Truly one of a kind, this exceptional home is nestled on a charming tree-lined street. It's just a short walk to vibrant downtown San Mateo, known for its excellent restaurants, shopping & nearby Central Park. Blending timeless character with modern comfort, the home offers a spacious & highly versatile floor plan with multiple living areas. The main level welcomes you through a striking carousel-shaped entry that opens to a bright & inviting living room, a formal dining room, office, full bathroom, and laundry room. The open kitchen flows seamlessly to the beautifully landscaped backyard. Upstairs are two spacious bedrooms, an additional full bathroom & a cozy bonus room currently used as a nursery. The lower level features an expansive bonus space with a full bathroom, dining area & a kitchenette (without stove). This flexible area is ideal for guests, a family or media room, or potential rental use. Outside, the property offers beautifully landscaped front & back yards, along with a long, gated, driveway leading to a large detached two-car garage. Above the garage is a charming, light-filled one-bedroom in-law unit, adding even more flexibility to this remarkable property. With its unique character, generous space and prime location, this special home is not to be missed.