Nestled on quiet, tree-lined Highland Avenue, just blocks from the sand, this gated compound blends historical character with modern upgrades across two distinct structures. The main residence is a two-story, four-bedroom, two-bath home of approximately 1,750 sq ft, capped by a private rooftop terrace with beautiful views. Across the courtyard from the main house stands a charming duplex built in 1989 boasting two single-level two-bedroom apartment homes, crowned by a shared 628 sq ft roof lounge that offers city, treetop, mountain, and partial Pacific views. Over the past several years, the duplex has undergone significant renovations: updated kitchens and baths, new windows, plumbing, electrical, HVAC, roofing, sundeck renewal, and refreshed landscaping. Each unit is separately metered for gas and electricity and equipped with separate water heaters, simplifying cost allocation. Both units are currently rented for $3,650 (2 bed 1 bath) and $3,750 (2 bed 2 bath) respectively, guaranteeing rental income from the onset. On the ground level of the rear building, you'll also find an unpermitted studio with 3/4 bath, perfect for a home office, guest suite, or potential permitting project. The existing four-car garage presents a unique opportunity for conversion to an ADU apartment, subject to City of Santa Monica approval. Outdoor living is prioritized through multiple private terraces, lush planting beds, and the expansive ocean-view roof deck, ideal for sunsets or weekend gatherings. The property is a short walk to Main Street cafes, Venice tech offices, local parks, and top-rated Santa Monica schools. Foundation and general inspection reports are on file and will be provided to verified parties upon request. Virtual tour is of the back two full level apartments and studio unit. Main house, front and back yard are in the virtual tour.