The two-acre North Shore estate that hosted the peak of Stratton Oakmont’s excess has just posted the highest price in its village this year — nearly three times what it fetched seven years ago.

From Stratton Oakmont to Biscayne Bay: Belfort’s Property Trail

Few American figures have a real estate history as closely tied to their rise and fall as Jordan Belfort. The Queens-born stockbroker built Stratton Oakmont into a Long Island brokerage known for aggressive penny-stock trading before investigations by the Securities and Exchange Commission and the FBI brought the operation to an end. Belfort pleaded guilty to securities fraud and money laundering in 1999, was ordered to repay roughly $110 million to investors, and served 22 months in federal prison. His memoirs and Martin Scorsese’s 2013 film adaptation, starring Leonardo DiCaprio, later turned his story into a lasting part of American financial culture.

Acquired in the early 1990s while Belfort was still in his twenties, the Old Brookville estate near Glen Head became the center of his lavish lifestyle. It served as his primary residence, a setting for parties and gatherings, and ultimately a tangible record of the wealth accumulated during his Stratton Oakmont years. The property was part of a larger collection that included a 167-foot yacht named after his then-wife, a Ferrari Testarossa and a helicopter associated with one of the more widely retold episodes from his years on Long Island.

Belfort’s second act has been considerably more restrained. Following his release in 2006, he rebuilt his career as a sales trainer, author and motivational speaker. During that period, he was associated with an oceanfront property on The Strand in Hermosa Beach, California. The roughly 4,000-square-foot residence was considerably smaller than his former Long Island estate, although its beachfront location placed it in one of Southern California’s most valuable residential markets.

In late 2021, Belfort relocated to South Florida with his wife, Argentine model Cristina Invernizzi. The couple settled near Biscayne Bay, marking another chapter in a property history that has moved from Long Island’s Gold Coast to Southern California and, eventually, Miami.

Belfort has not attempted to reacquire his former North Shore residence. Instead, the Old Brookville house has spent more than two decades changing hands, undergoing renovations and gradually developing an identity of its own. Its latest transaction represents the most valuable sale in that property’s long post-Belfort history.

A Quiet Deal on a Cul-de-Sac Ends the Estate’s Long Second Act

The mansion sold for $6,875,000 in an off-market transaction, making it the highest residential sale recorded in Old Brookville during the year. There was no public listing, open house or marketing campaign centered on its connection to Belfort. The sellers’ agent had been preparing to introduce the property to the market when a buyer searching for another property in the area expressed interest in the estate. The transaction was subsequently negotiated privately.

The discreet sale represents a notable contrast with the property’s earlier marketing history. For much of the past decade, its connection to Belfort and The Wolf of Wall Street was presented as part of its appeal. When the residence entered the market in March 2017 with a $3.4 million asking price, that association featured prominently. The property did not sell at that price.

By the summer of 2018, the asking price had been reduced to $2.89 million. Several months later, in October, the estate changed hands for $2.4 million — approximately $1 million below its original asking price.

The subsequent renovation changed the property’s position in the market. The buyers undertook extensive work, taking portions of the interiors down to the studs where systems required replacement and updating the layout and finishes throughout the main level. At the same time, they retained several architectural features associated with the original house, including the mahogany double doors, marble-floored dining room and double-height foyer with its circular staircase.

The improvements extended outdoors. The owners added an outdoor kitchen, constructed a separate pool house and rebuilt the landscaping surrounding the heated saltwater pool. After roughly seven years and a substantial renovation investment, the estate returned to the market at a dramatically higher value.

Part of that increase reflects the broader evolution of Old Brookville’s residential market. The village has limited housing supply, with large parcels and strict zoning contributing to the scarcity of available properties. Comparable homes on similarly sized lots can command multimillion-dollar prices, particularly when they have been comprehensively renovated.

