1 A new 757 will range anywhere from $60 to more than $90 million. 2  The price difference is as a result of the different models. 3  The 757-200, which retails for $70 to $80 million, enjoys great sales and tops the list as the most purchased Boeing 757.4  The price also varies after adding both delivery and customization costs. The price also varies after adding both delivery and customization costs. 2  A used 757 can cost $40 to $50 million. 3  In the past, Donald Trump purchased a used Boeing 757 for $100 from Microsoft co-owner, Paul Allen.