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About this home
4099 Island Lakes Dr is a 2006-built home in Island Lakes, Winter Haven. Inside you'll find 3 bedrooms, 2 bathrooms, and 1,603 square feet of living space. Listed at $379,000 (about $236/sqft), 562 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $50 quarterly.
One or more photo(s) has been virtually staged. NEW ROOF 2/9/2026 + $10K PRICE IMPROVEMENT on 7/24! Now offered at another improved price, this waterfront home on Lake Rochelle delivers the best value currently available on the Winter Haven Chain of Lakes. Located in the desirable Island Lakes community, this well-maintained 3-bedroom, 2-bath home combines lakefront living, major recent updates, and everyday functionality. A brand new roof was installed in February 2026, offering added peace of mind and potential insurance advantages for the next owner. Fresh landscaping and new sod create excellent curb appeal, while the open split-bedroom floorplan provides comfortable living with beautiful natural light throughout. The spacious primary suite overlooks the water and includes a private bath and walk-in closet. The living and dining areas flow easily into the kitchen, making the home ideal for entertaining, weekend guests, or simply enjoying the lake lifestyle. Step outside and enjoy direct access to the Chain of Lakes with boating, fishing, kayaking, and sunset views right from your backyard. Conveniently located near shopping, dining, medical facilities, and major roadways while still offering a peaceful waterfront setting. Whether you’re looking for a primary residence, winter retreat, or investment opportunity, this property checks all the boxes for Florida lakefront living. Schedule your private showing today.
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The essentials
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Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.
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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. HOA includes any condo dues reported on the listing. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.
Quick answers.
Price
$379,000
$236 per sq ft
Beds and baths
3 beds, 2 baths
Size
1,603 sq ft
Time on market
562 days
Year built
2006
Monthly payment
About $2,616/mo
That is 20% down on a 30-year fixed at 6.8%, plus the home's $5,194 annual tax bill, insurance, and the $50/qtr HOA fee.
HOA fee
$50/qtr
Managed by Highland Community.
Flood zone
Zone X
That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.
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