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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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  • 3022 HICKORY ST NW, WINTER HAVEN, FL 33881

    $265,000196 Days on yellowkey   MLS ID: A4674941

    REDUCED by $5,000 (1.9%) on 06/09/2026

    For Sale A4674941 - 3022 HICKORY ST NW, WINTER HAVEN, FL 33881 40 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1602
       Built: 1955   Tax: $1,866 (2024)
    Community: Biltmore Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,608 (change assumption)
    Mortgage ($1,452) + Taxes in 2024 ($156)


    Taxes:$1,866

    Elementary School: Auburndale Central Elem

    High School: Auburndale High School

    Tax Year: 2024

    Middle School: Westwood Middle


  • 1374 BENEVENTO DR, WINTER HAVEN, FL 33884

    $199,90091 Days on yellowkey   MLS ID: O6390730

    SHORT SALE O6390730 - 1374 BENEVENTO DR, WINTER HAVEN, FL 33884 3 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1849
       Built: 2020
    Monthly Fee: $15
       Tax: $5,650 (2025)
    Community: Villamar Ph 2
    Single Family


    Estimated Monthly Payment: $1,581 (change assumption)
    Mortgage ($1,095) + Fees ($15) + Taxes in 2025 ($471)


    Taxes:$5,650

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 153 STEVENSON RD, WINTER HAVEN, FL 33884

    $339,90086 Days on yellowkey   MLS ID: L4960685

    For Sale L4960685 - 153 STEVENSON RD, WINTER HAVEN, FL 33884 64 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1867
       Built: 1961   Tax: $4,041 (2025)
    Community: Garden Grove
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,199 (change assumption)
    Mortgage ($1,862) + Taxes in 2025 ($337)


    Taxes:$4,041

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1452 AXEL CIR, WINTER HAVEN, FL 33880

    $287,00027 Days on yellowkey   MLS ID: TB8513583

    REDUCED by $9,500 (3.2%) on 06/13/2026

    For Sale TB8513583 - 1452 AXEL CIR, WINTER HAVEN, FL 33880 16 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1842
       Built: 2022
    Monthly Fee: $71
       Tax: $3,731 (2025)
    Community: Pinnacle Point
    Single Family


    Estimated Monthly Payment: $1,954 (change assumption)
    Mortgage ($1,573) + Fees ($71) + Taxes in 2025 ($311)


    Taxes:$3,731

    Elementary School: Lake Shipp Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 381 SAN JOSE DR, WINTER HAVEN, FL 33884

    $237,50014 Days on yellowkey   MLS ID: S5151702

    For Sale S5151702 - 381 SAN JOSE DR, WINTER HAVEN, FL 33884 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1651
       Built: 1991
    Monthly Fee: $108
       Tax: $3,176 (2025)
    Community: Orchid Springs Patio Homes
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,674 (change assumption)
    Mortgage ($1,301) + Fees ($108) + Taxes in 2025 ($265)


    Taxes:$3,176

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 2235 LAKERIDGE DR, WINTER HAVEN, FL 33881

    $300,00076 Days on yellowkey   MLS ID: P4938412

    REDUCED by $5,000 (1.6%) on 06/13/2026

    For Sale P4938412 - 2235 LAKERIDGE DR, WINTER HAVEN, FL 33881 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1893
       Built: 2015
    Monthly Fee: $65
       Tax: $2,614 (2025)
    Community: Lakeridge Estates
    Single Family


    Estimated Monthly Payment: $1,927 (change assumption)
    Mortgage ($1,644) + Fees ($65) + Taxes in 2025 ($218)


    Taxes:$2,614

    Elementary School: Frank E. Brigham Academy

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: None


  • 1508 MAJESTIC LN, WINTER HAVEN, FL 33880

    $327,50034 Days on yellowkey   MLS ID: L4962086

    For Sale L4962086 - 1508 MAJESTIC LN, WINTER HAVEN, FL 33880 39 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1900
       Built: 2023
    Monthly Fee: $38
       Tax: $3,775 (2025)
    Community: Eagle Lndg Ph Ii
    Single Family


    Estimated Monthly Payment: $2,147 (change assumption)
    Mortgage ($1,794) + Fees ($38) + Taxes in 2025 ($315)


    Taxes:$3,775

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 136 LAKE RING DR, WINTER HAVEN, FL 33884

    $319,90055 Days on yellowkey   MLS ID: P4938606

    REDUCED by $5,000 (1.5%) on 05/29/2026

    For Sale P4938606 - 136 LAKE RING DR, WINTER HAVEN, FL 33884 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1728
       Built: 1975   Tax: $2,508 (2025)
    Community: Eloise Woods Lake Mariam Unit
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,962 (change assumption)
    Mortgage ($1,753) + Taxes in 2025 ($209)


    Taxes:$2,508

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5384 HOGAN LN, WINTER HAVEN, FL 33884

    $345,500346 Days on yellowkey   MLS ID: P4935506

    1 Days Off yellowkey (back on 6/13/2026)

    For Sale P4935506 - 5384 HOGAN LN, WINTER HAVEN, FL 33884 32 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1682
       Built: 2006
    Monthly Fee: $5

    Community: Lake Ashton West Ph 01
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,898 (change assumption)
    Mortgage ($1,893) + Fees ($5) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 448 ITUNA CIR, WINTER HAVEN, FL 33881

    $318,90013 Days on yellowkey   MLS ID: L4962701

    For Sale L4962701 - 448 ITUNA CIR, WINTER HAVEN, FL 33881 4 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1744
       Built: 2026
    Monthly Fee: $50

    Community: Harbor At Lake Henry
    Single Family


    Estimated Monthly Payment: $1,797 (change assumption)
    Mortgage ($1,747) + Fees ($50) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 505 MAGGIE CIR, WINTER HAVEN, FL 33880

