Woodside stands out as a rare enclave where wealth meets wilderness. Surrounded by redwoods and rolling hills, this secluded town is just minutes from Interstate 280, providing fast access to San Francisco, San Jose, and the heart of Silicon Valley. The town’s origins as a country retreat for San Francisco elites still shape its identity—large estate lots, horse properties, and strict development rules preserve its pastoral charm. While its commercial core is small, it offers essentials and high-quality dining in a tranquil setting. From country roads popular with cyclists to landmarks like the Filoli estate, Woodside maintains a quiet grandeur, attracting Stanford faculty, entrepreneurs, celebrities, and equestrians alike. The real estate market is defined by multi-acre properties with expansive custom homes, creating a uniquely private and refined lifestyle.