Penn Central Transp. Co. v. New York City
In Penn Central Transp. Co. v. New York City, 438 U.S. 104 (1978), the U.S. Supreme Court held that regulations against the private use of certain airspace does not constitute a categorical taking requiring compensation under the Fifth Amendment Taking Clause. This decision gave vast discretion to courts to rule against private property despite how regulations can deprive the value of the property from owners.
Justice Brennan held that a city may, as part of a comprehensive program to preserve historic landmarks and historic districts, place restrictions on the development of individual historic landmarks—in addition to those imposed by applicable zoning ordinances—without effecting a "taking" requiring the payment of "just compensation." Specifically, he held that the application of New York City's Landmarks Preservation Law to the parcel of land occupied by Grand Central Terminal has "taken" its owners' property in violation of the Fifth and Fourteenth Amendments.
The 5-3 decision by the Supreme Court in Murr v. Wisconsin (2017) complicated this test somewhat in the context of regulatory takings of private property.