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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Living Area Square Feet: 2000 to 2499

Winter Haven - 177 properties found

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  • 3142 WHISPERING TRAILS ST, WINTER HAVEN, FL 33884

    $370,00066 Days on yellowkey   MLS ID: O6386254

    For Sale O6386254 - 3142 WHISPERING TRAILS ST, WINTER HAVEN, FL 33884 56 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2203
       Built: 2006
    Monthly Fee: $95
       Tax: $3,991 (2025)
    Community: Whispering Trails Ph 01
    Single Family


    Estimated Monthly Payment: $2,455 (change assumption)
    Mortgage ($2,027) + Fees ($95) + Taxes in 2025 ($333)


    Taxes:$3,991

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 804 ANDREW ST, WINTER HAVEN, FL 33881

    $339,99035 Days on yellowkey   MLS ID: O6393645

    0 Days Off yellowkey (back on 4/23/2026)

    REDUCED by $26,700 (7.3%) on 04/07/2026

    For Sale O6393645 - 804 ANDREW ST, WINTER HAVEN, FL 33881 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2028
       Built: 2026
    Monthly Fee: $6
       Tax: $2,695 (2025)
    Community: Willowbrook North
    Single Family


    Estimated Monthly Payment: $2,094 (change assumption)
    Mortgage ($1,863) + Fees ($6) + Taxes in 2025 ($225)


    Taxes:$2,695

    Elementary School: Lake Alfred Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 5347 MICKEY AVE, WINTER HAVEN, FL 33884

    $349,99934 Days on yellowkey   MLS ID: S5146851

    INCREASED by $478 (0.1%) on 04/21/2026

    For Sale S5146851 - 5347 MICKEY AVE, WINTER HAVEN, FL 33884 18 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: $1,956 (change assumption)
    Mortgage ($1,918) + Fees ($38) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4656 MAGNOLIA PRESERVE LOOP, WINTER HAVEN, FL 33880

    $319,98939 Days on yellowkey   MLS ID: L4960603

    REDUCED by $4,911 (1.5%) on 04/23/2026

    For Sale L4960603 - 4656 MAGNOLIA PRESERVE LOOP, WINTER HAVEN, FL 33880 18 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2038
       Built: 2007
    Monthly Fee: $32
       Tax: $4,387 (2025)
    Community: Magnolia Preserve
    Single Family


    Estimated Monthly Payment: $2,151 (change assumption)
    Mortgage ($1,753) + Fees ($32) + Taxes in 2025 ($366)


    Taxes:$4,387

    Elementary School: Eagle Lake Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 264 RUBY LAKE LN, WINTER HAVEN, FL 33884

    $699,000201 Days on yellowkey   MLS ID: P4936678

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

    For Sale P4936678 - 264 RUBY LAKE LN, WINTER HAVEN, FL 33884 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2217
       Built: 1999
    Monthly Fee: $71
       Tax: $5,543 (2024)
    Community: Ruby Lake Ph 04
    Single Family


    Estimated Monthly Payment: $4,363 (change assumption)
    Mortgage ($3,830) + Fees ($71) + Taxes in 2024 ($462)


    Taxes:$5,543

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Denison Middle


  • 503 HAMILTON SHORES CT NE, WINTER HAVEN, FL 33881

    $525,00057 Days on yellowkey   MLS ID: L4960022

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

    For Sale L4960022 - 503 HAMILTON SHORES CT NE, WINTER HAVEN, FL 33881 45 photos

    Bed: 3   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2375
       Built: 1991
    Monthly Fee: $27
       Tax: $2,594 (2025)
    Community: Hamilton Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,120 (change assumption)
    Mortgage ($2,877) + Fees ($27) + Taxes in 2025 ($216)


    Taxes:$2,594

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 2285 AVENUE C SW, WINTER HAVEN, FL 33880

    $279,90090 Days on yellowkey   MLS ID: S5142523

    For Sale S5142523 - 2285 AVENUE C SW, WINTER HAVEN, FL 33880 33 photos

    Bed: 4   Bath: 2.0   Gar: 4
    Liv Area Sq Ft: 2325
       Built: 1962   Tax: $4,529 (2025)
    Community: West Winter Haven
    Single Family


    Estimated Monthly Payment: $1,911 (change assumption)
    Mortgage ($1,534) + Taxes in 2025 ($377)


    Taxes:$4,529

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 247 S LAKE PANSY DR, WINTER HAVEN, FL 33881

