WPF Span image across multiple listbox rows

Yes, it is possible. If a control is situated within a Canvas, it can be placed outside the bounds of the canvas. So essentially, you can use this feature to ensure that your control is not clipped. So, for example, you can do something like:

    <ListView ItemsSource="{Binding}">
        <ListView.ItemTemplate>
            <DataTemplate>
                <Grid>
                    <TextBlock Text="{Binding Text}" />
                    <Canvas>
                        <Rectangle Visibility="{Binding ShowOverlap}" Width="100" Height="100" Opacity="0.5">
                            <Rectangle.Fill>
                                <ImageBrush ImageSource="house2.png" Stretch="UniformToFill" />
                            </Rectangle.Fill>
                        </Rectangle>
                    </Canvas>
                </Grid>
            </DataTemplate>
        </ListView.ItemTemplate>
    </ListView>

With some code-behind of:

public partial class MainWindow : Window
{
    public class Item
    {
        public string Text { get; set; }
        public Visibility ShowOverlap { get; set; }
    }

    public MainWindow()
    {
        InitializeComponent();

        List<Item> items = new List<Item>();
        items.Add(new Item() { Text = "Test1", ShowOverlap = Visibility.Hidden });
        items.Add(new Item() { Text = "Test2", ShowOverlap = Visibility.Visible });
        items.Add(new Item() { Text = "Test3", ShowOverlap = Visibility.Hidden });
        DataContext = items;
    }
}

And you will see that a 100 x 100 rectangle, overlapping the ListViewItem appears. You can do the same thing, but put your image inside the Canvas.