We've lived in San Mateo (city) for the last seven years and about 20 years in the area.
Not sure what you are looking for in the way of housing, but the neighborhoods become more single family, larger houses and lots as you move west from the Bay. Smaller homes, apartments and condos are closer to El Camino, Caltrain and east towards the Bay. We live close to the downtown area and easily walk to shops, restaurants, movies, etc.
For cycling, a ride out Crystal Springs and Polhemus roads takes you to Canada road. From there you have access to the entire peninsula including climbs to the Santa Cruz Mountains (Kings Mountain, Old La Honda, Page Mill, Highway 9 etc) and rides to the coast. Many ways to do 1, 2, 3, 4 and 4+ hour loops with anywhere from 1,000 to 6,000 ft or more of climbing. Search on Strava or Garmin Connect to see tracks from a bunch of the local riders.
Happy to answer any specific questions.
Last edited by Markelp; 06-28-11 at 10:14 PM.