This article presents a comparative study of a pivotal case decided by the Lands Tribunal of Scotland, Strathclyde Joint Police Board v. The Elderslie Estates Ltd. The decision exemplifies how Scotland, one of the world’s leading mixed jurisdictions, addresses several fundamental property law issues. Should landowners be allowed to impose restrictions on the use of land that bind future owners in perpetuity? Should courts have any power to modify or terminate those land use restrictions if the passage of time appears to undermine their initial purpose and utility? Does the application of the European Convention on Human Rights change how a court must protect fundamental property rights? This comparative case study sheds light on how Scotland has answered all these questions, reflects on the costs and benefits of its solutions, and contrasts the Scottish approach with typical approaches under American law. The Lands Tribunal’s decision, the article also argues, demonstrates a powerful communitarian conception of property in Scottish law, one that has continued to surface even after the formal abolition of Scottish feudalism in 2004 and that differs substantially from the market based conception of property currently reigning in the United States.