A decline in the availability of opportunities for new entrants to agriculture is a recognised consequence of the agricultural restructuring process. Under the Common Agricultural Policy, various support schemes have attempted to address such concerns, with limited success. A number of these schemes focus on the provision of agricultural property rights for new entrants, but there appears to be limited justification for this. This paper argues the new entrant problem is as much about progression and exit as it is about entry, with such considerations generally not included in support frameworks. To develop this argument, the paper re-engages with the concept of ‘real’ regulation to examine rural property relationships on agricultural estates held by local authorities and county councils within England and Wales (i.e. the county farms estate). ‘Real’ regulation influences property-owner behaviour in three-ways: regulation of land occupancy; regulation of landowner behaviour; and, regulation of land use. These three regimes allow property owners to determine management strategies based on economic, social and environmental considerations. The flexibility afforded by ‘real’ regulation, and in particular, the regulation of land occupancy, and of landowner behaviour, allows property-owners the option to shift focus between these regimes, especially when faced with unfavourable market conditions. Analysis of different estate management strategies (consolidation, partial disinvestment, disinvestment), shows how this severely restricts the provision of property rights to new entrants and progressing tenants, as property-owners look to protect their interests. For these reasons, current new entrant support networks have limited success, irrespective of the political approach driving them.