Set in a peaceful, tree-filled setting just two blocks from the shops, restaurants, cafs, and everyday conveniences of downtown San Rafael, 7-9 Jessup offers the flexibility of a single-family residence with an ADU or a thoughtfully configured two-unit property. With approximately 1,575 square feet of living space, the property offers a variety of living arrangements, including owner occupancy with rental income, multigenerational living, or investment use. The main residence at 7 Jessup is a light-filled two-bedroom, one-bath unit featuring a spacious living room and open dining area that flow seamlessly to multiple outdoor living spaces. A wraparound deck, an expansive sunny patio ideal for outdoor dining and entertaining, and a shaded patio provide inviting spaces to enjoy throughout the day. Additional features include an in-unit washer and dryer, generous attic storage, and the potential to expand the attic into additional legal living space (buyer to verify). The lower residence at 9 Jessup is a charming studio with an open-concept kitchen and living area, a gas stove with the ambiance of a wood-burning fireplace, a full bath, and a private deck overlooking the surrounding trees. A dedicated laundry and storage room adds everyday convenience. Each unit has its own private driveway, providing flexibility and convenience. A bus route and dedicated bike lane are just steps away, while the Marin Transit Center and SMART Train station are approximately one mile from the property. Surrounded by mature trees, including magnificent Valley Oaks estimated to be approximately 200 years old, the property offers a unique natural setting. Beneath the tree canopy, a generous level terrace provides space for outdoor entertaining, gardening, relaxing, or enjoying the surrounding landscape. This versatile area may also offer opportunities for future improvements, including a potential ADU, detached office, fitness studio, or creative workspace (buyer to verify development potential). Combining flexible living options, inviting indoor-outdoor spaces, and a convenient location near downtown San Rafael, 7-9 Jessup presents a rare opportunity to enjoy the best of Marin living while offering a range of possibilities for future use.