Some waterfront homes in the Florida Keys come with a swimming pool and a dock. This sprawling compound in Tavernier, however, takes things several steps further with two residences, a protected marina basin, a 120-foot-long swimming pool, and 480 linear feet of ocean frontage. Positioned between Key Largo and Islamorada, the property is surrounded by bird sanctuaries, protected wildlife areas, and some of the region’s best boating and snorkeling waters. It’s also a short drive from the record-setting estate purchased by Barstool founder Dave Portnoy in 2025.

Spread across two adjoining parcels, the tropical retreat combines a recently completed contemporary mansion with a separate guesthouse, or caretaker’s residence. Altogether, the compound includes eight bedrooms, eight full bathrooms, and three half baths across more than 9,700 square feet. 

The primary home spans roughly 8,200 square feet with five bedrooms, six full bathrooms, and two powder rooms. Interiors are finished with white diamond marble, teak flooring, custom millwork, and walls of glass that frame the waterfront setting, while smart-home technology controls everything from the lighting to security and sound systems. Standout features include a vapor fireplace anchoring the main living area and an elevator connecting the home’s multiple levels.

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Just off the double-height living room, the kitchen is designed for both everyday living and entertaining, with two islands, dual dishwashers, a pair of farmhouse sinks, refrigerated drawers, wine storage, and custom mahogany countertops. Nearly every room opens onto covered terraces with sweeping water views.

Outside, the grounds are anchored by a dramatic 120-foot swimming pool equipped with spa features as well as both heating and cooling systems. A summer kitchen, cabana bath, and multiple lounge areas are thoughtfully spread across the property.

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In addition to a renovated three-bedroom, two-and-a-half-bath guesthouse completed in 2022, the secondary parcel spans more than three acres and includes a separate buildable lot, along with transferable development rights that could allow a future owner to expand the estate with an even larger primary residence.

For boating enthusiasts, the marina infrastructure may be the biggest draw. The protected basin currently offers 90 feet of dockage with room for expansion, as well as a 20,000-pound lift, a private boat ramp, and direct deep-water access to the ocean.

The property is listed for $40 million with Angel Nicolas and Courtney Conley of The Nicolas Group at Serhant.

Click here to see more photos of the oceanfront Florida Keys compound.