Sell Your Current Home
Most people can not afford to hold onto two homes at the same time, if you own the home you have now, you'll probably need to sell it.
When should you sell?
Seller's market: When there are lots of people looking for homes but not many for sale,
Buyer market: When there are lots of homes for sale and not many people buying them,
If you're selling one home and buying another, you don't really have to worry about playing the market. If you sell your existing home for a 'low' price, you're probably also buying at a low price.
Buy first or sell first? Many people are able to time their sale and purchase so they happen on the same "closing date". As a buyer, you can make your offer "conditional" on the sale of your existing home, so you're not paying for the upkeep of two homes. Or when selling, you can try to extend the "closing period" to give yourself more time to find your new home.