DirtyHarry

Skirting the Bayshore Freeway, Burlingame Gardens has a fair number of apartments and older homes. My favorite street here is leafy Winchester, where there is a stretch of cottage style bungalows. It is a really beautiful stretch of stately looking houses with high pitched roofs and often church castle style windows.

The median home price in Burlingame Gardens is around $875K—relatively affordable for Burlingame. The usual caveats for Burlingame apply: these are usually very old homes (pre-1950) of smaller sizes than most of us have become accustomed to, and the schools are great.

There are a lot of renters in the neighborhood as well. A one-bedroom goes for about $1800 on the really nice apartment complexes you will find on the northern end of the neighborhood.

The spot is also a great place for commuters, with the Broadway CalTrain station on its northwestern point.

Overall a pretty good neighborhood to spend a few years in but I don’t know if I would want to stay here forever.

With the Broadway CalTrain on the southeastern edge, Burlingame Gate is yet another Burlingame neighborhood with expensive older homes with great schools.

The median home price here is around $875K, which is relatively low for Burlingame. Prices range from from $700K to $1.4 million. Homes are smaller and older, with homes typically having between 1500 and 2000 ft of floor space and having been built before WWII.

There is also a sizable contingent of renters in this neighborhood, as you can tell from the number of boxy apartment complexes here. The average going rate for a one bedroom is around $1500 (you’ll find a number for $1450 though not much below that). Most of these apartments tend to be concentrated on El Camino and Broadway, the two bordering arteries of Burlingame Gate.

Because of the CalTrain station and all of the stores and activity on Broadway, Burlingame Gate does have slightly higher crime rates than other Burlingame neighborhoods. Mostly you will find thefts here—about one or two per week. In the last six months there have been a couple of assaults—but really nothing to worry much about.

The afore-mentioned stores along Broadway make this a good area for singles and young couples, as well. Not only are there two dozen plus restaurants, but you will also find art galleries, a good Irish pub (Behan’s) and even a dance studio for those preparing for weddings or who just want to learn how to get their groove on.

Overall, a pretty good neighborhood for renters, I think, though buying a house here might not quite be worth it for the value, imo.

Nestled right up against Hillsborough Hills, Burlingame Hills is like the less popular twin to its ritzy neighbor. Which is not to say that it isn’t nice in itself—only compared to Hillsborough would this neighborhood come up wanting.

It is, however, a pretty nice spot, nestled way up in the hills in a leafy area that makes you feel as if you are miles from anywhere. The homes here have a sort of 1960’s feel to them. As with other parts of Hillsborough, Hillsborough Hills is definitely million dollar home territory. In fact, homes here tend to climb closer to $1.5 million territory. This neighborhood is so stable, however, that few houses come on the market even in the volatile market we are currently experiencing.

Homes here tend to be on the larger side, 2000 ft and above, and to have more bedrooms, 4+. It is a fairly typical hillside neighborhood in that sense.

Of course, hillside living does come with its drawbacks such as nighttime visits from forest critters with penchant for destructive behavior such as shredding curbside garbage bags. Also, this is definitely car culture. You will have to drive to everything.

It is a nice spot for families and childrearing, except that the sidewalks are not really walkable or bike-able.

Burlingame Park is a slice of a neighborhood at whose center is Pershing Park. On the interior streets there are a lot of bungalows and older homes. Some of them are quite attractive and well-kept and some are a touch less so and show signs of age. Some of my favorite homes here are in the Spanish Revival style—the stucco and red-tiled roofs can be really attractive when well-kept.

As with other parts of Burlingame, the homes here way overpriced simply because they are in Burlingame. The median home here goes for about $1.25 million (although you can find some deals on foreclosures that sell for less than a million a make for great investment opportunities since they virtually automatically double or triple in value).

There are a number of boxy apartment buildings along El Camino—which, as you probably know, is the main avenue that cutting north south all the way down the Peninsula. It turns into a real mess during rush hour, pretty much becoming packed with commuters going to and from work.

There are a fair number of mediocre stores around here—supermarkets and drugstores and the like. Overall, however, this is pretty much your average Burlingame neighborhood, old overpriced homes with great schools and virtually no crime.

You might call it par for the course.

Burlingame Terrace is yet another Burlingame neighborhood packed with homes from pre-WWII. Some of them date back to the WWI, actually.

These are not the large stately homes that you encounter in Easton Addition. These are smaller homes—a lot more in the Bungalow vein than in the Tudor manor vein. There are exceptions to this general rule. In the narrow lane of Willborough Road at Willborough Place, there are some really attractive cottage style homes with thatched roofs and French style windows with decorative wood shutters. They don’t have much by way of yards and the lane separating them from their across the street neighbors is barely wide enough for one car—but this does give the location a certain cozy feel.

Now, if this neighborhood were in Berkeley or Oakland across the Bay you could probably slice property prices in half, but because this is Burlingame, the median home price here is $1 million. This definitely seems excessive, even by Peninsula standards, but that is what it is.

Of course, there are huge differences between the East Bay and the Peninsula. One big difference is the schools. McKinley Elementary, Crocker Middle School and Burlingame High have API’s in the 7 to 10 range. This is an outstanding educational system that ranks amongst the best in the country.

The other difference, of course, is crime. In the last six months this neighborhood has only experienced about a dozen thefts and 3 assaults (mostly along Broadway where the restaurants and the CalTrain station are located). That is closer to what certain places in the East Bay experience in one week.

That said, this is not just a residential neighborhood. Along the five blocks that make up Broadway you will find a number of restaurants and stores.

There are about 3 Mediterranean places (the best of which is probably Mivan in my opinion); there are also 3 places you can get a good “American” meal (Broadway Grill being the best—it double as a nightspot where you can take in some live jazz on certain nights); a pair of Italian places (Café Figaro and Rocca); and about a dozen East Asian places (the best and most expensive being Coucou Japanese Cuisine).

Many of those restaurants make for good date spots, but if you just want to hang out with friends and have a beer, Behan’s Irish Pub should certainly be your destination.

You can also find your usual assortment of peripheral stores here from a clothing boutique, to a hair stylist (Supercuts) and a nail salon to a coin store and liquor store. It’s one of those very walkable old fashion lanes that is pleasant to visit, on one’s day off.

Overall, this is pretty nice area that has something for everyone—from commuting professionals to singles who like to have a neighborhood bar to frequent to families looking for great schools.

Unfortunately the prices will make sure only the very well-off can manage to settle here permanently.

Burlingame Village, at the edge of Millbrae, is a small slice of a neighborhood made up mostly of smaller older homes. It is a flat neighborhood with streets that are slightly narrower than most you would see in neighborhoods these days.

On the northern end of the neighborhood along the final 2 blocks you get a combination of apartment buildings and office buildings. The office building include a mix of medical and governmental institutions such as the Peninsula Chiropractic Center, San Mateo Rape Trauma Services, Burlingame Police Department and Quest Diagnostics.

A one bedroom apartment around this area will run you about $1700 from what I’ve seen offered.

The Millbrae CalTrain is just three long blocks up so residents can, in theory walk, or even more easily bike and then commute to work in the city.

