Set on a 3.1 acre, private and gated lot in one of Woodside's most scenic settings, this exceptional, newly updated residence offers the perfect blend of refined luxury and modern comfort just minutes from town. Flooded with natural light from expansive floor to ceiling windows, the main home spans 3 levels and offers 4 bedroom suites, a library with fireplace, an office, and grand public spaces in +/ 5,555sf. The open concept living room boasts 24 foot ceilings, massive curved windows, a striking fireplace, and flows seamlessly into the sun filled dining room. The chef's kitchen opens to a huge family room with 10 foot ceilings, a dramatic fireplace, bar, and French doors opening to a patio perfect for indoor/outdoor living. Designed for everyday comfort and entertainment, the home offers multiple terraces, temperature controlled wine storage, and an expansive lower level replete with a gym, home theater, and full bath. Outdoor amenities include a pool with spa, tennis court, meandering paths that encircle the property, level lawns, and a vineyard. A detached 2BR/2BA, +/ 1,135sf guest house is ideal for extended family or visitors. Access to the top rated Woodside Elementary School completes this rare opportunity to experience a lifestyle of elegance, privacy, and convenience.