The Estonian economy and along with it the real estate market, especially housing market, has been in rapid development since its very existence in the 1990s. In resent years there have been repeated hints of an approaching real estate crash and of a possibility of extremely pessimistic development scenarios. The aim of this paper is to examine the possibilities of future development of housing market in Estonia. The development of the housing market has been investigated from three main aspects. Firstly, we evaluate the development and changes of Estonian economic environments and provide links to the general development of the whole real estate market and especially of housing market. Secondly, in greater detail we analyse demand and factors influencing it in housing market. Thirdly, we investigate supply of the housing market, the factors that facilitate and inhibit this development. The housing market development in Estonia, their differences and similarities with Latvia and Lithuania are also presented in the article. Statistical and econometric techniques are employed to find the drivers that influence the major housing market and its development in future.