Private Jet to Hillsborough

Hillsborough didn’t become one of the richest towns in the United States, it was born one. In fact, since the Gold Rush, Hillsborough, just over six square miles of hilly land and winding roads in Silicon Valley’s San Mateo County, has been the place where the wealthy have built mansions and summer estates.

Among its founders and earliest residents were 19th century millionaire bankers and railroad magnates.

Through the years, it has been home to the likes of William Randolph Hearst, Bing Crosby, politicians, celebrities, sports stars and Silicon Valley execs.

Today, the median home price in Hillsborough is $4.4 million with few for sale for less than $3 million.

Hillsborough’s Silicon Valley location on the San Francisco Peninsula, 17 miles south of San Francisco is only one of its attractions. It has an almost ideal climate with September highs around 78 degrees and December highs of about 60. In addition, the coastal mountains to its west shield it from the rain and fog common along much of the Pacific Coast in northern California. Hillsborough has 307 days of sunshine a year.

Hillsborough has no commercial zoning and no businesses in the city limits.

Homes must be at least 2,500 square feet and the lots – many of which are steep and wooded – must be at least half an acre. Those strict residential zoning laws keep out apartments and condominiums but they didn’t keep out The Flintstone House, much to the chagrin of many residents. The (in)famous orange bubble house, seen from the Doran Memorial Bridge of northbound Highway 280, was built in 1976 by spraying concrete over balloon-shaped forms. It lay in disrepair until retired media mogul Florence Fang bought it for $2.8 million in 2017 and remodeled it into a true Flintstone House, complete with a menagerie of dinosaur statues and a “Yabba Dabba Doo” sign. Residents were mortified and the town has been in court with her over it since she bought it.

There is, however, a famous property residents are proud of – the 65,000 square foot Gilded Age mansion, Carolands, which was built by Harriet Pullman Carolan, heiress to the Pullman railway car company. Visitors can see it for free – with one catch. Because of the extraordinary number of requests, a lottery system for is now being used for tours and it sounds as if it may be about as hard to score reservations as it is to win the real lotto.