The property’s history may also have become less of a commercial obstacle over time. In 2017 and 2018, the Belfort connection linked the residence to fraud, asset seizures and restitution. Years later, the association has taken on a different character. The property remains connected to one of the most recognizable financial scandals of its era, but that history now exists alongside a substantially renovated home rather than defining its entire market identity.

The estate’s ownership history also reflects the consequences of Belfort’s criminal case. He lived there during the 1990s with his then-wife, Nadine Macaluso, and their two children. Federal authorities seized the property in 2001 following his guilty plea, and it was subsequently sold as part of efforts to satisfy the restitution ordered to his victims. The property reportedly fetched approximately $2.5 million at the time.

Since then, each private owner has held the property independently of Belfort’s original ownership. The latest transaction therefore represents not a return to its former identity, but another stage in the property’s evolution.

One common misconception is also worth clarifying: although the Old Brookville residence was Belfort’s actual home, it was not the primary house seen in The Wolf of Wall Street. The film used other Long Island properties for various scenes, including a mock-Tudor estate in Oyster Bay and a waterfront property in Port Washington for the pool-party sequence.

As a result, visitors expecting the exact cinematic setting may find that the real residence is somewhat different from its Hollywood portrayal. Its significance lies less in being a film set than in the genuine history attached to the property.

Eight Bathrooms, a Glass Racquetball Court and the Safe That Stayed

Built in 1986 and positioned at the end of a private cul-de-sac, the residence encompasses approximately 8,706 square feet on two landscaped acres. The current configuration includes five bedrooms and eight bathrooms, along with a three-car garage.

The floor plan is designed around entertaining. A two-story entrance foyer features marble flooring and a circular staircase rising through a turret. Elsewhere, the home includes a large living room, den, lounge and billiards spaces arranged as an expansive entertainment wing.

The amenities extend beyond the home’s main living areas. The interior includes a home gym, wine cellar and glass-enclosed racquetball court — a distinctive feature that reflects the property’s original era while remaining unusual in today’s luxury market.

Outside, a bluestone terrace extends across the rear of the house and leads toward the landscaped grounds. The property includes a heated saltwater pool, detached pool house, outdoor kitchen, putting green and treehouse.

Several original details have also been preserved. The formal dining room retains its marble flooring, while the mahogany double doors at the entrance remain part of the house’s original character.

Perhaps the most unusual remnant of the Belfort era is the built-in safe. Rather than removing it during the renovation, the previous owners left it in place, allowing it to remain with the property.

It is a small feature compared with the estate’s extensive amenities, but it neatly captures the balance between old and new that now defines the house: a thoroughly updated Gold Coast residence that still carries visible traces of the history that made it famous.

How the Pin Oak Court Estate Got Here

1986: The approximately 8,706-square-foot residence is constructed on a two-acre parcel at the end of a private cul-de-sac in Old Brookville, near Glen Head.
Early 1990s: Jordan Belfort acquires the estate during the height of Stratton Oakmont and lives there with his then-wife, Nadine Macaluso, and their two children.
1998–1999: Belfort is arrested and pleads guilty to securities fraud and money laundering. The court orders roughly $110 million in restitution.
2001: Federal authorities seize the property and sell it for approximately $2.5 million as part of efforts to satisfy Belfort’s restitution obligations.
March 2017: The estate enters the public market with a $3.4 million asking price, with its connection to The Wolf of Wall Street forming part of the property’s marketing.
August 2018: The asking price is reduced by $510,000 to $2.89 million after the property remains unsold.
October 2018: The estate sells for $2.4 million, approximately $1 million below its original asking price.
2019–2024: The owners undertake an extensive renovation, retaining features such as the mahogany doors, marble dining room and built-in safe while adding an outdoor kitchen, pool house and redesigned landscaping.
Autumn 2025: The estate sells off-market for $6,875,000, reportedly setting the year’s highest residential sale in Old Brookville. The new owners are expected to undertake additional work on the property.