One or more photo(s) has been virtually staged. 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 & 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 & other beautiful wildlife. The home itself offers a thoughtfully designed single-story layout with over 1,800 square feet, featuring 3 bedrooms & 3 bathrooms. An open-concept living space is filled with natural light and showcases stunning lake views, while a split-bedroom design provides comfort & 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 its oversized driveway & 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 & 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 & unwind in one of Florida’s most iconic lakefront settings. Book your showing today!
- Built in 1948
- $224.29/sqft
- Lot size: 16,365 sqft
- 166 days on market
- Directions: 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.
- County: Polk
- Geo subdivision: EAST VIEW PKWY
Nearby Schools
Auburndale Central Elem
Westwood Middle
Auburndale High School
Features
Interior
Exterior
Utilities
Structure
Pets, Accessibility & Amenities
Financial
Lease Information
Tax, Legal & Financing
Let's get in touch!
Let's get in touch!

Steven Koleno
Consumer-First Real Estate Architect
- Source: Stellar MLS
- MLS #: S5146723
Listing updated: September 10, 2026 at 3:29PM
Listing provided by: Patricia De Graaff, LLC, RE/MAX HERITAGE PROFESSIONALS
Last checked 4 hours ago
Listing provided by: Patricia De Graaff, LLC, RE/MAX HERITAGE PROFESSIONALS
Last checked 4 hours ago
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.







