Addis Ababa has been subjected to different kinds of urban developments which are undertakenrnat different times: past and present. The city is now witnessing the product of these two kinds ofrnurban developments. The places created by these two urban development activities varyrnsignificantly; some places in the past developments arguably, to a certain level, have good placernattributes which can be prototypes. They have good physical setting, activities and impart strongrnmeanings. On the other hand the present developments lack strong place attributes. They havernproblems in the physical setting, in the activities that take place in these areas and in thernmeanings they impart.rnThis requires proper investigation in to which places do people prefer, to what extent the pastrnurban development areas are having the place attributes and recent urban development areas arernlacking them.rnThe investigation was made by studying two places selected from the rapidly growing urbanrnareas in Addis Ababa and the other from the past developments. That is, Captain H/G/SellassiernStreet (CHAGS) and Lagar Railway Station-Beherawi Theatre (LRS-BT) areas respectively.rnThe study was made by measuring the two places with place preference (attachment) indicatorsrnand place attributes or urban design qualities which are collected from different sources. Thesernwere further refined in to two pillars of evaluation. The first was questionnaires for users of placernin each location and the second was the expert evaluation format with which an expert evaluationrnwas made in the two places. The target of questionnaires was to find out important componentsrnof places as answered by respondents in the two case study areas: the place preference ofrnrespondents and their opinions on place attributes (urban design qualities). The place preferencerncomponent targeted to find out place preference, reason for place preference and the level ofrnattachment. On the other hand the place attributes component of the questionnaire dealt with thernlevel of place attributes as indicated by respondents. As to investigation on place attachment,rnquestions were that deal with place preference, reason of preference, level and kind of placernattachment were added to the questionnaires