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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Living Area Square Feet: 1500 to 1999

Winter Haven - 311 properties found

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  • 555 LUCERNE BLVD, WINTER HAVEN, FL 33881

    $280,000108 Days on yellowkey   MLS ID: S5145385

    2 Days Off yellowkey (back on 6/11/2026)

    REDUCED by $10,000 (3.4%) on 05/18/2026

    For Sale S5145385 - 555 LUCERNE BLVD, WINTER HAVEN, FL 33881 38 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1980
       Built: 2016
    Monthly Fee: $49
       Tax: $2,414 (2025)
    Community: Lakes/Lucerne Park Ph 4
    Single Family


    Estimated Monthly Payment: $1,784 (change assumption)
    Mortgage ($1,534) + Fees ($49) + Taxes in 2025 ($201)


    Taxes:$2,414

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 900 LAKE JESSIE DR, WINTER HAVEN, FL 33881

    $450,00089 Days on yellowkey   MLS ID: S5146723

    REDUCED by $19,900 (4.2%) on 06/06/2026

    For Sale S5146723 - 900 LAKE JESSIE DR, WINTER HAVEN, FL 33881 50 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1828
       Built: 1948   Tax: $4,023 (2025)
    Community: East View Pkwy
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,801 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($335)


    Taxes:$4,023

    Elementary School: Auburndale Central Elem

    High School: Auburndale High School

    Tax Year: 2025

    Middle School: Westwood Middle


  • 524 HAINES TRL, WINTER HAVEN, FL 33881

    $315,00056 Days on yellowkey   MLS ID: L4961454

    REDUCED by $14,000 (4.3%) on 06/11/2026

    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: $1,982 (change assumption)
    Mortgage ($1,726) + 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


  • 4454 GLENNS LNDG, WINTER HAVEN, FL 33884

    $249,000115 Days on yellowkey   MLS ID: P4938011

    1 Days Off yellowkey (back on 6/11/2026)

    REDUCED by $10,000 (3.9%) on 05/13/2026

    For Sale P4938011 - 4454 GLENNS LNDG, WINTER HAVEN, FL 33884 48 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1526
       Built: 1991
    Monthly Fee: $83
       Tax: $2,292 (2025)
    Community: Cypress Landing Ph 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,638 (change assumption)
    Mortgage ($1,364) + Fees ($83) + Taxes in 2025 ($191)


    Taxes:$2,292

    Elementary School: Garden Grove Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 4669 OSPREY WAY, WINTER HAVEN, FL 33881

    $319,50068 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


  • 551 LAKE SMART BLVD, WINTER HAVEN, FL 33881

    $344,90087 Days on yellowkey   MLS ID: S5146731

    REDUCED by $15,000 (4.2%) on 05/30/2026

    For Sale S5146731 - 551 LAKE SMART BLVD, WINTER HAVEN, FL 33881 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1936
       Built: 2020
    Monthly Fee: $50
       Tax: $4,211 (2025)
    Community: Lake Smart Pointe
    Single Family


    Estimated Monthly Payment: $2,291 (change assumption)
    Mortgage ($1,890) + Fees ($50) + Taxes in 2025 ($351)


    Taxes:$4,211

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 321 SQUIRES GROVE DR, WINTER HAVEN, FL 33880

    $229,90016 Days on yellowkey   MLS ID: TB8517299

    For Sale TB8517299 - 321 SQUIRES GROVE DR, WINTER HAVEN, FL 33880 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1616
       Built: 2007
    Monthly Fee: $52
       Tax: $1,217 (2025)
    Community: Squires Grove
    Single Family


    Estimated Monthly Payment: $1,413 (change assumption)
    Mortgage ($1,260) + Fees ($52) + Taxes in 2025 ($101)


    Taxes:$1,217

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 1109 BRIMSTONE CIR, WINTER HAVEN, FL 33884

    $299,00015 Days on yellowkey   MLS ID: P4939014

    For Sale P4939014 - 1109 BRIMSTONE CIR, WINTER HAVEN, FL 33884 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1697
       Built: 2023
    Monthly Fee: $30
       Tax: $3,769 (2025)
    Community: Harmony/Lk Eloise Ph 1
    Single Family


