NASA’s Commercial Orbital Transportation Services (COTS) program radically changed the space industry, igniting private-sector partnerships for delivering cargo and crew to the International Space Station (ISS). With the ISS nearing retirement, NASA aims to extend that same commercial spirit toward ensuring continued access to low Earth orbit (LEO). The Commercial Low-Earth Orbit Development Program seeks to foster privately owned and operated space destinations where agencies and commercial customers can purchase services and conduct research in the post-ISS era. This chapter examines how select companies have embraced the challenge of becoming “orbital real estate” developers. It begins with early endeavors like the Industrial Space Facility and Bigelow Aerospace’s pioneering inflatable modules, showcasing commercial LEO ventures’ potential. Next, it focuses on NASA’s pressing need to replace the ISS and details proposals from several aspiring contenders. Axiom Space Station aims to transition from attached ISS modules into an independent platform; Blue Origin and Sierra Space’s Orbital Reef aspires to become a multipurpose commercial habitat; and Voyager’s Starlab envisions a fully integrated station catering to scientific and industrial pursuits. These endeavors demonstrate how NASA’s evolving relationship with the private sector is reshaping the future of human spaceflight and LEO utilization.