Carolands

Situated along the southwestern fringe of Hillsborough, Carolands is one of the most affluent neighborhoods in the area. As a result, the median resident’s age is around 47 and has a deep bank account. For those looking to become such, you have quite a variety of homes to choose from. There is everything from more traditional, mid-20th century homes, to a fewer new and larger homes (that share little of its old-style theme) that have popped up in recent years. But both share one crucial characteristic...money. And these residences are separated by leafy, communal spaces and long, thin country roads curving around the landscape, which makes for a relatively sparse community population.

If you trek through the district, you’ll find it to be a very polished Hillsborough neighborhood. The district is outfitted with older, more traditional ranch style homes saturating the area. But many of these original homes have been upgraded and expanded since their development in the 1950 and 60’s. Properties also vary in size and shape. There are some large, usually of the half-acre type and offer well-groomed front yards and half circle driveways. They are usually either hidden beneath the tree-line or protected by elegant metal fencing. Older homes, however, have some bushy properties which tend to overcrowd front yards, but still have some quaint house fronts. These house values in Carolands deviate drastically in price. Some homes come in just under $2 million while others are priced up to eight figures.

As you might expect from this wealthy community, its school system is of the highest caliber. West Elementary School, which is situated within walking distance, has scored a 9-out-of-10 on greatschools.net. Elsewhere, Burlingame Country Club skirts the northern edge and provides all the essentials a private, high-class country club should have. The district is also situated relatively close to Highway 280, which makes for a convenient commuter option.

Carolands is the neighborhood just to the south of the Skyfarm neighborhood. Unlike Skyfarm it is a much more densely populated area with many more homes in closer proximity to each other and fewer forested areas.

Like Skyfarms, however, the Carolands neighborhood is also named after an old mansion. Carolands—the mansion not the neighborhood—was built in 1914 for the daughter of George Pullman, the famous Chicago rail coach tycoon. The mansion itself however is a bit cursed. Pullman’s daughter barely lived there, fighting with her husband over it. The property changed hands several times, was vandalized and for a while was treated as the local haunted house. (In one of the worst incidents a pair of teenage girls were kidnapped and sexually assaulted by a security guard at the estate—one of them dying in the ordeal.)

It is quite a beautiful property, however, and was once considered as a possible site for a West Coast White House.
Unfortunately it is not kept as a museum and remains in private hands bought by a group of wealthy investors.

Much of the surrounding land has since been developed. There are other smaller, more modern mansions in this section of Hillsborough. Most of the larger homes are on the eastern end of the neighborhood. There is, for example, an arced roof postmodern sort of deal on Robin Drive which looks a little bit like a mix between a garage and airplane hangar to me, but to each his own. (It’s got a great view by the way, and the unusual architecture includes a long thin pool that stretches under the street level driveway so that the pool is always partly shaded.)

Carolands is also home to West Hillsborough Elementary—the neighborhood school which, like every other school in Hillsborough as far as I know—is outstanding. (I always hear those on the Right saying that “throwing money” at education won’t help the problem, but it sure doesn’t seem to hurt.)

There are some other features of Carolands that make it a bit different than many other neighborhoods in Hillsborough.
Carolands, for example, connects with Highway 280. This may seem like no big deal but, if you live in a neighborhood like
Hillsborough Hills, having the make the extra trek to get on the freeway everyday can be a bit of pain.

Being a fan of European style traffic circles, one of the features of Carolands that I really appreciate is the circle right of the Highway 280 on Hayne Road.

These are just little things, but it makes this neighborhood feel a lot more homey and regular than a lot of other Hillsborough neighborhoods that just feel way too hoity-toity for a lot of us folks.

So what does it cost to live here?

On the low end you can find a 3000 foot home for about $1.8 million. These are about as small as homes get here in Hillsborough. On the high end you can buy one of those east side mansions I mentioned before for about $16 million. There is a Tudor style mansion right now going for $16.5 million.

Over all, this is possibly my favorite Hillsborough neighborhood. Though I don’t know if I could ever justify footing the bill for living here. You really would have to be fabulously rich to even consider it.