Earlier this year, Dave Portnoy, a well-known property enthusiast and founder of the Barstool Sports media empire, made a significant real estate acquisition when he purchased a modest ranch-style house in the Saratoga Springs neighborhood of Upstate New York, conveniently located near the region’s renowned thoroughbred race track.
In another substantial addition to his already impressive real estate portfolio, Dave Portnoy, a veteran sports personality, has invested in a grand manner. According to official records, he acquired a waterfront estate in the Monomoy area of Nantucket in an off-market transaction, paying a staggering $42 million for the property. In addition to the property itself, he also acquired furniture and other items for an extra $2 million.
The Wall Street Journal was the first to report this significant transaction, which has set a new record for the most expensive residential real estate deal ever documented on Nantucket, as well as in Portnoy’s home state of Massachusetts. This substantial purchase easily surpasses the $38.1 million transaction involving another waterfront estate in Nantucket, which was acquired by venture capitalist Evan Jones and his wife Cindy in June of this year.
The sellers of this remarkable property are two trusts known as MAK Daddy and MAK Shack, both associated with hedge fund manager Mike Colby and his wife Kathi, as indicated in records. Mike Colby, a longtime executive at Ray Dalio’s Bridgewater Associates, initially acquired two parcels covering 1.2 acres for slightly over million back in 2016. Subsequently, the couple demolished the existing structures on the site and enlisted the services of the architecture and design firm Workshop/APD to create an entirely new and impressive compound.
The project was completed around 2018 and features a stunning four-bedroom main house with a design that marries casual comfort with understated elegance. The residence showcases a double-height entry foyer with a striking sculptural staircase and bi-folding glass doors that provide sweeping views of Nantucket Harbor.
Notable elements of the property include a living room graced with a freestanding fireplace and two chandeliers with sunburst-inspired designs. Additionally, there’s a dining area, a kitchen equipped with a marble-topped eat-in island, and a primary bedroom suite that opens onto a private terrace complete with an outdoor shower. The property also boasts a pool area and a detached guesthouse, which features a gym and a media room.
The sellers were represented by Shellie Dunlap of Lee Real Estate, while the buyer received representation from Peter Engen, also of Lee Real Estate.
In summary, Dave Portnoy’s latest real estate acquisition is a testament to his continued interest in upscale and prestigious properties. This waterfront estate in Nantucket, with its luxurious features and breathtaking views, represents a new record in residential real estate transactions on the island and in the state of Massachusetts, underscoring Portnoy’s commitment to acquiring remarkable and noteworthy properties.
