What is your price range? This will dictate whether you will be able to buy an SFR in Santa Clara County in the abovementioned areas or Milpitas/Campbell/SJ.
Obviously, SFR’s in some areas in both San Mateo County (as flu mentioned) and SC County will likely be out of your reach. Have you considered looking at major fixers (even structural) in out-of-way places such as Pacifica or Half Moon Bay area (not fwy close)?
What is your level of home-improvement expertise?
I personally don’t think prices will “crash” in SV as there will never be any more land and the vast open space on the peninsula will never be developed (yes, I said, “never”). There are a few (VERY few) distressed properties still on the market but would imagine they are snapped up quickly after being listed.
I also noticed SFR’s in one of my choice retirement areas, Saratoga, has nearly DOUBLED in price in the last two years, condition be damned. Obviously, being one of the last downzoned bastions of mid-century ranches on large lots, buyers have recently realized this. Campbell is my second choice but is currently soaring in value.
Except for some parts of SJ and below, the condo/townhome market appears to me to be infinitely easier to get into for the borrower who doesn’t have $300K+ to put down.
As a soon-to-be-“retiree,” I’m probably priced out of SV forever as a single buyer for what I want so have now begun to study the “Lamorinda” area (CC Co) and Montclair/Piedmont (Oakland). But I won’t have a SV job to commute to, like you do :=}
I regret not being able to buy a property in SM/SC Counties in the last 1-2 years and lease it until I am ready to occupy it.