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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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  • 112 PAINE DR, WINTER HAVEN, FL 33884

    $315,000148 Days on yellowkey   MLS ID: L4957763

    REDUCED by $35,000 (10.0%) on 04/21/2026

    For Sale L4957763 - 112 PAINE DR, WINTER HAVEN, FL 33884 36 photos

    Bed: 5   Bath: 2.0
    Liv Area Sq Ft: 2078
       Built: 1965   Tax: $3,343 (2024)
    Community: Fla Highlands Co Sub
    Single Family


    Estimated Monthly Payment: $2,005 (change assumption)
    Mortgage ($1,726) + Taxes in 2024 ($279)


    Taxes:$3,343

    Elementary School: Garden Grove Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Denison Middle


  • 689 VITTORIO DR, WINTER HAVEN, FL 33884

    $315,000189 Days on yellowkey   MLS ID: O6353926

    2 Days Off yellowkey (back on 1/20/2026)

    For Sale O6353926 - 689 VITTORIO DR, WINTER HAVEN, FL 33884 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2053
       Built: 2021
    Monthly Fee: $19
       Tax: $5,951 (2025)
    Community: Villamar Ph 2
    Single Family


    Estimated Monthly Payment: $2,241 (change assumption)
    Mortgage ($1,726) + Fees ($19) + Taxes in 2025 ($496)


    Taxes:$5,951

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Mclaughlin Academy Of Excellence


  • 5171 KINSLEY DR, WINTER HAVEN, FL 33884

    $339,999252 Days on yellowkey   MLS ID: S5133352

    INCREASED by $3,100 (0.9%) on 04/21/2026

    For Sale S5133352 - 5171 KINSLEY DR, WINTER HAVEN, FL 33884 20 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2050
       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


  • 5135 KINSLEY DR, WINTER HAVEN, FL 33884

    $314,999342 Days on yellowkey   MLS ID: S5127745

    REDUCED by $951 (0.3%) on 04/21/2026

    For Sale S5127745 - 5135 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


  • 3820 TRADITIONS BLVD N, WINTER HAVEN, FL 33884

    $380,00035 Days on yellowkey   MLS ID: P4938275

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

    For Sale P4938275 - 3820 TRADITIONS BLVD N, WINTER HAVEN, FL 33884 45 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2400
       Built: 2006
    Monthly Fee: $485
       Tax: $2,300 (2025)
    Community: Traditions Ph 01
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,759 (change assumption)
    Mortgage ($2,082) + Fees ($485) + Taxes in 2025 ($192)


    Taxes:$2,300

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4612 REYNOSA DR SW, WINTER HAVEN, FL 33880

    $320,000270 Days on yellowkey   MLS ID: V4944212

    1 Days Off yellowkey (back on 4/21/2026)

    SHORT SALE V4944212 - 4612 REYNOSA DR SW, WINTER HAVEN, FL 33880 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1716
       Built: 1984   Tax: $4,573 (2024)
    Community: Plaza Sub
    Single Family


    Estimated Monthly Payment: $2,134 (change assumption)
    Mortgage ($1,753) + Taxes in 2024 ($381)


    Taxes:$4,573

    Elementary School: Lake Shipp Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Westwood Middle


  • 1658 TEAGAN LN, WINTER HAVEN, FL 33884

    $315,99026 Days on yellowkey   MLS ID: S5146407

    For Sale S5146407 - 1658 TEAGAN LN, WINTER HAVEN, FL 33884 30 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1933
       Built: 2024
    Monthly Fee: $16
       Tax: $4,170 (2025)
    Community: Peace Creek Reserve
    Single Family


    Estimated Monthly Payment: $2,095 (change assumption)
    Mortgage ($1,731) + Fees ($16) + Taxes in 2025 ($348)


    Taxes:$4,170

    Elementary School: Wahneta Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 3863 BEDFORD AVE, WINTER HAVEN, FL 33884