Most of the residential homes are on the southern end of the neighborhood, where the median prices seems to be about $875K. As throughout Burlingame, the higher prices are largely due to location. Burlingame’s great schools, low crime, and ease of access to both San Francisco and Silicon Valley make it a favorite for commuting power couples.

Overall a pretty nice spot.

With its big old homes, Easton is definitely one of the most exclusive neighborhoods in Burlingame. The median home price here is around $1.2 million. More than half the homes here date to the Roaring Twenties, each with its own unique architecture. You can sense the wealth as you drive through the streets here.

There are classic manors, with their square build and the overhanging flat roofs with attractive trim. Many of the homes here have Tudor accents such as half timbering. Others are more of the Mediterranean style with red tiled roofs and stucco walls.
The homes here also range in sizes with some small bungalow style homes offering barely more than 1000 feet, while some of the larger manors range up to 4000 feet. (These are also the more expensive homes.)

The front lawns often are decorated with interesting topiary—often incorporating English style hedges or rose bushes.

You will also find some 60’s style boxy apartment buildings along El Camino—the kind of apartment buildings that have the name to the building written sideways in fancy script.

Easton Drive, the main artery, is perhaps one of the most compelling of the lanes as well, having towering trees lining the narrow lane—there large bases taking up huge portions of the sidewalks.

As you might expect, this is also a very safe neighborhood (nothing to report accept petty thefts in the last six months) and the schools are fantastic, as throughout Burlingame.

The other nice thing about this neighborhood is that with Broadway just beyond El Camino sporting a half dozen restaurants and a pleasant walk, you are right by the action. You can get a beer Behan’s and a bite at the Broadway Grill.

Also, with the Broadway CalTrain just a few blocks down Broadway, you could actually avoid using a car from most homes in Easton.

Overall, I would say that this is probably the best residential neighborhood in all of Burlingame. Though, of course, you will definitely pay for the privilege of living here.

Stretching out just to the south of SFO, the Ingold/Milldale “neighborhood”—I have to put quotation marks around it since I don’t think anyone actually lives here—is known for being home to a ton of hotels. Doubletree, Red Roof Inn, Embassy Suites, Hilton, Crowne Plaza, Holiday Inn and the Vagabond Inn all look to take advantage of SFO’s proximity.

You can roughly divide the Ingold/Milldale neighborhood into 2 sections. There is the long watery stretch which has very little other than airport parking and hotels, except for a Kincaid’s, a classic steak joint right by the side of the bay. It’s the pricey sort of place that people of a certain generation used to go to celebrate anniversaries.

The other section is farther to the north and surrounds the Bayshore Freeway. It too has a more significant proportion of hotels. Here, too, there are a number of restaurants here too. Many of them are popular chain restaurants that travelers are likely to recognize, such as Benihana, El Torito, Max’s Opera Café (if you go for the singing waiter thing) and the Elephant Bar.

Others are more unique to this area: Fandorin is a Russian influenced continental restaurant that sits right at the edge of the bay, giving you an excellent view of the airplanes and landing and taking off. Gulliver’s is another restaurant that I think is unique to Burlingame—it is basically a steakhouse similar to Kincaid’s.

For those of a more active mindset, there is also Caribbean Gardens, a salsa place where you can get lessons or just go to get your Latin groove on. And if you prefer sports, there is the Badminton Center—which deals in all things badminton.

There are a number of commercial businesses here, too. For example: Simply Perfect, a catering place; ABC Supply, a roofing and window’s supplier; and Vector Labs, a medical supplier that specializes in detection and labeling products.

Now, like a lot of places like this it is not that attractive—lots of squat commercial offices south and west of the freeway, and hotels dominating the skyline on the eastern side.

Overall, however, it is not a bad place to go if you want to grab a bite to eat.

Lyon Hoag is definitely one of the oldest parts of Burlingame. About half of the homes here date back to first quarter of the 20th Century. So these are smaller homes (lots of bungalows and similar style homes), which in your average East Bay neighborhood would not go for more than $500K. But since we are in the Penninsula, prices start at around $700K, with the median price hovering around $850K.

Lyon Hoag is more of a middle class neighborhood, and as such, you do find a bit of an uptick in crime. It is not a huge problem, but still one worth noting. In the last six months, there have been a handful of assaults and more than dozen thefts.

One very nice thing about his neighborhood is its location. The proximity to the downtown means that just about everything that you need to live in this neighborhood is right at hand. You can do everything from go out for a meal to take the Caltrain up to work.

Overall, however, this is one of the more affordable neighborhoods in Burlingame, at just the right price point for smaller families trying to make in the Peninsula, I think.

The main artery at the center of Mills Estates is Trousdale Drive. It is a long, relatively straight lane that climbs up the hills towards Highway 280. Mills Estates is mostly made up of homes from the late 50’s and early 60’s on wide, slightly curving streets. On the western end of the neighborhood, you get some pretty great views of the flatlands leading to the Bay. The homes are nice—very slick and stylish in a 60’s modish style. (You get some fairly stylish Eichlers mixed in up here that conjure America during the Kennedy Era neatly.) They are also larger than homes in a lot of neighborhoods in Burlingame, averaging about 2,250 street—which sounds average but is pretty good when compared to some of the smaller older houses in other neighborhoods.

The median home price is about $1.25 Million.

The area is super safe with only the occasional vehicle break-in or petty theft. Schools are also great—as you would expect for Burlingame.

You definitely need a car up here in order to make it to the freeway. Overall, I would highly recommend it for families and professionals, although it is definitely on the expensive side.

Oak Grove Manor/Burlingables is a small brick shaped neighborhood, squeezed between California Drive and the Bayshore Freeway.

Judging from the age of the homes, this neighborhood dates from around WWII when most of these homes were built. As with many homes dating to this period, the homes are a bit on the smallish side with the typical home being about 1200 feet.

Despite this somewhat small size, the homes here go for close to $1 million. Of course, it re-affirms that old chestnut about real estate being all about “location, location, location.”

One of the great benefits of most of Burlingame—and this neighborhood is no exception—are the amazing schools. Washington Elementary, Crocker Middle School and Burlingame High certainly don’t disappoint in this regard. And even if they did, there are a number of excellent private schools in the area as well.

The streets are clean and have that older feel to them, which can be nice—especially if you have kids.

Burlingame High School is a part of this neighborhood so if you have high school age kids they can walk right to school. Burlingame High is regularly ranked in the top 250 high U.S. high schools for academic excellence. And if you’re a Glee fan, you may also be excited to note that Diana Agron is also an alum.

The neighborhood borders Downtown Burlingame, as well, so you can basically walk over to where all the action is.

Overall, a nice neighborhood, though perhaps a bit too close to the Bayshore Freeway on the eastern end.

Ray Park in Burlingame, California is home to Mills Peninsula Health Center on its northern end, Burlingame intermediate
school on its western end, and Lincoln Elementary on its southern in (by Ray Park proper).

This is a neighborhood that popped up in the post WWII period. The homes here all date back to the late 40’s or very early 50’s and they are quite modern by our modern days standards with none of them that I could find exceeding 2000 sq. ft.
Despite these modest offerings, however, these homes regularly sell for about $1 million.

Why the high prices?

As always, the key is location. Ray Park and Burlingame in general is a great spot for SF commuters looking to get just far enough away to escape the problems of the city. The neighborhood has virtually no crime (only a pair of assaults near the hospital in the past 6 months). You are only about a mile from two separate CalTrains stations, as well.

