Right-click anywhere on the Now Playing screen and chooseEnhancements>Crossfading and Auto Volume Leveling.

A new window will pop open with options for crossfading.

PressTurn on Crossfadingto enable it.

Windows Media Player 12 on Windows 10

Use the slider on the window to set the duration of the overlap between songs.

When you’re done, kill the window and return to your music.

Alternatively, hold down the[CTRL]key and press[1].

Windows Media Player switch to Now Playing

To start playing songs in one of your playlists, simply double-punch one to begin.

While a track is playing, switch to the Now Playing screen, as before.

Recheck the crossfade again between the next two songs in your playlist and repeat the above step if necessary.

Windows Media Player open Crossfade options

Windows Media Player Crossfade options

Windows Media Player set crossfade duration

Windows Media Player seek to end of song