    $345,00027 Days on yellowkey   MLS ID: O6396509

    REDUCED by $10,000 (2.8%) on 04/16/2026

    For Sale O6396509 - 3863 BEDFORD AVE, WINTER HAVEN, FL 33884 33 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1797
       Built: 2017
    Monthly Fee: $485
       Tax: $4,293 (2025)
    Community: Traditions Ph 02
    Single Family


    Estimated Monthly Payment: $2,733 (change assumption)
    Mortgage ($1,890) + Fees ($485) + Taxes in 2025 ($358)


    Taxes:$4,293

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2775 SAN MARCO WAY, WINTER HAVEN, FL 33884

    $332,99014 Days on yellowkey   MLS ID: O6400845

    For Sale O6400845 - 2775 SAN MARCO WAY, WINTER HAVEN, FL 33884 7 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1564
       Built: 2026
    Monthly Fee: $193
       Tax: $3,035 (2025)
    Community: Villamar Ph 5
    Single Family


    Estimated Monthly Payment: $2,270 (change assumption)
    Mortgage ($1,825) + Fees ($193) + Taxes in 2025 ($253)


    Taxes:$3,035

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 528 CODY CALEB DR, WINTER HAVEN, FL 33884

    $304,50014 Days on yellowkey   MLS ID: L4961233

    For Sale L4961233 - 528 CODY CALEB DR, WINTER HAVEN, FL 33884 60 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2250
       Built: 2005
    Monthly Fee: $23
       Tax: $4,538 (2025)
    Community: Savannah Estates
    Single Family


    Estimated Monthly Payment: $2,070 (change assumption)
    Mortgage ($1,668) + Fees ($23) + Taxes in 2025 ($378)


    Taxes:$4,538

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 123 ELOISE OAKS DR, WINTER HAVEN, FL 33884

    $390,00033 Days on yellowkey   MLS ID: L4960769

    1 Days Off yellowkey (back on 4/20/2026)

    REDUCED by $5,000 (1.3%) on 04/16/2026

    For Sale L4960769 - 123 ELOISE OAKS DR, WINTER HAVEN, FL 33884 52 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2029
       Built: 2018
    Monthly Fee: $56

    Community: Eloise Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,193 (change assumption)
    Mortgage ($2,137) + Fees ($56) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 1192 NORMANDY HEIGHTS CIR, WINTER HAVEN, FL 33880

    $344,90017 Days on yellowkey   MLS ID: L4961188

    For Sale L4961188 - 1192 NORMANDY HEIGHTS CIR, WINTER HAVEN, FL 33880 48 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2093
       Built: 2009
    Monthly Fee: $50
       Tax: $4,839 (2025)
    Community: Normandy Heights
    Single Family


    Estimated Monthly Payment: $2,343 (change assumption)
    Mortgage ($1,890) + Fees ($50) + Taxes in 2025 ($403)


    Taxes:$4,839

    Elementary School: Lake Shipp Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 5445 CHANDLER DR, WINTER HAVEN, FL 33884

    $319,50048 Days on yellowkey   MLS ID: S5146003

    For Sale S5146003 - 5445 CHANDLER DR, WINTER HAVEN, FL 33884 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3010
       Built: 2006
    Monthly Fee: $48
       Tax: $5,827 (2025)
    Community: Bentley Place
    Single Family


    Estimated Monthly Payment: $2,284 (change assumption)
    Mortgage ($1,751) + Fees ($48) + Taxes in 2025 ($486)


    Taxes:$5,827

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3890 BEDFORD AVE, WINTER HAVEN, FL 33884

    $395,00016 Days on yellowkey   MLS ID: L4961088

    For Sale L4961088 - 3890 BEDFORD AVE, WINTER HAVEN, FL 33884 68 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2322
       Built: 2019
    Monthly Fee: $485
       Tax: $5,156 (2025)
    Community: Traditions Ph 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,079 (change assumption)
    Mortgage ($2,164) + Fees ($485) + Taxes in 2025 ($430)


