diff --git a/src/Markup/Avalonia.Markup.Xaml/Data/Binding.cs b/src/Markup/Avalonia.Markup.Xaml/Data/Binding.cs
index eb5f87ea2a..8ba637de50 100644
--- a/src/Markup/Avalonia.Markup.Xaml/Data/Binding.cs
+++ b/src/Markup/Avalonia.Markup.Xaml/Data/Binding.cs
@@ -66,7 +66,7 @@ namespace Avalonia.Markup.Xaml.Data
         /// <summary>
         /// Gets or sets the binding path.
         /// </summary>
-        public string Path { get; set; }
+        public string Path { get; set; } = "";
 
         /// <summary>
         /// Gets or sets the binding priority.
@@ -93,53 +93,51 @@ namespace Avalonia.Markup.Xaml.Data
             bool enableDataValidation = false)
         {
             Contract.Requires<ArgumentNullException>(target != null);
-
             anchor = anchor ?? DefaultAnchor?.Target;
-
-            var pathInfo = ParsePath(Path);
-            ValidateState(pathInfo);
+            
             enableDataValidation = enableDataValidation && Priority == BindingPriority.LocalValue;
-
+            
             ExpressionObserver observer;
 
-            if (pathInfo.ElementName != null || ElementName != null)
+            if (ElementName != null)
             {
                 observer = CreateElementObserver(
                     (target as IControl) ?? (anchor as IControl),
-                    pathInfo.ElementName ?? ElementName,
-                    pathInfo.Path);
+                    ElementName,
+                    Path);
             }
             else if (Source != null)
             {
-                observer = CreateSourceObserver(Source, pathInfo.Path, enableDataValidation);
+                observer = CreateSourceObserver(Source, Path, enableDataValidation);
             }
             else if (RelativeSource == null || RelativeSource.Mode == RelativeSourceMode.DataContext)
             {
                 observer = CreateDataContexObserver(
                     target,
-                    pathInfo.Path,
+                    Path,
                     targetProperty == Control.DataContextProperty,
                     anchor,
                     enableDataValidation);
             }
             else if (RelativeSource.Mode == RelativeSourceMode.Self)
             {
-                observer = CreateSourceObserver(target, pathInfo.Path, enableDataValidation);
+                observer = CreateSourceObserver(target, Path, enableDataValidation);
             }
             else if (RelativeSource.Mode == RelativeSourceMode.TemplatedParent)
             {
-                observer = CreateTemplatedParentObserver(target, pathInfo.Path);
+                observer = CreateTemplatedParentObserver(target, Path);
             }
             else if (RelativeSource.Mode == RelativeSourceMode.FindAncestor)
             {
-                if (RelativeSource.AncestorType == null)
+                if (RelativeSource.Tree == TreeType.Visual && RelativeSource.AncestorType == null)
                 {
-                    throw new InvalidOperationException("AncestorType must be set for RelativeSourceModel.FindAncestor.");
+                    throw new InvalidOperationException("AncestorType must be set for RelativeSourceMode.FindAncestor when searching the visual tree.");
                 }
 
                 observer = CreateFindAncestorObserver(
                     (target as IControl) ?? (anchor as IControl),
-                    pathInfo.Path);
+                    RelativeSource,
+                    Path);
             }
             else
             {
@@ -168,53 +166,6 @@ namespace Avalonia.Markup.Xaml.Data
             return new InstancedBinding(subject, Mode, Priority);
         }
 
-        private static PathInfo ParsePath(string path)
-        {
-            var result = new PathInfo();
-
-            if (string.IsNullOrWhiteSpace(path) || path == ".")
-            {
-                result.Path = string.Empty;
-            }
-            else if (path.StartsWith("#"))
-            {
-                var dot = path.IndexOf('.');
-
-                if (dot != -1)
-                {
-                    result.Path = path.Substring(dot + 1);
-                    result.ElementName = path.Substring(1, dot - 1);
-                }
-                else
-                {
-                    result.Path = string.Empty;
-                    result.ElementName = path.Substring(1);
-                }
-            }
-            else
-            {
-                result.Path = path;
-            }
-
-            return result;
-        }
-
-        private void ValidateState(PathInfo pathInfo)
-        {
-            if (pathInfo.ElementName != null && ElementName != null)
-            {
-                throw new InvalidOperationException(
-                    "ElementName property cannot be set when an #elementName path is provided.");
-            }
-
-            if ((pathInfo.ElementName != null || ElementName != null) &&
-                RelativeSource != null)
-            {
-                throw new InvalidOperationException(
-                    "ElementName property cannot be set with a RelativeSource.");
-            }
-        }
-
         private ExpressionObserver CreateDataContexObserver(
             IAvaloniaObject target,
             string path,
@@ -271,12 +222,13 @@ namespace Avalonia.Markup.Xaml.Data
 
