Woodside has a storied history, first as a campsite for Spanish explorers led by Gaspar de Portolà, then as a milltown “producing building materials for a booming San Francisco,” said Wikipedia. It was in the late 19th century that the California Gold Rush begot a land rush. And soon, country estates began dotting the land of Woodside.

Today, select properties in this hamlet on the San Francisco Peninsula between San Jose and San Francisco, just adjacent to Silicon Valley, inspire a similar land rush. Properties say, like 389 Moore Road. This exceptional Woodside estate is spread out over 21 acres of rolling hills, landscaped grounds, and oak, redwood, and pine trees, creating a natural park environment. Yet among this pastoral land is every imaginable outdoor amenity: a swimming pool with waterfall and clubhouse, basketball court, newly re-paved tennis court, numerous patio areas, and a spa deck with sweeping views spanning Woodside and framed by scenic mountains.

Woodside is also zoned “equestrian,” affording residents a unique opportunity to have horses on their land. “Horses are part of the local culture. Numerous residents keep horses, and the town government maintains a network of horse trails,” said Wikipedia. This home offers the finest equestrian facilities, with stables for numerous horses, a barn, and an immense riding arena.

This Grand Monterey colonial on 21 acres presents seven bedrooms, including two master suites and a two-bedroom staff apartment. There is also a private guest house/caretaker’s quarters on the grounds.

Built in 1939 and retaining a mix of original character with colonial details, updated technology, and hillside beauty with sweeping views of coastal hills and sunlight flooding in through numerous windows and French doors, the home offers a floorplan deal for formal entertaining and everyday living. Three floors of spacious rooms, large public spaces, and special touches include a huge chef’s kitchen, a recreation/media room, a dining room with custom wood bar room tucked away behind, a wine cellar, and a fitness center with sauna.

A town that offers the privacy, prestige, acreage and convenience of Woodside does not remain a secret for long. And, indeed, Woodside has been home to many a mover, shaker, and superstar who fall for the “rural residential character, though it is a short commute to Silicon Valley” as well as San Francisco via nearby Highway 280.

“Among the wealthiest small towns in the United States,” according to Wikipedia, Woodside is or has been home to everyone from Larry Ellison, CEO of Oracle Corporation, Gordon E. Moore, co-founder of Intel musician Neil Young, actress Michelle Pfeiffer, singer Joan Baez, and Apple Inc. co-founder Steve Jobs.

Woodside has also been a draw for Hollywood productions looking for a scenic town in which to film. Movies including Bicentennial Man, Heaven Can Wait, The Game, and The Wedding Planner, as well as the TV show Dynasty, were all filmed in the town.

389 Moore Road  is listed for $12,000,000 with Scott Dancer of Coldwell Banker Residential Brokerage in Woodside.

389 Moore Rd., Woodside

389 Moore Road, Woodside

389 Moore Rd., Woodside