Welcome to 28 Caballeros Rd - a rare offering in the gated hillside enclave of Rolling Hills, where sprawling parcels, hiking and horse trails, and lush greenery set the stage for true resort-style living above the clouds. This exceptional 5,874 sq ft estate (4,727 sq ft main house plus a ~1,147 sq ft guest house) offers 5 bedrooms and 5.75 baths, fully reimagined by Kim Lapin Interiors and Canyon Homes in a modern Montecito Ranch aesthetic. Enter through a private courtyard with a running fountain into a home defined by vaulted ceilings and thoughtful flow throughout. Curated natural, vintage, and hand-crafted finishes are found at every turn - Calacatta Viola marble, solid white oak and walnut cabinetry with unlacquered brass and polished nickel hardware, zellige and sand-cast brick, warm hardwood floors, and four fireplaces. A formal living room opens directly to the stunning backyard, with views of the Queen's Necklace and twinkling city lights setting the tone for indoor-outdoor living. The North side of the home holds the kitchen, dining, and family living room - a warm, easy space built for lazy days together. The chef's kitchen features double ovens and a sunny breakfast nook, opening naturally into the family room beyond. The South side offers four bedrooms, each with its own ensuite bath for maximum privacy. The primary suite is a true sanctuary, with soaring vaulted ceilings and natural light pouring in, its own fireplace, a walk-in closet, and a spa-like primary bath designed for a quiet retreat. Downstairs, a bonus den awaits with a projector screen, bar area, and direct access outside, along with a laundry room and additional office space. The existing ADU - which includes the 5th bedroom, bath, and kitchenette with sweeping views - was expanded by 500 sq ft. The result is a fully built-out gym with white oak floors, mirrored walls, and minimal-frame Titoni sliding doors opening to views of the horse corral. Outside, enjoy a fenced yard with pool, spa, fire pit, and BBQ area, plus full horse facilities and direct access to the Purple Canyon trail - a true equestrian and entertainer's dream in one of the South Bay's most coveted communities.