Perched atop the coveted north slope of Telegraph Hill, this exceptional San Francisco compound offers breathtaking views of Coit Tower, the San Francisco Bay, the Golden Gate Bridge, the Bay Bridge, the TransAmerica Pyramid, and Downtown. Set on an oversized lot with dual street frontage on Chestnut and Whiting Street, this rare property includes a 3-bed, 3-bath main house and a 1-bed, 1-bath guest cottage, both fully detached for abundant natural light and sweeping views. The main house features a sunlit interior with rich hardwood floors, a south-facing kitchen with walls of glass, and a stunning roof deck showcasing panoramic 360-degree views. The guest cottage includes a full kitchen and a dedicated home office, ideal for remote work. A private courtyard oasis separates the two residences, creating a serene retreat. Additional highlights include a 2-car garage, a rare luxury in this location. Just steps from Coit Tower, North Beach, and the SF waterfront, this home is surrounded by world-class dining, parks, and cafes. Offering an unparalleled blend of elegance, privacy, and iconic views, this is a one-of-a-kind opportunity in one of San Francisco's most desirable neighborhoods.