Dave Portnoy of Barstool just bought the most expensive home ever on Nantucket

Table Of Content

• Barstool Founder Dave Portnoy Buys Most Expensive Home In Massachusetts History—This $42 Million Nantucket Mansion
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• A West Hollywood Penthouse Just Sold for $24 Million, One of L.A.’s Biggest Condo Deals in Years
• Rhode Island News
• Barstool’s Dave Portnoy purchases most expensive home in Massachusetts history
• Dave Portnoy's $42 million Nantucket home breaks record

An additional $2 million worth of furniture and other items were also included in the sale, The WSJ reported. The deal was conducted off-market and Shellie Dunlap of Lee Real Estate represented the sellers, a pair of trusts known as MAK Daddy Trust and MAK Shack Trust, according to records. Lee Real Estate called the sale “a new benchmark for residential real estate on Nantucket,” The Boston Globe reported. “I went from being able to afford renting for a day to a weekend to a week to a month to renting for the entire summer to buying a house to now buying a house beyond even my wildest imaginations.

Barstool Founder Dave Portnoy Buys Most Expensive Home In Massachusetts History—This $42 Million Nantucket Mansion

Brady Wilson is the Founder and CEO of Pampr, a hospitality startup that is trying to transform the guest experience for vacation homes. Wilson graduated from Wake Forest University in 2021 and launched Pampr in 2022. Pampr has been piloting its services on Nantucket for two summer seasons and is preparing to launch its first new market this winter. Dave Portnoy bought a record-setting $42 million home in Nantucket, The Wall Street Journal reported, citing people familiar with the deal. The company declined to confirm reports that Portnoy had purchased the estate, identifying the buyer as Ferry Views LLC and the seller as Mak Daddy Trust & MAK Shack Trust.

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The 1.2-acre property, located in the Monomoy area, sprawls along the Nantucket Harbor waterfront. The owners bought two parcels in 2016 for a combined $13.3 million and custom-built the compound following the demolition of two existing homes. The sale set a residential real estate record for the island as well as the entire state of Massachusetts, according to the Nantucket Current. She cited the robust state of the real estate market and the current demand for move-in ready homes on Nantucket as key factors. In January, Portnoy announced the Chernin Group had bought a majority stake in Barstool Sports. It’s estimated he raked in about $15 million from the deal, though it appears he got a head start on spending that money since he bought the summer house a few months prior.

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On a cloudy day, walk the charming streets in town, among steepled churches and buildings with weathered grey shingles. The Whaling Museum tells the story of the dangerous and dramatic 18th-century whaling industry. Nantucket Looms weaves textiles at their own studio, including cashmere throws and mohair wraps. Townpool is a quirky souvenir shop that stacks an entire wall floor-to-ceiling with rubber ducks and sells rope bracelets, artsy maps, and cozy knits.

Portnoy, who is from Massachusetts, has previously invested in Nantucket real estate, having bought a property for around $2 million. He recently reacquired Barstool for $550 million after selling it to Penn Entertainment. He’s also known for appearing in headlines nearly as much as his media company generates them. In 2021, he faced allegations of sexual misconduct from several women, which he denied.

Barstool’s Dave Portnoy purchases most expensive home in Massachusetts history

The hotel landscape on Nantucket is distinguished by plenty of posh stays and bed-and-breakfasts alike. The Nantucket Hotel (from $295 per night), which bills itself as the island’s only year-round stay, is a shingle mansion with a spacious wraparound porch, and has a past life as the 1891 Point Breeze hotel. Besides the hotel’s history, its homemade popovers, plush bathrobes, and complimentary ferry pick-up and drop-off service contribute to a feeling of home. The Wauwinet (from $240 per night), a Relais & Chateaux hotel, a sister to the White Elephant, and Nantucket’s grande dame, is located on the more remote northeastern tip of the island.

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With changing stations, a plastic mat that leads from the parking lot to the water, showers, volleyball nets, and a playground, Jetties is accessible and stress-free. Take its sloping cobblestone streets, pink lady’s slipper orchids splitting the sandy soil, and glowing Christmas trees floating on boats in December. It is the world of Herman Melville’s Moby Dick, a natural splendor where rare species—such as double-crested cormorants and piping plovers—gather, and for travelers, it is a world-class destination ideal for kicking back. So much more than just a summer town, Nantucket is a beauty in winter, fall, and spring.

Both declined requests for comment from The Real Deal on the transaction. The Nantucket Current reported yesterday that Dave Portnoy, founder of Barstool Sports, paid $42 million for the Monomoy Road compound. This broke the most recent record for the most expensive property sale on Nantucket. Other standout features include a living room sporting a freestanding fireplace and pair of sunburst-inspired chandeliers, as well as a dining area, kitchen outfitted with a marble eat-in island, and primary bedroom suite with a private terrace that has an outdoor shower.

