Protected by tall gates and surrounded by exclusive privacy, the multi-million-dollar estates and rolling neighborhood streets of Hillsborough cater to an elevated lifestyle in the Bay Area. This high-income town is one of the wealthiest in the region and the nation, with highly rated public schools and upscale delights. Filled almost entirely with large single-family homes, you won’t find any condos, townhomes or even entry-level homes for sale in Hillsborough. Instead, buyers are treated to generously sized homes sitting on large lots and surrounded by hundreds of acres of reserved open space. Found to the east of 280, the picturesque town is marked by rolling streets and the convenience of bordering both nearby San Mateo and Burlingame.
Oversized lots are the norm across Hillsborough, where private gates and tall trees bring an enhanced sense of privacy and exclusiveness to the Bay Area. You won’t find sidewalks in Hillsborough, but buyers can expect to uncover some of the region’s finest homes and neighborhoods, with a mix of older and newer homes for buyers to choose from. While there aren’t any restaurants, shops or commercial offerings in Hillsborough either, some of its neighborhoods are close enough to enjoy the delights of surrounding communities. Closest to the shops and restaurants of Burlingame Avenue, the northern neighborhood of Ryan Tract is also close to the Burlingame Caltrain and is home to some of the town’s original estates. Not far away, homes rarely hit the market in County Club Manor, where buyers are sure to uncover large, mostly pre-war estates in the multi-million-dollar range.
Closest to Downtown San Mateo, Brewer Subdivision is where you’ll find mid-century ranches mixed in with some even larger and newer homes. Hillsborough Park, meanwhile, is known for its winding streets and tree filled lots, where some of Hillsborough’s newest and grandest homes exist. Other options include low-density Skyfarm and Tobin Clark Estate. Virtually surrounded on all sides by San Mateo, newer homes are the norm in this desirable, southern Hillsborough neighborhood.

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