From HttpListener source code 

http://www.dotnetframework.org/default.aspx/DotNET/DotNET/8@0/untmp/whidbey/REDBITS/ndp/fx/src/Net/System/Net/HttpListenerResponse@cs/2/HttpListenerResponse@cs

line 525

                              UnsafeNclNativeMethods.HttpApi.HttpSendHttpResponse(
                                    HttpListenerContext.RequestQueueHandle,
                                    HttpListenerRequest.RequestId,
                                    (uint)flags,
                                    pResponse,
                                    null,
                                    null,
                                    SafeLocalFree.Zero,
                                    0,
                                    asyncResult==null ? null : asyncResult.m_pOverlapped,
                                    null );

http://msdn.microsoft.com/en-us/library/windows/desktop/aa364499(v=vs.85).aspx

Argument 5 is the CACHE_POLICY. It is set to null which means no caching.

SO NO YOU DO NOT USE KERNEL MODE CACHING WITH HTTP LISTENER