Barstool Sports Founder Dave Portnoy’s $42 M Home in Nantucket, MA-(bsfDPh1220)

Nestled in the exclusive Monomoy Harbor, Dave Portnoy’s newly acquired estate redefines luxury and exclusivity on Nantucket Island.

Spanning 1.2 acres, the property, which includes two homes, has set a new state record at $42 million, making it the most expensive residential purchase in Massachusetts history.

Situated in a neighborhood known for attracting billionaires and celebrities, the estate blends coastal charm with modern opulence, becoming a symbol of grandeur.

Indoor-Outdoor Masterpiece

At the heart of the estate lies a 5,200-square-foot main house, designed to blur the boundaries between indoor and outdoor living.

Floor-to-ceiling accordion glass walls open up to 180-degree views of the harbor, Nantucket town, and the sparkling waters of Nantucket Sound.

Each room is bathed in natural light, allowing residents to enjoy panoramic vistas from sunrise to sunset.

With multiple bedrooms, this home offers a perfect balance of sophistication and comfort, while expansive living areas are ideal for both intimate gatherings and large-scale entertaining.

A Luxurious Guest House

Perched on a hill behind the main residence, the two-bedroom guest house serves as a luxurious retreat with the same attention to detail and design as the main home.

From its elevated position, guests are treated to sweeping views of the harbor, infinity pool, and lush surroundings, providing an intimate yet private space for visitors.

The Private Beachfront Retreat

Boasting 140 feet of private beach, this estate offers the perfect backdrop for oceanfront living.

Whether for a leisurely swim or a scenic boat ride, the beach is an invitation to embrace the natural beauty of the Atlantic.

The infinity pool, designed to capture the island’s iconic sunsets, provides a serene escape with uninterrupted views stretching over the harbor.

Unparalleled Outdoor Spaces

The estate’s outdoor areas are meticulously crafted for both relaxation and entertainment.

Perfectly positioned for spectacular views of the July 4th fireworks, starlit nights, and ferries sailing past Brant Point, the outdoor spaces are as functional as they are breathtaking.

This is more than just a home—it’s a lifestyle, offering the ultimate Nantucket experience.

A Harborfront Elegance

Designed by the renowned Andrew Kotchen of Workshop/APD and constructed by Reid Builders, this estate encapsulates the essence of harborfront living.

Combining natural beauty with architectural brilliance, this Monomoy retreat stands as a rare opportunity to experience the finest that Nantucket has to offer.

Scroll down to see stunning photos of this property.

Photos of Dave Portnoy’s Home

The front of the house features three dormer windows and a welcoming entryway underneath a clear blue sky.

An aerial view of the property reveals its stunning location nestled in greenery, with a private path leading directly to the beach, surrounded by other luxurious estates.

A sleek outdoor lounge area features stylish sun loungers beneath a pergola, with a view of the harbor and distant pier, creating a relaxing setting.

The master bedroom opens directly to a private outdoor space, featuring large glass doors that offer a seamless transition between indoor and outdoor living.

Sitting on a large, beautifully manicured lawn overlooking the harbor, the house offers panoramic water views that stretch out to the horizon.

A wooden deck wraps around the back of the house, ideal for enjoying views of the serene harbor and the boats anchored in the distance.

Leading to the front door, a neatly trimmed hedge archway adds privacy and charm to the entryway, with a classic brick pathway lined by vibrant plants.

A cozy outdoor seating area on the wooden deck provides an uninterrupted view of the sparkling blue waters of Nantucket Sound.

Weaving through the coastal grasses, a private boardwalk leads directly to the property’s exclusive 140 feet of sandy beach.

Framed by neatly trimmed hedges, the side view of the house provides both privacy and a quaint coastal aesthetic, with glimpses of the harbor in the background.

An elevated viewpoint showcases the harbor dotted with sailboats, offering a peaceful backdrop for this waterfront property.

A stunning aerial view of the property highlights its prime location right on Monomoy Harbor, with a wide circular driveway and a garage tucked on the side.

The wooden deck in the backyard overlooks a lush green lawn that seamlessly blends into the natural surroundings with the calm harbor just beyond.

Featuring large picture windows, the back of the house provides uninterrupted views of the expansive green yard and the water, creating an ideal coastal retreat.

A private sandy path lined with coastal grasses leads directly from the house to the property’s 140 feet of secluded beachfront.

The coastal greenery and dunes frame the shoreline, giving the property an unspoiled natural charm while overlooking Monomoy Harbor.

A scenic view of the nearby dock extending into the harbor, with boats gently floating on the water, complements the home’s prime waterfront setting.

Designed for relaxation, with elegant lounge seating and a view of the harbor, a luxurious pool area captures the perfect balance between modern amenities and natural beauty.

The backyard boasts an inviting outdoor dining space under a pergola, with a large swimming pool and lounge area that offer a relaxing spot to take in the ocean views.

A beautifully set outdoor table overlooks lush greenery and the harbor, offering a peaceful setting with soft evening light glinting off the water in the distance.

The sun sets over the harbor, reflecting off the large windows of the house and illuminating the modern pergola and cozy outdoor seating area.

Showcasing a perfectly balanced design with expansive glass doors, the back of the house is a spacious patio, offering multiple seating areas.

The home is set against lush landscaping, with its clean architectural lines and multiple outdoor patios blending seamlessly into the natural surroundings.

Glowing under string lights, with a pergola offering shade by day and ambiance by night, the outdoor dining space complements the serene poolside setting.

Grand Interiors

The living room features large windows that fill the space with natural light and offer beautiful views of the harbor, complemented by hardwood floors and coastal decor.

A cozy sitting area by the fireplace offers a comfortable space with wicker chairs and nautical accents, creating a warm, inviting atmosphere with water views.

The open-concept living space flows into the dining area, featuring a striped couch with cheerful pillows and a rustic dining table, perfect for casual coastal living.

Offering a stunning harbor view through large glass doors framed by soft curtains, the cozy living room features a decorative telescope, creating a seamless connection to the outdoors.

The modern kitchen opens to an outdoor dining space, with a sleek island and a large chandelier providing a stylish touch, all overlooking a comfortable patio with a fireplace.

A serene dining area bathed in natural light features a modern wood table and sleek chairs, complemented by floor-to-ceiling windows with garden views.

Opening directly to the harbor, with accordion glass walls blurring the lines between indoor and outdoor living, a spacious bedroom creates a peaceful retreat.

A stylish staircase enclosed in rope-detailed railings adds a unique design element to the minimalist interior, enhancing the home’s modern aesthetic.

Featuring a cozy bed with a textured throw, a beautifully designed bedroom boasts a natural wood nightstand and a rustic mirror.

The bathroom showcases a sleek design with a concrete sink and a glass-enclosed shower, featuring stylish herringbone tile and modern fixtures for a sophisticated feel.

A spacious living room bathed in natural light features floor-to-ceiling windows and cozy, plush seating with modern hanging light fixtures.

The living area boasts a central suspended fireplace, with expansive windows framing uninterrupted harbor views, creating a serene yet luxurious atmosphere.

Elegantly designed with dual sinks, sleek marble finishes, and modern fixtures, the bathroom offers a spa-like retreat.

The open-plan kitchen and dining area features a marble island and built-in seating, combining modern design with functional elegance.

A cozy sitting room offers direct access to a balcony with sweeping views of the harbor, framed by chic French doors.

Accented by deep blue sectional seating and patterned ottomans, with a modern shelving system, a cozy lounge area adds warmth and style to the room.

Framed by large windows that offer views of the surrounding greenery, with a long dining table and plush leather chairs, a stylish dining area creates an inviting atmosphere.