Set on an oversized lot in prestigious Ingleside Terraces, 440 Monticello Street offers the perfect balance of classic Spanish Mediterranean architecture, thoughtful updates, and beautiful indoor-outdoor flow. This fully detached residence features five bedrooms and four bathrooms across a flexible, light-filled floor plan designed for modern living. Timeless 1925 details original moldings, soaring terrace ceilings, and a striking marble fireplace blend seamlessly with an updated chef's kitchen outfitted with a Viking 6-burner range, Grohe fixtures, and a custom quarter-circle island. The main level includes three spacious bedrooms and two bathrooms, opening onto a private redwood deck and a professionally designed backyard oasis ideal for dining, relaxing, or entertaining. The lower level offers an oversized primary suite, a generous family room, sauna, and ample storage, providing excellent flexibility for a variety of lifestyles. Additional highlights include dual-pane windows, central heating, a tandem garage with paved driveway access, and a beautifully landscaped lot. Ideally located near West Portal Village, Stonestown Galleria, parks, and MUNI and freeway connections, 440 Monticello offers comfort, character, and convenience in one of SF's most loved neighborhoods.