    $479,90021 Days on yellowkey   MLS ID: TB8496517

    For Sale TB8496517 - 247 S LAKE PANSY DR, WINTER HAVEN, FL 33881 56 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2247
       Built: 1986
    Monthly Fee: $136
       Tax: $2,948 (2025)
    Community: Hartridge Hills
    Single Family


    Estimated Monthly Payment: $3,011 (change assumption)
    Mortgage ($2,630) + Fees ($136) + Taxes in 2025 ($246)


    Taxes:$2,948

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 708 GLAD RD, WINTER HAVEN, FL 33880

    $114,99518 Days on yellowkey   MLS ID: P4938461

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

    For Sale P4938461 - 708 GLAD RD, WINTER HAVEN, FL 33880 14 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2000
       Built: 1967   Tax: $2,704 (2025)
    Community: Jan Phyl Village
    Single Family


    Estimated Monthly Payment: $855 (change assumption)
    Mortgage ($630) + Taxes in 2025 ($225)


    Taxes:$2,704

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5357 HOGAN LN, WINTER HAVEN, FL 33884

    $440,000264 Days on yellowkey   MLS ID: P4935902

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

    For Sale P4935902 - 5357 HOGAN LN, WINTER HAVEN, FL 33884 71 photos

    Bed: 3   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2363
       Built: 2006
    Monthly Fee: $5
       Tax: $6,216 (2024)
    Community: Lake Ashton West Ph 01
    Single Family


    Estimated Monthly Payment: $2,934 (change assumption)
    Mortgage ($2,411) + Fees ($5) + Taxes in 2024 ($518)


    Taxes:$6,216

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1987 8TH ST SE, WINTER HAVEN, FL 33880

    $261,222348 Days on yellowkey   MLS ID: P4934891

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

    SHORT SALE P4934891 - 1987 8TH ST SE, WINTER HAVEN, FL 33880 1 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2363
       Built: 1959   Tax: $1,648 (2024)
    Community: Laha Wa Manor
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $1,569 (change assumption)
    Mortgage ($1,431) + Taxes in 2024 ($137)


    Taxes:$1,648

    Elementary School: None

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: None


  • 3904 GIORGIO DR, WINTER HAVEN, FL 33884

    $305,000335 Days on yellowkey   MLS ID: O6313349

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

    For Sale O6313349 - 3904 GIORGIO DR, WINTER HAVEN, FL 33884 37 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2168
       Built: 2025
    Monthly Fee: $15

    Community: Villamar
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,686 (change assumption)
    Mortgage ($1,671) + Fees ($15) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 5444 SAN PIETRO DR, WINTER HAVEN, FL 33884

    $324,99938 Days on yellowkey   MLS ID: TB8491382

    REDUCED by $10,000 (3.0%) on 04/21/2026

    For Sale TB8491382 - 5444 SAN PIETRO DR, WINTER HAVEN, FL 33884 33 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2226
       Built: 2025
    Monthly Fee: $53
       Tax: $2,689 (2025)
    Community: Villa Mar
    Single Family


    Estimated Monthly Payment: $2,058 (change assumption)
    Mortgage ($1,781) + Fees ($53) + Taxes in 2025 ($224)


    Taxes:$2,689

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 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


  • 446 TERRANOVA ST, WINTER HAVEN, FL 33884

    $425,00070 Days on yellowkey   MLS ID: P4937910

    REDUCED by $10,000 (2.3%) on 04/21/2026

    For Sale P4937910 - 446 TERRANOVA ST, WINTER HAVEN, FL 33884 37 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2121
       Built: 2004
    Monthly Fee: $664
       Tax: $2,816 (2025)
    Community: Terranova Ph 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,227 (change assumption)
    Mortgage ($2,329) + Fees ($664) + Taxes in 2025 ($235)


    Taxes:$2,816

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 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


  • 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


  • 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


  • 292 SPIRIT LANDINGS CIR, WINTER HAVEN, FL 33880

    $280,000368 Days on yellowkey   MLS ID: O6305100

    REDUCED by $19,000 (6.4%) on 04/20/2026

    SHORT SALE O6305100 - 292 SPIRIT LANDINGS CIR, WINTER HAVEN, FL 33880 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2332
       Built: 2023
    Monthly Fee: $102
       Tax: $4,760 (2024)
    Community: Spirit Lndgs
    Single Family


    Estimated Monthly Payment: $2,033 (change assumption)
    Mortgage ($1,534) + Fees ($102) + Taxes in 2024 ($397)


    Taxes:$4,760

    Elementary School: None

    High School: None

    Tax Year: 2024

    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.