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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Living Area Square Feet: 1500 to 1999

Winter Haven - 281 properties found

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  • 536 ITUNA CIR, WINTER HAVEN, FL 33881

    $320,35574 Days on yellowkey   MLS ID: L4959563

    1 Days Off yellowkey (back on 4/16/2026)

    For Sale L4959563 - 536 ITUNA CIR, WINTER HAVEN, FL 33881 3 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1545
       Built: 2026
    Monthly Fee: $50

    Community: Harbor At Lake Henry
    Single Family


    Estimated Monthly Payment: $1,805 (change assumption)
    Mortgage ($1,755) + Fees ($50) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2037 LAKERIDGE DR, WINTER HAVEN, FL 33881

    $305,00027 Days on yellowkey   MLS ID: L4960883

    1 Days Off yellowkey (back on 4/16/2026)

    For Sale L4960883 - 2037 LAKERIDGE DR, WINTER HAVEN, FL 33881 31 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1824
       Built: 2014
    Monthly Fee: $65
       Tax: $2,106 (2025)
    Community: Lakeridge Estates
    Single Family


    Estimated Monthly Payment: $1,912 (change assumption)
    Mortgage ($1,671) + Fees ($65) + Taxes in 2025 ($176)


    Taxes:$2,106

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 440 KENSINGTON VIEW DR, WINTER HAVEN, FL 33880

    $263,000141 Days on yellowkey   MLS ID: G5105497

    1 Days Off yellowkey (back on 4/15/2026)

    INCREASED by $23,000 (9.6%) on 04/15/2026

    SHORT SALE G5105497 - 440 KENSINGTON VIEW DR, WINTER HAVEN, FL 33880 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1688
       Built: 2020
    Monthly Fee: $53
       Tax: $3,809 (2024)
    Community: Kensington View
    Single Family


    Estimated Monthly Payment: $1,812 (change assumption)
    Mortgage ($1,441) + Fees ($53) + Taxes in 2024 ($317)


    Taxes:$3,809

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2415 BRASSIE CT, WINTER HAVEN, FL 33884

    $289,00020 Days on yellowkey   MLS ID: P4938435

    For Sale P4938435 - 2415 BRASSIE CT, WINTER HAVEN, FL 33884 51 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1629
       Built: 2022
    Monthly Fee: $18
       Tax: $2,101 (2025)
    Community: Villamar Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,777 (change assumption)
    Mortgage ($1,584) + Fees ($18) + Taxes in 2025 ($175)


    Taxes:$2,101

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 4140 SOPHIA BLVD, WINTER HAVEN, FL 33880

    $279,90021 Days on yellowkey   MLS ID: TB8495461

    For Sale TB8495461 - 4140 SOPHIA BLVD, WINTER HAVEN, FL 33880 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1711
       Built: 2017
    Monthly Fee: $25
       Tax: $4,540 (2025)
    Community: Buckeye Ridge
    Single Family


    Estimated Monthly Payment: $1,937 (change assumption)
    Mortgage ($1,534) + Fees ($25) + Taxes in 2025 ($378)


    Taxes:$4,540

    Elementary School: Elbert Elem

    High School: Chain of Lakes Collegiate High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 3901 GIORGIO DR, WINTER HAVEN, FL 33884

    $331,26098 Days on yellowkey   MLS ID: O6375585

    INCREASED by $20 (0.0%) on 04/14/2026

    For Sale O6375585 - 3901 GIORGIO DR, WINTER HAVEN, FL 33884 6 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1840
       Built: 2026
    Monthly Fee: $154
       Tax: $2,005 (2026)
    Community: Villamar
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,136 (change assumption)
    Mortgage ($1,815) + Fees ($154) + Taxes in 2026 ($167)


    Taxes:$2,005

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2026

    Middle School: Denison Middle


  • 1729 PEBBLE BEACH ST, WINTER HAVEN, FL 33881

    $299,00030 Days on yellowkey   MLS ID: P4938335

    0 Days Off yellowkey (back on 4/14/2026)

    For Sale P4938335 - 1729 PEBBLE BEACH ST, WINTER HAVEN, FL 33881 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1865
       Built: 2013
    Monthly Fee: $34
       Tax: $4,596 (2026)
    Community: Country Club Trails
    Single Family


