Oddly Affordable explored the potential for infill development on city-owned nonconforming or "odd" lots to support affordable housing in New York City and Philadelphia. The study examined how historical planning decisions led to irregularities in parcel shapes and dimensions, each city’s current strategies for addressing these challenging sites, and the barriers to and recommendations for future development. Both Philadelphia and New York are at crossroads in their approach to developing on these odd lots, motivated by a shared need for increased investment in affordable housing. This research demonstrates that these sites, which may initially seem unsuitable for development, can hold significant value in meeting housing demands. Through data-driven analysis, the highest and best use of each site can be determined, whether for infill development or as a community asset. The research finds that the primary challenges lie not in the physical constraints of the sites, but in the chosen design approach by the architects, the construction methods, and the complexities of navigating regulatory restrictions that pose significant barriers to smaller-scale developments.