Chestnut St, Russian Hill

For those singles and young couples who have the wherewithal to aspire to such things, Russian Hill is one of the most desirable locations in all of SF. And of the streets in this highly affluent area, one of the most attractive to residents is Chestnut, where you will find one of the very most expensive home sales in the entire city in the past year--a 3-story Victorian that went for nearly $5 mil.

One of the attractions of Chestnut is its variety. On the far western end is Van Ness Avenue, Chestnut Avenue climbs up from that busy avenue, crowded on either side with the 3-story Victorians that are so attractive and so typical of SF. Bay windows and first floor garage doors are the rule of the day here.

After two blocks however, Chestnut gives way to the Chestnut Street Steps which climb up through a small woody area. (This is, of course, just one of several such steps in SF, with the Vallejo Steps perhaps being one of the most famous.)

On the other side of the steps, Chestnut picks up again, though the character of the street has somewhat changed just on the other side. The feel on this first block is much more like what you find in Nob Hill to the south. There are tall residential buildings of the kind you find in metropolitan centers like New York, but that are less typical of SF. This section of Chestnut has a very European feel to it, with buildings being recessed behind high walls with gated entrances and having private green spaces also enclosed within; or, varying the 3-story structures with balconies and cornices rather than bay windows. You are just one block north of the famous Crookedest Street in the World at this point and there is in fact a set of stairs that will lead you right to the street. (Which also makes this a very highly frequented section of Chestnut.)

You also start getting some amazing views of the waters just beyond the Golden Gate. As Chestnut starts making its descent that is where you find what appears to be a mission or church but is actually San Francisco Art Institute. Designed by the same architect who designed Coit Tower, the SFAI facilities are beautiful replica of the kind of architecture the Spanish brought here. They also have a mural by Diego Rivera here.

At the eastern end of Chestnut Street it crosses over Columbus. This is where you find Bimbos, the classic music venue made famous in the 60’s. It is just a very cool set-up inside. To give you a flavor of the kind of acts that perform at Bimbos, here is what is coming up next for them: they have a couple of nights with Sandra Bernhardt if you are into a night of amusing talk; if you prefer to rock like it is the Reagan Era, then come on one of the Tainted Love nights such as on the Stung night when they do all Police tribute songs.

Put simply, this is a pretty amazing run of blocks.

What does it cost to live here?


The average condo in and around Chestnut Street goes for around $1 million. As far as renting goes, 2 and 3 bedrooms run in the $5000 to $6000 range. A studio might go for $2500.

The schools in the area are also strong, with famous schools like the Yick Wo Alternative Elementary making its home here.

Crime is a little bit of a mixed bag. Although on Chestnut Street and in the immediate surroundings it is relatively quiet with only about a dozen burglaries and half a robberies in six months, the area is surrounded by high traffic, high crime areas where burglaries, assaults and robberies abound. Overall, however, you should be okay while on Chestnut itself so long as you use common sense. (No late night walks by yourself, or staring at your phone instead of being aware of your surroundings.)

You can’t beat this location however. You are right in the center of the best part of the city and within minutes of everything from a cool North Beach bar to a live theater event. It is one of the best places to live in the world if you aren’t quite ready to completely settle down yet and have a high powered (and high salaried) job.