Add Oreos to a baggie and smash with a rolling pin until desired sizes. Set aside.
Add heavy cream to a bowl and mix with an electric hand mixer until stiff peaks form. Set aside.
In a separate bowl, add in the condensed milk and vanilla. Mix well.
Fold about a cup of the whip cream into the condensed milk gently.
Gently fold the condensed milk mixture into the rest of the whip cream. Make sure to fold from the bottom to the top gently so it stays fluffy.
Once smooth, gently fold in most of the Oreos, leaving some for adding on top of the ice cream.
Add to a freezer safe container then top with the remaining crushed Oreos.
Place in freezer 6-7 hours or overnight.