Richmond
If you work in Richmond, then you can probably live on the bay/river with a reasonable (1-1.5 hour) commute. The waterfront property down in the areas near here are high, but have not caught up with many markets around the US. You will probably think it is dirt cheap coming from San Jose. They are going to start to develop Urbanna, VA with a nice new neighborhood area www.rosegill.com (<1 hr to Richmond).I know folks that commute from Deltaville, VA (1:15 to 1:30 to Richmond). Also, wonderful town to live would be Irvington, VA - I would love to live there. Both are on the Rappahannock River and close to the Bay. All are close to Richmond with little traffic for your commute though it may be 70 miles from Richmond. Slip fees will run probably around $2k for a 36 footer around here.Near DC, I would just forget about it. Traffic is absolutely terrible! It would be great to live in Annapolis, but would probably take you forever to get into DC - not sure about how long from there to Baltimore with traffic though. Think big bucks up in this neck of the woods both for your house and your boat. I am not as familiar with that area since I live down in Richmond.Maybe look at the Hampton, Norfolk, Newport News, Yorktown area. There you can live close to work, boat, etc. It is not as quaint as the less populated areas and traffic is once again terrible, but may offer more of what you are looking for.Are you looking for a specific location, or just general area recommendations?