An exceptional offering of two adjacent, detached homes tucked away on a private cul-de-sac on Telegraph Hill - functioning as a primary residence plus guest cottage. Entering through a gated front garden to 69 Telegraph Place, this home offers a fabulous dining room with Bay views, an inviting den with fireplace, an updated kitchen with deluxe appliances, a pantry and a breakfast area. The primary suite boasts 4 closets and a lovely ensuite bath. On the upper level is a spectacular family/living room with fireplace and a walk-out deck with Bay and Alcatraz views. Around the corner is a private view office, and a sunny, south-facing deck. On the lower level are 2 bedrooms, an attractive bath with shower, laundry room, wine storage, and a 2-car garage. 339 Lombard Street presents an inviting studio, complete with a built-in Murphy bed, gas fireplace, full kitchen, and a renovated bath with shower. Downstairs is a multi-use room with laundry and a wet bar, opening to a serene brick garden with a cascading fountain. Upstairs showcases an expansive landscaped roof terrace, featuring sweeping Bay views. Whether paired as a main residence with a guest cottage, or a multi-generational living opportunity or studio workspace, this is a rare gem in San Francisco's most iconic neighborhood.