Hi Leo! Timing the real estate market is like timing the stock market- not something most people do successfully. The answer is not a simple yes or no, but rather to look at the reasons you are thinking of selling, where you would go from here in Oak Park (I''ve been here over 20 years!) Are you over 55? Depending on where you are moving to, you may be able to take advantage of proposition 60/90- which allows a one time transfer of your property tax base, if you meet certain guidelines and requirements.