As I happen to live about an hour out of New York City, I know a little bit about this area's real estate market. Here's what I know. If you are buying a property in the City, meaning Manhattan Island, it is almost guaranteed that you will not lose money. However, condominiums (there are almost no houses left in Big Apple) are very expensive, as you might already know. A two bedroom 1.5 bath will easily cost anywhere from half a Mil to 800K in most livable parts of the island. If you go up to the Upper West or even East side, don't expect anything for less than a Mil. I would avoid Bronx, Brooklyn and even Queens, but that is just me. You might like it there. If you venture out a bit, say into New Jersey, there are lot of neighborhoods that are very livable. But I suggest you live near the NJ Transit train station as the traffic can be horrendous if you have to commute to work in the City. For around 600K, about the same price you would fork over for a tiny condo in Manhattan, you can get a decent single family home in a town such as Summit, New Providence, Berkeley Heights, etc. And the home prices tend to go up in these parts, even during recession, because of the relatively close proximity to NYC (1 hour by train) and the excellent schools. As for the time to buy, I would say, if you plan to live in the house for at least 5 years, buy now. Interest rates are relatively low. Housing prices are almost at rock bottom. Provided that you have good credit (above 720 Fico score), steady and sufficient income with the history of same for past few years, have enough saved to put 20% down payment (or at least 10%), you can easily find a good home loan at around 6% interest rate. If you are looking to sell, I would say wait at least until latter half of 2009 when the real estate market is estimated to pick up. I am not a realtor, this is just from my own experience. So if you are serious, it might behoove you to do some research and get yourself a real estate agent (a good one, mind you, as there are many who are just after the commission).