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For sale
    • $399,000

    4099 Island Lakes Dr, Winter Haven, FL 33881

    3beds
    1,603sqft
    : 
    Single Family Residence
    Built in 2006
    0.4 Acres Lot
    $-- Zestimate®
    $249/sqft
    $17/mo HOA

    What's special

    Enhances curb appealDirect lake accessBreathtaking waterfront viewsGenerous closet space
    One or more photo(s) has been virtually staged. NEW ROOF 2/9/2026 + $40,000 PRICE IMPROVEMENT! Lakefront living on the Chain of Lakes just became an incredible opportunity. Welcome to 4099 Island Lakes Dr — a well-maintained 3 bedroom, 2 bath block home offering breathtaking waterfront views and direct access to the Chain of Lakes. Major updates already handled with a brand new roof installed February 9, 2026, giving buyers peace of mind and potential insurance benefits. Combine that with a significant $40K price reduction, and this property stands out in today’s market. Inside, you’ll find a bright and open layout filled with natural light. The spacious living area flows seamlessly into the kitchen and dining space, ideal for entertaining or relaxing after a day on the water. The primary suite features beautiful lake views, a private bath, and generous closet space. Step outside to freshly installed sod and updated landscaping that enhances curb appeal and creates the perfect setting for outdoor gatherings. With direct lake access, enjoy boating, fishing, kayaking, and stunning sunset views right from your backyard. Whether you're searching for a full-time residence, seasonal escape, or lakefront investment, this Chain of Lakes home offers location, lifestyle, and value. Schedule your private showing today.
    378 days
    |
    437
    |
    32
    |

    Zillow last checked:

    Listing updated:

    Listing Provided by:

    Don Jerue 863-259-9550,

    KELLER WILLIAMS REALTY SMART 1 863-508-3000

    Source: Stellar MLS,MLS#: P4934266MLS LogoOriginating MLS: East Polk

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 2
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: First
      Bedroom 2
      • Features: Built-in Closet
      • Level: First
      Bedroom 3
      • Features: Built-in Closet
      • Level: First
      Kitchen
      • Level: First
      Living room
      • Level: First
      Heating
      • Central
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Microwave, Range, Refrigerator
      • Laundry: Inside
      Features
      • Cathedral Ceiling(s), Ceiling Fan(s), In Wall Pest System, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Split Bedroom, Vaulted Ceiling(s), Walk-In Closet(s)
      • Flooring: Laminate
      • Has fireplace: No
      Interior area
      • Total structure area: 2,252
      • Total interior livable area: 1,603 sqft
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      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage - Attached
      • Attached garage spaces: 2
      Features
      • Levels: One
      • Stories: 1
      • Patio & porch: Covered, Front Porch, Rear Porch, Screened
      • Exterior features: Lighting
      • Has view: Yes
      • View description: Lake
      • Has water view: Yes
      • Water view: Lake
      • Waterfront features: Lake - Chain of Lakes, Lake Privileges, Skiing Allowed
      • Body of water: LAKE ROCHELLE
      Lot
      • Size: 0.4 Acres
      • Features: City Lot
      Details
      • Parcel number: 262809530005000430
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Block, Stucco
      • Foundation: Slab
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 2006

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Electricity Connected, Water Connected

      Community & HOA

      Community
      • Pet fee: $0 monthly
      • Subdivision: ISLAND LAKES
      HOA
      • Has HOA: Yes
      • HOA fee: $17 monthly
      • HOA name: Highland Community
      • HOA phone: 863-940-2863
      Location
      • Region: Winter Haven

      Financial & listing details

      • Price per square foot: $249/sqft
      • Tax assessed value: $272,497
      • Annual tax amount: $5,193
      • Date on market: 4/1/2025
      • Cumulative days on market: 378 days
      • Listing terms: Cash,Conventional,FHA,VA Loan
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved
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        Estimated market value

        Not available

        Estimated sales range

        Not available

        $1,828/mo

        Price history

        Price history
        DateEventPrice
        10/7/2025Price change$399,000-2.4%$249/sqft
        Source: Stellar MLS #P4934266 Report a problem
        5/27/2025Price change$409,000-6.8%$255/sqft
        Source: Stellar MLS #P4934266 Report a problem
        4/1/2025Listed for sale$439,000-5%$274/sqft
        Source: Stellar MLS #P4934266 Report a problem
        7/11/2024Listing removed$462,000$288/sqft
        Source: Stellar MLS #P4928402 Report a problem
        4/30/2024Listing removed--
        Source: Zillow Rentals Report a problem
        4/2/2024Listed for rent$2,200$1/sqft
        Source: Zillow Rentals Report a problem
        2/6/2024Price change$462,000-3.5%$288/sqft
        Source: Stellar MLS #P4928402 Report a problem
        12/11/2023Listed for sale$479,000+40.9%$299/sqft
        Source: Stellar MLS #P4928402 Report a problem
        10/24/2023Sold$340,000+3%$212/sqft
        Source: Stellar MLS #P4927062 Report a problem
        10/2/2023Pending sale$330,000$206/sqft
        Source: Stellar MLS #P4927062 Report a problem
        8/23/2023Listed for sale$330,000+19.8%$206/sqft
        Source: Stellar MLS #P4927062 Report a problem
        8/27/2007Sold$275,400$172/sqft
        Source: Public Record Report a problem

        Public tax history

        Public tax history
        YearProperty taxesTax assessment
        2024$5,194 +5.9%$272,497 +9.6%
        2023$4,907 +7.5%$248,523 +10%
        2022$4,562 +10.1%$225,930 +10%
        2021$4,145 -1.3%$205,391 -0.7%
        2020$4,200 +6.9%$206,893 +9.2%
        2019$3,929 $189,505 +2.9%
        2018$3,929 +2.5%$184,187 +10.8%
        2017$3,834 +23.1%$166,298 +7.7%
        2016$3,114 +7.4%$154,361 +9.3%
        2015$2,900 +12.9%$141,172 +9.5%
        2014$2,569 +3.9%$128,970 +10%
        2013$2,471 +7.3%$117,245 +7.1%
        2012$2,304 -24.1%$109,503 -23.5%
        2011$3,037 -3.9%$143,234 -2.6%
        2010$3,159 -9.1%$147,132 -5.5%
        2009$3,474 -22.5%$155,691 -26.4%
        2008$4,480 $211,395
        2007-- --
        2006$1,207 --

        Find assessor info on the county website

        Monthly payment

        Est. payment
        $2,482/mo
        Principal & interest
        $1953
        Property taxes
        $512
        HOA Fees
        $17
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          Climate risks

          Neighborhood: 33881

          Getting around

          9 / 100
          Car-Dependent
          41 / 100
          Somewhat Bikeable

          Nearby schools

          GreatSchools rating

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