Oberoi Realty Limited (ORL) has been a success story in Mumbai’s premium real estate space and has created a strong brand value over the years. However, the company has primarily focussed on the high-end category and on specific locations in Mumbai. Over the past 15 years, the high demand for prime real estate properties has been sustained with robust income growth of the economy. However, the economic slowdown since 2018 and the COVID-19 pandemic have created huge uncertainty in the real estate market, particularly in Mumbai. This, along with the government’s active push, has led to a change in preference of consumers for owning affordable houses. On one hand, the inventory is piling up, and, on the other, affordable housing on the outskirts of Mumbai is gaining momentum. ORL is facing the dilemma of whether to diversify its portfolio at the cost of possible brand dilution or to continue with its earlier strategy of offering exclusive, brand-oriented luxury housing for high-income individuals. This case is all about this strategic dichotomy in the real estate business.