    Estimated Monthly Payment: $1,982 (change assumption)
    Mortgage ($1,638) + Fees ($30) + Taxes in 2025 ($314)


    Taxes:$3,769

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4129 GIORGIO DR, WINTER HAVEN, FL 33884

    $279,90015 Days on yellowkey   MLS ID: O6415782

    For Sale O6415782 - 4129 GIORGIO DR, WINTER HAVEN, FL 33884 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2026
    Monthly Fee: $18
       Tax: $3,035 (2025)
    Community: Villamar
    Single Family


    Estimated Monthly Payment: $1,805 (change assumption)
    Mortgage ($1,534) + Fees ($18) + Taxes in 2025 ($253)


    Taxes:$3,035

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 1454 GRAND CAYMAN CIR, WINTER HAVEN, FL 33884

    $249,99081 Days on yellowkey   MLS ID: O6396319

    REDUCED by $10,000 (3.8%) on 06/10/2026

    For Sale O6396319 - 1454 GRAND CAYMAN CIR, WINTER HAVEN, FL 33884 50 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1596
       Built: 1987
    Monthly Fee: $45
       Tax: $2,901 (2025)
    Community: Lake Dexter Moorings
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,656 (change assumption)
    Mortgage ($1,370) + Fees ($45) + Taxes in 2025 ($242)


    Taxes:$2,901

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 140 SOLIS DR, WINTER HAVEN, FL 33880

    $314,900232 Days on yellowkey   MLS ID: S5137785

    0 Days Off yellowkey (back on 6/10/2026)

    REDUCED by $500 (0.2%) on 05/28/2026

    For Sale S5137785 - 140 SOLIS DR, WINTER HAVEN, FL 33880 38 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1814
       Built: 2019
    Monthly Fee: $65
       Tax: $2,678 (2024)
    Community: Solis Gardens
    Single Family


    Estimated Monthly Payment: $2,014 (change assumption)
    Mortgage ($1,725) + Fees ($65) + Taxes in 2024 ($223)


    Taxes:$2,678

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Denison Middle


  • 4952 KAIA AVE, WINTER HAVEN, FL 33884

    $281,900281 Days on yellowkey   MLS ID: O6345029

    REDUCED by $2,000 (0.7%) on 06/10/2026

    For Sale O6345029 - 4952 KAIA AVE, WINTER HAVEN, FL 33884 25 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1665
       Built: 2025
    Monthly Fee: $17
       Tax: $1,047 (2025)
    Community: Villamar
    Single Family


    Estimated Monthly Payment: $1,649 (change assumption)
    Mortgage ($1,545) + Fees ($17) + Taxes in 2025 ($87)


    Taxes:$1,047

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 4081 GIORGIO DR, WINTER HAVEN, FL 33884

    $281,90017 Days on yellowkey   MLS ID: O6414935

    REDUCED by $4,000 (1.4%) on 06/10/2026

    For Sale O6414935 - 4081 GIORGIO DR, WINTER HAVEN, FL 33884 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2026
    Monthly Fee: $18
       Tax: $3,036 (2025)
    Community: Villamar
    Single Family


    Estimated Monthly Payment: $1,816 (change assumption)
    Mortgage ($1,545) + Fees ($18) + Taxes in 2025 ($253)


    Taxes:$3,036

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 4160 GIORGIO DR, WINTER HAVEN, FL 33884

    $291,900190 Days on yellowkey   MLS ID: O6366024

    REDUCED by $5,090 (1.7%) on 06/10/2026

    For Sale O6366024 - 4160 GIORGIO DR, WINTER HAVEN, FL 33884 27 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1665
       Built: 2025
    Monthly Fee: $18
       Tax: $3,035 (2025)
    Community: Villamar Phase 6 And Phase 6D
    Single Family


    Estimated Monthly Payment: $1,870 (change assumption)
    Mortgage ($1,599) + Fees ($18) + Taxes in 2025 ($253)


