In a large jar, whisk together heavy cream and condensed milk.
Pour the mixture onto a large baking tray.
Add Oreo cookies on top of the ice cream mixture, and use two steel spatulas to chop the cookies into small crumbs and mix them with the ice cream base. (It may take a few minutes, but make sure to mix them thoroughly. This will make sure that your ice cream has a smooth consistency.)
Spread the mixture evenly on the tray, and place the tray in the freezer. Freeze for 5 hours or overnight until it’s solid. (It’s very important to make sure your tray lay flat in the freezer.)
When ready to serve, arrange the rolling space ahead of time as it’s very important for you to move as fast as possible to avoid the ice cream from melting. Place the tray on the counter. You can put it against a wall so that your tray’s secured during rolling. Alternatively, you can roll your ice cream in the freezer (if it’s possible).
Using your steel spatula, roll the ice cream from one end towards the other until it forms a nice spiral shape. Repeat with the rest.
Gently transfer the rolls into a serving bowl or cup.
Top with whipped cream, Oreo cookie, and crushed Oreos, and raspberries. Serve and enjoy immediately.