Designed around light, views, and an effortless connection between indoor and outdoor living, 2229 Castilian Drive is perched at the top of a hillside in the highly desirable Outpost Estates in the Hollywood Hills. Throughout the home, large Fleetwood sliding glass door systems open the living spaces to expansive terraces, creating an atmosphere that feels equally suited for quiet mornings overlooking the canyon or unforgettable evenings entertaining friends. At the heart of the home, the dining room features a wall of floor to ceiling windows, giving the sensation of floating above the canyon while dining. The living spaces flow naturally outdoors, where multiple decks, a fire feature, a large hot tub, and generous gathering areas create a private retreat that feels worlds away from the city while remaining just minutes from Sunset Boulevard, The Hollywood Bowl, and the studios. Designed with wellness in mind, the outdoor experience continues with a newly constructed steam room and a large sunken tiled hot tub. A private exterior staircase connects directly to the primary suite, where a Japanese soaking tub and oversized walk-in rain shower create a true sanctuary at the end of the day. Completed in 2023, the detached ADU offers remarkable flexibility with its own entrance, full kitchen, laundry, luxury appliances, and a 120-inch 4K projection system. Whether used as guest accommodations, a creative studio, executive office, multigenerational living space, or an income-producing residence, it offers a level of independence rarely found in the Hollywood Hills. The home has been extensively enhanced by its current owners with thoughtful improvements that prioritize both comfort and convenience. Smart home technology includes Lutron lighting, distributed audio, motorized shades, motorized retractable exterior screens, DoorBird entry, AquaLink spa controls, ADT security hardware, and four-zone climate control. A new roof, tankless water heaters, Toto heated bidet toilets, custom garage cabinetry, and dual level 2 charging outlets further reflect the attention to detail found throughout the property. Blending contemporary architecture with exceptional privacy, dramatic canyon views, and a seamless indoor-outdoor lifestyle, 2229 Castilian Drive offers a rare opportunity to experience one of the Hollywood Hills’ most compelling modern residences.