Sweeping Bay and San Mateo Bridge views define this expansive Hillsborough residence, cherished by the same owners for more than 40 years. Recently refreshed and updated, the home features newly painted interiors, hardwood floors and a dramatic great room with walls of glass overlooking the pool and expansive deckan exceptional setting for everyday living and entertaining. Designed with multigenerational living in mind, the residence offers two kitchens, two laundry rooms, flexible living areas and separate exterior access. The main level includes two primary suites, a powder room and a view-oriented kitchen with beautiful stone countertops, a generous island, an eating area and fireplace. A nearby office offers the opportunity for a fifth bedroom or expansion of the primary suite. The lower level includes two additional bedrooms, a full bath, second kitchen, dining area and a flexible bonus room that can serve as a second office, with direct access to the patio, pool and outdoor spacesideal for extended family, guests, caregivers or a private retreat. A wine cellar, workshop area, attached two-car garage, oversized driveway and generous storage complete this rare offering with exceptional views, scale and versatility.