11. 18001 Wagner Road, Los Gatos – $14.498 million
This massive Los Gatos estate has six bedrooms, more than 20,000 square feet of space, two pool houses, a tennis court, and a helicopter landing pad. The garage has room for up to 15 cars.
10. 291 Atherton Avenue, Atherton – $14.85 million
This seven-bedroom home in ritzy Atherton has a sweeping driveway lined with palm trees. Inside, you’ll find high ceilings, dramatic chandeliers, and a gourmet kitchen. Additional amenities include a sauna, swimming pool, and tennis court.
9. 333 Atherton Avenue, Atherton – $16.8 million
Located about three minutes further south on the same Atherton street, this property includes a two-bedroom guesthouse in addition to the six-bedroom main house.
8. 132 Isabella Avenue, Atherton – $18.35 million
This Atherton home has more than 17,300 square feet of space. Amenities include a home theater, wine cellar, two-bedroom guesthouse, and an elevator to access all three floors.
7. 1225 San Raymundo Road, Hillsborough – $19.75 million
Further up the Peninsula in Hillsborough, this 12-bedroom home sits on a three-acre lot. It has some pretty extravagant decor — including intricately molded ceilings — and a vineyard in the backyard.
6. 1 Faxon Road, Atherton – $20.7 million
With more than 12,000 square feet of space, this Atherton home would make for a lavish family retreat that is just minutes away from “tech giants,” according to the listing. There’s a large pool, putting green, and a wine cellar that can hold up to 5,000 bottles.
5. 11627 Dawson Drive, Los Altos Hills – $23.995 million
The “Rancho San Antonio” estate, located on a hilltop 5.6-acre lot, has six bedrooms and 11 bathrooms. There’s also a two-bedroom guesthouse, pool, spa, and tennis court.
4. 21116 Comer Drive, Saratoga – $24.5 million
In the southern part of Silicon Valley, this 13,000-square-foot Saratoga home has a dramatic entryway. Inside, you’ll find seven bedrooms, 12 bathrooms, a home theater, infinity pool, cabana, and an au pair suite.
3. 52 Atherton Avenue, Atherton – $28 million
This 9,000-square-foot home in Atherton belongs to a prominent Silicon Valley financier. The house sits on nearly three acres of land, complete with a guest house, pool, tennis court, and expansive gardens.
2. 700 Kings Mountain Road, Woodside – $28.89 million
This 14,000-square-foot mansion is set on park-like grounds in Woodside. According to the listing, the home boasts four separate master suites, a 13,000-bottle wine cellar, and “award-winning gardens.”
1. 331 Greer Road, Woodside – $39.98 million
Built in 1941, the Flood Estate sits on more than 40 acres of gorgeous rolling hills. The property includes plentiful gardens, a gatehouse, tennis court, swimming pool, and colonial-style main house with nine bedrooms. Previously listed for $85 million in 2012, the price was chopped to $69.8 million in 2013, and then to $39.98 million in May 2015.