diff --git a/src/Avalonia.Animation/AnimationInstance`1.cs b/src/Avalonia.Animation/AnimationInstance`1.cs
index 6f601a3e13..0e1882ce75 100644
--- a/src/Avalonia.Animation/AnimationInstance`1.cs
+++ b/src/Avalonia.Animation/AnimationInstance`1.cs
@@ -5,6 +5,7 @@ using Avalonia.Animation.Animators;
 using Avalonia.Animation.Utils;
 using Avalonia.Data;
 using Avalonia.Reactive;
+using JetBrains.Annotations;
 
 namespace Avalonia.Animation
 {
@@ -45,8 +46,9 @@ namespace Avalonia.Animation
             _onCompleteAction = OnComplete;
             _interpolator = Interpolator;
             _baseClock = baseClock;
-            _neutralValue = (T)_targetControl.GetValue(_animator.Property);
+            control.PropertyChanged += ControlPropertyChanged;
 
+            UpdateNeutralValue();
             FetchProperties();
         }
 
@@ -216,5 +218,22 @@ namespace Avalonia.Animation
                 }
             }
         }
+
+        private void UpdateNeutralValue()
+        {
+            var property = _animator.Property;
+            var baseValue = _targetControl.GetBaseValue(property, BindingPriority.LocalValue);
+
+            _neutralValue = baseValue != AvaloniaProperty.UnsetValue ?
+                (T)baseValue : (T)_targetControl.GetValue(property);
+        }
+
+        private void ControlPropertyChanged(object sender, AvaloniaPropertyChangedEventArgs e)
+        {
+            if (e.Property == _animator.Property && e.Priority > BindingPriority.Animation)
+            {
+                UpdateNeutralValue();
+            }
+        }
     }
 }
diff --git a/src/Avalonia.Input/KeyboardDevice.cs b/src/Avalonia.Input/KeyboardDevice.cs
index 79152e20d2..a159b19026 100644
--- a/src/Avalonia.Input/KeyboardDevice.cs
+++ b/src/Avalonia.Input/KeyboardDevice.cs
@@ -217,12 +217,31 @@ namespace Avalonia.Input
                         {
                             var bindings = (currentHandler as IInputElement)?.KeyBindings;
                             if (bindings != null)
+                            {
+                                KeyBinding[]? bindingsCopy = null;
+
+                                // Create a copy of the KeyBindings list if there's a binding which matches the event.
+                                // If we don't do this the foreach loop will throw an InvalidOperationException when the KeyBindings list is changed.
+                                // This can happen when a new view is loaded which adds its own KeyBindings to the handler.
                                 foreach (var binding in bindings)
                                 {
-                                    if (ev.Handled)
+                                    if (binding.Gesture?.Matches(ev) == true)
+                                    {
+                                        bindingsCopy = bindings.ToArray();
                                         break;
-                                    binding.TryHandle(ev);
+                                    }
+                                }
+
+                                if (bindingsCopy is object)
+                                {
+                                    foreach (var binding in bindingsCopy)
+                                    {
+                                        if (ev.Handled)
+                                            break;
+                                        binding.TryHandle(ev);
+                                    }
                                 }
+                            }
                             currentHandler = currentHandler.VisualParent;
                         }
 
diff --git a/src/Avalonia.Styling/Styling/Activators/PropertyEqualsActivator.cs b/src/Avalonia.Styling/Styling/Activators/PropertyEqualsActivator.cs
index 9e30e4fa14..8d446ebc9c 100644
--- a/src/Avalonia.Styling/Styling/Activators/PropertyEqualsActivator.cs
+++ b/src/Avalonia.Styling/Styling/Activators/PropertyEqualsActivator.cs
@@ -33,6 +33,6 @@ namespace Avalonia.Styling.Activators
 
         void IObserver<object>.OnCompleted() { }
         void IObserver<object>.OnError(Exception error) { }
-        void IObserver<object>.OnNext(object value) => PublishNext(Equals(value, _value));
+        void IObserver<object>.OnNext(object value) => PublishNext(PropertyEqualsSelector.Compare(_property.PropertyType, value, _value));
     }
 }
diff --git a/src/Avalonia.Styling/Styling/PropertyEqualsSelector.cs b/src/Avalonia.Styling/Styling/PropertyEqualsSelector.cs
index cdd985ac80..5d9c3fe56b 100644
--- a/src/Avalonia.Styling/Styling/PropertyEqualsSelector.cs
+++ b/src/Avalonia.Styling/Styling/PropertyEqualsSelector.cs
@@ -1,4 +1,6 @@
 using System;
+using System.ComponentModel;
+using System.Globalization;
 using System.Text;
 using Avalonia.Styling.Activators;
 