The schools are also excellent with both Lincoln and Franklin elementaries having the highest API’s possible while Burlingame Middle School and Mills High are also close to perfect. (And that is not to mention the outstanding choices in private schools as well.)

As far as entertainment and similar matters, you are also pretty close to some restaurants and not far from the downtown areas of both Burlingame and Millbrae. If you are in the mood for a sandwich you might try the Little Lucca Sandwich Shop or the American Bull Bar and Grill which is right by Little Lucca.

As to the medical center that lies on its northern end?

I don’t exactly how I should judge such a facility except to say that it looks like they are a full service hospital that includes most every service from surgery to and ER, but that what perhaps sets it apart is perhaps its inclusion of psychiatric services as part of its offerings.

Overall a pretty nice, though way overpriced upper middle class neighborhood.

Though not as large as San Mateo’s Downtown, Downtown Burlingame has quite a bit to offer its upper middleclass residents.

You will find a number of restaurants worth visiting here. Here are my favorites:

--Ecco: Great Classy American Joint. Try the Salmon with a good California Wine.
--Stella Alpina Osteria: Pricey Italian place, but well worth it.
--Straits: An Asian Fusion restaurant. Rendang Beef and the Butter Chicken.
And here are a few less pricey choices:

--Kabul Afghanistan: Great for a change of pace and exploring new things.
--Trapeze European Cuisine: Try the linguine and clams and a good wine.
--Coconut Bay Caribbean: Yeah, man!
--Barracuda Sushi: Good sushi with no frills.

So those are some of the restaurants. For nightspots, try these:

--Barrelhouse
--the Alibi
--Vinyl Room

Most of these have dancing. Vinyl Room is my favorite.

There are also the usual assortment of boutiques, etc.

For women there are the usual Therapy and Anthropologie; and there are also Francesca’s, Les Deux Compines, and Picasso’s Closet. And all the usual chain stores and similar places.

Put simply, you don’t have to leave Burlingame to fulfill your consumerist urges.

This is also, by the way, an amazingly safe downtown with very little crime of any kind.

Brookside Park is yet another of these woody Portola Valley neighborhoods where homes pop up in the middle of winding woody lanes.

Homes here run between about $1 million and $2.5 million for the most part. These are not huge homes and they would certainly cost a lot less if they were not in Portola Valley. You will find a mix of homes here dating from the 50’s to the 90’s, with older homes tending to be smaller (around 2250 ft.) and newer homes tending to be bigger (~3500 ft.) and prices following a similar pattern.

The area feels very secluded and remote, though you are within a half hour’s drive (maybe less?) of Palo Alto, so although Portola Valley does not have much of anything to offer in terms of entertainment or nightlife, you are close enough to Palo Alto, San Jose and San Francisco where you can go and come back even on a busy weekend.

The schools are good. The neighbors are wealthy, or at least fairly well off. Over all, fairly typical Portola Valley.

If you like feeling as if you are out at the edge of the city in a semirural area, you will probably like Central Portola Valley.

Many of the street names here are themed around Native American tribe names: Iroquois Trail, Cherokee Way, Cheyenne
Point, and Shawnee Pass to just name a few. Homes here are on the larger side and range from around $1 million to $5 million. Most of the homes for $2 million and less are for sale in the more densely packed on the southern end of the neighborhood while the homes that go for $4 and $5 million are in the rest of the neighborhood where homes are more spread apart.

Most of the homes in this area are contemporary style homes and are very luxurious inside.

Overall this is a good spot but a bit on the remote side.

The Ladera neighborhood is yet another leafy Portola Valley neighborhood. This is basically just a hillside so the farther west you go, the higher the elevation and the better the views.

Of course, as you get farther up into the hills prices go up along with the elevation. Near the top where the views are the best, home prices average $2 million. These are largely remodeled 1960’s era homes which though not terribly attractive from the outside tend to have magnificent interiors.

On the far eastern end of the neighborhood is Alpine Road (and then Highway 280). Alpine Road is where you will find the Ladera Shopping Center, which is basically just a sort of strip mall anchored by Bianchini’s Market, the local supermarket.
There are a couple of rather mediocre restaurants here—Mike’s Café and the The Ladera Lobster Shack—but this is mostly just the same old same old in terms of supermarket strip malls. You can get the basics, and maybe grab a bite if you don’t feel like heading into Stanford, but that is about it.

(The best place to get a bite is the Amigos Grill, imo.)

The schools here are pretty great and the proximity to Palo Alto makes it a prime location for Silicon Valley types. If you can afford it, it is a great location. For most people though it is simply beyond their means.

Los Trancos Woods and Vista Verde are the farthest south that you can go in Portola Valley. Much of this area is actual forest (open preserve) and is filled with trails. If you love being outdoors, this is a great place for it. You can go hiking virtually any time that you are home and the wild life is all around. At night time you are no doubt to see the deer and hear other animals as they rummage about. (Be sure to keep your garbage cans well sealed.)

But there are also a number of homes nestled into the trees along these seemingly remote country roads. I do not have enough of a sampling of how much these homes cost, but I sense they are comparatively modest in terms of Portola Valley and the Peninsula. One that is on sale here is currently going for $1.2 million. That is for a home that has 3 bedroom and only has 1700 ft.

There is not much else here, of course. So if you are into living close to anything, this is not the place where you want to set down your stakes.

Portola Valley Ranch is one of the neighborhoods on the far south western reaches of Portola Valley, which basically means that in a city which is already about as remote as it gets, this is one of the remotest areas of it. Put simply, if you want to live here, it is because you really, really want to get away from it all when you go home at night from work.

The homes in the Portola Valley Ranch neighborhood are not, for the most part, the large homes on extensive properties that characterize some of the other Portola Valley neighborhoods. These are more average sized homes. What makes the neighborhood distinct, however, are the turnabout cul-de-sacs; there are a bunch of them and they give a certain consistency to the neighborhood.

In fact, Portola Valley Ranch is a planned community run by a home-owners association that helps in the upkeep. They have a number of facilities that they share as part of living in this community, including a big event facility, swimming pools, tennis courts and even a working vineyard which produces a very competent Pinot Noir (one of my favorites).

There are also some great trails that wind around the valley.

Homes here run about $3 million for a 5600 ft. home with 6 bedrooms. Anywhere else that might be a bit on the high side, but given the astronomical prices you come across in other sections of Portola Valley, this sounds like par for the course.

Corte Madera School is also here. It handles grades 4 to 8 (which is a little weird since most middle schools only do grades 6 to 8 in California) and it is very highly rated with an API of 10 (the highest possible) and standardized test scores that routinely place their students near or over the 90% percentile. (Very amazing!)

So, if like living in community that is more than a little bit off the beaten track, you will probably love it here in the Portola Valley Ranch neighborhood.

The Westridge neighborhood is a long arcing stretch of a neighborhood that stretches from Portola Road all the way to Alpine Road (nearly to Highway 280), all along the northern side of Westridge Drive. There are homes spread throughout the neighborhood, but virtually every lot has quite a bit of land so that no homes are right against each other. It is the sort of place where your neighbors will probably not know your business.

