There is good news here. You are realistic about the market and you are a "move up" buyer. First you need to contact a Realtor to find out what you can realistically expect to sell your home for. Second, be weary of agents that will try to "buy" your listing. In other words, tell you an unrealistic price so you list your home with them. Third, from the agent you should expect hard numbers, market trends, absorption rates, and current solds and actives. Try to make your condo the best deal out there. It sounds like you have done a great deal of updates and Buyers love that but it doesn't always make your home more valuable but it does make it more saleable. The rest of the good news is you are a "move up" Buyer so you will save in the long run. If you paid 285k for your condo and end up selling for less you will buy for less too and your savings will be more on a 500k house. This is just anj example but say you sell for 270k and you buy for 500k. The house you would be buying may have been more like 575k. So you actually made 50k in the deal. Buying and selling is really just transferring equity so the short answer is it seems as though you are in a good position to buy. If you wait for your townhome to appreciate the home you want to buy will too and it will cost you more in the long run.