    $249,90037 Days on yellowkey   MLS ID: P4938744

    0 Days Off yellowkey (back on 6/12/2026)

    For Sale P4938744 - 505 MAGGIE CIR, WINTER HAVEN, FL 33880 65 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1592
       Built: 1973   Tax: $2,729 (2025)
    Community: Jan Phyl Village
    Single Family


    Estimated Monthly Payment: $1,597 (change assumption)
    Mortgage ($1,369) + Taxes in 2025 ($227)


    Taxes:$2,729

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 614 SIDNEY CIR, WINTER HAVEN, FL 33880

    $399,99021 Days on yellowkey   MLS ID: O6413011

    For Sale O6413011 - 614 SIDNEY CIR, WINTER HAVEN, FL 33880 26 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1908
       Built: 1968   Tax: $3,517 (2025)
    Community: Jan Phyl Village
    Single Family


    Estimated Monthly Payment: $2,485 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($293)


    Taxes:$3,517

    Elementary School: Sandhill Elem

    High School: Haines City Senior High

    Tax Year: 2025

    Middle School: Daniel Jenkins Academy of Technology Middle


  • 6103 GREY HERON DR, WINTER HAVEN, FL 33881

    $295,00056 Days on yellowkey   MLS ID: O6403532

    REDUCED by $9,999 (3.3%) on 06/12/2026

    For Sale O6403532 - 6103 GREY HERON DR, WINTER HAVEN, FL 33881 13 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1828
       Built: 2018
    Monthly Fee: $15
       Tax: $5,214 (2025)
    Community: Lakeside Landings Ph 01
    Single Family


    Estimated Monthly Payment: $2,066 (change assumption)
    Mortgage ($1,616) + Fees ($15) + Taxes in 2025 ($434)


    Taxes:$5,214

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 780 OVERLOOK GROVE DR, WINTER HAVEN, FL 33884

    $272,50057 Days on yellowkey   MLS ID: L4960255

    REDUCED by $22,500 (7.6%) on 06/12/2026

    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: $1,889 (change assumption)
    Mortgage ($1,493) + Fees ($38) + Taxes in 2025 ($358)


    Taxes:$4,294

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3357 TIMBERLINE RD W, WINTER HAVEN, FL 33880

    $279,00014 Days on yellowkey   MLS ID: O6416140

    For Sale O6416140 - 3357 TIMBERLINE RD W, WINTER HAVEN, FL 33880 15 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1675
       Built: 1983   Tax: $2,765 (2024)
    Community: Timber Wood
    Single Family


    Estimated Monthly Payment: $1,759 (change assumption)
    Mortgage ($1,529) + Taxes in 2024 ($230)


    Taxes:$2,765

    Elementary School: Clarence Boswell Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Westwood Middle


  • 2540 14TH ST SE, WINTER HAVEN, FL 33884

    $369,90029 Days on yellowkey   MLS ID: O6411362

    2 Days Off yellowkey (back on 6/12/2026)

    For Sale O6411362 - 2540 14TH ST SE, WINTER HAVEN, FL 33884 30 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1753
       Built: 1956   Tax: $3,789 (2025)
    Community: South Roy Shores
    Single Family


    Estimated Monthly Payment: $2,343 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($316)


    Taxes:$3,789

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 1195 TYLER LOOP, WINTER HAVEN, FL 33884

    $299,997168 Days on yellowkey   MLS ID: O6371574

    For Sale O6371574 - 1195 TYLER LOOP, WINTER HAVEN, FL 33884 21 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1933
       Built: 2024
    Monthly Fee: $16
       Tax: $7,112 (2025)
    Community: Peace Crk Reserve
    Single Family


    Estimated Monthly Payment: $2,252 (change assumption)
    Mortgage ($1,644) + Fees ($16) + Taxes in 2025 ($593)


    Taxes:$7,112

    Elementary School: South Pointe Elementary

    High School: None

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 909 CAMBRIDGE DR, WINTER HAVEN, FL 33881

    $271,90069 Days on yellowkey   MLS ID: G5111142

    REDUCED by $5,000 (1.8%) on 06/11/2026

    SHORT SALE G5111142 - 909 CAMBRIDGE DR, WINTER HAVEN, FL 33881 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1506
       Built: 2022
    Monthly Fee: $13
       Tax: $3,310 (2025)
    Community: Lucerne Park Reserve
    Single Family


    Estimated Monthly Payment: $1,779 (change assumption)
    Mortgage ($1,490) + Fees ($13) + Taxes in 2025 ($276)


    Taxes:$3,310

    Elementary School: Fred G. Garnier Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 3873 GIORGIO DR, WINTER HAVEN, FL 33884

    $274,990338 Days on yellowkey   MLS ID: O6327569

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

    REDUCED by $15,000 (5.2%) on 04/02/2026

    For Sale O6327569 - 3873 GIORGIO DR, WINTER HAVEN, FL 33884 31 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1988
       Built: 2025
    Monthly Fee: $15

    Community: Villamar
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,522 (change assumption)
    Mortgage ($1,507) + 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


  • 4 GROVE CT SE, WINTER HAVEN, FL 33884

    $424,90056 Days on yellowkey   MLS ID: O6401108

    REDUCED by $5,000 (1.2%) on 06/10/2026

    For Sale O6401108 - 4 GROVE CT SE, WINTER HAVEN, FL 33884 49 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 1983
       Built: 1977   Tax: $2,779 (2025)
    Community: Lake Winterset Acres
    Single Family


    Estimated Monthly Payment: $2,560 (change assumption)
    Mortgage ($2,328) + Taxes in 2025 ($232)


    Taxes:$2,779

    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.