There are a few outright mansions in this area. For example, right now there is an 8,000 ft. 4-bedroom on the western end of Westridge that is going for $25 million. It sits on an 11.5+ acre lot and has a pool, tennis court and what looks like a vineyard. (By the way, in case you are wondering, your estimated monthly payment on a $25 million house is $121,000 PER MONTH—now that’s what I call a mortgage payment.)

Of course, most homes here in Westridge are not $25 million mansions, but none is inexpensive. For example right now, the least expensive home for sale here is on the market at $1.8 million. That is no where near $25 million, but it is not exactly cheap. The home, which is located on the far eastern end of the neighborhood near the freeway, is basically an elongated Ranch home on a big lot.

In the middle, the median priced home is just below $5 million. For that price you can get a pretty good home here, with nice views, a pool and a relatively manageable 2 and a half acre property.

On the far eastern end of the Westridge neighborhood you find yourself right by the Ladera marketplace where you can do things like get groceries and pick up a pizza. None of this is fantastic in itself, but given the remoteness of things here, it is always good for you to know that you can get the basics of life without having to drive too far.

Alpine is also the road that you follow to get to Highway 280 to head to work. (I’m not sure there is really anything by way of public transportation here.)

The nearest schools are Ormandale Elementary, La Entrada Middle School and Woodside High—all of which are above average schools.

Put simply, if you are loaded and like your privacy—you will probably love the Westridge neighborhood.

Woodside Highlands—not to be confused with either Woodside Hills or Woodside Heights which are actually in neighboring Woodside, is actually a tiny Portola Valley neighborhood. It is basically made up of a half dozen or so woody lanes nestled up in the hills in northwest Portola Valley.

Homes here are, of course, expensive. Portola Valley is the number 6 most expensive location in California (in terms of home prices, I believe). Currently there is only one home for sale here currently. It is a 3000 ft. 3 bedroom home with pretty nice view and a wooden deck. It is going for $2.5 million.

This is a very leafy area with narrow roads (some unpaved) winding up to very nice homes. You definitely do feel that you are away from it all. And this is about as un-walkable as it gets, narrow winding roads with no sidewalks basically force you to get into your car for just about everything—even if you just need to go into to town for the paper or cup of Jo.

You are actually not that far from Palo Alto and other centers; which is good because there isn’t much in Portola Valley itself.

Overall, a nice neighborhood, but I’m not sure it is worth the ridiculously high home prices.

Woodside Hills, located just to the south of Canada College (the local two year college) and just to the north of Woodside High, is about what it sounds like, a hilly neighborhood with large, overpriced homes in a very affluent community.

The most expensive home currently on sale in this neighborhood is Le Soleil (the “sun”), which is an actual mansion (in a French Chateau style). It is currently listed for just shy of $13 million. It was built in 1929 and looks like the sort of place where they could have set scenes from The Great Gatsby. It has 7 bedrooms and 7 baths, a front driveway fountain, a pool, symmetrically shaped topiary gardens and a tennis court.

It will be going on sale on June 14 of this year, with bids starting at $8 million. (The home was originally listed at $21 million.)
So we will have to keep an eye on how that turns out.)

The vast majority of homes in this area however are not in the mansion category. The median home in this area runs $2.5 million, which is hardly chump change, but is nowhere in the same galaxy as Le Soleil. These other homes also get a special bump because of being in affluent Woodside. For one of these mid-level homes you get perhaps 4000 ft., pool and koi pond and 4 bedrooms. Pretty nice, I suppose and worth it if you work in Silicon Valley and would like to shorten your commute.

Unlike a lot of Woodside, most of the homes here come right up near the streets they are on so that you can get a good look at them. Many of the homes here have U-shaped driveways in front and tennis courts in the back.
Home styles vary, ranging from large, luxuriously kept Ranch Style homes to Mediterranean villas to imposing manors. On the far eastern end of the neighborhood you will find the Buck Estate. It is a basically an English style mansion of the kind where you could film Pride and Prejudice without too much strain of credibility.
It happens to currently be on sale for just shy of $11 million. Homes here tend not to rise to this level for the most part, however, with a fair number of homes for around $2.5 million. These prices tend to be for large 50’s style Ranch homes which, anywhere else, would probably not break $1 million. As they say in real estate, however, location is everything.
On the far eastern end by the Buck Estate, you also find Woodside High, Woodside’s main high school. Woodside is an above average school with an API of 7. This is good but not as good as many other nearby Peninsula high schools whose APIs are 9s and 10s.
I am not sure why Woodside should be slightly below its neighboring high schools. Parents seem fairly involved and administrators and teachers are praised for their involvement with and commitment to students. It may simply be one of those stats that is true for a year or two and then will disappear again. (And, of course, above average is not failure.)
Overall, this is one of the highly coveted neighborhoods in all of the Peninsula. I would certainly not have minded having the wherewithal to move here.

Leaning up against the western side of Highway 280, Woodside Glens is one of those neighborhoods where narrow roads creep off into dead ends. The main artery through this neighborhood is Canada Road, which is long and straight and has several surface streets that slide off it to the homes in Woodside Glens.

Homes here run from just over $1 million to $4.25 million, with the median being around $3 million. The desirability of this location is reflected in the meticulous upkeep of the homes here. You can find everything from a classic Mediterranean style home here to an East Coast style manner. Most homes here take full advantage of the location to high light cottage like elements of their architectural styles. That means lots of exposed timbering, wood porches, and stonework.

You are not quite as isolated here in Woodside Glens as you are in other parts of Woodside. With the freeway on one side and the “downtown” Woodside area on the other, Woodside Glens just generally feels more populated and more active than other locations in Woodside. The “downtown” area has a supermarket and few restaurants and all the basics that you need to live. So if you live here it is possible, in theory, to go weeks without leaving Woodside.

There isn’t much more to it than this however, and if given the affluence of Woodside residents, I doubt many of them go long without heading out for some entertainment.

It is a very nice spot, though prices definitely make it out of the reach of most of us.

If you like that woodsy timber town feel like you are on the edge of some old western mining town, perhaps, you will love this neighborhood in Woodside. Though right here, it feels less like it should be called “woodside” than just “woods”.

Right at the junction of Highway 35 and La Honda Road (Highway 84), you have a little trading post sort of area where you will find some restaurants and other kinds of stores you would expect in a place like Big Bear. This is a popular area with outdoorsy types and bikers.

The main restaurant here is Alice’s—a burger and sandwich sort of place with simple fair and laid back attitude; more Santa Cruz than Woodside really. They sometimes have live music on Thursdays, featuring the kind of folksy performers no one has ever heard of. It’s the kind of place that is perfect as a pit stop on your way somewhere else, but not a destination in itself.

Across the street from Alice’s is Mountain Terrace, a favorite location for weddings and corporate events. (They also have dance lessons for those brides and grooms who unfortunately have a pair of left feet.)

Though hidden behind tree cover there are a number of hillside homes mostly dating from the 1960’s. These homes have a sort of ski resort sort of a feel to them—often with a bit of modish modernist sleekness (straight lines and lots of glass for greater clarity of sight). They have high ceilings and exposed timbering and kitchens that connect right onto the dining room and look out over decks, usually onto lush greenery. Redwoods abound providing large patches of shading grooves and magnificent light shows from the tree tops.