    Estimated Monthly Payment: $2,055 (change assumption)
    Mortgage ($1,638) + Fees ($34) + Taxes in 2026 ($383)


    Taxes:$4,596

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2026

    Middle School: Denison Middle


  • 1596 LEAMINGTON LN, WINTER HAVEN, FL 33884

    $270,000305 Days on yellowkey   MLS ID: P4935416

    SHORT SALE P4935416 - 1596 LEAMINGTON LN, WINTER HAVEN, FL 33884 46 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1851
       Built: 2022
    Monthly Fee: $15
       Tax: $6,017 (2024)
    Community: Villamar Ph 3
    Single Family


    Estimated Monthly Payment: $1,996 (change assumption)
    Mortgage ($1,479) + Fees ($15) + Taxes in 2024 ($501)


    Taxes:$6,017

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 441 SAN JOSE DR, WINTER HAVEN, FL 33884

    $275,000360 Days on yellowkey   MLS ID: P4934776

    REDUCED by $10,000 (3.5%) on 04/14/2026

    For Sale P4934776 - 441 SAN JOSE DR, WINTER HAVEN, FL 33884 37 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1843
       Built: 1984
    Monthly Fee: $5
       Tax: $1,000 (2024)
    Community: Orchid Springs Patio Homes
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,595 (change assumption)
    Mortgage ($1,507) + Fees ($5) + Taxes in 2024 ($83)


    Taxes:$1,000

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3349 COSTELLO CIR, WINTER HAVEN, FL 33884

    $249,990153 Days on yellowkey   MLS ID: O6364268

    0 Days Off yellowkey (back on 4/14/2026)

    REDUCED by $1,000 (0.4%) on 04/03/2026

    For Sale O6364268 - 3349 COSTELLO CIR, WINTER HAVEN, FL 33884 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1516
       Built: 2023
    Monthly Fee: $17
       Tax: $6,563 (2024)
    Community: Villamar Ph 5
    Single Family


    Estimated Monthly Payment: $1,934 (change assumption)
    Mortgage ($1,370) + Fees ($17) + Taxes in 2024 ($547)


    Taxes:$6,563

    Elementary School: Chain O Lakes Elem

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5543 TAVERNA, WINTER HAVEN, FL 33884

    $269,990119 Days on yellowkey   MLS ID: O6371052

    2 Days Off yellowkey (back on 4/14/2026)

    For Sale O6371052 - 5543 TAVERNA, WINTER HAVEN, FL 33884 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2025
    Monthly Fee: $53
       Tax: $3,300 (2025)
    Community: Villamar Phase 7
    Single Family


    Estimated Monthly Payment: $1,807 (change assumption)
    Mortgage ($1,479) + Fees ($53) + Taxes in 2025 ($275)


    Taxes:$3,300

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Mclaughlin Middle


  • 120 GROVE BRANCH RD, WINTER HAVEN, FL 33880

    $304,900160 Days on yellowkey   MLS ID: P4937143

    For Sale P4937143 - 120 GROVE BRANCH RD, WINTER HAVEN, FL 33880 49 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1851
       Built: 2020
    Monthly Fee: $57
       Tax: $4,019 (2024)
    Community: Squires Grove
    Single Family


    Estimated Monthly Payment: $2,063 (change assumption)
    Mortgage ($1,671) + Fees ($57) + Taxes in 2024 ($335)


    Taxes:$4,019

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1228 DENALI DR, WINTER HAVEN, FL 33881

    $315,000243 Days on yellowkey   MLS ID: P4936142

    For Sale P4936142 - 1228 DENALI DR, WINTER HAVEN, FL 33881 24 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1707
       Built: 2023
    Monthly Fee: $73
       Tax: $4,208 (2024)
    Community: Lake Lucerne Ii
    Single Family


    Estimated Monthly Payment: $2,150 (change assumption)
    Mortgage ($1,726) + Fees ($73) + Taxes in 2024 ($351)


    Taxes:$4,208

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2518 14TH CT SE, WINTER HAVEN, FL 33884

