diff --git a/src/Microsoft.OpenApi.OData.Reader/Edm/ODataPathProvider.cs b/src/Microsoft.OpenApi.OData.Reader/Edm/ODataPathProvider.cs
index 0c9b8276..868fd881 100644
--- a/src/Microsoft.OpenApi.OData.Reader/Edm/ODataPathProvider.cs
+++ b/src/Microsoft.OpenApi.OData.Reader/Edm/ODataPathProvider.cs
@@ -391,10 +391,10 @@ private void RetrieveMediaEntityStreamPaths(IEdmEntityType entityType, ODataPath
                 }
             }
 
-            /* Create a /$value path only if entity has stream and
+            /* Append a $value segment only if entity (or base type) has stream and
              * does not contain a structural property named Content
              */
-            if (createValuePath && entityType.HasStream)
+            if (createValuePath && (entityType.HasStream || ((entityType.BaseType as IEdmEntityType)?.HasStream ?? false)))
             {
                 currentPath.Push(new ODataStreamContentSegment());
                 AppendPath(currentPath.Clone());
diff --git a/src/Microsoft.OpenApi.OData.Reader/Microsoft.OpenAPI.OData.Reader.csproj b/src/Microsoft.OpenApi.OData.Reader/Microsoft.OpenAPI.OData.Reader.csproj
index 89bd34d7..d2b1b7de 100644
--- a/src/Microsoft.OpenApi.OData.Reader/Microsoft.OpenAPI.OData.Reader.csproj
+++ b/src/Microsoft.OpenApi.OData.Reader/Microsoft.OpenAPI.OData.Reader.csproj
@@ -26,6 +26,7 @@
 - Checks whether path exists before adding it to the paths dictionary #343
 - Strips namespace prefix from operation segments and aliases type cast segments #348
 - Return response status code 2XX for PUT operations of stream properties when UseSuccessStatusCodeRange is enabled #310
+- Adds $value segment to paths with entity types with base types with HasStream=true #314
     </PackageReleaseNotes>
     <AssemblyName>Microsoft.OpenApi.OData.Reader</AssemblyName>
     <AssemblyOriginatorKeyFile>..\..\tool\Microsoft.OpenApi.OData.snk</AssemblyOriginatorKeyFile>
diff --git a/test/Microsoft.OpenAPI.OData.Reader.Tests/Edm/ODataPathProviderTests.cs b/test/Microsoft.OpenAPI.OData.Reader.Tests/Edm/ODataPathProviderTests.cs
index 868120c9..ab810ce0 100644
--- a/test/Microsoft.OpenAPI.OData.Reader.Tests/Edm/ODataPathProviderTests.cs
+++ b/test/Microsoft.OpenAPI.OData.Reader.Tests/Edm/ODataPathProviderTests.cs
@@ -52,9 +52,18 @@ public void GetPathsForGraphBetaModelReturnsAllPaths()
 
             // Assert
             Assert.NotNull(paths);
+            Assert.Equal(18054, paths.Count());
+            AssertGraphBetaModelPaths(paths);
+        }
+
+        private void AssertGraphBetaModelPaths(IEnumerable<ODataPath> paths)
+        {
+            // Test that $count and microsoft.graph.count() segments are not both created for the same path.
             Assert.Null(paths.FirstOrDefault(p => p.GetPathItemName().Equals("/drives({id})/items({id1})/workbook/tables/$count")));
             Assert.NotNull(paths.FirstOrDefault(p => p.GetPathItemName().Equals("/drives({id})/items({id1})/workbook/tables/microsoft.graph.count()")));
-            Assert.Equal(18024, paths.Count());
+
+            // Test that $value segments are created for entity types with base types with HasStream="true"
+            Assert.NotNull(paths.FirstOrDefault(p => p.GetPathItemName().Equals("/me/chats({id})/messages({id1})/hostedContents({id2})/$value")));
         }
 
         [Fact]
@@ -75,7 +84,7 @@ public void GetPathsForGraphBetaModelWithDerivedTypesConstraintReturnsAllPaths()
 
             // Assert
             Assert.NotNull(paths);
-            Assert.Equal(18675, paths.Count());
+            Assert.Equal(18705, paths.Count());
         }
 
         [Fact]