I haven’t been here enough to know for sure, but it also seems like an area that doesn’t get that much fog--being just far enough from the coast.

Of course, whenever you live in the middle of woods like this, forest fires, critters and hillside erosion (to a lesser extent given the dryness) are a concern. Also, you will definitely be spending a lot more time getting groceries and that kind of thing in this area.

In a nutshell, if you are an earthy crunchy sort of a guy or gal, and want to live right in nature, this is the sort of place that you will love. If you want big city action—this place will bore you to tears.

If there is a relatively affordable area in Woodside it is around here. These are no longer the woodsy mansions that you get farther up into the hills—these are far more modest homes in comparison. The neighborhood mostly looks like many others in the Peninsula—perhaps just a touch more upscale than some of the others in the area, but certainly nothing in comparison to say Hillsborough or even neighboring Atherton.

Home prices in the Selby neighborhood are much more affordable—still over $500 K but not in the multi-million dollar range like in much of the rest of Woodside. The streets are mostly flat and laid out in a grid, with homes built one next to another.

On one end of the neighborhood is Selby Elementary, while on the other you find Woodside High. Selby is unfortunately not a very well performing school, with an API of 3. Woodside High is quite a bit better, with an API of 7.

This is also not quite as safe a neighborhood as many others in Woodside, with many of the surrounding areas having problems with burglaries and even a couple of assaults in nearby Redwood City.

That said, this is still a pretty good area, though still a bit overpriced, in my opinion.

You might mistakenly believe that you are way out in the country when you come into Woodside. This neighborhood is fairly typical in that—from the roads it seems like you are way out at the edge of forrest (which you sort of are, given the Wunderlich Park makes up the western border of this neighborhood)—you know the feel, lots of wood posts for fences and private roads winding up to what you might believe are farmhouses and that sort of thing.

With a median household income of nearly $200k, Woodside is one of the wealthiest cities in all of California. And that is represented in this neighborhood as well.

What does the median priced home cost in this neighborhood?

$6.25 million.

On the high end homes rise to $19 million (or you can buy uncultivated land for $29 million if you are an ambitious real estate developer).

What do you get for say $16 million? For $16 million you can get a 6000 ft. English manor house with 3 bedrooms. It is the kind of place where the bedroom is bigger than most peoples entire homes. Very luxurious and not afraid to show it.

But don’t worry about only having 3 bedrooms—there are 2 separate guest houses and your own private vineyard.

What about on the low end?

You can get a 4 bedroom home nestled in the trees. It is smaller at 3500 feet but still very attractive.

What about schools?

Woodside Elementary and La Entrada Middle School are both outstanding schools with API’s of 10 each, while Woodside High School is only somewhat above average.

And, of course, it goes without saying that the area is virtually crime free.

Overall, this is the kind of place you go to live if you sold your start-up for enough money that you will never have to work again. Otherwise, you might as well just keep on dreaming—only the 1% can afford to live here.

This is one of those areas of the Peninsula where nature becomes a real inspiration. You can find some really beautiful redwood trees here and beautiful homes.

The homes here are built with their wild surroundings in mind. Many of them have wild front lawns and gardens that go well with the green surroundings.

This is a pretty small area, but because it is so quiet it can be quite a draw. Unfortunately it is way out of the reach financially for most. A 6000 ft. home up here, goes for $7.5 million.

The schools around here are pretty strong as you might expect, with the local elementary school getting the highest possible score on its API.

Overall, this definitely a great place to live , if you can afford it.

These large hillside homes can fetch over $1 million when they are not on the market for foreclosure. You can find some real beauties up here, with hardwood decks, large Jacuzzi like bath tubs, and wine cellars. It’s that kind of a neighborhood. When you are driving up here you are often not quite aware of just how big some of these homes actually are. That is because the roads up here are very windy, narrow and blocked by tree cover. This offers the residents a bit of cover for their luxurious life styles.

Now the roads up here are narrow and there are not any sidewalks so this is in no way a walkable neighborhood if you are into that.

There is a little town area here where you can do things like get gas, or put someone up for the night at the local “inn”. There is a taco place and a strip mall at this location as well. It isn’t super fancy but it does have the air of authenticity about it.
Schools, of course, are great and crime is low. Overall this is really nice neighborhood, well worth it if you have the means.

Located deep in the hills to the north west of Woodside and west of Redwood City, Emerald Lake Hills is one of the two neighborhood that make up Emerald Hills. As you might guess from the fact that this neighborhood is far up in the hills on the Peninsula, this is an expensive location.

So what do these hillside homes with great views of the bay cost?

Well let’s start with renting. To rent a home up here, a 2-bedroom will run you about $4000 and a 4-bedroom for $6000.

As you might expect, if you want to own a home, you are looking at multi-million dollars to settle down here. These are largely newer homes, often built in the 90’s or 00’s and they offer a lot of space—often on the order of 6000 feet. Though not as expensive as the homes you will find in Hillsborough, these homes are pretty magnificent by virtually any other comparison.

Even an 1800 foot home built in the 1950’s will still run you a good $800 K.

In terms of schools, this is, as you might expect, a really good neighborhood with Roy Cloud Elementary and Woodside High having very high API’s. And it is a very safe neighborhood as well, with only the rare crime of note.

Overall this is a fantastic place to live, if you are very, very rich.

Cipriani is the neighborhood at the very heart of Belmont. It is a somewhat hilly neighborhood, with somewhat narrow streets that curve along gentle sloops. The homes here are older and not very flashy but nice, and the neighborhood gives you a feeling of shelter from the outside world.

Just past the eastern end of the neighborhood is Twin Pines Park (perhaps Belmont’s best park) and on the western end is Laurelwood Park (perhaps the largest Belmont park). Ralston, the main east-west artery for Belmont, marks its southern border.

The median home price here is about $800K but don’t let this fool you into thinking this is the kind of neighborhood where you will find a multimillion dollar mansion at the end of your block. The ceiling for homes in Cipriani seems to be around $1.25 million (right now there is one home going for $1.27 million, but that is just the asking price).

As with most fairly affluent areas, the foreclosure rate is much lower here than in other neighborhoods, with only about 1 in 3 homes on sale due to foreclosure. Homes here are nice, largely dating from the 50’s, 60’s and 70’s as far as I can tell and the more expensive ones tend to be on the larger side (about 3000 sq. ft.).

One of the nice things about this area is that there is a fairly wide variety of homes for sale, so you are likely to find something that you like (so long as you aren’t looking for a brand new construction or one built in the last generation).

The schools are very strong as well, with Cipriani Elementary and Ralston Middle School being the local public options. (There are also a number of private options.)

This is about as safe a neighborhood as you will come across as well, with barely a domestic dispute to report for the last six months.

Overall, I would say that is a perfect little neighborhood for families where one of the parents has a relatively high paying Silicon Valley tech job.

Homeview is a bit of an ugly strip of a residential neighborhood that straddles the southern end of Ralston between El
Camino and the Bayshore Freeway. The homes here day way back to the post WWII era and a fair number of the residents here are still the original owners. This was clearly the kind of middle class neighborhood that the GI Bill helped to build. The homes are small, barely 1200 sq. ft. many of them and they are a bit cramped in any way that you view them. Also because they are built on a fat grid, they feel more than a little bit generic.