         private ExpressionObserver CreateFindAncestorObserver(
             IControl target,
+            RelativeSource relativeSource,
             string path)
         {
             Contract.Requires<ArgumentNullException>(target != null);
 
             return new ExpressionObserver(
-                ControlLocator.Track(target, RelativeSource.AncestorType, RelativeSource.AncestorLevel -1),
+                ControlLocator.Track(target, relativeSource.Tree, relativeSource.AncestorLevel - 1, relativeSource.AncestorType),
                 path);
         }
 
@@ -328,6 +280,7 @@ namespace Avalonia.Markup.Xaml.Data
         {
             public string Path { get; set; }
             public string ElementName { get; set; }
+            public RelativeSource RelativeSource { get; set; }
         }
     }
-}
\ No newline at end of file
+}
diff --git a/src/Markup/Avalonia.Markup.Xaml/Data/RelativeSource.cs b/src/Markup/Avalonia.Markup.Xaml/Data/RelativeSource.cs
index f77df6853b..825d3b8ba5 100644
--- a/src/Markup/Avalonia.Markup.Xaml/Data/RelativeSource.cs
+++ b/src/Markup/Avalonia.Markup.Xaml/Data/RelativeSource.cs
@@ -87,5 +87,7 @@ namespace Avalonia.Markup.Xaml.Data
         /// Gets or sets a value that describes the type of relative source lookup.
         /// </summary>
         public RelativeSourceMode Mode { get; set; }
+
+        public TreeType Tree { get; set; } = TreeType.Visual;
     }
 }
\ No newline at end of file
diff --git a/src/Markup/Avalonia.Markup.Xaml/MarkupExtensions/BindingExtension.cs b/src/Markup/Avalonia.Markup.Xaml/MarkupExtensions/BindingExtension.cs
index 8984498393..c6705cbb4b 100644
--- a/src/Markup/Avalonia.Markup.Xaml/MarkupExtensions/BindingExtension.cs
+++ b/src/Markup/Avalonia.Markup.Xaml/MarkupExtensions/BindingExtension.cs
@@ -29,20 +29,167 @@ namespace Avalonia.Markup.Xaml.MarkupExtensions
 
         public override object ProvideValue(IServiceProvider serviceProvider)
         {
+            var descriptorContext = (ITypeDescriptorContext)serviceProvider;
+
+            var pathInfo = ParsePath(Path, descriptorContext);
+            ValidateState(pathInfo);
+
             return new Binding
             {
                 Converter = Converter,
                 ConverterParameter = ConverterParameter,
-                ElementName = ElementName,
+                ElementName = pathInfo.ElementName ?? ElementName,
                 FallbackValue = FallbackValue,
                 Mode = Mode,
-                Path = Path,
+                Path = pathInfo.Path,
                 Priority = Priority,
-                RelativeSource = RelativeSource,
+                RelativeSource = pathInfo.RelativeSource ?? RelativeSource,
                 DefaultAnchor = new WeakReference(GetDefaultAnchor((ITypeDescriptorContext)serviceProvider))
             };
         }
 
