When it was completed in 1913, the Cass Gilbert–designed Woolworth Building was the tallest skyscraper in the world, immediately making it a New York icon. While the 58-story office tower may no longer be the world’s tallest, it is still decidedly impressive, especially now that the top 30 floors have been converted into condos by acclaimed architect Thierry Despont. The Pinnacle Penthouse takes up the top five floors of this landmark building, encompassing the structure’s distinctive copper roof and a private observatory. With this 408-sq-ft observatory, a 9,710-sq-ft interior and ceilings reaching up to 24ft, space in the penthouse is abundant, and a private elevator can whisk you between each of its floors. Elsewhere in the tower, you’ll find the original 50-ft pool — thoughtfully updated by Despont — a sauna and hot tub, fitness studio, the 29th floor’s Gilbert Lounge, and a wine cellar and tasting room. Each residence has its own 185-bottle wine locker.