Hillsborough Park

Burrowed deep into Hillsborough’s woodlands, Hillsborough Park is a neighborhood set aside for the rich and upper-class. Most of us 99%, maybe 98%, only dream of living within this community. But for those who can afford it, you’d be living in luxury. It has everything from multi-million dollar homes to gated and roughly secluded properties. As a whole, the district spans about 0.7 square miles of leafy residential terrain. And according to the 2010 US Census, the population is relatively sparse, circling around 1,000. Demographically speaking, the community is largely white with a somewhat sizable asian minority.

If you drive into Hillsborough Park’s residential space, you’ll get a glimpse of a quiet, blissful existence. Homes tend to vary in size and shape. There are a collection of 1920 and 1930 Tudors and Mediterranean-style residences that make up the foundation of the community. These are considered more modest looking homes, as compared to other Hillsborough homes. But in the last 25 years, newer developments (that reflect more modern times) have been popping up in every nook and cranny of Hillsborough Park. As a result, these chic homes have drastically ascended the local real-estate market. But either or, residences grant about 3,000 to 4,000 square feet of interior living space and lots that stretch up to one square acre. And as you might expect, residential listings are few and far between. Of those that do make it to market, expect house values to be in the vicinity of $2-3 million dollars.

Hillsborough Park’s communal residential space is one of the nicer things about the neighborhood. The community is very sparse, with homes sometimes separated by acres. Properties are usually protected by attractive metal gates, white picket fences or walls patterned by vines as if it was intentional. They lay ground to narrow streets winding through the bushy terrain. It is also nestled along Crystal Springs Road which makes for a secluded area, but also has the convenient connectivity to both Highway 280 and downtown San Mateo. And for recreation, Vista Park has undergone a facelift in the past couple years and offers a fresh grown youth baseball field, a playground and newly constructed picnic areas.

As the name indicates, there is a park in Hillsborough Park—Vista Park. It is a pretty good park with a soccer field, basketball court and pretty extensive play area which is fenced in to make sure the little guys and gals don’t run out into the street.

Of course you are in Hillsborough so there is hardly a great need for a play area given that most people who live here have their own swimming pools, large yards and often even their own tennis courts.

The other reason Vista Park is notable is because I really can’t think of too many other parks in Hillsborough. I know there is Pershing Park, but I can’t remember if that is still Hillsborough or not.

As to the rest of the neighborhood, it is a pretty typical Hillsborough neighborhood. You get lots of large homes and some outright mansions. It is hilly enough where you get a bit of a view.

The best view in the area, however, can currently be found from the roof of Chiltern—the most expensive home currently on sale in Hillsborough. It is basically a castle on a hill and it is going for $44 million. It basically looks like the set of Eyes Wide Shut, both inside and out. It is really massive and includes a garden and hot house and all the rest of it. You could house an army there.

Most homes in Hillsborough are not quite as massive as this however. Typically, homes in this area seem to run around $2 million for a contemporary style house. There is a fair amount of newer construction here.

The area is generally one of the woodsier areas in Hillsborough, so it appeals to those who like a bit of a more natural setting. And with the typically great schools that you get here, it is a good spot for families too.