+        private class PathInfo
+        {
+            public string Path { get; set; }
+            public string ElementName { get; set; }
+            public RelativeSource RelativeSource { get; set; }
+        }
+
+        private void ValidateState(PathInfo pathInfo)
+        {
+            if (pathInfo.ElementName != null && ElementName != null)
+            {
+                throw new InvalidOperationException(
+                    "ElementName property cannot be set when an #elementName path is provided.");
+            }
+
+            if (pathInfo.RelativeSource != null && RelativeSource != null)
+            {
+                throw new InvalidOperationException(
+                    "ElementName property cannot be set when a $self or $parent path is provided.");
+            }
+
+            if ((pathInfo.ElementName != null || ElementName != null) &&
+                (pathInfo.RelativeSource != null || RelativeSource != null))
+            {
+                throw new InvalidOperationException(
+                    "ElementName property cannot be set with a RelativeSource.");
+            }
+        }
+
+        private static PathInfo ParsePath(string path, ITypeDescriptorContext context)
+        {
+            var result = new PathInfo();
+
+            if (string.IsNullOrWhiteSpace(path) || path == ".")
+            {
+                result.Path = string.Empty;
+            }
+            else if (path.StartsWith("#"))
+            {
+                var dot = path.IndexOf('.');
+
+                if (dot != -1)
+                {
+                    result.Path = path.Substring(dot + 1);
+                    result.ElementName = path.Substring(1, dot - 1);
+                }
+                else
+                {
+                    result.Path = string.Empty;
+                    result.ElementName = path.Substring(1);
+                }
+            }
+            else if (path.StartsWith("$"))
+            {
+                var relativeSource = new RelativeSource
+                {
+                    Tree = TreeType.Logical
+                };
+                result.RelativeSource = relativeSource;
+                var dot = path.IndexOf('.');
+                string relativeSourceMode;
+                if (dot != -1)
+                {
+                    result.Path = path.Substring(dot + 1);
+                    relativeSourceMode = path.Substring(1, dot - 1);
+                }
+                else
+                {
+                    result.Path = string.Empty;
+                    relativeSourceMode = path.Substring(1);
+                }
+
+                if (relativeSourceMode == "self")
+                {
+                    relativeSource.Mode = RelativeSourceMode.Self;
+                }
+                else if (relativeSourceMode == "parent")
+                {
+                    relativeSource.Mode = RelativeSourceMode.FindAncestor;
+                    relativeSource.AncestorLevel = 1;
+                }
+                else if (relativeSourceMode.StartsWith("parent["))
+                {
+                    relativeSource.Mode = RelativeSourceMode.FindAncestor;
+                    var parentConfigStart = relativeSourceMode.IndexOf('[');
+                    if (!relativeSourceMode.EndsWith("]"))
+                    {
+                        throw new InvalidOperationException("Invalid RelativeSource binding syntax. Expected matching ']' for '['.");
+                    }
+                    var parentConfigParams = relativeSourceMode.Substring(parentConfigStart + 1).TrimEnd(']').Split(';');
+                    if (parentConfigParams.Length > 2 || parentConfigParams.Length == 0)
+                    {
+                        throw new InvalidOperationException("Expected either 1 or 2 parameters for RelativeSource binding syntax");
+                    }
+                    else if (parentConfigParams.Length == 1)
+                    {
+                        if (int.TryParse(parentConfigParams[0], out int level))
+                        {
+                            relativeSource.AncestorType = null;
+                            relativeSource.AncestorLevel = level + 1;
+                        }
+                        else
+                        {
+                            relativeSource.AncestorType = LookupAncestorType(parentConfigParams[0], context);
+                        }
+                    }
+                    else
+                    {
+                        relativeSource.AncestorType = LookupAncestorType(parentConfigParams[0], context);
+                        relativeSource.AncestorLevel = int.Parse(parentConfigParams[1]) + 1;
+                    }
+                }
+                else
+                {
+                    throw new InvalidOperationException($"Invalid RelativeSource binding syntax: {relativeSourceMode}");
+                }
+            }
+            else
+            {
+                result.Path = path;
+            }
+
+            return result;
+        }
+
+        private static Type LookupAncestorType(string ancestorTypeName, ITypeDescriptorContext context)
+        {
+            var parts = ancestorTypeName.Split(':');
+            if (parts.Length == 0 || parts.Length > 2)
+            {
+                throw new InvalidOperationException("Invalid type name");
+            }
+
+            if (parts.Length == 1)
+            {
+                return context.ResolveType(string.Empty, parts[0]);
+            }
+            else
+            {
+                return context.ResolveType(parts[0], parts[1]);
+            }
+        }
 
         private static object GetDefaultAnchor(ITypeDescriptorContext context)
         {
diff --git a/src/Markup/Avalonia.Markup/ControlLocator.cs b/src/Markup/Avalonia.Markup/ControlLocator.cs
index de8415d6db..1a82c0a4fd 100644
--- a/src/Markup/Avalonia.Markup/ControlLocator.cs
+++ b/src/Markup/Avalonia.Markup/ControlLocator.cs
@@ -11,6 +11,21 @@ using Avalonia.VisualTree;
 
