The wide-spread adoption of the Smart City concept has introduced a new era of computing paradigm with opportunities for city administrators and stakeholders in various sectors to re-think the concept of urbanization and development of healthy cities. With the world population rapidly becoming urban-centric especially amongst the emerging economies, social innovation will assist greatly in deploying emerging technologies to address the development challenges in core sectors of the future cities. In this context, sustainable health-care delivery and improved quality of life of the people is considered at the heart of the healthy city agenda. This paper examines the Boston innovation landscape from the perspective of smart services and innovation ecosystem for sustainable development, especially in transportation and healthcare. It investigates the policy implementation process of the Healthy City agenda and eHealth economy innovation based on the experience of Massachusetts’s City of Boston initiatives. For this purpose, three emerging areas are emphasized, namely the eHealth concept, the innovation hubs, and the emerging technologies that drive innovation. This was carried out through empirical analysis on results of public sector and industry-wide interviews/survey about Boston’s current initiatives and the enabling environment. The paper highlights few potential research directions for service integration and social innovation for deploying emerging technologies in the healthy city agenda. The study therefore suggests the need to prioritize social innovation as an overarching strategy to build sustainable Smart Cities in order to avoid technology lock-in. Finally, it concludes that the Boston example of innovation economy is unique in view of the existing platforms for innovation and proper understanding of its dynamics, which is imperative in building smart and healthy cities where quality of life of the citizenry can be improved.