If you’re disappointed about missing out on America’s priciest home in Southwest Florida listed for $295 million, there’s still an opportunity to consider the next best thing in Naples. Available now is a recently remodeled penthouse priced at nearly $33 million, potentially setting a record for the highest resale unit in the affluent area.

An elevator lobby opening to the foyer.
The dining area.
The kitchen.
The family room.
An outdoor kitchen off the main living area.
A morning room.
The primary bedroom.
A spa surrounded by a “living” wall on the primary terrace.
One of two primary bathrooms.
A dressing area.
A sauna-equipped fitness studio.
The study.
The Seasons at Naples Cay.
An aerial view of the property.

Previously purchased for $11 million in fall 2022, the residence underwent extensive renovations led by Dick Portillo, the founder of Portillo’s restaurant chain. Collaborating with C&E Builders and Theory Design’s Ruta Menaghlazi, Portillo transformed the 2002-built penthouse located on the 20th floor of The Seasons at Naples Cay. Marketed by The Earls | Lappin Team of John R. Wood Christie’s International Real Estate, the luxurious abode offers nearly 12,000 square feet of living space with five bedrooms and seven baths.

The living room.

Highlights of the penthouse include herringbone oak floors, high ceilings, and designer lighting throughout. Floor-to-ceiling glass walls and over 4,800 square feet of outdoor terraces provide breathtaking panoramic views from the Gulf of Mexico and Outer Clam Bay to the city lights of Naples. The interior features an elevator-accessible foyer leading to an open-plan great room encompassing a fireside living room, dining area, and a gourmet kitchen with champagne eucalyptus cabinetry, white Macaubas quartzite countertops, and top-tier Miele appliances.

A fireside lounge area.

The master wing offers a water vapor fireplace, wraparound balcony with a spa, morning lounge, sauna-equipped fitness studio, and dual dressing rooms and baths. Additional amenities include four en-suite bedrooms, a backlit onyx entertainment bar, glass-encased wine vault, and a study with a fireplace. Community perks encompassed in the $11,563 monthly HOA fee feature a guard-gated entry, 24-hour doorman, swimming pool, fitness center, and billiards room.

An entertainment bar.

Portillo, a self-made billionaire and seasoned real estate investor, also owns another condo in Naples and has undertaken numerous property renovations in the Chicago area.

A glass-encased wine vault.
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