVEN, FL 33881

    $340,00091 Days on yellowkey   MLS ID: O6379127

    For Sale O6379127 - 643 GROVE ST, WINTER HAVEN, FL 33881 16 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1853
       Built: 2022
    Monthly Fee: $50
       Tax: $5,200 (2024)
    Community: Inman Groves
    Single Family


    Estimated Monthly Payment: $2,346 (change assumption)
    Mortgage ($1,863) + Fees ($50) + Taxes in 2024 ($433)


    Taxes:$5,200

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Denison Middle


  • 5147 KINSLEY DR, WINTER HAVEN, FL 33884

    $314,999341 Days on yellowkey   MLS ID: S5127810

    REDUCED by $3,636 (1.1%) on 04/21/2026

    For Sale S5127810 - 5147 KINSLEY DR, WINTER HAVEN, FL 33884 17 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1919
       Built: 2025
    Monthly Fee: $38

    Community: Seasons At Annabelle Estates
    Single Family


    Estimated Monthly Payment: $1,764 (change assumption)
    Mortgage ($1,726) + Fees ($38) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 215 SANTA ROSA DR, WINTER HAVEN, FL 33884

    $329,90028 Days on yellowkey   MLS ID: TB8494313

    REDUCED by $20,000 (5.7%) on 04/21/2026

    For Sale TB8494313 - 215 SANTA ROSA DR, WINTER HAVEN, FL 33884 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2355
       Built: 1988
    Monthly Fee: $46
       Tax: $3,255 (2025)
    Community: Overlook Estates
    Single Family


    Estimated Monthly Payment: $2,125 (change assumption)
    Mortgage ($1,808) + Fees ($46) + Taxes in 2025 ($271)


    Taxes:$3,255

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 1144 HIGH SEAS ST, WINTER HAVEN, FL 33880

    $319,000160 Days on yellowkey   MLS ID: B4902112

    For Sale B4902112 - 1144 HIGH SEAS ST, WINTER HAVEN, FL 33880 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1716
       Built: 2016
    Monthly Fee: $68
       Tax: $1,443 (2024)
    Community: Shores At Lake Sears
    Single Family


    Estimated Monthly Payment: $1,936 (change assumption)
    Mortgage ($1,748) + Fees ($68) + Taxes in 2024 ($120)


    Taxes:$1,443

    Elementary School: Lake Shipp Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Westwood Middle


  • 720 OVERLOOK GROVE DR, WINTER HAVEN, FL 33884

    $300,00066 Days on yellowkey   MLS ID: O6386447

    3 Days Off yellowkey (back on 4/29/2026)

    For Sale O6386447 - 720 OVERLOOK GROVE DR, WINTER HAVEN, FL 33884 41 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1892
       Built: 2014
    Monthly Fee: $38
       Tax: $5,040 (2025)
    Community: Overlook Ridge
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,102 (change assumption)
    Mortgage ($1,644) + Fees ($38) + Taxes in 2025 ($420)


    Taxes:$5,040

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 140 1ST ST, WINTER HAVEN, FL 33880

    $309,50052 Days on yellowkey   MLS ID: TB8484176

    REDUCED by $500 (0.2%) on 04/26/2026

    For Sale TB8484176 - 140 1ST ST, WINTER HAVEN, FL 33880 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1682
       Built: 2026   Tax: $292 (2025)
    Community: Leslie J A Sub
    Single Family


    Estimated Monthly Payment: $1,720 (change assumption)
    Mortgage ($1,696) + Taxes in 2025 ($24)


    Taxes:$292

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5352 NICKLAUS DR, WINTER HAVEN, FL 33884

    $349,90033 Days on yellowkey   MLS ID: L4960750

    REDUCED by $10,000 (2.8%) on 04/29/2026

    For Sale L4960750 - 5352 NICKLAUS DR, WINTER HAVEN, FL 33884 66 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2354
       Built: 2007
    Monthly Fee: $5
       Tax: $5,617 (2025)
    Community: Lake Ashton West Ph 01
    Single Family


    Estimated Monthly Payment: $2,390 (change assumption)
    Mortgage ($1,917) + Fees ($5) + Taxes in 2025 ($468)


    Taxes:$5,617

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6040 NAVONA WAY, WINTER HAVEN, FL 33884

    $357,999221 Days on yellowkey   MLS ID: TB8431485

    0 Days Off yellowkey (back on 3/26/2026)

    For Sale TB8431485 - 6040 NAVONA WAY, WINTER HAVEN, FL 33884 25 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2470
       Built: 2025
    Monthly Fee: $18
       Tax: $8,495 (2025)
    Community: Villa Mar
    Single Family


    Estimated Monthly Payment: $2,688 (change assumption)
    Mortgage ($1,962) + Fees ($18) + Taxes in 2025 ($708)


    Taxes:$8,495

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison 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.