You did not mention whether you are looking to rent or purchase, and I would suggest that you rent for at least six months, before purchasing. There is so much diversity in the Bay Area, and each city is very different. The answers below are all on target.
I would like to mention that you are looking at a commute of about an hour, from Palo Alto/Cupertino area to UC Berkeley. I used to commute from Palo Alto to Oakland, and it was not a bad commute because I was going against traffic. But the cities are not right next to each other. Good luck.
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weather is pretty subjective but I can say from living in the Bay area all my life that Cupertino and Palo Alto are pretty similar with their weather patterns. If you want sunny, little fog, rain and clouds stay inland. If you travel up the Penninsula you will get the fog and clouds. Anywhere in the valley is outstanding. San Jose in whole is awesome. I would say that if you look in Los Gatos all the way to mid-Penninsula (Redwood City) you will get the great weather. If you go south towards the coast (Santa Cruz) or north (Half Moon Bay, San Mateo, Bay) it gets chillier. East Bay tends to get a little warmer, but it's pretty temperate.
I understand SAD. I moved to WA state for 3 years and couldn't get back to my native CA quick enough. There are areas which get more fog and these are usually areas nearer the water. So if you go inland and south you'll have more sunny days. The temperatures get warmer in some areas, such as Fremont, Almaden Valley, Morgan Hill, etc. Weather websites will give you days of rain, sun, etc. then hook up with a Realtor to assist you with the other factors in your decision.
How about Fremont? Lots of things to do, house prices varies (low to high end), lots of shops and activities, Bart to go to Berkeley.
A place to check into and let me know if I can help you.
I would love to let you know what area would be probably best for you. But I'm not sure what home price range you are looking for. Please feel free to contact me so I can help you find the best place for you to live in.
Each area of Silicon Valley beautiful and each one has its own perks. From a small town feel to a secluded get away to a vibrant down town area. You'll probably see that weather won't be your main concern in the Valley.
Don't hesitate to call me directly at (408) 863.3179. Until then, have a great day.
Carlos Rafael Cruz
REALTOR | DRE# 01865777
Intero Real Estate Services
12900 Saratoga Avenue
Saratoga, CA 95070
+1 (408) 786-5179 (Cell)
+1 (408) 863.3179 (Office)
+1 (408) 877.1595 (Fax)
I agree with the guys below on the areas, I'd also like to point out that in Los Gatos, or in the mountains the fog burns off first and you have bright clear days. Also there is a dryer climate here than the Northeast. although not as dry as AZ.
Hook up with a realtor who works these areas so that you will feel confident when you make a purchase.
There are some VERY good realtors right here on trulia, just look over the profiles and answers of a few of us and contact the ones who you feel will represent you well.