Introducing a generational opportunity to own two of the most desirable penthouse units at Anacapa Villas that seamlessly blends into one, creating one of the most unique downtown compounds to ever hit the market. Behind a private gated entrance in the heart of downtown, two contemporary single level penthouses come together to create a compound of 5 bedrooms, 5 baths, approximately 5,779 square feet of living space and over 800 sq. ft. of 3 separate outdoor patio spaces with expansive views from each one. An elevator rises from the 2-car garage directly into the home, so every arrival is completely private. The 3 bed 3 bath 3,762 sq. ft. penthouse is among the largest single units in downtown Santa Barbara. It features an open floor plan with large living spaces, two living rooms, a dedicated office space, a direct view of the American Riviera from your patio, and dramatic finishes throughout. The chef's kitchen is made for entertaining, with custom cabinetry, an oversized island with granite counters, and professional-grade stainless appliances, including a Viking range. The primary bath is a true spa retreat, the size of a bedroom with Kohler infinity-edge sinks and a large walk in shower. The 2,017 sq. ft. upper unit penthouse offers 2 bedrooms and 2 baths in an equally open contemporary design. It features wood floors, a living room fireplace, a gourmet kitchen with a large island and pantry, and graceful patios at each end frame sweeping views of the Riviera, the city, and peeks of the ocean. Together, the two residences are ideal for multigenerational living, a private guest wing, a home office or studio, or simply an unmatched lock-and-leave lifestyle. Located one block from State Street, cafés, galleries, and acclaimed dining, and just five blocks from East Beach, the Funk Zone, and Stearns Wharf. Don't miss this generational opportunity to own one of Santa Barbara's most iconic penthouse offerings.