    Taxes:$5,156

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6337 BOTTICELLA BLVD, WINTER HAVEN, FL 33884

    $332,71016 Days on yellowkey   MLS ID: W7884986

    For Sale W7884986 - 6337 BOTTICELLA BLVD, WINTER HAVEN, FL 33884 16 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2370
       Built: 2026
    Monthly Fee: $19

    Community: Villa Mar
    Single Family


    Estimated Monthly Payment: $1,842 (change assumption)
    Mortgage ($1,823) + Fees ($19) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 292 MEREDITH BLVD, WINTER HAVEN, FL 33881

    $329,990111 Days on yellowkey   MLS ID: G5106667

    0 Days Off yellowkey (back on 4/19/2026)

    For Sale G5106667 - 292 MEREDITH BLVD, WINTER HAVEN, FL 33881 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2110
       Built: 2025
    Monthly Fee: $75
       Tax: $500 (2025)
    Community: Willowbrook North
    Single Family


    Estimated Monthly Payment: $1,925 (change assumption)
    Mortgage ($1,808) + Fees ($75) + Taxes in 2025 ($42)


    Taxes:$500

    Elementary School: Fred G. Garnier Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 4669 OSPREY WAY, WINTER HAVEN, FL 33881

    $319,50016 Days on yellowkey   MLS ID: R4911042

    For Sale R4911042 - 4669 OSPREY WAY, WINTER HAVEN, FL 33881 27 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1992
       Built: 2019
    Monthly Fee: $35
       Tax: $5,100 (2025)
    Community: St James Xing
    Single Family


    Estimated Monthly Payment: $2,211 (change assumption)
    Mortgage ($1,751) + Fees ($35) + Taxes in 2025 ($425)


    Taxes:$5,100

    Elementary School: Walter Caldwell Elem

    High School: Auburndale High School

    Tax Year: 2025

    Middle School: None


  • 441 MCKENNA DR, WINTER HAVEN, FL 33881

    $363,00024 Days on yellowkey   MLS ID: O6398240

    For Sale O6398240 - 441 MCKENNA DR, WINTER HAVEN, FL 33881 36 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2360
       Built: 2021
    Monthly Fee: $17
       Tax: $6,548 (2025)
    Community: Lucerne Park Reserve
    Single Family


    Estimated Monthly Payment: $2,552 (change assumption)
    Mortgage ($1,989) + Fees ($17) + Taxes in 2025 ($546)


    Taxes:$6,548

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2352 TWIN LAKE VIEW RD, WINTER HAVEN, FL 33881

    $314,90057 Days on yellowkey   MLS ID: L4960041

    REDUCED by $2,500 (0.8%) on 04/18/2026

    For Sale L4960041 - 2352 TWIN LAKE VIEW RD, WINTER HAVEN, FL 33881 23 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1994
       Built: 2020
    Monthly Fee: $23
       Tax: $4,127 (2025)
    Community: Eagle Crest
    Single Family


    Estimated Monthly Payment: $2,092 (change assumption)
    Mortgage ($1,725) + Fees ($23) + Taxes in 2025 ($344)


    Taxes:$4,127

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 239 GOLF AIRE BLVD, WINTER HAVEN, FL 33884

    $399,000179 Days on yellowkey   MLS ID: P4936940

    For Sale P4936940 - 239 GOLF AIRE BLVD, WINTER HAVEN, FL 33884 87 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2263
       Built: 1998
    Monthly Fee: $500
       Tax: $2,634 (2024)
    Community: Lake Bess Country Cc
    Single Family


    Estimated Monthly Payment: $2,906 (change assumption)
    Mortgage ($2,186) + Fees ($500) + Taxes in 2024 ($220)


    Taxes:$2,634

    Elementary School: Frank E. Brigham Academy

    High School: Winter Haven Senior

    Tax Year: 2024

    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.