Yankees legend Derek Jeter’s former castle-like lakeside retreat in New York’s Hudson Valley is officially on Airbnb—meaning you can live like the Hall of Famer even without his $400 million net worth!
The guesthouse of the famous Greenwood Lake property—known as Tiedemann Castle—has just opened for short-term rentals, offering fans the chance to step inside a piece of Yankee history while enjoying luxury Hudson Valley charm.
Originally built in 1903 by Dr. Rudolph Gudewill for his wife, the sprawling castle has passed through several owners, including Jeter’s grandfather, but its fame skyrocketed when Derek Jeter purchased it in 2003.
The Yankee shortstop invested $3 million into renovations to restore the century-old estate, which sits on four acres and 700 feet of private shoreline in Greenwood Lake, one of the Hudson Valley’s most elite summer escapes. The listing reads:
Greenwood Lake’s only castle and guest house is filled with local lore and a legendary past. From the Gudewills it was sold to the Tiedemanns, but the property’s fame came when NY Yankee Derek Jeter purchased the castle compound in 2003. The torch has passed once again and now for the first time in history the lakefront castle guest house is available for short term rental.
Jeter re-listed the sprawling home for $14.75 million in 2018. After years on the market and a failed auction, the home sold in June 2024 for $5.1 million.
And now, for the first time ever, the one-bedroom guesthouse is available to book on Airbnb!
Though Jeter hasn’t lived there for over a year, the property features quite the list of amenities you’d expect in the home of any former Yankees shortstop. Blending turn-of-the-century character with modern touches, it features:
- A stone façade with medieval-style turrets and German-inspired battlements (designed by artisans brought from Europe)
- A turret that hides a yoga studio and sauna
- Direct lakefront access with a private dock
- A cozy fireplace and outdoor fire pit
Guests can expect boutique concierge services, curated local excursions, and even private yoga classes.
Meanwhile, the full estate includes a 9,000-square-foot main house with 24 rooms, a baseball diamond-shaped infinity pool, a 1,500-square-foot pool house, and even a replica of the Statue of Liberty. Eventually, the owners plan to rent out the whole estate.
Renting Derek Jeter’s Former Hudson Valley Castle
The Hudson Valley castle guesthouse is currently listed at just over $1,300 per night on Airbnb. Perfect for a one-of-a-kind getaway, it allows fans to experience life like Derek Jeter once did—just minus the World Series rings.
So if you’ve ever dreamed of staying in a castle on the lake, this is your chance to check in where the Yankees captain once called home.
How To Get To Derek Jeter’s Hudson Valley Castle From NYC
The castle guesthouse is located at 14 Lake Shore Road in Greenwood Lake, NY—less than two hours from Manhattan—making it an easy escape from the city.
- 🚗 By car: Take I-87 North toward Harriman, then follow Route 17A to Greenwood Lake – about 90 minutes depending on traffic
- 🚌 By bus: NJ Transit runs buses from Port Authority to Greenwood Lake – just under two hours
- 🛤️ By train: You can also take NJ Transit’s Bergen Line to Tuxedo Station, then grab a short cab or rideshare to the property
Whether you’re coming from the Upper West Side or Brooklyn, it’s a quick trip from NYC to this Hudson Valley hideaway. Perfect timing too, considering the Hudson Valley was just named America’s number one fall foliage destination!
Book your stay here.