 namespace Avalonia.Markup
 {
+    /// <summary>
+    /// The type of tree via which to track a control.
+    /// </summary>
+    public enum TreeType
+    {
+        /// <summary>
+        /// The visual tree.
+        /// </summary>
+        Visual,
+        /// <summary>
+        /// The logical tree.
+        /// </summary>
+        Logical,
+    }
+
     /// <summary>
     /// Locates controls relative to other controls.
     /// </summary>
@@ -27,13 +42,13 @@ namespace Avalonia.Markup
         {
             var attached = Observable.FromEventPattern<LogicalTreeAttachmentEventArgs>(
                 x => relativeTo.AttachedToLogicalTree += x,
-                x => relativeTo.DetachedFromLogicalTree += x)
+                x => relativeTo.AttachedToLogicalTree -= x)
                 .Select(x => ((IControl)x.Sender).FindNameScope())
                 .StartWith(relativeTo.FindNameScope());
 
             var detached = Observable.FromEventPattern<LogicalTreeAttachmentEventArgs>(
                 x => relativeTo.DetachedFromLogicalTree += x,
-                x => relativeTo.DetachedFromLogicalTree += x)
+                x => relativeTo.DetachedFromLogicalTree -= x)
                 .Select(x => (INameScope)null);
 
             return attached.Merge(detached).Select(nameScope =>
@@ -68,37 +83,75 @@ namespace Avalonia.Markup
         /// <param name="relativeTo">
         /// The control relative from which the other control should be found.
         /// </param>
-        /// <param name="ancestorType">The type of the ancestor to find.</param>
+        /// <param name="tree">The tree via which to track the control.</param>
         /// <param name="ancestorLevel">
         /// The level of ancestor control to look for. Use 0 for the first ancestor of the
         /// requested type.
         /// </param>
-        public static IObservable<IControl> Track(IControl relativeTo, Type ancestorType, int ancestorLevel)
+        /// <param name="ancestorType">The type of the ancestor to find.</param>
+        public static IObservable<IControl> Track(IControl relativeTo, TreeType tree, int ancestorLevel, Type ancestorType = null)
+        {
+            return TrackAttachmentToTree(relativeTo, tree).Select(isAttachedToTree =>
+            {
+                if (isAttachedToTree)
+                {
+                    if (tree == TreeType.Visual)
+                    {
+                        return relativeTo.GetVisualAncestors()
+                            .Where(x => ancestorType?.GetTypeInfo().IsAssignableFrom(x.GetType().GetTypeInfo()) ?? true)
+                            .ElementAtOrDefault(ancestorLevel) as IControl; 
+                    }
+                    else
+                    {
+                        return relativeTo.GetLogicalAncestors()
+                            .Where(x => ancestorType?.GetTypeInfo().IsAssignableFrom(x.GetType().GetTypeInfo()) ?? true)
+                            .ElementAtOrDefault(ancestorLevel) as IControl;
+                    }
+                }
+                else
+                {
+                    return null;
+                }
+            });
+        }
+
+        private static IObservable<bool> TrackAttachmentToTree(IControl relativeTo, TreeType tree)
+        {
+            return tree == TreeType.Visual ? TrackAttachmentToVisualTree(relativeTo) : TrackAttachmentToLogicalTree(relativeTo);
+        }
+
+        private static IObservable<bool> TrackAttachmentToVisualTree(IControl relativeTo)
         {
             var attached = Observable.FromEventPattern<VisualTreeAttachmentEventArgs>(
                 x => relativeTo.AttachedToVisualTree += x,
-                x => relativeTo.DetachedFromVisualTree += x)
+                x => relativeTo.AttachedToVisualTree -= x)
                 .Select(x => true)
                 .StartWith(relativeTo.IsAttachedToVisualTree);
 
             var detached = Observable.FromEventPattern<VisualTreeAttachmentEventArgs>(
                 x => relativeTo.DetachedFromVisualTree += x,
-                x => relativeTo.DetachedFromVisualTree += x)
+                x => relativeTo.DetachedFromVisualTree -= x)
                 .Select(x => false);
 
