diff --git a/cpp/CMakeLists.txt b/cpp/CMakeLists.txt
index 7de7e714..13b16449 100644
--- a/cpp/CMakeLists.txt
+++ b/cpp/CMakeLists.txt
@@ -16,6 +16,13 @@
 # along with YouCompleteMe.  If not, see <http://www.gnu.org/licenses/>.
 
 cmake_minimum_required( VERSION 2.8 )
+
+# Disable CMake legacy mode for Cygwin, since the build doesn't depend on
+# WIN32 being set for Cygwin, and this property being unset causes a
+# warning in Cygwin.
+# Remove when CMake >= 2.8.4 is required, since that implicitly sets this
+set( CMAKE_LEGACY_CYGWIN_WIN32 0 )
+
 project( YouCompleteMe )
 
 option( UNIVERSAL "Build universal mac binary" OFF )
diff --git a/cpp/ycm/CMakeLists.txt b/cpp/ycm/CMakeLists.txt
index b7bbbe53..ff35f783 100644
--- a/cpp/ycm/CMakeLists.txt
+++ b/cpp/ycm/CMakeLists.txt
@@ -318,9 +318,21 @@ set_target_properties( ${CLIENT_LIB} PROPERTIES PREFIX "")
 set_target_properties( ${SERVER_LIB} PROPERTIES PREFIX "")
 
 if ( WIN32 OR CYGWIN )
-  # This is the extension for compiled Python modules on Windows
-  set_target_properties( ${CLIENT_LIB} PROPERTIES SUFFIX ".pyd")
-  set_target_properties( ${SERVER_LIB} PROPERTIES SUFFIX ".pyd")
+  # DLL platforms put dlls in the RUNTIME_OUTPUT_DIRECTORY
+  set_target_properties( ${CLIENT_LIB} PROPERTIES
+  RUNTIME_OUTPUT_DIRECTORY ${PROJECT_SOURCE_DIR}/../../python )
+  set_target_properties( ${SERVER_LIB} PROPERTIES
+  RUNTIME_OUTPUT_DIRECTORY ${PROJECT_SOURCE_DIR}/../../python )
+
+  if ( WIN32 )
+    # This is the extension for compiled Python modules on Windows
+    set_target_properties( ${CLIENT_LIB} PROPERTIES SUFFIX ".pyd")
+    set_target_properties( ${SERVER_LIB} PROPERTIES SUFFIX ".pyd")
+  elseif ( CYGWIN )
+    # This is the extension for compiled Python modules in Cygwin
+    set_target_properties( ${CLIENT_LIB} PROPERTIES SUFFIX ".dll")
+    set_target_properties( ${SERVER_LIB} PROPERTIES SUFFIX ".dll")
+  endif()
 else()
   # Even on macs, we want a .so extension instead of a .dylib which is what
   # cmake would give us by default. Python won't recognize a .dylib as a module,