Of course, this combination also means that prices drop lower than in other neighborhoods, with the median home here going for about $500K. These are the kind of homes where half the driveway I is taken by asphalt.

Overall, however, this is a nice neighborhood with very low crime and good schools. I’m still not sure the high sticker price is justifiable in the neighborhood like this, but I can understand why some would go with it anyway.

The majority of this McDougal is taken up by Twin Pines Park, whose shady trails and nice play area make it a favorite for locals. The neighborhood stretches along the southern edge of Ralston just to the west of El Camino Real.

Ironically, I suppose, the neighborhood is named after the park on the western end of the neighborhood where kids go to play baseball, but which is nowhere near as expansive a park as Twin Pines Park.

The neighborhood is hilly and woody, which gives the nicely kept Ranch homes a nicer feel than they might otherwise have.

This is one of those fairly nice neighborhoods that people moved out to in the 1970’s and 1980’s in order to raise their kids.

If you like quaint little Depression Era homes (some of them Mission style, some Tudors), then it is likely you will like McDougal to the east of the park as it approaches El Camino Real. The homes here are mostly nicely kept, but you can tell they were built nearly a century ago.

As you get farther up into the hills the homes get newer and bigger.
Prices throughout the neighborhood vary. You will find some million dollar homes and above, but most near but do not reach this amount.

Schools are great, and crime is virtually non-existent. It is clearly a good neighborhood for families.

Sliced between El Camino Real and the Bayshore Freeway, the Sterling Downs neighborhood is a flat relatively nice middle class neighborhood. There are a fair number of homes on the eastern end of Sterling Flats that would be considered tract homes, I suppose. These are Ranch style homes with red tiled roofs and stucco walls (although that makes it sound worse than it actually is). The streets in these sections are wide and the front lawns are well kept often with well-maintained topiary.
Basically Sterling Downs is quiet though fairly average neighborhood.

Other sections of the eastern end of the neighborhood also have similarly nicely kept Ranch homes. The homes on the southern end of the neighborhood tend to be a little bit shabbier than those on the northern end.

About 90% of the homes for sale in this neighborhood right now are on sale due to foreclosure. The median price for a home here is around $550K.

There are also some apartment buildings on the western end of this neighborhood. I believe they go for about $2200 for a 2-bedroom.

This is, however, a very safe neighborhood with little more than the occasional theft from a vehicle and the schools are strong, from Union Elementary through Carlmont High School.

The main drag in this section of Belmont is El Camino Real, where you can find a number of businesses including a ballet school and a restaurant or two—a sushi place, a creperie and a tavern. It is not a particularly attractive area, but it pretty much gets the job done as far as being a functional neighborhood.

The Central Belmont neighborhood wraps around the northern end of Notre Dame de Namur University.

This is a big hilly neighborhood filled with a variety of home types, from Eichler houses to Tudor variations. Many of the homes here run well over $1 million dollars, although the median price is closer to $750K. Generally in this neighborhood, the higher up in the hills you go, the more expensive the homes.

On the far eastern end of the neighborhood, is El Camino Real, the major avenue that runs north south across most of San Mateo County and the Peninsula. You will find quite a few businesses along, and just off, El Camino Real Blvd. including the Bel Monte Bowl up on the north of the neighborhood and Workplace Innovations—a business that helps companies set up their offices for maximum efficiency.

There are also a number of restaurants on El Camino Real as well. (Some right around the bend on Ralston.) These include places like Jack Prime (a burger place), the Sushi Monster, Shalazar (a Persian joint) and M.E.N.U.

Because the Belmont Caltrain station is on the eastern end of this neighborhood, you might expect that this is an environmentally strong neighborhood, where people could lower their emissions by walking to the Caltrains’ station.
Unfortunately, because there are no sidewalks, this neighborhood is simply not conducive to pedestrian traffic of any kind.

Trying to walk to the Caltrains Station is possible and you could probably get there safely if you kept your wits about you, but

I doubt many residents of Central want to walk in this defensive fashion day after day.

Overall this is a pretty nice place to live.

What determines whether you like this neighborhood is whether you put a high premium on the look of the place where you are. The homes here are far from spectacular; they are mostly Ranch homes of the kind you can find throughout the Western US. Many of these homes are more nicely kept than Ranch homes usually are, but they are still basically just Ranch homes.

What sets this place apart is that you are up in the hills in a fairly woodsy area—though there is not quite enough wood cover to really make this as attractive as it might otherwise be. You are, however, fairly removed from society at large and do feel somewhat secluded. If you like this, then you might like living here in Plateau Skymont.

Homes run around $750 K in this area. A bit on the expensive side when it comes to just getting a Ranch home, but as they say in Real Estate, it’s all about “location, location, location.”

Appropriately named, the Western Hills neighborhood of Belmont stretches out on the far western section of Belmont. This area is largely made up of hilly streets, many of which have apartment buildings.

You could roughly divide the Western Hills neighborhood into three sections. On the lowest section you find the main artery in the area, Alameda de las Pulgas, which forms the eastern border of the neighborhood and has a number of stores including the local supermarket, Lunardi’s. (There is also a Safeway just north of Ralston.)

There are also a good half dozen restaurants right off Avenida de las Pulgas. You have an Italian restaurant named Vivace, a Subway, a pizza place, and a Mexican food place. These are nothing to write home about but they will do the job as far as local suburban eats go.

Close to Avenida de las Pulgas, there are a number of apartment buildings and creeping up the hill are a number of apartment buildings dating largely from the 1970’s. These are run of the mill apartments that happen to be located in a pretty good spot. They are a bit too boxy to really be too attractive, but given the nice wide streets and the hillside feel, they seem a lot nicer to me than might otherwise be the case.

In terms of Peninsula prices, rents are really affordable, running between $800 on the low end for a studio and $2500 for a two-bedroom.

A bit farther up from the apartments, you find a number of Ranch homes. Homes here run in the $800 to $900 K range—largely because of the location’s appearance and great schools.

Overall, a pretty good spot for both renters and homeowners—pretty unusual in that sense.

The Farallon neighborhood in Belmont, stretching from just north of the Oracle HQ down to Twin Dolphins Drive along the Bayshore Freeway, is mostly known for its hotels. In and around this neighborhood, you will find hotels from the likes of the Radisson, to the Holiday Inn to Motel 6. Largely it is about the positioning here—right by the San Carlos Airport and located seemingly equidistant from SF, Oakland and San Jose –it is the perfect crossroads for hotels.

By far, however, the best of these joints, however, is the Sofitel, one of the really great hotels in the Peninsula (possibly in the Bay Area). It is a beautiful sprawling international hotel of the kind you expect in SF or in Europe more than at this spot. Rooms, in case you’re wondering, start at $265 per night. Many choose it for their weddings—it is definitely the place for getting back in tune with your significant other.

There are also a handful of companies here. Asera, Inc., for example, is a tech company that consults with companies to offer them internet service solutions; and Actiance, another Farallon tech company helps financial companies use the web for marketing and communications.

On the far northern end of the neighborhood, you will also find a couple of townhome neighborhoods where all the homes have the same homogenous look—giving these neighborhoods a very clean uniformity that is both their strength and their great drawback, since everything just seems a little too premeditated.

