In the UK, around 55% of householdsí net worth is in housing. More than 70% of households in the UK own a house and holding such a large amount of undiversified real asset poses risk. It is not always that a house would appreciate in value, though a housing investment has been recognised as a good hedge against inflation. This paper assesses the risks associated with housing investment by performing following tasks: (i) analyse the association of return on individual housing with sub-market return, overall Aberdeen housing return and Scotland housing return, (ii) analyse the role of atypicality of individual properties and bargaining power of sellers on housing returns, (iii) estimate the probability of loss and (iv) the role of bargaining power of sellers and atypicaility of properties in determining probability of loss. The data used for the analysis is the Aberdeen Solicitor and Property Centre (ASPC) transaction data for the period 1984 to 2002.