@@ -75,11 +77,37 @@ namespace Avalonia.Styling
             }
             else
             {
-                var result = (control.GetValue(_property) ?? string.Empty).Equals(_value);
-                return result ? SelectorMatch.AlwaysThisInstance : SelectorMatch.NeverThisInstance;
+                return Compare(_property.PropertyType, control.GetValue(_property), _value)
+                    ? SelectorMatch.AlwaysThisInstance
+                    : SelectorMatch.NeverThisInstance;
             }
+            
         }
 
         protected override Selector? MovePrevious() => _previous;
+
+        internal static bool Compare(Type propertyType, object propertyValue, object? value)
+        {
+            if (propertyType == typeof(object) &&
+                propertyValue?.GetType() is Type inferredType)
+            {
+                propertyType = inferredType;
+            }
+
+            var valueType = value?.GetType();
+
+            if (valueType is null || propertyType.IsAssignableFrom(valueType))
+            {
+                return Equals(propertyValue, value);
+            }
+
+            var converter = TypeDescriptor.GetConverter(propertyType);
+            if (converter?.CanConvertFrom(valueType) == true)
+            {
+                return Equals(propertyValue, converter.ConvertFrom(null, CultureInfo.InvariantCulture, value));
+            }
+
+            return false;
+        }
     }
 }
diff --git a/tests/Avalonia.Input.UnitTests/KeyboardDeviceTests.cs b/tests/Avalonia.Input.UnitTests/KeyboardDeviceTests.cs
index df0a077c7f..7730cee78c 100644
--- a/tests/Avalonia.Input.UnitTests/KeyboardDeviceTests.cs
+++ b/tests/Avalonia.Input.UnitTests/KeyboardDeviceTests.cs
@@ -1,5 +1,9 @@
-using Avalonia.Input.Raw;
+using System;
+using System.Windows.Input;
+using Avalonia.Controls;
+using Avalonia.Input.Raw;
 using Avalonia.Interactivity;
+using Avalonia.UnitTests;
 using Moq;
 using Xunit;
 
@@ -86,5 +90,45 @@ namespace Avalonia.Input.UnitTests
 
             focused.Verify(x => x.RaiseEvent(It.IsAny<TextInputEventArgs>()));
         }
+
+        [Fact]
+        public void Can_Change_KeyBindings_In_Keybinding_Event_Handler()
+        {
+            var target = new KeyboardDevice();
+            var button = new Button();
+            var root = new TestRoot(button);
+            var raised = 0;
+
+            button.KeyBindings.Add(new KeyBinding
+            {
+                Gesture = new KeyGesture(Key.O, KeyModifiers.Control),
+                Command = new DelegateCommand(() =>
+                {
+                    button.KeyBindings.Clear();
+                    ++raised;
+                }),
+            });
+
+            target.SetFocusedElement(button, NavigationMethod.Pointer, 0);
+            target.ProcessRawEvent(
+                new RawKeyEventArgs(
+                    target,
+                    0,
+                    root,
+                    RawKeyEventType.KeyDown,
+                    Key.O,
+                    RawInputModifiers.Control));
+
+            Assert.Equal(1, raised);
+        }
+
+        private class DelegateCommand : ICommand
+        {
+            private readonly Action _action;
+            public DelegateCommand(Action action) => _action = action;
+            public event EventHandler CanExecuteChanged;
+            public bool CanExecute(object parameter) => true;
+            public void Execute(object parameter) => _action();
+        }
     }
 }
diff --git a/tests/Avalonia.Styling.UnitTests/SelectorTests_PropertyEquals.cs b/tests/Avalonia.Styling.UnitTests/SelectorTests_PropertyEquals.cs
index e149410152..7689a458ae 100644
--- a/tests/Avalonia.Styling.UnitTests/SelectorTests_PropertyEquals.cs
+++ b/tests/Avalonia.Styling.UnitTests/SelectorTests_PropertyEquals.cs
@@ -22,6 +22,23 @@ namespace Avalonia.Styling.UnitTests
             Assert.False(await activator.Take(1));
         }
 
+        [Theory]
+        [InlineData("Bar", FooBar.Bar)]
+        [InlineData("352", 352)]
+        [InlineData("0.1", 0.1)]
+        public async Task PropertyEquals_Matches_When_Property_Has_Matching_Value_And_Different_Type(string literal, object value)
+        {
+            var control = new TextBlock();
+            var target = default(Selector).PropertyEquals(TextBlock.TagProperty, literal);
+            var activator = target.Match(control).Activator.ToObservable();
+
+            Assert.False(await activator.Take(1));
+            control.Tag = value;
+            Assert.True(await activator.Take(1));
+            control.Tag = null;
+            Assert.False(await activator.Take(1));
+        }
+
         [Fact]
         public void OfType_PropertyEquals_Doesnt_Match_Control_Of_Wrong_Type()
         {
@@ -40,5 +57,11 @@ namespace Avalonia.Styling.UnitTests
 
             Assert.Equal("TextBlock[Text=foo]", target.ToString());
         }
+
+        private enum FooBar
+        {
+            Foo,
+            Bar
+        }
     }
 }