Los Altos Hills is very desirable compared to most areas in California for all of the reasons mentioned here.
However, like all housing in the US in the last 20 years, Los Altos Hills experienced a "Bubble" where purchase prices broke free of "real" demand. Prices became based on speculation instead of actual desirability.
The easy way to see this is price-to-rent ratio (look this up on Google).
Rent reflects what a house is really "worth" from a pure demand perspective. People pay high rents for desirable areas and lower rents for less desirable areas.
In Los Altos Hills you can expect to pay anywhere from $4,000 to $10,000 per month in rent (based on a quick browsing of Craig's List).
That's a lot of money for rent, and this reflects actual demand: this is what people are willing to pay to live in this town.
But here's the catch: based on the asking prices of homes here, these rents are actually incredibly LOW.
I just looked at Craig's list and found a home at 26173 Rancho Manuella. It is listed there for $7,500 per month. The price of this home when it was listed was $5 million! (Google the address).
Think about that: imagine renting a $5 million item for ONLY $90,000 per year. That would be like renting a $250,000 Ferrari for $400 per month! Where can I sign up for that? :-)
What's the catch? The catch is that while RENTS in Los Altos Hills reflect the actual market, PRICES here reflect SPECULATION.
The famous "US Housing Bubble of 2007" has burst. Anybody who believes that we're going to return to the Bubble years is either deluded or has been living on Mars for the last three years. Prices are falling everywhere and the will be flat for the next decade at least.
Why? Just like the Bubble made "prices go up because prices are going up", the deflating of the Bubble will make prices go down for the same reason.
So you can say that rents in Los Altos Hills are insanely LOW, but they reflect actual market demand. You can't move that side of the equal sign :-). So if that side of the equal sign is not going to move, it means the OTHER SIDE has to. That means purchase prices.
In short, based on price-to-rent ratio, houses in Los Altos Hills are between 2x and 3x OVERPRICED right now.
If you take the house on Manuella, the correct price-to-rent ratio would price that house at $1.5 million, not $5 million! Even if you assume that owning might be "better in a lot of ways" it still isn't going to be THREE TIMES better. 20% better if you are lucky (a lot of people don't like paying property taxes and paying for upkeep, remember).
Using a combination of Trulia and Craig's List you can find a dozen more examples of this.
Los Altos Hills prices are sitting on a cliff which can fall in at any moment. The only reason prices here haven't fallen YET is because people here can wait a lot longer to sell (in some cases, virtually forever).
There are two things that will finally drive prices in Los Altos Hills to fall:
1. Owner education. In other words, the Smart money will leave sooner than the dumb money. The more owners are educated about the realities of the market, the more they will pull out. This means we'll see houses here actually priced to SELL rather than sit on MLS for six months only to move to Craig's List for rent after that. When owners understand that there is no light at the end of this tunnel, they will actually move. The smart money will leave first (and enjoy the best sales prices, albeit down from peak).
2. Foreclosures. Los Altos Hills is an expensive area reserved for rich people. During the Bubble times, however, a lot of mere "well to do" people moved in. These were working professionals that could make high payments. Bubble financing allowed somebody making $300,000 per year to leverage into a $3 million home. Option ARM payments could be as low as $4000/million and banks would allow you to allocate virtually all of your income to your payments. And there was virtually no down payment requirement. And if you paid a little extra, they wouldn't ask any questions (no-doc loans).
You can imagine how this is going to end. Why pay $12,000 per month for an underwater home when you are paying interest only (or less) with absolutely no hope of ever getting above water in your lifetime? Better to rent the same (or bigger) home for half of that and start saving for your future.