Hillsborough Oaks

Hillsborough Oaks is an elite, rarely visited community fairly protected from the outside world. Its aesthetic inventory consists of graceful neighborhood quarters, small estates, polished house fronts and thick green foliage overhanging long residential lanes. It is also a relatively small community, only spanning about 0.4 square miles with a sparse population totaling 800. Demographically speaking, the community is overwhelmingly white (about 80%), with a mixed race minority population.

Although exclusively residential, Hillsborough Oaks has everything you want in a community. For starters, perspective residents have a variety of homes to choose from, all built within different decades (1930-1980). There are a cluster of elaborate English Country homes and Spanish-style villas that are sort of atypical of other Hillsborough communities. Also, you can find your fair share of pre-war homes which tend to sell lower than the city’s pricey median average. The typical resident has enough space for up to 5 bedrooms, (ranging from 3,000 to 4,000) which can nicely accommodate a large family and maybe a couple more house guests. But if you’re looking to live here, median house listings are typically around the $2 million dollar range while its priciest house can rise to $7 million. I hope you can afford it.

Aesthetically speaking, lots tend to offer crisp landscaping with sizable front lawns/little gardens and driveways that run deep into properties. These large lots are, however, hidden from the general public, whether that be behind bushy trees or protected by large walls and tasteful steel fencing. And you also won’t hear much from your neighbors. Homes can be separated by thick foliage and large stretches of woodsy terrain, but scan still maintain that ritzy aesthetic charm.

Although you might not think there’s much to do in Hillsborough Oaks, you have more than enough at your disposal. First, the prestigious Burlingame Country Club is just up the road from its community quarters. Although pricey, many residents can afford its $50,000 initiation fee because they themselves rake in a median household income of $200,000/year. Also, the neighborhood is within walking distance to both El Camino Real and the Burlingame Broadway Downtown district. Both of which grant you easy access to great shopping, dining and entertainment.

The Hillsborough Oaks (a.k.a., Hillsborough Oakbridge) neighborhood is one of the leafier and more sheltering of Hillsborough neighborhoods. Many of the curving lanes of this neighborhood provide a shady canopy of branches above so that you get that tunnel like feeling as you drive through. It really does make you feel protected from the troubles of the outside world. (Of course, if you live in Hillsborough there is high probability that you have sizeable enough ban account where you are protected from the vast majority of outside problems.)

Behind the branches and decoratively choreographed ivy patterns along the walls you catch glimpses of large homes beyond. The mansions are mostly confined to the northern end of the neighborhood where you can find your share of Tudor styles and classical revival style homes (think little White Houses and you get the idea).

The effect is really quite pleasing.

If you love looking at residential architecture this is really a great neighborhood in which to take a walk (though there aren’t really any sidewalks and luxury vehicles swoosh by as if driven by maniacs so watch out). One of my favorite spots is on the Eden Way cul-de-sac where there is this one home whose gate is ensconced between two thick grooved redwoods—its stone steps slipping between to faded stone wall with a wooden curved door of the kind you find in storybooks. This is the kind of door you expect Snow White to answer should you knock on it.

This door doesn’t actually lead into the house however, whose second story French Colonial style balcony you can see peeking out from over the top of the ivy carpeted wall that stretches roadside. In fact, it seems as if the main entrance to the house is through a doorway to the right of the three garage doors just beyond--above which you see a hint of the European style windows and the home’s red-tiled roof. (The window that you do see is pretty attractive being an inset square with a column in the center and two pairs of casements windows behind those.) Beyond the open arch of the doorway—which is attractively set in between two large stone flower pots with tall rose bushes growing from them—you just make out tiled steps rising up to what I assume is the front entrance to the home.

It is definitely one of the most intriguing set-ups I have ever seen for a home, tantalizing the imagination in anticipation of the home that awaits beyond.

What does it cost to live in Hillsborough Oaks?

There aren’t very many homes on the market here. From the ones which are on sale the prices seem to run between $2 million and $7 million, though I am sure that once you get into the larger mansions they run more than this. On the high end right now, there is a New England Colonial style home dating from 1914 going for just under $7 million. So that gives you a sense of prices.