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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Price: $400,000 to $499,000

Winter Haven - 67 properties found

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  • 446 TERRANOVA ST, WINTER HAVEN, FL 33884

    $419,900121 Days on yellowkey   MLS ID: P4937910

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

    REDUCED by $5,100 (1.2%) on 05/12/2026

    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: $55
       Tax: $2,816 (2025)
    Community: Terranova Ph 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,590 (change assumption)
    Mortgage ($2,301) + Fees ($55) + 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


  • 5122 KINSLEY DR, WINTER HAVEN, FL 33884

    $422,948138 Days on yellowkey   MLS ID: S5143312

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

    For Sale S5143312 - 5122 KINSLEY DR, WINTER HAVEN, FL 33884 21 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3030
       Built: 2026
    Monthly Fee: $38

    Community: Seasons At Annabelle Estates
    Single Family


    Estimated Monthly Payment: $2,355 (change assumption)
    Mortgage ($2,317) + Fees ($38) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1908 CROSSROADS BLVD, WINTER HAVEN, FL 33881

    $419,000328 Days on yellowkey   MLS ID: P4935563

    REDUCED by $900 (0.2%) on 05/30/2026

    For Sale P4935563 - 1908 CROSSROADS BLVD, WINTER HAVEN, FL 33881 54 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2781
       Built: 2008
    Monthly Fee: $133
       Tax: $3,762 (2024)
    Community: Crossroads At Lake Region
    Single Family


    Estimated Monthly Payment: $2,742 (change assumption)
    Mortgage ($2,296) + Fees ($133) + Taxes in 2024 ($314)


    Taxes:$3,762

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Denison Middle


  • 225 FRANKLIN CT, WINTER HAVEN, FL 33881

    $427,500153 Days on yellowkey   MLS ID: L4958723

    0 Days Off yellowkey (back on 5/24/2026)

    For Sale L4958723 - 225 FRANKLIN CT, WINTER HAVEN, FL 33881 57 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2362
       Built: 2014
    Monthly Fee: $74
       Tax: $5,287 (2025)
    Community: Hampton Cove
    Single Family


    Estimated Monthly Payment: $2,857 (change assumption)
    Mortgage ($2,342) + Fees ($74) + Taxes in 2025 ($441)


    Taxes:$5,287

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 1096 SANDPIPER LOOP, WINTER HAVEN, FL 33881

    $442,50084 Days on yellowkey   MLS ID: S5146706

    2 Days Off yellowkey (back on 5/28/2026)

    For Sale S5146706 - 1096 SANDPIPER LOOP, WINTER HAVEN, FL 33881 44 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2536
       Built: 2022
    Monthly Fee: $60
       Tax: $739 (2025)
    Community: Chestnut Crk
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,546 (change assumption)
    Mortgage ($2,425) + Fees ($60) + Taxes in 2025 ($62)


    Taxes:$739

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4048 PHOENICIAN WAY, WINTER HAVEN, FL 33884

    $435,000219 Days on yellowkey   MLS ID: O6361389

    REDUCED by $10,000 (2.2%) on 04/20/2026

    For Sale O6361389 - 4048 PHOENICIAN WAY, WINTER HAVEN, FL 33884 54 photos

    Bed: 3   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2354
       Built: 2007
    Monthly Fee: $5
       Tax: $8,124 (2024)
    Community: Lake Ashton West Ph 01
    Single Family


    Estimated Monthly Payment: $3,065 (change assumption)
    Mortgage ($2,384) + Fees ($5) + Taxes in 2024 ($677)


    Taxes:$8,124

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1854 ELOISE COVE DR, WINTER HAVEN, FL 33884

    $440,000153 Days on yellowkey   MLS ID: L4958664

    0 Days Off yellowkey (back on 5/23/2026)

    REDUCED by $5,000 (1.1%) on 05/19/2026

    For Sale L4958664 - 1854 ELOISE COVE DR, WINTER HAVEN, FL 33884 67 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2888
       Built: 2006
    Monthly Fee: $94
       Tax: $3,516 (2025)
    Community: Eloise Cove
    Single Family


