There is a low supply of the missing middle housing types (MMH) in walkable urban core neighborhoods. That is, a variety of compact low- to mid-rise housing in walkable areas that are accessible to entertainment, recreational and other amenities. The largest demographic, the millennials, followed by the baby boomers, prefer the MMH types. The MMH types is a new name for a variety of compact housing types that existed in traditional neighborhoods in urban areas pre-World War II. However, due to changes in housing preferences after World War II, the requisite land use and zoning changes facilitated larger single-family homes phasing out the MMH types. Efforts to reintroduce the MMH types is these areas are met with opposition. This research investigates increasing the supply of the MMH types in walkable urban core neighborhoods. The literature review reveals, prior to this one, no academic study at this level was done to understand how to increase the supply of MMH types in these areas. This research explores the views of stakeholders in urban planning and various professions related to housing and the MMH types in the Tampa Bay Area, to better understand the issues involved in the low supply of the MMH types in urban core areas. The data for this qualitative research was guided by a grounded theory methodology (Corbin & Strauss, 2014) and was derived from thirty-nine semi-structured interviews with stakeholders to find out what factors inhibit and ways to improve the supply of the MMH types in the Tampa Bay area.