Place your mixing bowl and mixer attachment(s) in the freezer for at least 20 minutes before beginning to allow them to chill.
While the mixing bowl is in the freezer, place the cookies in a zip top bag and crush them with a rolling pin until you have small to medium pieces. Do not turn them to crumbs or your ice cream will be gray.
Add the heavy whipping cream and sugar to the cold mixing bowl and mix with a hand (or stand) mixer until it becomes the consistency of whipped cream.
Add in the vanilla and sweetened condensed milk. Mix again until smooth.
Stir in the crushed oreos by hand and then pour into a 9x5 loaf pan.
Set the loaf pan in the freezer and allow to freeze for 3+ hours. 3 hours will give you a nice, almost soft serve texture, freezing longer will give you a ‘harder’ ice cream.
If freezing longer than 3 hours, let ice cream set out at room temperature for 5 minutes to soften up until easy to scoop and serve.
Notes
The oreos should be crushed, in small to medium sized pieces, not turned into crumbs. They should also be stirred in with a spoon, not using a mixer, otherwise you run the risk of the ice cream turning a gray color from the Oreos.Store ice cream in a covered dish for up to 2 weeks in the freezer. We like the classic Oreo flavor best, but you can use any variety you prefer.