    Estimated Monthly Payment: $2,798 (change assumption)
    Mortgage ($2,411) + Fees ($94) + Taxes in 2025 ($293)


    Taxes:$3,516

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 104 SANDERLING DR, WINTER HAVEN, FL 33881

    $419,00092 Days on yellowkey   MLS ID: O6392989

    REDUCED by $6,000 (1.4%) on 05/02/2026

    For Sale O6392989 - 104 SANDERLING DR, WINTER HAVEN, FL 33881 39 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2277
       Built: 2004
    Monthly Fee: $34
       Tax: $6,245 (2025)
    Community: Hamilton West Ph 01
    Single Family


    Estimated Monthly Payment: $2,850 (change assumption)
    Mortgage ($2,296) + Fees ($34) + Taxes in 2025 ($520)


    Taxes:$6,245

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 183 LAKE THOMAS, WINTER HAVEN, FL 33880

    $460,000127 Days on yellowkey   MLS ID: P4937839

    For Sale P4937839 - 183 LAKE THOMAS, WINTER HAVEN, FL 33880 52 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2385
       Built: 2005   Tax: $5,292 (2024)
    Community: Lake Thomas Woods Eight Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,961 (change assumption)
    Mortgage ($2,520) + Taxes in 2024 ($441)


    Taxes:$5,292

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5110 KINSLEY DR, WINTER HAVEN, FL 33884

    $420,10433 Days on yellowkey   MLS ID: S5150452

    For Sale S5150452 - 5110 KINSLEY DR, WINTER HAVEN, FL 33884 26 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3030
       Built: 2026
    Monthly Fee: $38

    Community: Seasons At Annabelle Estates
    Single Family


    Estimated Monthly Payment: $2,340 (change assumption)
    Mortgage ($2,302) + Fees ($38) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5118 KINSLEY DR, WINTER HAVEN, FL 33884

    $418,95033 Days on yellowkey   MLS ID: S5150451

    For Sale S5150451 - 5118 KINSLEY DR, WINTER HAVEN, FL 33884 26 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3030
       Built: 2026
    Monthly Fee: $38

    Community: Seasons At Annabelle Estates
    Single Family


    Estimated Monthly Payment: $2,334 (change assumption)
    Mortgage ($2,296) + Fees ($38) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 194 S LAKE MARIAM DR, WINTER HAVEN, FL 33884

    $400,000127 Days on yellowkey   MLS ID: L4959447

    For Sale L4959447 - 194 S LAKE MARIAM DR, WINTER HAVEN, FL 33884 30 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1538
       Built: 2000   Tax: $3,770 (2025)
    Community: Valencia Wood Estates First Add
    Single Family


    Estimated Monthly Payment: $2,506 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($314)


    Taxes:$3,770

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1018 BRIMSTONE CIR, WINTER HAVEN, FL 33884

    $475,00046 Days on yellowkey   MLS ID: P4938672

    For Sale P4938672 - 1018 BRIMSTONE CIR, WINTER HAVEN, FL 33884 99 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2457
       Built: 2025
    Monthly Fee: $33
       Tax: $3,218 (2025)
    Community: Harmony/Lk Eloise Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,904 (change assumption)
    Mortgage ($2,603) + Fees ($33) + Taxes in 2025 ($268)


    Taxes:$3,218

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 1757 HUMMINGBIRD RD, WINTER HAVEN, FL 33884

    $423,99041 Days on yellowkey   MLS ID: O6406366

    For Sale O6406366 - 1757 HUMMINGBIRD RD, WINTER HAVEN, FL 33884 30 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2336
       Built: 2026
    Monthly Fee: $30
       Tax: $2,632 (2025)
    Community: Harmony On Lake Eloise Phase 4
    Single Family


