It feels like something out of a storybook—Derek Jeter’s castle-style estate in the Hudson Valley. Situated near the border of New York and New Jersey, this sprawling lakefront property came into Jeter’s possession in the early 2000s. The luxurious estate includes a main house, guest house, pool house, and boathouse. With lush gardens, a private lagoon, and breathtaking views over Greenwood Lake, it seemed destined to be snapped up quickly once it hit the market. But surprisingly, it lingered unsold for six years and ultimately sold for far less than the original asking price. So what went wrong?
Jeter initially listed the home for $14.75 million in early 2018, even though he had reportedly purchased it for just over $400,000 in 2013. Despite the massive price difference and potential for profit, no buyers came forward. Listings at the time described the property as offering sweeping lake views, rooftop access via turret stairs, ample entertainment space, and luxurious amenities such as a pool house and a Great Room.
However, nearby residents challenged the image portrayed in the listings, saying the home wasn’t as secluded as it appeared in photos. According to location data, the estate is only about 0.2 miles from the busy Greenwood Lake Marina, with boats frequently passing by—something not highlighted in the marketing. Many prospective buyers realized this during their visits and walked away. Additionally, the price was considered far too high for the Greenwood Lake area, which limited the pool of potential buyers.
During the COVID-19 pandemic, the home was briefly taken off the market for unclear reasons. When it returned in 2021, the asking price was reduced to $12.75 million, but still failed to attract serious interest. Eventually, the property was moved to an auction with a starting bid of $6.5 million. It remained unsold even then.
Finally, in May 2024, the home was relisted at a steep discount—45% below the original asking price—at $6.3 million. That price adjustment ultimately led to a sale, though it closed for roughly $8 million less than what Jeter originally hoped to earn.
In contrast to Jeter’s real estate troubles, Milwaukee Bucks player Pat Connaughton has built a highly successful property empire. Drafted by the Baltimore Orioles in 2014, Connaughton received a $428,000 signing bonus which he used to make smart investments. Over the span of just seven years, he amassed a $550 million real estate portfolio.
Connaughton began by investing in properties around his college campus, which laid the foundation for his future success. He later co-founded a real estate company called “Three Leaf Partners.” This firm manages around 700,000 square feet of industrial property and specializes in multi-family units designed to add long-term value to communities.
Connaughton has proven to be multi-talented—not only excelling in professional baseball and basketball, but also establishing himself as a savvy businessman in real estate. His disciplined approach and long-term vision have turned him into a standout success off the court.