400 Flagship DR

About this Property

AN EXCEPTIONALLY RARE NAPLES OFFERING! This three-bedroom Regatta penthouse brings together sweeping Gulf and bay views, a short walk to the beach, a pet-friendly community and a private two-car garage—a combination that’s hard to find in Naples. Add the opportunity for private beach club membership and boat slips available separately, and you have a place to enjoy the Naples lifestyle from the water to the sand.  Perfectly positioned on the top floor, this captivating residence showcases unobstructed water views, soaring 10.5-foot ceilings and floor-to-ceiling sliders that fill the home with natural light. The open-concept kitchen, dining and living areas flow effortlessly onto the expansive lanai, creating an ideal setting for relaxing, entertaining and enjoying unforgettable sunsets. Enhanced with new light fixtures and accessories, the residence is meticulously maintained and offered beautifully turnkey furnished with a refined tropical-coastal flair. Regatta’s outstanding amenities include a gated entry, resort-style waterfall pool, grilling area and 55-slip marina for boating enthusiasts. Enjoy an extraordinary walk-to-the-beach lifestyle near Vanderbilt Beach, Delnor-Wiggins Pass State Park, The Ritz-Carlton, tennis and pickleball courts, restaurants, entertainment and more. Regatta is also pet-friendly. AND THE DEAL GETS EVEN BETTER: The buyer has the opportunity to become a member of Paraíso Beach Club at Vanderbilt Beach, an exciting new private club planned around beachfront service, Gulf-view dining, saltwater pools, wellness experiences and member events. Imagine a day on the sand followed by a sunset dinner just moments from home. This opportunity comes with no initiation fee or transfer fee, and a special membership fee—an extraordinary addition to the Naples coastal lifestyle.

Listing Details

MLS #

226034232

Board

Southwest Florida

Market

florida

Property Type

Residential

Style

High Rise (8+)

Year Built

2000

Garage Spaces

2

Parking Spaces

2

Heating

Central Electric

Cooling

Ceiling Fan(s), Central Electric

Pool

Community

Annual Taxes

$13,106/yr

Maint. Fee

$18,484/mo

Listed By

William Raveis Real Estate

Listed On

September 23, 2026

Days on Market

7

Features & Extras