Photos courtesy of Stephen Dolinsky
Here’s a chance to stay in the lakeside guesthouse of a castle-like Hudson Valley estate once owned by Yankees legend Derek Jeter. As first reported by the New York Post, the guesthouse at the historic Greenwood Lake property known as Tiedemann Castle was listed on Airbnb last month for just over $1,300 per night. After Jeter sold the sprawling home in 2024, its new owners converted the one-bedroom guesthouse into a rental, adding upscale concierge services while preserving the estate’s 19th-century character.
Constructed in the early 1900s by a New York doctor, Tiedemann Castle sits on Greenwood Lake, which at the time was one of the era’s most popular summer escapes for New York City’s elite.
The guesthouse retains elements of the period, with a stone facade and medieval-style turrets and battlements crafted by artisans in the style of German castles. The turret is partially accessible to guests and features a yoga space and sauna at its base.
Guests can also book luxury amenities such as private yoga classes, in-house catering, and local excursions, according to the Post.
As 6sqft previously reported, the estate has familial significance for Jeter, who retired in 2014 and has since moved to Miami. His grandfather, Sonny Connors, the adopted son of John and Julia Tiedemann, who bought the home in 1952, was raised on the property.
As a child, Jeter spent his summers at the property, according to the 2011 book, “The Captain: The Journey of Derek Jeter,” by Ian O’Connor.
Jeter purchased the property in 2003 and spent 15 years renovating it before relisting the castle for $14.75 million in 2018. After several years on the market and a failed auction in 2022, the estate finally sold last June for $5.1 million.
The massive property rests along 700 feet of shoreline and across four acres. Besides the guesthouse, the estate features a 9,000-square-foot main house with 24 rooms and a 1,500-square-foot pool house.
As 6sqft previously reported, the home includes a six-foot stone wall at its entrance gate, a replica of the Statue of Liberty guarding over the home, a roof with a “widow’s walk,” and a baseball diamond-shaped infinity pool.
Lisa Mulcahy, founder of the luxury short-term rental firm Upstate Luxe, told the Post the estate’s current owners use it as a vacation home and plan to eventually list the full property on the rental market.
RELATED:
