Societal changes are forcing us to reconsider how healthcare is delivered and ICT can support this reimagining of healthcare delivery. One of the emerging trends in this area is Connected Health. However, the evaluation of Connected Health technologies is crucial to assess whether their implementation has had a positive impact on healthcare delivery. To support this assessment process, we developed, an exploratory framework for the evaluation of Connected Health technologies in healthcare settings. This framework was developed after having critically appraised the existing findings of health information system evaluation studies. It also builds on previous models of Information Systems evaluation, in particular, the Information Systems Success Model. Our framework incorporates the concept of assessment from multiple perspectives. Furthermore, the framework identifies the primary stakeholders and extends the assessment based on their concerns. Finally, we elaborate on the framework, detailing its application to a Connected Health solution for primary care based dementia patients in Ireland.