Dave Portnoy's $42 million Nantucket home breaks record

Portnoy’s reported purchase tops the summer sale of a nearby home that went for $38.1 million. In a post on X, formerly known as Twitter, Portnoy appeared to confirm the purchase of the property. Peter Engen of Lee Real Estate, who represented Portnoy in the deal, declined to provide comment when reached by Insider. "In the big markets, people who are paying cash for $3 million homes want something that no one else has," Ron Syrnyk, an interior designer who had designed a tunnel to a wine cave for a client, told the Journal at the time. Examples of tunnels featured in other homes include an "Alice in Wonderland"-inspired tunnel that leads to a children's playroom and a 70-foot tunnel that crosses under a road to grant easier access to the beach.

The properties at 72 and 68 Monomoy Road were sold in March 2016 by the Anathan family to two blind trusts for a combined $13.3 million. The existing dwellings were then torn down and the properties were completely redeveloped. Both the buyer and the seller were represented in the deal by the Nantucket firm Lee Real Estate. Broker Shellie Dunlap represented the seller, while agents Peter Engen and Bruce Beni represented Portnoy.

Wauwinet guests are often couples or families, content to be in a quiet area. Life House (from $239 per night), which opened last summer, has all the appeal of a bed-and-breakfast, but with modern digs, a daily complimentary happy hour, and a beautifully designed patio where locals and hotel guests mingle. On Friday, the Boston Herald reported the sale of a Nantucket home to Portnoy, though he bought the house in November 2015. According to land records, he coughed up $2 million for the grey-shingled four bedroom.

The buyer on the deed is listed as Ferry Views LLC, registered to local attorney John Brescher. The seller was listed as Steven Cohen as trustee of the Mak Daddy Trust and trustee of the MAK Shack Trust, according to property records. Nestled in the coveted Monomoy area, this prime piece of real estate sprawls across approximately 1.2 acres, showcasing views of Nantucket Harbor. Portnoy is best known for Barstool Sports, the company he started about two decades ago.

For example, when it comes to trash removal and collection, instead of placing your refuse in bins outside of your home to be gathered by a waste management company, homeowners must keep the garbage in bins or barrels away from the curb until scheduled pickup days. According to the Myles Reis trucking company's website, this is "due to the historic nature of the island." When Dave first purchased the home in 2016, he also uploaded a series of videos entitled "Nantucket Living" on YouTube, showing what life on the island is like. Portnoy appeared Tuesday on "Varney & Co," where host Stuart Varney at one point asked the Barstool Sports founder whether he had chosen Nantucket versus Martha’s Vineyard based on politics.

The company is targeting transient resort-style communities that are home to a large number of short-term vacation rental properties. They will be launching their first new market in November in a West Coast location with a high volume of short-term vacation rentals. And in summer 2024, they are aiming to expand to a new East Coast market in addition to Nantucket.

A Nantucket 200-Year-Old Home Lists for Sale for $25 Million - Observer

A Nantucket 200-Year-Old Home Lists for Sale for $25 Million.

Posted: Mon, 16 Oct 2023 07:00:00 GMT [source]

PENN sold Barstool back to Portnoy last month as part of a $1.5 billion agreement the Pennsylvania-based company landed with ESPN for a new sportsbook called ESPN Bet. Portnoy filed a defamation lawsuit against Insider in February 2022, claiming the outlet “knowingly disregard[ed] the truth.” The suit was dismissed in November. The 1.2-acre pair of waterfront properties at 68 and 72 Monomoy Road feature a 5,200-square-foot main estate with a two-bedroom guest house and pool in Nantucket’s Monomoy neighborhood, giving the homeowner a sunset view over Nantucket Harbor and the island’s historic downtown. The mansion and guest quarters have six bedrooms, nine full baths and two half baths among them, according to Lee Real Estate’s listing. In the main house, it features "multiple sets of accordion glass walls evoking the feeling of being one with the harbor when open," the listing said.

Barstool Sports founder Dave Portnoy reportedly purchased a waterfront mansion on Nantucket for $42 million -- the most expensive real estate transaction in the history of the island and the entire state. “At $42 million, the sale has set a new benchmark for residential real estate on Nantucket,” Lee Real Estate said in announcing the sale of the Monomoy Road mansion. The 1.2-acre estate has three dwellings with private beach access, the company said. Dunlap spilled the details, revealing that the main house features four bedrooms, complete with a primary suite offering an indoor/outdoor shower and foldaway glass doors that open up to harbor views. The 1.2-acre property features the main dwelling that’s connected to a guesthouse via an underground tunnel, as well as a recently finished pool. The combined 1.2-acre property features a waterside main dwelling, a guesthouse, and a pool that were completed in 2018 and 2019 by the Nantucket construction firm Reid Builders and designed by architect Andrew Kotchen of Workshop/APD and landscape architect Miroslava Ahern.