900 Lake Jessie Drive

Live the ultimate lakefront lifestyle on Lake Jessie. This beautifully maintained single-story home on a 189 acre lake on the South end of Winter Haven's famed Chain of Lakes offers a rare combination of privacy, recreation, and breathtaking views — all just minutes from downtown and a quick trip to Central Florida’s top attractions.
Key Features:
•. metal roof 2019
• Updated interior with modern finishes
• Spacious layout with 3 bedrooms and 3 bathrooms
• Open-concept living area with large windows and lake views
• Bedrooms thoughtfully separated from common areas for privacy
• East-facing rear exposure for stunning morning sunrises
• Large, flat front and back yards — ideal for games, entertaining, or outdoor yoga
• Covered patio and private dock overlooking the lake
Lake Life at Your Doorstep:
• Direct access to Lake Jessie for boating, fishing, kayaking, paddleboarding, waterskiing, wakeboarding, and barefoot skiing
• Close to multiple slalom courses and a seaplane base
• Watch bald eagles, herons, osprey, and other tropical birds from your backyard
• Cruise the Chain of Lakes to dine at on-the-water restaurants and bars
Prime Location:
• 8 minutes to downtown Winter Haven restaurants, theaters, and Central Park events
• 20 minutes to LEGOLAND
• 30–45 minutes to Walt Disney World and Universal Orlando
• Access to top-tier waterski and barefooting schools nearby

Take a look at 900 Lake Jessie Dr. The home has 3 bedrooms and 3 bathrooms and over 1800 square feet, making this move-in-ready lakefront home the perfect pick as a primary residence, vacation retreat, or investment property in the heart of Florida’s water-sports paradise. With a private entrance in-law suite, this would also make a great multi-generational house, or income possibility.

This Chain of Lakes home offers an open floor plan that offers a great split layout to allow privacy to the bedrooms. Stunning views of the lake are available from most windows in the home.
Schedule your private tour today and start living the lakefront dream!