Using a hand or standing mixer, whip cream cheese, Cool Whip and powdered sugar until thick and fluffy. Add in vanilla and mix to combine.
Fold in crushed Oreos.
Spoon half of the mixture evenly into 4 dessert dishes. Cover with raspberries. Spoon the rest on top of the berries. Chill until ready to serve. (Suggested chill time is at least 30 minutes)
Top with whipped cream and more crushed Oreos before serving. Enjoy!