-            return attached.Merge(detached).Select(isAttachedToVisualTree =>
-            {
-                if (isAttachedToVisualTree)
-                {
-                    return relativeTo.GetVisualAncestors()
-                        .Where(x => ancestorType.GetTypeInfo().IsAssignableFrom(x.GetType().GetTypeInfo()))
-                        .ElementAtOrDefault(ancestorLevel) as IControl;
-                }
-                else
-                {
-                    return null;
-                }
-            });
+            var attachmentStatus = attached.Merge(detached);
+            return attachmentStatus;
+        }
+
+        private static IObservable<bool> TrackAttachmentToLogicalTree(IControl relativeTo)
+        {
+            var attached = Observable.FromEventPattern<LogicalTreeAttachmentEventArgs>(
+                x => relativeTo.AttachedToLogicalTree += x,
+                x => relativeTo.AttachedToLogicalTree -= x)
+                .Select(x => true)
+                .StartWith(relativeTo.IsAttachedToLogicalTree);
+
+            var detached = Observable.FromEventPattern<LogicalTreeAttachmentEventArgs>(
+                x => relativeTo.DetachedFromLogicalTree += x,
+                x => relativeTo.DetachedFromLogicalTree -= x)
+                .Select(x => false);
+
+            var attachmentStatus = attached.Merge(detached);
+            return attachmentStatus;
         }
     }
 }
diff --git a/tests/Avalonia.Markup.Xaml.UnitTests/Xaml/BindingTests_RelativeSource.cs b/tests/Avalonia.Markup.Xaml.UnitTests/Xaml/BindingTests_RelativeSource.cs
index 9125e1e643..095aae7742 100644
--- a/tests/Avalonia.Markup.Xaml.UnitTests/Xaml/BindingTests_RelativeSource.cs
+++ b/tests/Avalonia.Markup.Xaml.UnitTests/Xaml/BindingTests_RelativeSource.cs
@@ -3,6 +3,7 @@
 
 using Avalonia.Controls;
 using Avalonia.UnitTests;
+using System;
 using Xunit;
 
 namespace Avalonia.Markup.Xaml.UnitTests.Xaml
@@ -77,6 +78,77 @@ namespace Avalonia.Markup.Xaml.UnitTests.Xaml
             }
         }
 
+        [Fact]
+        public void Binding_To_First_Ancestor_Without_AncestorType_Throws_Exception()
+        {
+            using (UnitTestApplication.Start(TestServices.StyledWindow))
+            {
+                var xaml = @"
+<Window xmlns='https://github.com/avaloniaui'
+        xmlns:x='http://schemas.microsoft.com/winfx/2006/xaml'
+        xmlns:local='clr-namespace:Avalonia.Markup.Xaml.UnitTests.Xaml;assembly=Avalonia.Markup.Xaml.UnitTests'>
+    <Border Name='border1'>
+      <ContentControl Name='contentControl'>
+        <Button Name='button' Content='{Binding Name, RelativeSource={RelativeSource AncestorLevel=1}}'/>
+      </ContentControl>
+    </Border>
+</Window>";
+                var loader = new AvaloniaXamlLoader();
+                Assert.Throws<InvalidOperationException>( () => loader.Load(xaml));
+            }
+        }
+
+        [Fact]
+        public void Binding_To_First_Ancestor_With_Shorthand_Works()
+        {
+            using (UnitTestApplication.Start(TestServices.StyledWindow))
+            {
+                var xaml = @"
+<Window xmlns='https://github.com/avaloniaui'
+        xmlns:x='http://schemas.microsoft.com/winfx/2006/xaml'
+        xmlns:local='clr-namespace:Avalonia.Markup.Xaml.UnitTests.Xaml;assembly=Avalonia.Markup.Xaml.UnitTests'>
+    <Border Name='border1'>
+      <Border Name='border2'>
+        <Button Name='button' Content='{Binding $parent.Name}'/>
+      </Border>
+    </Border>
+</Window>";
+                var loader = new AvaloniaXamlLoader();
+                var window = (Window)loader.Load(xaml);
+                var button = window.FindControl<Button>("button");
+
+                window.ApplyTemplate();
+
+                Assert.Equal("border2", button.Content);
+            }
+        }
+
+        [Fact]
+        public void Binding_To_First_Ancestor_With_Shorthand_Uses_LogicalTree()
+        {
+            using (UnitTestApplication.Start(TestServices.StyledWindow))
+            {
+                var xaml = @"
+<Window xmlns='https://github.com/avaloniaui'
+        xmlns:x='http://schemas.microsoft.com/winfx/2006/xaml'
+        xmlns:local='clr-namespace:Avalonia.Markup.Xaml.UnitTests.Xaml;assembly=Avalonia.Markup.Xaml.UnitTests'>
+    <Border Name='border'>
+      <ContentControl Name='contentControl'>
+        <Button Name='button' Content='{Binding $parent.Name}'/>
+      </ContentControl>
+    </Border>
+</Window>";
+                var loader = new AvaloniaXamlLoader();
+                var window = (Window)loader.Load(xaml);
+                var contentControl = window.FindControl<ContentControl>("contentControl");
+                var button = window.FindControl<Button>("button");
+
+                window.ApplyTemplate();
+                
+                Assert.Equal("contentControl", button.Content);
+            }
+        }
+
         [Fact]
         public void Binding_To_Second_Ancestor_Works()
         {
@@ -102,6 +174,108 @@ namespace Avalonia.Markup.Xaml.UnitTests.Xaml
             }
         }
 