    $209,00024 Days on yellowkey   MLS ID: L4961012

    0 Days Off yellowkey (back on 4/10/2026)

    For Sale L4961012 - 2518 14TH CT SE, WINTER HAVEN, FL 33884 16 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1806
       Built: 1970   Tax: $1,875 (2025)
    Community: South Roy Shores
    Single Family


    Estimated Monthly Payment: $1,301 (change assumption)
    Mortgage ($1,145) + Taxes in 2025 ($156)


    Taxes:$1,875

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5520 TAVERNA LOOP, WINTER HAVEN, FL 33884

    $279,999270 Days on yellowkey   MLS ID: TB8415205

    0 Days Off yellowkey (back on 4/13/2026)

    REDUCED by $10,000 (3.4%) on 04/07/2026

    For Sale TB8415205 - 5520 TAVERNA LOOP, WINTER HAVEN, FL 33884 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1615
       Built: 2025
    Monthly Fee: $18
       Tax: $2,292 (2025)
    Community: Villa Mar
    Single Family


    Estimated Monthly Payment: $1,743 (change assumption)
    Mortgage ($1,534) + Fees ($18) + Taxes in 2025 ($191)


    Taxes:$2,292

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 1629 NANTUCKET WAY, WINTER HAVEN, FL 33884

    $303,90040 Days on yellowkey   MLS ID: TB8490344

    For Sale TB8490344 - 1629 NANTUCKET WAY, WINTER HAVEN, FL 33884 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1526
       Built: 2025
    Monthly Fee: $95

    Community: Peach Crossings
    Single Family


    Estimated Monthly Payment: $1,760 (change assumption)
    Mortgage ($1,665) + Fees ($95) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Denison Middle


  • 2708 ATTWATER LOOP, WINTER HAVEN, FL 33884

    $269,99932 Days on yellowkey   MLS ID: O6395048

    3 Days Off yellowkey (back on 4/13/2026)

    For Sale O6395048 - 2708 ATTWATER LOOP, WINTER HAVEN, FL 33884 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1561
       Built: 2017
    Monthly Fee: $486
       Tax: $769 (2025)
    Community: Traditions Ph 02
    Single Family


    Estimated Monthly Payment: $2,029 (change assumption)
    Mortgage ($1,479) + Fees ($486) + Taxes in 2025 ($64)


    Taxes:$769

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1802 WHITE ELEPHANT LOOP, WINTER HAVEN, FL 33884

    $344,900408 Days on yellowkey   MLS ID: TB8364884

    For Sale TB8364884 - 1802 WHITE ELEPHANT LOOP, WINTER HAVEN, FL 33884 20 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1863
       Built: 2025
    Monthly Fee: $95

    Community: Peach Crossings
    Single Family


    Estimated Monthly Payment: $1,985 (change assumption)
    Mortgage ($1,890) + Fees ($95) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Denison Middle


  • 4747 MANDOLIN LOOP, WINTER HAVEN, FL 33884

    $299,900166 Days on yellowkey   MLS ID: P4937079

    REDUCED by $5,000 (1.6%) on 04/13/2026

    For Sale P4937079 - 4747 MANDOLIN LOOP, WINTER HAVEN, FL 33884 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1506
       Built: 2011
    Monthly Fee: $42
       Tax: $4,813 (2024)
    Community: Mandolin 02
    Single Family


    Estimated Monthly Payment: $2,086 (change assumption)
    Mortgage ($1,643) + Fees ($42) + Taxes in 2024 ($401)


    Taxes:$4,813

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5840 GREY HERON DR, WINTER HAVEN, FL 33881

    $257,00030 Days on yellowkey   MLS ID: L4960838

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale L4960838 - 5840 GREY HERON DR, WINTER HAVEN, FL 33881 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1747
       Built: 2016
    Monthly Fee: $10
       Tax: $3,990 (2025)
    Community: Lakeside Landings Ph 01
    Single Family


    Estimated Monthly Payment: $1,751 (change assumption)
    Mortgage ($1,408) + Fees ($10) + Taxes in 2025 ($333)


    Taxes:$3,990

    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.