I had a business partner who lived up here so I would occasionally come up into this neighborhood and hang out—mix with each other’s families, plot how we were going to take over the world, that sort of thing.

I really love this little neighborhood and would not have minded living here myself. The houses here are not eye-popping or spectacular by normal standards, but they are definitely distinctive. The homes here largely date from the 1950’s and 60’s.
These are really nice, large homes

There is one house there that is sort of like a Cape Cod, with a gambrel roof over the front facing garage, wood thatch roof, with white trimmed casement windows and a gnarled old tree highlighted by the perfectly green lawn that surrounds it.

Many of the homes here are in this sort of style—kind of an upper class Eisenhower era sort of a feel to them.

So what is the price tag for a home here?

These beautiful houses average about a million bucks, which is about what you expect for the Peninsula.

If it were not for the eye-popping price tag, you might even consider this perfect neighborhood for families, given its outstanding schools and the nice sheltered feel it has. The local elementary, Fox; middle school, Ralston; and high school, Carlmont; are all outstanding. And those are just the public school choices. There are a number of private schools—both religious and secular—in the area as well.

The other nice thing about this part of Belmont is Water Dog Park whose mountain biking and hiking trails are pretty great.

If one had to pick one qualm for this area, it is that it is a bit out of the way from nightlife and that sort of thing. Overall though, if you are raising a family this is a great spot—if you can afford it.

Ryan Tract is a little nook of a neighborhood just to the northeast of the Burlingame Golf Course. It is a pretty old neighborhood and you can find a number of homes that date back at least as far back as the Swinging 20’s. A lot of these are in the English Country Cottage style with the kind of Tudor timbering that makes it seem so old worldly.

These older homes are really well maintained and usually go for around $5 million—which seems to be the going rate for homes in Ryan Tract.

Overall this is pretty nice little Hillsborough neighborhood—if you can afford it, but of course, that goes without saying in Hillsborough.

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.

The Hillsborough Heights neighborhood, located just to the north of the Brewer Subdivision neighborhood, is one of the oldest neighborhoods in Hillsborough. A large majority of the homes here date back to the 1930’s and some are even older.
You will find a fair number of homes here in classic styles such as French Provincial and Spanish Villa styles. These are not quite mansions but they are larger homes and quite attractive, both inside and out.

You will even find some Depression Era homes here designed by William Wurster, who Cal students will recognize from Wurster Hall—the architecture building on campus which, ironically, also happens to have the distinction of being the ugliest building on campus. (The one I am familiar with is designed in the French Provincial style.)

There are also some larger properties here as well, including a mansion that is currently on the market for $25 million. On average, however, most homes in this neighborhood go for about $3 million as far as I can tell.

With Crystal Springs just to the south this is a pretty good area for raising kids as well. The streets are helpful in this regard, having sidewalks. (A lot of neighborhoods in California no longer have this convenience.) Though, I suspect if you live here, you certainly don’t lack for space in your home.

Overall, a great historic neighborhood, well suited to raising kids—as most of Hillsborough is.

The Parrot Drive Area is mostly an undeveloped forest area. There are a couple of streets that creep up into it, and you do have a big mansion deep in this forested area, up on a hill. (I don’t know who lives there. But pretty much that is it for this neighborhood.)

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.

The Country Club Manor neighborhood is mostly taken up by the Hillsborough Country Club and its sprawling golf course.
Not being a member of this club (they are a private country club) I can’t tell you much about this facility other than it looks pretty nice from the outside.

There are some homes in this neighborhood. They are mostly on the eastern end of the golf course though some of them encroach onto the range dividing it into two promontories. I suppose if you live here you should be ready for the occasional golf ball through the window.

There are some really attractive homes here, including Eichlers and Mediterranean style homes. Very well kept and beautiful.

What’s the price tag?

I don’t know because no homes are for sale in the neighborhood right now, but given this is Hillsborough, you are probably talking in the millions for even the smallest of homes here.

Straddling San Mateo College on the northern end, Tobin Clark Estate offers hillside homes with great bay views. This is one of those long east to west neighborhoods that slowly creeps up the hillside the farther that it goes, stretching from Aragon High School to the western end of San Mateo College.

On its eastern end, Tobin Clark is made up largely of long squat homes with perfectly manicured lawns. Though this sounds like your typical Ranch home neighborhood from that description, these are not really Ranch homes. You are aware that you are in an unusual neighborhood throughout this area, partly because the homes are larger than normal, partly because each has its own style, and mostly just because every brick and grass blade seems perfectly placed.

As you get farther up the hill, you get the hillside homes with the best views. This is the area where you get some of the most attractive McMansions in the area, most of them made in imitation of classic styles some actually dating for the 1930’s.
Many sprawl out along the hillside facing out over the Peninsula and Bay.

On the western end of Tobin Clark, you don’t get the spectacular bay views, but you still do get some really attractive—well manicured homes with attractively maintained lawns and just a general feeling of wealth.

Tobin Clark is a mix of contemporary style homes (the squat homes I described earlier) and 1930’s style mansions, with a few English country cottages thrown in for good measure as well.

So what does it cost to live here?

On the low end you can find one of those squat contemporaries for around $2 million. On the high end, one of those giant classic mansions with the views could run you close to $29 million. The median price however is closer to $3.75 million.

The schools here are—as you would expect—pretty outstanding as well. Aragon is a pretty strong high school, maybe just slightly worse than the really outstanding high schools that make up the Penninsula schools.

Overall, I would say that if you are the sort of family for which cost is not much of a consideration (that is, you are filthy rich), that this would definitely be a popular destination for you.

And in case you are wondering where the name Tobin Clark comes from, the area was named after Celia Tobin Clark. The Clarks were a prominent though now pretty much forgotten, Bay Area family. The original estate was designed by famous Chicago architect David Adler.

Of Hillsborough neighborhoods, Lakeview is the one that looks the most average. You get lots of large Ranch homes here of the kind that are not that unusual in many neighborhoods.

In addition, the hilly streets really do look as if they are a part of the surrounding forest rather than having the immaculate look of many of the manicured streets of Hillsborough. In part, perhaps this difference is due to this neighborhood being so far away from the heart of Hillsborough.

So does this mean that prices will be significantly lower than the usual $2-$3 million you would expect in other Hillsborough neighborhoods?

No such luck. The cheapest home you will currently find in Lakeview is going for $1.5 million. It is just a Ranch home dating from 1950. (It is actually below the usual Hillsborough requirement that homes be at least 2500 feet—probably managed to escape this because of its age.)

On the high end, you can find a 5000 foot Mediterranean style home for about $4.25 million—that is relatively low as a cap for Hillsborough, but most homes are in the mid $2 million range, so this is not really much of deal.

Hillsborough Knolls is a tiny neighborhood just to the south of the neighborhoods of Carolands and Homeplace. The homes here are on the large side, though only slightly above average perhaps for Hillsborough.

As usual there is a mix of home styles—from Tudors to Mediterranean styles. The roads are narrow and windy, and it is very secluded.

What does it cost to live here?

You can get a lot here for about $1.2 million, while a 6000 ft. Spanish style home will go for around $5 million. Pretty typical Hillsborough.

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.