+        [Fact]
+        public void Binding_To_Second_Ancestor_With_Shorthand_Uses_LogicalTree()
+        {
+            using (UnitTestApplication.Start(TestServices.StyledWindow))
+            {
+                var xaml = @"
+<Window xmlns='https://github.com/avaloniaui'
+        xmlns:x='http://schemas.microsoft.com/winfx/2006/xaml'
+        xmlns:local='clr-namespace:Avalonia.Markup.Xaml.UnitTests.Xaml;assembly=Avalonia.Markup.Xaml.UnitTests'>
+    <ContentControl Name='contentControl1'>
+      <ContentControl Name='contentControl2'>
+        <Button Name='button' Content='{Binding $parent[1].Name}'/>
+      </ContentControl>
+    </ContentControl>
+</Window>";
+                var loader = new AvaloniaXamlLoader();
+                var window = (Window)loader.Load(xaml);
+                var contentControl1 = window.FindControl<ContentControl>("contentControl1");
+                var contentControl2 = window.FindControl<ContentControl>("contentControl2");
+                var button = window.FindControl<Button>("button");
+
+                window.ApplyTemplate();
+
+                Assert.Equal("contentControl1", button.Content);
+            }
+        }
+
+        [Fact]
+        public void Binding_To_Ancestor_Of_Type_With_Shorthand_Works()
+        {
+            using (UnitTestApplication.Start(TestServices.StyledWindow))
+            {
+                var xaml = @"
+<Window xmlns='https://github.com/avaloniaui'
+        xmlns:x='http://schemas.microsoft.com/winfx/2006/xaml'
+        xmlns:local='clr-namespace:Avalonia.Markup.Xaml.UnitTests.Xaml;assembly=Avalonia.Markup.Xaml.UnitTests'>
+    <Border Name='border1'>
+      <Border Name='border2'>
+        <Button Name='button' Content='{Binding $parent[Border].Name}'/>
+      </Border>
+    </Border>
+</Window>";
+                var loader = new AvaloniaXamlLoader();
+                var window = (Window)loader.Load(xaml);
+                var button = window.FindControl<Button>("button");
+
+                window.ApplyTemplate();
+
+                Assert.Equal("border2", button.Content);
+            }
+        }
+
+        [Fact]
+        public void Binding_To_Second_Ancestor_With_Shorthand_And_Type_Works()
+        {
+            using (UnitTestApplication.Start(TestServices.StyledWindow))
+            {
+                var xaml = @"
+<Window xmlns='https://github.com/avaloniaui'
+        xmlns:x='http://schemas.microsoft.com/winfx/2006/xaml'
+        xmlns:local='clr-namespace:Avalonia.Markup.Xaml.UnitTests.Xaml;assembly=Avalonia.Markup.Xaml.UnitTests'>
+    <Border Name='border1'>
+      <Border Name='border2'>
+        <Button Name='button' Content='{Binding $parent[Border; 1].Name}'/>
+      </Border>
+    </Border>
+</Window>";
+                var loader = new AvaloniaXamlLoader();
+                var window = (Window)loader.Load(xaml);
+                var button = window.FindControl<Button>("button");
+
+                window.ApplyTemplate();
+
+                Assert.Equal("border1", button.Content);
+            }
+        }
+
+        [Fact]
+        public void Binding_To_Second_Ancestor_With_Shorthand_Works()
+        {
+            using (UnitTestApplication.Start(TestServices.StyledWindow))
+            {
+                var xaml = @"
+<Window xmlns='https://github.com/avaloniaui'
+        xmlns:x='http://schemas.microsoft.com/winfx/2006/xaml'
+        xmlns:local='clr-namespace:Avalonia.Markup.Xaml.UnitTests.Xaml;assembly=Avalonia.Markup.Xaml.UnitTests'>
+    <Border Name='border1'>
+      <Border Name='border2'>
+        <Button Name='button' Content='{Binding $parent[1].Name}'/>
+      </Border>
+    </Border>
+</Window>";
+                var loader = new AvaloniaXamlLoader();
+                var window = (Window)loader.Load(xaml);
+                var button = window.FindControl<Button>("button");
+
+                window.ApplyTemplate();
+
+                Assert.Equal("border1", button.Content);
+            }
+        }
+
         [Fact]
         public void Binding_To_Ancestor_With_Namespace_Works()
         {