The PropertyGrid is an old grumpy beast. It needs the non-generic IList explicit implementation, not the generic one.

As a site note, you could derive ZoneCollection directly from List<Zone>, and you don't need any ICustomTypeDescriptor / PropertyDescriptor, with regards to this PropertyGrid issue.

Here is an implementation that seems to work:

public class ZoneCollection : IList<Zone>, IList
{
    private List<Zone> _list = new List<Zone>();

    public ZoneCollection()
    {
    }

    public int IndexOf(Zone item)
    {
        return _list.IndexOf(item);
    }

    public void Insert(int index, Zone item)
    {
        _list.Insert(index, item);
    }

    public void RemoveAt(int index)
    {
        _list.RemoveAt(index);
    }

    public Zone this[int index]
    {
        get
        {
            return _list[index];
        }
        set
        {
            _list[index] = value;
        }
    }

    public void Add(Zone item)
    {
        _list.Add(item);
    }

    public void Clear()
    {
        _list.Clear();
    }

    public bool Contains(Zone item)
    {
        return _list.Contains(item);
    }

    public void CopyTo(Zone[] array, int arrayIndex)
    {
        _list.CopyTo(array, arrayIndex);
    }

    public int Count
    {
        get { return _list.Count; }
    }

    public bool IsReadOnly
    {
        get { return ((IList)_list).IsReadOnly; }
    }

    public bool Remove(Zone item)
    {
        return _list.Remove(item);
    }

    public IEnumerator<Zone> GetEnumerator()
    {
        return _list.GetEnumerator();
    }

    IEnumerator IEnumerable.GetEnumerator()
    {
        return GetEnumerator();
    }

    int IList.Add(object value)
    {
        int index = Count;
        Add((Zone)value);
        return index;
    }

    bool IList.Contains(object value)
    {
        return Contains((Zone)value);
    }

    int IList.IndexOf(object value)
    {
        return IndexOf((Zone)value);
    }

    void IList.Insert(int index, object value)
    {
        Insert(index, (Zone)value);
    }

    bool IList.IsFixedSize
    {
        get { return ((IList)_list).IsFixedSize; }
    }

    bool IList.IsReadOnly
    {
        get { return ((IList)_list).IsReadOnly; }
    }

    void IList.Remove(object value)
    {
        Remove((Zone)value);
    }

    object IList.this[int index]
    {
        get
        {
            return this[index];
        }
        set
        {
            this[index] = (Zone)value;
        }
    }

    void ICollection.CopyTo(Array array, int index)
    {
        CopyTo((Zone[])array, index);
    }

    bool ICollection.IsSynchronized
    {
        get { return ((ICollection)_list).IsSynchronized; }
    }

    object ICollection.SyncRoot
    {
        get { return ((ICollection)_list).SyncRoot; }
    }
}