In a large bowl, beat the softened cream cheese until smooth and creamy. Gradually add the powdered sugar, vanilla extract, and peppermint extract. Mix until fully combined.
Using a cold mixing bowl and beaters, whip the heavy cream until soft peaks form. This means the cream holds shape but curls over slightly when the beaters are lifted.
Gently fold the whipped cream into the cream cheese mixture using a spatula. Be careful not to deflate the whipped cream; the goal is a light, fluffy filling.
Spread a thin layer of the peppermint cream mixture on the bottom of your baking dish. Place 6 Oreo cookies in a single layer over the cream. Spread a generous layer of the peppermint filling over the cookies. Repeat layers two more times, ending with a layer of filling on top.
Sprinkle crushed peppermint candies over the top layer of filling for a festive, crunchy finish.
Cover the dish with plastic wrap and refrigerate for at least 8 hours, preferably overnight. This allows the Oreos to soften and absorb the creamy filling, creating that perfect icebox cake texture.
Slice into squares and serve chilled. This dessert is rich, creamy, and bursting with minty chocolate goodness.
