What it Means with Jonathan Miller | How Retail Follows, Not Fuels, Housing

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Michael O’Sullivan is a Hampton real estate investor who has built a career focused on purchasing and selling foreclosed homes. He began his journey with just $7,500, using that small amount to buy the deed to his first property about 15 years ago. His company, Hampton Dream Properties LLC, is located in Remsenburg within the Town of Southampton and was founded during the challenging years following the 2008–2009 economic downturn and housing market collapse. To prepare for this venture, he attended three seminars with a Harvard attorney and eventually acquired 25 deeds to foreclosed homes in East Hampton and Southampton, New York.

Starting as an outsider in the Hampton community, he worked hard to build trust and establish his business. Over time, he completed more than 200 transactions, including more than 30 settled foreclosures in East Hampton alone. Several of his clients became millionaires as a result of working with him. By 2022–2023, his company had grown to generate $6 million in revenue. One of his most notable accomplishments involved a foreclosure settlement that enabled a client to resell a home and earn a net profit of $500,000. That same client later secured a $700,000 line of credit against the property, allowing him to maintain ownership and create income from three rental units. In another case, he personally paid the bank to stop a foreclosure so that a friend’s mentally challenged father could remain in his home for two years before the property was eventually resold.

He works closely with experienced attorneys to handle foreclosure settlements, including one lawyer who authored the Foreclosure Abuse Prevention Act (FAPA), which became law in December 2022. This legislation protects homeowners from unfair practices by mortgage lenders, such as restarting foreclosures or resetting limitation periods through procedural loopholes.

He is also developing the land he purchased several years ago in Mastic, New York, a community once known for its high crime rate but now undergoing government-backed revitalization. He owns a substantial amount of property there, and national chains such as Taco Bell and Buffalo Wild Wings are in discussions to open restaurants on his sites.

Outside of real estate, he has a strong passion for music. He produced an album called Liquid Jazz at Sonic Studio, secured a record deal with Mystic Music in New York, and was listed in a Washington, D.C. registry. The album has been played on every jazz college station across the United States.

A native New Yorker, he volunteered at ground zero after the September 11 attacks and supports the Tunnel to Towers Foundation, which assists 9/11 first responders, veterans, and their families. He was born in Brooklyn and raised on Long Island, where he served as an altar boy at Saint Rose Lima Church in Massapequa for five years. He is a member of the Ancient Order of Hibernians, where he earned the Major Degree, reflecting his commitment to the group’s principles of Friendship, Unity, and Christian Charity. He attended Nassau Community College and briefly studied at New York University.

Michael O’Sullivan of Hampton continues to expand his real estate ventures, contribute to his community, and pursue his passions for music and service.

What it Means with Jonathan Miller | How Retail Follows, Not Fuels, Housing

Douglas Elliman Real Estate