Hillsborough vs. Woodside (San Mateo, Redwood City, Alameda: apartment, rentals, big house)

[herazeus]

Can anyone give me comparisons between the cities of Hillsborough and Woodside? I'm wondering what the people are like and what there is to do in town.

[humboldtrat]

Got money? Both Hillsborough and Woodside are very upscale communities where most homes start at $5 million. There are no rentals or apartment buildings in either town. There's not much to do in either town since both towns are almost completely residential with a minimum of commercial or retail establishments in either town.

Lots in Woodside tend to be larger so that residents can keep horses which require out buildings such as a barn or stable. No one in Hillsborough seems to have horses that I have ever seen.

[sonarrat]

There are some smaller rentals between Canada Road and 280 in Woodside.. cottages and small apartment buildings. Woodside is really in the forest, and it has a heavy rural flavor. You'll still find some older properties without electricity and water. Hillsborough is not so secluded, but the town goes to extreme lengths to set it apart from the surrounding communities (which are, themselves, quite prosperous). There are no multi-family properties in the entire town.

[DMenscha]

The coolest thing to do in Woodside is have a meal at Buck's Cafe. Jamis and Margaret have been doing things right there for a long time. I stop there every time I'm in the neighborhood.

Buck's of Woodside

[krudmonk]

Neil Young chose Woodside. Go hang out with him.

[gizmo980]

I grew up next to Hillsborough (in San Mateo Park), and went to school there for most of my life... then my mother moved to Woodside after getting divorced, and lived there for 10 years - so I know both towns very well! Like the others said, they're both very expensive areas, but I'm sure you already know that. Woodside is definitely more rural & woodsy, and they are zoned for horses, so you'll often see people riding down Canada Rd. Hillsborough is mostly just big houses on hills, and there are NO commercial properties allowed... therefore there's no "downtown," restaurants, stores, etc., and you have to drive to San Mateo or Burlingame to find that stuff. Woodside does have a downtown, small as it may be, with Robert's Grocery, Buck's (I second that YUMMMMMY), and a few other things. Then you have a multitude of stores down Woodside Road, as it hits Redwood City - Safeway, Petco, Blockbuster, restaurants, etc. I'd personally choose Woodside, since I like the old-town feel & shopping options. Hillsborough is very nice, but feels more isolated and snotty, and has a lot of neighborhood "rules" that can get annoying.

[Peninsula gal]

Hillsborough has no business district, Woodside does. Hillsborough is an incorporated town sitting between El Camino and 280 Burlingame and San Mateo. Woodside does have some areas with the mail address of Woodside but unincorporated and those are east of 280 abutting the Alameda in Redwood City. Woodside is horse friendly, with large estate, large homes, loads of land, horse trails, and old, old money. Hillsborough does not allow horses, has a half acre minimum for each lot, also has old money, but not as old as in Woodside. Woodside's weather is a bit warmer, as it's further south on the Peninsula. Do not believe the comment about $5m to buy in. You can get into either town under $2m, which isn't cheap change, but sure a lot less than $5m. Both are very upscale areas and safe from crime. Hillsborough had many old estates that were carved up for the land and now have homes whereas Woodside still does have some of those old estates.

[gizmo980]

Originally Posted by Peninsula gal

Do not believe the comment about $5m to buy in. You can get into either town under $2m, which isn't cheap change, but sure a lot less than $5m.

Yes, you are correct... my mother's house off Jefferson Ave. cost about $950K 10 years ago, and she sold it for $1.5M last year. It was a 5-bedroom house with a good-sized backyard (just under 1/2 acre, I think), so you can definitely get something for less than $2M. Hillsborough is a little bit cheaper overall, but has plenty of $10-15M houses among the "less expensive" ones.

[herazeus]

Is there shopping nearby to these cities? Grocery stores like Whole Foods?

[herazeus]

Originally Posted by gizmo980

I grew up next to Hillsborough (in San Mateo Park), and went to school there for most of my life... then my mother moved to Woodside after getting divorced, and lived there for 10 years - so I know both towns very well! Like the others said, they're both very expensive areas, but I'm sure you already know that. Woodside is definitely more rural & woodsy, and they are zoned for horses, so you'll often see people riding down Canada Rd. Hillsborough is mostly just big houses on hills, and there are NO commercial properties allowed... therefore there's no "downtown," restaurants, stores, etc., and you have to drive to San Mateo or Burlingame to find that stuff. Woodside does have a downtown, small as it may be, with Robert's Grocery, Buck's (I second that YUMMMMMY), and a few other things. Then you have a multitude of stores down Woodside Road, as it hits Redwood City - Safeway, Petco, Blockbuster, restaurants, etc. I'd personally choose Woodside, since I like the old-town feel & shopping options. Hillsborough is very nice, but feels more isolated and snotty, and has a lot of neighborhood "rules" that can get annoying.

So are you saying that Hillsborough has no downtown area and Woodside does? If you live in either of the towns do you ever see your neighbors or are you totally isolated?