Hillsborugh

There are no apartments, condominiums, or townhouses in Hillsborough; Forbes calculates the median home price at $5.1 milion. Notable residents past and present include entertainer Bing Crosby; publisher William Randolph Hearst; the king of Tonga, George Tupou V; diet guru Jenny Craig; former Major League Baseball players J.T. Snow, Rickey Henderson, and Greg Maddux; and New England Patriots quarterback and San Mateo County native Tom Brady.

There are no commercial districts in Hillsborough. As a wealthy suburb of San Francisco, 17 miles to the north, life in the town is unhurried and quiet. The relaxed atmosphere is enhanced by tree-lined streets that don’t follow a grid pattern and instead wind around the hilly landscape. There are few traffic signals. 

The town covers six square miles and is bounded by Burlingame to the north, San Mateo to the east and south, and Interstate 280 to the west.