A rare Jefferson Park offering: two vacant separate craftsman bungalows on one lot, each with its own address. This is not a primary residence with a later-added ADU, but rather two distinct homes offering exceptional flexibility for rental income, multigenerational living, guests, or a dedicated work-from-home retreat. The spacious 3 bedroom plus an office front home pairs its original Craftsman exterior with a thoughtful modern interior update, creating an airy, open layout with soaring vaulted ceilings, beautifully updated living spaces, and abundant natural light from period windows. The kitchen opens to a generous deck for easy indoor-outdoor living, while multiple bedrooms, including a private primary suite and several flexible rooms provide space for family, guests, work, and play. Tucked behind the main house, the separate one-bedroom residence is filled with lovingly preserved period character, including original wood floors, built-ins, substantial crown moldings, period light fixtures, and an impressive original Murphy bed. With its own private entrance, kitchen, bath, laundry, and outdoor space, it offers everything buyers often seek in an ADU income potential, independence, and privacy already built as a legal second residence, without the need to create or permit an additional dwelling unit. Another, separate, bonus structure is divided into two private spaces, giving each residence its own additional space outside the home. Use each as an art or design studio, home office, yoga or workout room, workshop, creative retreat, or simply exceptional storage. Both homes feature updated plumbing and electrical systems, laundry, central heat and AC, and separate meters. The backyard is shaded by mature, fruit-bearing Hass avocado trees and can remain open as one shared garden, or be divided to create distinct private outdoor spaces for each residence. Perfectly situated near USC, Culver City, and Downtown Los Angeles, with easy Metro access, the property is also close to neighborhood favorites, including Fuegos, Johnny's Pastrami, Cafe 5, and the Papi's Tacos walk-up window. Set within the Jefferson Park Historic Preservation Overlay Zone, this is a true urban retreat with the flexibility buyers are searching for: live in one and rent the other, accommodate extended family, or enjoy two completely separate homes on one historic Los Angeles property. Also listed as an income property, MLS #26908829.