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900 LAKE JESSIE DRIVE

Winter Haven, FL, 33881

Active

$425,000

3

Bedrooms

3

Bathrooms

1,828 sqft

Living Area

1948

Year Built

16,365

Lot Size (sqft)

151

Days on Market

Dock Score™

DockOnly
50
Fair

What shaped this score

Ocean Access
Dock present
Fits boats up to ~60ft (est.)
deep water, private dock

DockOnly.com rating, not provided by the MLS or listing broker.

Dock & Water AccessMLS

Lake - Chain of Lakes

AI Aerial Imagery Detection

Dock DetectedSeawall DetectedDeep Water Indicators~51-69 ft dock

Detected by AI from open-source aerial mapping imagery and may not reflect current conditions. This information was not provided by the MLS or listing broker. Always verify dock infrastructure with the listing agent.

Navigation RouteDockOnly

Data sources: SFWMD AHED waterway polygons · FHWA National Bridge Inventory 2024 · Not provided by the MLS or listing broker.

Description

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!

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Location

Winter Haven, FL, 33881

No price history available for this property.

Displayed by Blue Mar Real Estate Group Inc., Licensed Florida Real Estate Broker (DBPR CQ1018554) · [email protected]

Listing courtesy of RE/MAX HERITAGE PROFESSIONALS via Stellar MLS

Last checked: 11 hours ago

Listing updated: August 26, 2026

© 2026 Stellar MLS. All rights reserved. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) program of Stellar MLS. Information is deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change, or withdrawal.

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FEMA Flood Zone X

Minimal Flood Hazard

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Mortgage Calculator

Estimate your monthly payment for this waterfront property

20%

$85,000 down

%
Principal & Interest$2,205/mo
Property Tax (est. ~1.2%, varies by county)$425/mo
Home Insurance (est.)$250/mo
Total Monthly Payment$2,880
Loan Amount: $340,000Rate: 6.75%
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$425,000Tour the dockSchedule a Showing
Navigation note: Navigation routes show the shortest mapped path to open water. A vessel taller than the binding bridge clearance may still reach open water via a longer alternate route that we don't currently map. Verify navigability with a local captain or surveyor before relying on it.