The challenging task of providing high-quality workforce housing is further complicated in a rent-stabilized housing market such as New York City. Socially conscious, fiscally responsible landlords must conduct major capital improvements and apartment maintenance with an eye toward creating a safe and attractive living environment while also meeting investors’ return expectations. How does a for-profit company add value to its portfolio while managing to keep rents affordable? This case study of Urban American, LLC, examines how one company’s operational model works within rent stabilization laws to create healthy returns and reinvigorate the workforce housing stock in and around New York City. The author would like to thank Urban American, LLC, and especially James Eisenberg, Joshua Eisenberg, Philip Eisenberg, Ann Heath, and Frost Travis for their guidance and goodwill during the course of preparing this case study. Any errors of fact or interpretation are the author’s alone.