How social structures and relations influence entrepreneurship is an enduring puzzle. The history of land ownership in Scotland is marked by tensions between the institutional legacy of private landlordism and community embeddedness in place. In this paper I examine the development of a community venture that was established to buy and commit land that was formerly privately-owned into community ownership, and then manage the land in perpetuity for community benefit. The methodology employs archival, interview and observation data to investigate how institutional legacy social structures and relations motivated and shaped community entrepreneurship. The Scottish historical context elaborates the influence of institutional legacy on the embeddedness in place perspective, and the effects of transcending institutional legacy on entrepreneurial flourishing and institutional change