    Taxes:$3,035

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 5561 TAVERNA LOOP, WINTER HAVEN, FL 33884

    $276,90080 Days on yellowkey   MLS ID: O6396753

    REDUCED by $2,090 (0.7%) on 06/10/2026

    For Sale O6396753 - 5561 TAVERNA LOOP, WINTER HAVEN, FL 33884 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2026
    Monthly Fee: $53
       Tax: $2,689 (2025)
    Community: Villamar Phase 7
    Single Family


    Estimated Monthly Payment: $1,794 (change assumption)
    Mortgage ($1,517) + Fees ($53) + Taxes in 2025 ($224)


    Taxes:$2,689

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 3807 POMELO DR, WINTER HAVEN, FL 33880

    $312,900184 Days on yellowkey   MLS ID: O6369075

    REDUCED by $2,000 (0.6%) on 06/10/2026

    For Sale O6369075 - 3807 POMELO DR, WINTER HAVEN, FL 33880 17 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1672
       Built: 2025
    Monthly Fee: $69
       Tax: $2,605 (2025)
    Community: Harmony On Lake Eloise Phase 4
    Single Family


    Estimated Monthly Payment: $2,001 (change assumption)
    Mortgage ($1,714) + Fees ($69) + Taxes in 2025 ($217)


    Taxes:$2,605

    Elementary School: John Snively Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 3815 POMELO, WINTER HAVEN, FL 33884

    $307,900122 Days on yellowkey   MLS ID: O6384844

    REDUCED by $2,000 (0.6%) on 06/10/2026

    SHORT SALE O6384844 - 3815 POMELO, WINTER HAVEN, FL 33884 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1672
       Built: 2026
    Monthly Fee: $30
       Tax: $155 (2025)
    Community: Harmony On Lake Eloise
    Single Family


    Estimated Monthly Payment: $1,730 (change assumption)
    Mortgage ($1,687) + Fees ($30) + Taxes in 2025 ($13)


    Taxes:$155

    Elementary School: John Snively Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 3316 WHITE INDIGO RD, WINTER HAVEN, FL 33884

    $287,900108 Days on yellowkey   MLS ID: O6389109

    REDUCED by $2,000 (0.7%) on 06/10/2026

    For Sale O6389109 - 3316 WHITE INDIGO RD, WINTER HAVEN, FL 33884 27 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2026   Tax: $155 (2025)
    Community: Harmony On Lake Eloise
    Single Family


    Estimated Monthly Payment: $1,590 (change assumption)
    Mortgage ($1,577) + Taxes in 2025 ($13)


    Taxes:$155

    Elementary School: John Snively Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 3310 WHITE INDIGO RD, WINTER HAVEN, FL 33884

    $296,900122 Days on yellowkey   MLS ID: O6385000

    REDUCED by $2,000 (0.7%) on 06/10/2026

    For Sale O6385000 - 3310 WHITE INDIGO RD, WINTER HAVEN, FL 33884 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1665
       Built: 2026
    Monthly Fee: $69
       Tax: $2,310 (2025)
    Community: Harmony On Lake Eloise Phase 4
    Single Family


    Estimated Monthly Payment: $1,888 (change assumption)
    Mortgage ($1,627) + Fees ($69) + Taxes in 2025 ($193)


    Taxes:$2,310

    Elementary School: John Snively Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 3105 FIREBRUSH LN, WINTER HAVEN, FL 33884

    $287,900168 Days on yellowkey   MLS ID: O6372244

    REDUCED by $2,000 (0.7%) on 06/10/2026

    For Sale O6372244 - 3105 FIREBRUSH LN, WINTER HAVEN, FL 33884 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2025
    Monthly Fee: $69
       Tax: $2,310 (2025)
    Community: Harmony On Lake Eloise
    Single Family


    Estimated Monthly Payment: $1,839 (change assumption)
    Mortgage ($1,577) + Fees ($69) + Taxes in 2025 ($193)


    Taxes:$2,310

    Elementary School: John Snively 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.