Real estate covenant regimes are a form of common pool resource in which property owners retain ultimate ownership but contractually surrender some rights to the use of their land into a commons. The pooled rights generate surplus for the owners. This article explores the efficiency of legal rules protecting covenants, applying three perspectives: the property/contract interface, incomplete contracts and common pool resource literatures. Efficiency is considered at two points: when the initial investment decision is made (ex ante); and at a later point (ex post) when a new use would be higher-valued and the covenant should be modified or terminated. Covenants are interests along the property/contract interface: promises with respect to the use of land. The choice between property or contract status is determined by which will maximize investment while minimizing the sum of holdout and transaction costs on renegotiation. When investment incentives predominate, this favors property status protected by property rules. When the later risks of high transaction costs and holdouts predominate, this favors contract status, which allows easy breakage protected by liability rules. Because real estate is an investment-intensive asset class, covenants are generally given property status and governed by property rules protected by injunctions. The investment induced by property status generates an expectation of surplus for each unit owner; when these rights are defeated, the result may be demoralization leading to underinvestment. The primary conclusions are first, that for most covenant violations, courts should give greater respect to the private ordering of remedies, such as fines, self-help and expulsion. These remedies provide lower-cost enforcement than the current regime of injunctive relief and limit the inefficient erosion of covenant regimes. Second, over decades, covenant regimes are likely to be inefficiently rigid, a problem made worse because the rise of the community association has radically lowered enforcement costs. This results in an anticommons where fragmented control prevents transfers of property to more efficient uses. Third, to combat this, courts should use mixed property-liability rules in the form of supercompensatory damages for major use violations occurring more than 40 years after creation of the covenant regime. Supercompensatory damages would limit demoralization from defeated investment expectations (if contract status protected by a liability rule applied) or excessive performance of an uneconomic promise (if property status protected by injunctive relief applied).