# 4099 ISLAND LAKES Drive, Winter Haven, FL 33881 > **TL;DR:** 3bd/2ba single family, $379,000 ($236/sqft), built 2006, 1,603 sqft. > Waterfront, View, A/C, 2-car garage. Est. $2,027/mo. Listed 575 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $379,000 | | Price/sqft | $236 | | Bedrooms | 3 | | Bathrooms | 2 full | | Square Feet | 1,603 | | Year Built | 2006 | | Lot Size | 17,424 sqft (0.40 acres) | | Stories | 1 | | Garage | 2-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 575 | ## Why This Home Stands Out - **Waterfront** - Waterfront location listed - **Views** - Lake ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $1,916 | | Estimated Insurance | $111 | | **Total** | **$2,027** | ## Key Amenities - Waterfront - View - A/C - 2-car garage ## Property Highlights - Built in 2006 - 0.40 acre lot - Waterfront ## Description ### Agent Description 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. ## Location - **Address:** 4099 ISLAND LAKES Drive, Winter Haven, FL 33881 - **County:** Polk - **Neighborhood:** ISLAND LAKES - **Coordinates:** 28.067429, -81.726016 - **Google Maps:** https://www.google.com/maps?q=28.067429,-81.726016 ## Virtual Tour & Media - **Video Tour:** https://www.propertypanorama.com/instaview/stellar/P4934266 ## Listing Agent - **Name:** Don Jerue - **Brokerage:** Smart Realty of Winter Haven LLC - **Broker Phone:** (863) 508-3000 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/4099-Island-Lakes-Dr_Winter-Haven_FL_33881_M69986-57642?f=listhub&s=MFRMLSFL&m=P4934266&c=propsimple) ## Photos ![4099 ISLAND LAKES Drive - Photo 1](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f1526379858r.jpg) ![4099 ISLAND LAKES Drive - Photo 2](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f2952061450r.jpg) ![4099 ISLAND LAKES Drive - Photo 3](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f1874607324r.jpg) ![4099 ISLAND LAKES Drive - Photo 4](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f1052536522r.jpg) ![4099 ISLAND LAKES Drive - Photo 5](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f1666829114r.jpg) ![4099 ISLAND LAKES Drive - Photo 6](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f4234417918r.jpg) ![4099 ISLAND LAKES Drive - Photo 7](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f1587877753r.jpg) ![4099 ISLAND LAKES Drive - Photo 8](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f2855081529r.jpg) ![4099 ISLAND LAKES Drive - Photo 9](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f1068503419r.jpg) ![4099 ISLAND LAKES Drive - Photo 10](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f3963094908r.jpg) ![4099 ISLAND LAKES Drive - Photo 11](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f2278382624r.jpg) ![4099 ISLAND LAKES Drive - Photo 12](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f4272065216r.jpg) ![4099 ISLAND LAKES Drive - Photo 13](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f2995076952r.jpg) ![4099 ISLAND LAKES Drive - Photo 14](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f4081013704r.jpg) ![4099 ISLAND LAKES Drive - Photo 15](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f1842867011r.jpg) ![4099 ISLAND LAKES Drive - Photo 16](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f2910648265r.jpg) ![4099 ISLAND LAKES Drive - Photo 17](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f2105186393r.jpg) ![4099 ISLAND LAKES Drive - Photo 18](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f1154258682r.jpg) ![4099 ISLAND LAKES Drive - Photo 19](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f824242220r.jpg) ![4099 ISLAND LAKES Drive - Photo 20](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f2299798064r.jpg) ![4099 ISLAND LAKES Drive - Photo 21](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f2475747140r.jpg) ![4099 ISLAND LAKES Drive - Photo 22](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f3936968246r.jpg) ![4099 ISLAND LAKES Drive - Photo 23](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f2698868534r.jpg) ![4099 ISLAND LAKES Drive - Photo 24](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f4188373900r.jpg) ![4099 ISLAND LAKES Drive - Photo 25](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f3250848003r.jpg) ![4099 ISLAND LAKES Drive - Photo 26](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f1393232258r.jpg) ![4099 ISLAND LAKES Drive - Photo 27](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f3637009308r.jpg) ![4099 ISLAND LAKES Drive - Photo 28](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f4116470612r.jpg) ![4099 ISLAND LAKES Drive - Photo 29](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f1923107159r.jpg) ![4099 ISLAND LAKES Drive - Photo 30](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f1511010752r.jpg) ![4099 ISLAND LAKES Drive - Photo 31](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f1602310150r.jpg) ![4099 ISLAND LAKES Drive - Photo 32](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f457021775r.jpg) ![4099 ISLAND LAKES Drive - Photo 33](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f1917376749r.jpg) ![4099 ISLAND LAKES Drive - Photo 34](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f1884784760r.jpg) ![4099 ISLAND LAKES Drive - Photo 35](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f3937044118r.jpg) ![4099 ISLAND LAKES Drive - Photo 36](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f1785347659r.jpg) ![4099 ISLAND LAKES Drive - Photo 37](http://lh.rdcpix.com/48a65a7482e0fb6c2334e146c9508de5l-f591762181r.jpg) --- **MLS#:** P4934266 | **Updated:** 2026-10-25 **Source:** listhub *Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://staging.propertysimple.ai/listing/4099-island-lakes-drive-winter-haven-fl-33881-41e8fe808a22405d9537564fdff00f83) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/4099-island-lakes-drive-winter-haven-fl-33881-41e8fe808a22405d9537564fdff00f83#listing", "url": "https://staging.propertysimple.ai/listing/4099-island-lakes-drive-winter-haven-fl-33881-41e8fe808a22405d9537564fdff00f83", "name": "4099 ISLAND LAKES Drive, Winter Haven, FL 33881", "description": "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. 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