Skyfarm is a largely wooded neighborhood just to the west of the Burlingame Country Club. For those who dig a bit of history, this is the location of the old Crocker Mansion, which is now the Nueva Day School (I am told). Crocker was one of the big four magnates that pretty much made their money in SF (Hearst and Stanford were two of the others—the fourth is not coming to me right now other than to remember that he has a hotel in Nob Hill named after him).

Anyway Crocker built his Shangri-La here at what he dubbed Sky-Farm. They say the Mediterranean style buildings that make up Nueva Day School are the old Crocker Mansion buildings, but I think that more likely the old abandoned mansion up in the middle of the water district area is more likely the mansion. It looks like an old style mansion that has been abandoned. If you look at it in Google maps you can see that it meets up perfectly with where the Old Crocker mansion is supposed to be.

The mansion was supposed to be at 2270 Reddington Road and if you look at where that is, the abandoned mansion is fits perfectly. Nueva School is a lot farther up. (Perhaps there were two mansions? I understand that there was a fire in the old mansion and maybe this precipitated the Crocker family erecting a new mansion? I don’t know really.)

Anyway, Nueva School is a compelling reason to move here anyway. Nueva School is an alternative co-educational day school. It is kind like a Montessori style school that is completely student centered, helping to teach students how to think critically and creatively. Basically preparing them to become the same kinds of titans of industry as their parents are. Of course, it will cost you to send you kid here--$36K in tuition per year is about as much as it will cost you to send your kid to Stanford. On the other hand, if you live in Hillsborough, cost might not be your central concern.

My daughter’s best friend from CSUS lived here in Homeplace, so I got to know this neighborhood relatively well from dropping her off and exploring a bit afterwards on a couple of occasions. This neighborhood is deep into Hillsborough, located just to the south of Crocker Middle School and the Burlingame Country Club.

As throughout the rest of Hillsborough, the homes here are (as mandated by city ordinance) large—usually around 3500 ft.

One of the nice the nice things about this neighborhood is the sprinkling of French chateau style homes, with Tudor accents like faux half-timbering, bow windows, weathered brickwork and thatch tiled roof. The look is elegant and makes you feel like you are in the south of France more than in California. The narrow streets and high hedges also add somewhat to this continental feel.

For the most part this area is hooked on classically symmetrical styles with a fair number of Corinthian columns, square paned windows, and walls of various kinds. It’s a nice clean look.

What’s the price tag?

On the low end, for a 3-bedroom, 3000 ft. house dating from the around 1950, you are looking at $2 million. On the high end, for a 1920s Mediterranean style mansion on a 1.25 acre lot, you are looking at $15 million. On average you are looking at around $5 million in this area.

In another neighborhood review I spoke of the Hillsborough Hills generically. There is, as you have no doubt noticed by now, also a Hillsborough Hills that is an actual designated neighborhood in Hillsborough. It is way up near Highway 280 about as far west as you can get and still be in Hillsborough, although the nearest on ramp for the freeway is up by Trousdale Dr. I believe. So you will definitely have a bit of trek when you want to head out to work or anything else of this nature.

If you like being in a neighborhood where you will only see those who live or work there (ie, gardeners and housecleaners), this is definitely the place. No one really comes up here on their way anywhere else.

The homes that crop up here are of a fairly unusual species. Although you have your fairly classic looking contemporary style homes, you will also find larger mansions in varying styles. There is one, for example, that looks like some kind of institute from the outside with a large wrought iron gate leading to a glass paneled square-ish building that looks as if it could house a laboratory. Yet it is, as you can tell from aerial views a personal residence with a pool and the whole shebang.

Other homes up here have more of a European feel with thatched roof and French windows, framed by elaborate stonework and wrought iron fences. Outside you find large lawns and fairly expansive grounds.

When you are not nestled into leafy hills, you will find some spots here where you will get some fairly magnificent views out over the bay towards Hayward and Fremont. It is really a pretty amazing spot.

So what will it cost you to live up here?

On the low end, you can find a 3700 ft. Mediterranean style home with pretty good views for around $2.5 million.

On the high end (currently anyway), you can get about 4 acres and a home for about $8 million.

So, as with everything else in Hillsborough, it ain’t cheap or even moderately reasonable in terms of price.

And, of course, for any kind of basics, such as groceries, you will have to make the drive down to San Mateo.

I believe the elementary that serves this area is Roosevelt and the Middle School is Crocker Middle School. Both outstanding.

Overall, a good area if you want to live slightly away from it all and have the kind of money most people only dream of.

For me, this neighborhood is all about Crystal Springs Upland High School, which is the school my daughter attended back when we lived in this area. Not to be confused with the Sacramento State college with the same acronym, CSUS is one of those amazing prep schools that makes its students feel as if they are already halfway in college.

Partly this has to do with the mansion in which the college is located—it feels like Mills College or a similar sort of college.
he white Corinthian columns that shoulder the entryway and the neo-classical building can feel a bit intimidating when students first arrive. (My daughter was certainly a little intimidated at first.) But the small student body (just 350 students) and the 6 to 1 student teacher ratio make this the kind of ideal learning environment ideally suited for drawing the most from your child and preparing him or her for the challenges of our highly competitive world.

My daughter certainly thrived at CSUS. Largely this is because they not only focus on academics but also emphasize the arts (dancing and music in my daughter’s case).

You are also surrounded by students who have for the most part had all the benefits of the best that education has to offer. So the environment itself is outstanding for learning.

Crystal Springs is definitely the main feature of this neighborhood, the campus and mansion being the largest structures in the Brewer Subdivision.

CSUS is not, however, the only school in Brewer Subdivision. South Hillsborough Elementary is also an outstanding school—as you would expect in such a wealthy community as Hillsborough.

Nor is the CSUS mansion, the only mansion in the Brewer Subdivision of Hillsborough. You can see the top of another mansion right by South Hillsborough Elementary—its top floor popping up above the high hedges that keep the long pool and rows of manicured trees private from probing eyes. If you are such a big fan of Downton Abbey that you want to live in what feels like a replica of the manor, you have found the location to do just that.

Of course, they aren’t all just mansions here. There some relatively regular sized homes by Hillsborough standards. These are not tiny hovels of course. These are large homes with multiple rooms. (As you probably know you won’t find any apartment buildings in Hillsborough because of city ordinance that all homes must be larger than 2500 feet. One of the ways they keep the riff-raff like us out.)

And in case you are wondering, on the low end a 3500 ft. Ranch style home here with 4 bedrooms and baths will run you just shy of $3 mil.

On the high end, you can find a 9000 ft. Italian Palladian style home with 6 bedrooms, pool, screening room, tennis court and all the usual amenities you would expect for close to $7 million.

Of course, those mansions I mention would considerably raise the high end if they ever went on sale.

One of the other draws of the neighborhood, is its proximity to Downtown San Mateo, which helps both for commuting purposes and for shopping. The more you get up into the Hillsborough hills the more of drag it becomes getting things done, I imagine.

Though, of course, if you are rich enough to live high up in the Hillsborough hills then it is doubtful that you worry too much about how much time it takes to drive down (or for your chauffeur to drive you down) to the supermarket.

Overall, one of my favorite neighborhoods in Hillsborough. I suppose, I wouldn’t mind living here with all the other snooty Hillsborough residents.