This chapter builds a model for homestay businesses for senior women entrepreneurs and seeks to understand the possibility and challenges of commercialization of existing endowments at one’s disposal for a possible profitable venture. The chapter focuses on women homeowners in the age bracket of 60 years or more. In India, most people retire from active employment around 60 years of age, and it becomes increasingly difficult for most of them to find avenues of income generation that accommodate their age-related physical and mental challenges. This is all the more true for senior women. The authors argue that homestay businesses can fill this gap. A homestay business model falls in the category of sustainable innovation as it offers the woman the opportunity to monetize both her experience as a homemaker and the home itself. Thus, it paves the way for social and economic empowerment for women in their advanced age. An exploratory model is built to understand the intention of senior women homeowners to translate their functionality into capability and the underlying challenges thereof. Since homestay businesses offer an opportunity to utilize their existing skill sets and resources, the newly created entrepreneurs can become agents of change. This could, therefore, become a sustainable business venture for senior women, utilizing their pre-existing facility and functional ability for their socio-economic well-being. The chapter develops a conceptual framework to explore the idea that the functional knowledge that women homemakers possess is an expertise that can enhance the capability of becoming a successful entrepreneur. Furthermore, the chapter explores the possible challenges and policy interventions that can encourage more elderly women to optimize the commercial opportunity of converting their existing residences to homestay businesses.