Background: People have various and changing needs as they age, and the number of people living with some form of dementia is steadily increasing. Smart homes have a unique potential to provide assisted living but are often designed rigidly with a specific and fixed problem in mind. Objectives: To make smart-ready homes and communities that can be adaptively and easily updated over time to support varying user needs and to deliver the needed assistance, empowerment, and living independence. Method: The design and deployment of programmable assistive environment for older adults. Results: The use of platform technology (a special form of what is known today as the Internet of Things or IoT) has enabled the decoupling of goal setting and application development from sensing and assistive technology deployment and insertion in the assistive environment. Personalising a smart home or changing its applications and its interfaces dynamically as the user needs change was possible and has been demonstrated successfully in one house – the Gator Tech Smart House. Scaling up the platform technology approach to a planned living community is underway at one of UK’s National Health Services (NHS) Healthy New Town projects. Conclusions: There is a great need to integrate technology with living spaces to provide assistance and independent living, but to smarten these spaces for lifelong living, the technology and the smart home applications must be flexible, adaptive, and changeable over time. However, people do not just live at home, they live in communities. Looking at the big picture (communities), as well as the small (homes), we consider how to progress beyond smart-ready homes towards smart-ready communities.