Timeless 1918 Craftsman charm meets incredible modern flexibility in this extensively expanded (1988) Midtown estate. Perfect for multi-generational living or a high-yield four-unit rental portfolio, this unique property offers a main residence configured as two independent units, a permitted garage conversion, and a detached cottage. Totaling approx. 3,440 sq. ft. with 3 full kitchens, 1 kitchenette, and 4 bathrooms. Main house unit1-Lower with elevated wisteria covered front porch, enclosed sunroom, hardwood floors, wood-framed windows, spacious living & formal dining rooms, updated kitchen, 2 bedrooms & an office. Main house unit 2 - Upper accessed via interior/exterior staircase, featuring 2 bedrooms, 1 bathroom, light-filled living & dining spaces, lots of wood windows and a full kitchen. Unit 3-Attached permitted garage conversion with high ceilings, a loft, full kitchen & 1 bath. Unit 4-Detached cottage with cozy retreat featuring a kitchenette, i bathroom, Murphy bed, and heated floors. Enhanced by beautiful outdoor living spaces, mature fruit trees, ample of off-street parking. All in a desirable Midtown location close to Hoover park, shopping, dining & excellent Palo Alto schools.