    Estimated Monthly Payment: $2,573 (change assumption)
    Mortgage ($2,323) + Fees ($30) + Taxes in 2025 ($219)


    Taxes:$2,632

    Elementary School: John Snively Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 1051 LENA RUN CT, WINTER HAVEN, FL 33880

    $477,555133 Days on yellowkey   MLS ID: L4959294

    1 Days Off yellowkey (back on 5/14/2026)

    For Sale L4959294 - 1051 LENA RUN CT, WINTER HAVEN, FL 33880 43 photos

    Bed: 4   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2428
       Built: 2016
    Monthly Fee: $123
       Tax: $3,613 (2025)
    Community: Hidden Creek
    Single Family


    Estimated Monthly Payment: $3,041 (change assumption)
    Mortgage ($2,617) + Fees ($123) + Taxes in 2025 ($301)


    Taxes:$3,613

    Elementary School: Eagle Lake Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 1108 SAWGRASS DR, WINTER HAVEN, FL 33884

    $422,99948 Days on yellowkey   MLS ID: S5149437

    REDUCED by $2,001 (0.5%) on 05/14/2026

    For Sale S5149437 - 1108 SAWGRASS DR, WINTER HAVEN, FL 33884 33 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1533
       Built: 2021
    Monthly Fee: $5
       Tax: $9,972 (2025)
    Community: Lake Ashton West Ph Ii South
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,154 (change assumption)
    Mortgage ($2,318) + Fees ($5) + Taxes in 2025 ($831)


    Taxes:$9,972

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1151 CAREFREE COVE DR, WINTER HAVEN, FL 33881

    $425,000212 Days on yellowkey   MLS ID: TB8450979

    REDUCED by $10,000 (2.3%) on 05/11/2026

    For Sale TB8450979 - 1151 CAREFREE COVE DR, WINTER HAVEN, FL 33881 25 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1734
       Built: 1984   Tax: $4,375 (2024)
    Community: Carefree Cove
    Single Family


    Estimated Monthly Payment: $2,693 (change assumption)
    Mortgage ($2,329) + Taxes in 2024 ($365)


    Taxes:$4,375

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2734 ROCHELLE DR, WINTER HAVEN, FL 33881

    $450,00045 Days on yellowkey   MLS ID: G5109004

    For Sale G5109004 - 2734 ROCHELLE DR, WINTER HAVEN, FL 33881 38 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2829
       Built: 2006
    Monthly Fee: $21
       Tax: $5,183 (2025)
    Community: Lake Rochelle Estates
    Single Family


    Estimated Monthly Payment: $2,919 (change assumption)
    Mortgage ($2,466) + Fees ($21) + Taxes in 2025 ($432)


    Taxes:$5,183

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 461 FISH HAWK DR, WINTER HAVEN, FL 33884

    $425,000152 Days on yellowkey   MLS ID: O6376115

    REDUCED by $10,000 (2.3%) on 05/08/2026

    For Sale O6376115 - 461 FISH HAWK DR, WINTER HAVEN, FL 33884 60 photos

    Bed: 6   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3920
       Built: 2006
    Monthly Fee: $45
       Tax: $6,577 (2024)
    Community: Hart Lake Cove Ph 02
    Single Family


    Estimated Monthly Payment: $2,922 (change assumption)
    Mortgage ($2,329) + Fees ($45) + Taxes in 2024 ($548)


    Taxes:$6,577

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6165 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884

    $469,000205 Days on yellowkey   MLS ID: P4937082

    1 Days Off yellowkey (back on 4/30/2026)

    For Sale P4937082 - 6165 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884 99 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2045
       Built: 2019
    Monthly Fee: $5
       Tax: $4,742 (2025)
    Community: Lake Ashton West Ph Ii North
    Single Family


    Estimated Monthly Payment: $2,970 (change assumption)
    Mortgage ($2,570) + Fees ($5) + Taxes in 2025 ($395)


    Taxes:$4,742

    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.