The legend of Derek Jeter continues to grow after his retirement. The former Yankee captain was also the captain of cool, and that was before we knew he owned a castle. Located in Orange County, New York, the castle was built in 1915 and was purchased by the former Yankee shortstop in 2003. He paid $425,000 for it. It’s now selling for $14.75 million. Not a bad investment. Complete with 700 feet of shoreline, 6′ stone walls, and turret stairs, the castle is a relaxing retreat that also keeps out invading armies of fans. On the property are multiple structures, a pool house, boat house, infinity pool, and plenty of outdoor space for a stellar barbecue. Inside are high ceilings, a wood-burning fireplace, and a tower for all your archers.