For what it's worth, home prices have fallen considerably in the SF Bay area as well as the rest of California in the past year.
As for cycling in the SF Bay area, we can do it pretty much year round.
We've entered the rainy season now
, and around here, when it rains, it pours! We don't so much get the steady drizzle that our friends in western OR and WA experience. Luckily for us (but, not necessarily for the water supply), the rains diminish come March and are pretty much over come April, and then they don't start up again until December. Roughly speaking of course.
Sometimes, like right now, temperatures in the SF Bay area can drop into the 30's but that's somewhat unusual. The farther inland you go they experience more winter-like weather, then of course a few hours east of us you have the ski areas.
Our summers don't get particularly hot, especially if you're right near the coast (where it can be downright chilly thanks to the fog blowing in from the ocean) although temperatures can get into the 100's the further inland you go. "But it's a dry heat".
And the cycling around here is great - you've probably seen some of our ride reports in the Northern CA forum.
Good luck in your search.
2009 Lynskey R230 Houseblend - Brooks Team Pro
2007 Rivendell Bleriot - Rivet Pearl