Dave Portnoy, the founder of Barstool Sports, has just purchased a breathtaking Nantucket compound for a cool $42 million. This sale sets a new residential record for the island and the state of Massachusetts. But it’s not just the price tag that’s turning heads—it’s the story behind Portnoy’s journey to this incredible property.
In this article, we’ll take you through the details of this remarkable estate and explore the story of how Portnoy turned his dreams into a reality.
A Dream Come True for Portnoy
“Nantucket has always been my favorite place on earth. The best day of my year was heading to the island for vacation. The worst day was taking the ferry back home. I used to dream of buying a place where I could watch the ferry come and go, a place where I could have privacy and cherish every second I got to spend on the island.”
These are the words of Dave Portnoy, reflecting on his recent purchase of a $42 million Nantucket compound. Portnoy, the founder of Barstool Sports, has long had a special connection to the island, and his journey to owning a piece of it is nothing short of inspiring.
In a social media post, Portnoy shared his excitement and gratitude for this new chapter in his life:
“Once Barstool started taking off, my dreams of owning a place on Nantucket became a reality. What started as renting for a day turned into a weekend, then a week, and eventually, I was able to rent for the entire summer. And now, I’m beyond grateful to call this incredible place my home.”
Portnoy’s post not only celebrates his success but also acknowledges the hard work and dedication that made it possible. It’s a testament to his journey and a reminder that with perseverance, dreams can become a reality.
A Record-Breaking Purchase
The $42 million price tag isn’t just a personal milestone for Portnoy—it sets a new residential record for Nantucket and the entire state of Massachusetts. The previous record was set just a few months ago, in June, when a nearby compound on Berkeley Avenue sold for $38 million.
The property includes two separate lots, 72 and 68 Monomoy Road, which were developed as a single, fully furnished estate. The sale was handled by the Nantucket firm Lee Real Estate, with Shellie Dunlap representing the seller and Peter Engen and Bruce Beni representing Portnoy.
The closing price also includes approximately $2 million worth of furniture and amenities, showcasing the level of luxury and attention to detail that this estate offers.
A Waterfront Escape
The crown jewel of Nantucket.
Located on the coveted Monomoy Road, this waterfront estate offers unparalleled views and privacy. The combined 1.2-acre property features a waterside main dwelling, a guest house, and a pool—providing the ultimate escape for Portnoy and his guests.
Completed in 2018 and 2019, the main house and guest house were designed by architect Andrew Kotchen of Workshop/APD, with landscape architecture by Miroslava Ahern. The result is a breathtaking estate that seamlessly blends indoor and outdoor living.
One of the property’s most unique features is the underground tunnel connecting the two houses, providing a seamless and private way to move between them.
Inside the Main House
As you step into the main house, you’re greeted by a bright and airy interior that showcases the surrounding waterfront views. The living room, with its floor-to-ceiling windows, offers a peaceful space to relax and take in the beauty of Nantucket Harbor.
The dining room and kitchen continue the theme of waterfront views, with a seamless flow between indoor and outdoor spaces. The kitchen, a chef’s dream, features state-of-the-art appliances and a spacious layout, making it perfect for entertaining.
The main house also includes multiple bedrooms and bathrooms, offering a comfortable and luxurious retreat for Portnoy and his guests.
The Guest House and Outdoor Spaces
A haven for relaxation and entertainment.
The guest house provides additional space for Portnoy to host family and friends. It features a fully equipped kitchen, bedrooms, and a studio space, ensuring guests have all the comforts of home.
Stepping outside, the property truly shines. A peaceful waterfront deck offers the perfect spot for al fresco dining or simply soaking in the sun. The pool area, surrounded by lush greenery, invites you to take a dip or lounge poolside while enjoying the breathtaking views.
The landscape design by Miroslava Ahern enhances the natural beauty of the property, creating a harmonious blend of architecture and nature.
A Property Shrouded in Privacy
Seclusion at its finest.
One of the most notable aspects of this estate is the level of privacy it affords. The property is carefully designed to provide a secluded escape for Portnoy and his guests. The use of landscaping and natural barriers ensures that the outdoor spaces can be enjoyed with utmost privacy.
Additionally, the underground tunnel connecting the main house and guest house allows for discreet movement between the two, further enhancing the sense of seclusion.
The Journey to $42 Million
From renting to buying, a dream was fulfilled.
Portnoy’s journey to owning this $42 million estate is a testament to his hard work and the success of Barstool Sports. He first fell in love with Nantucket as a rental visitor to the island, and his affection for it only grew over the years.
His previous real estate ventures on the island included a property on High Brush Path off Hummock Pond Road. However, his new purchase on Monomoy Road takes his Nantucket experience to a whole new level.
The two lots that make up the compound, 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 property was completely redeveloped, resulting in the breathtaking estate it is today.
A Place to Call Home
More than just a house, it’s a sanctuary.
For Portnoy, this $42 million purchase isn’t just about the luxurious amenities or the record-breaking price tag. It represents a deep connection to Nantucket and a realization of his dreams.
In his social media post, Portnoy shared his emotions:
“This house is beyond even my wildest imaginations. It’s a place where I can truly relax and enjoy every second I spend on this island. It’s a place I’m proud to call home, and I’m grateful for the journey that led me here.”
This purchase signifies more than just a real estate transaction—it’s a symbol of Portnoy’s success, a place where he can create new memories, and a sanctuary where he can escape the hustle and bustle of his busy life.
| Feature | Description |
|---|---|
| Location | The property is located in the Monomoy area of Nantucket, Massachusetts, on a 1.2-acre oceanfront site. |
| Main House | The main house is a 5,200-square-foot estate with four bedrooms, including a primary suite with an indoor-outdoor shower and private terrace. |
| Guest Quarters | The estate includes a two-bedroom guesthouse and a separate studio, connected by an underground tunnel. |
| Bathrooms | The mansion and guest quarters have a total of six bedrooms, nine full baths, and two half baths. |
| Living Room | Features a freestanding fireplace and sunburst-inspired chandeliers. |
| Kitchen | Outfitted with a marble eat-in island. |
| Pool Area | Includes an infinity pool and various decks. |
| Gym and Media Room | Located in the detached guesthouse. |
| Views | Offers sunset views over Nantucket Harbor and the island’s historic downtown. |
| Design and Construction | Designed by Andrew Kotchen of Workshop/APD and built by Reid Builders in 2018. |
| Furniture | The purchase included $2 million worth of furniture and amenities. |
Final Thoughts
A dream home, a record-breaking sale, and an inspiring journey.
Dave Portnoy’s $42 million Nantucket compound is more than just a luxurious estate—it represents a journey of hard work, dedication, and a deep connection to a place that has always felt like home.
From renting for a day to now owning a piece of Nantucket’s history, Portnoy’s story serves as an inspiration to dream big and never give up. His purchase sets a new standard for residential real estate on the island and showcases the power of perseverance.
As Portnoy settles into his new home, we can only imagine the memories he will make and the impact this special place will continue to have on his life.
So, there you have it—a glimpse into the remarkable $42 million Dave Portnoy house and the inspiring story behind it.
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