The quality of software has an important bearing on the financial and safety aspects in our daily life. Assessing quality of software at the design level will provide ease and higher accuracy for users. However, there is a great gap between the rapid adoption of Object Oriented (OO) techniques and the slow speed of developing corresponding object oriented metric measures, especially object oriented design measures. To tackle this issue, we look into measuring the quality of Object Oriented designs during both software development and re-development processes. A set of OO design metrics has been derived from the existing work found in literature and been further extended. The paper also presents software tools for assisting software re-engineering using the metric measures developed; this has been illustrated with an example of the experiments conducted during our research, finally concluded with the lessons learned and intended further work.