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.
More Home
Our Favorite Finds From Bespoke Post’s Fourth of July Sale
Up to 50% off. These are the pieces we'd grab before they're gone.
Black Book: 13 Products Our Editors Loved in June 2026
The products our editors have been obsessed with in June 2026.
Italy From Home
How to stock your pantry, fridge, and bar cart like an Italian.