900 LAKE JESSIE DRIVE WINTER HAVEN, FL 33881
update time: 04/11/2026 18:05:05
Welcome to a place where everyday life feels like a getaway. Set along the peaceful shores of Lake Jessie, part of Winter Haven’s renowned Chain of Lakes, this lakefront retreat is more than just a home, it’s a lifestyle defined by water, sunshine, and unforgettable experiences. Start your mornings with breathtaking sunrises shimmering across the lake, coffee in hand from your private dock or patio. Spend your days exactly how you choose, cruising the Chain of Lakes by boat, casting a line in some of Central Florida’s best freshwater fishing, or enjoying world-class watersports like skiing, wakeboarding, and paddleboarding right from your backyard. With nearby slalom courses and open water, this is truly a paradise for water enthusiasts. Lake Jessie is especially cherished for its tranquil atmosphere, offering a rare sense of calm while still being full of life. One of its most unique features is the seaplane activity, where you can watch planes gracefully land and take off across the water, an experience that never gets old and adds to the charm of lakeside living. Nature lovers will also appreciate the frequent sightings of all kinds of birds and other beautiful wildlife. The home itself offers a thoughtfully designed single-story layout with over 1,800 square feet, featuring 3 bedrooms and 3 bathrooms. An open-concept living space is filled with natural light and showcases stunning lake views, while a split-bedroom design provides comfort and privacy. A private in-law suite with its own entrance adds flexibility for guests, multi-generational living, or additional income potential. This residence offers plenty of parking space with it's oversized driveway and an additional carport providing covered parking as well. The home has been updated with modern finishes and includes a metal roof installed in 2019. This home would make a perfect full time residence, investment property or second home. Beyond the water, the location is just as appealing. You’re right around the corner from a brand new Publix store and minutes from the heart of Winter Haven, where you’ll find charming local restaurants, shops, parks, and community events. Legoland Florida Resort is just a short drive away and there is convenient access to both Tampa and Orlando, so world-class attractions, dining, and entertainment are always within reach. Whether you're seeking adventure, relaxation, or a smart investment, this Lake Jessie property delivers it all, offering the rare opportunity to live, play, and unwind in one of Florida’s most iconic lakefront settings. Book your showing today!
From Havendale Blve NW in Winter Haven, turn right onto Jersey Rd, turn right onto E Derby Ave, turn left onto Lake Jessie Dr. Property will be on your right.
Property Details
Location
+Interior Features
+Exterior Features
+School
+Additional Information
+Nearby Properties
Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website comes in part from the Stellar MLS. Listings identified with the Stellar MLS logo are not necessarily those of the website owner. If you believe any Stellar MLS listing contains material that infringes your copyrighted work, please click hereto review the Stellar MLS DMCA policy and learn how to submit a takedown request. © 2026 Stellar MLS. All rights reserved. Stellar MLS data last updated at 2026-04-11 18:05:05. For issues with IDX contact stdreamer123@gmail.com