You’ve seen the headlines. You know the name. But honestly, most of the chatter around Jordon Hudson real estate is missing the point. People get so hung up on the age gap with Bill Belichick that they overlook a fairly sophisticated series of business maneuvers.
She isn't just "buying houses." At 24, she’s built an $8 million portfolio in about 18 months. That's fast. Like, remarkably fast.
The scale of this thing is wild. We are talking about four properties—mostly multi-family units in and around Boston—purchased in a dizzying sprint between late 2023 and early 2024. If you're looking for the typical celebrity "mansion flex," you won't find it here. This looks much more like a cold-blooded cash flow play than a vanity project.
The Strategy Behind Jordon Hudson Real Estate
Most people think real estate is just about picking a pretty building. It’s not. It’s about the "stack." Hudson’s stack involves a very specific type of asset: the multi-family townhouse. These aren't single-family suburban homes with white picket fences. They are income engines.
Take her Dorchester properties. In December 2023, she closed on two different townhouses on the exact same day.
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- Property A: A $2.2 million townhouse.
- Property B: A $2.3 million townhouse.
Both were already converted into three separate apartments. Both were renovated "to the studs" before she even signed the paperwork. By the time she took out the $1.2 million mortgages on these units, they were already primed for the Boston rental market. One unit alone was reportedly listed for $5,000 a month. Do the math on six units across two buildings, and you start to see why this isn't just a hobby.
Smart Hygiene or Overkill?
Hudson didn't just buy these in her own name. She used a series of LLCs—Trouble Cub Enterprises, Gingerbread Apartments, and others. To a casual observer, it looks like a mess of paperwork. To a pro, it’s standard risk mitigation. If a pipe bursts and floods a unit in Dorchester, the liability (theoretically) stays within that specific LLC. It doesn't sink the $3 million property she owns in Roxbury Crossing.
This is what seasoned investors call "financial hygiene." It’s a bit unusual to see a 24-year-old former cheerleader with a cosmetology background navigating these waters so cleanly. Whether she’s being advised by Belichick’s legal team or she’s a natural-born shark, the structure is objectively professional.
The $8 Million Portfolio Breakdown
Let's look at the actual numbers because they’re kind of staggering. The portfolio didn't grow slowly. It exploded.
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- The Harwich Cottage: This was the "cheap" one. Purchased in October 2023 for $610,000. It’s a two-bedroom spot on Cape Cod. It serves as her primary residence on most of her legal filings.
- The Dorchester Double: As mentioned, these two townhouses cost a combined $4.5 million.
- The Roxbury Crossing Giant: This is the crown jewel of the income side. A $3 million multi-family dwelling with 15 bedrooms and 8.5 bathrooms.
When you add it up, the monthly rental income from the Roxbury property alone was reportedly hitting $17,675. That’s over $212,000 a year from one building.
Where is the money coming from?
This is the elephant in the room. Public records show Hudson as the "borrower" on these mortgages. However, critics point out that she was a 24-year-old student and model just months before these multi-million dollar deals closed. While there's no public proof Belichick cut the checks, the timing—roughly two years into their relationship—is what fuels the skepticism.
But here’s the nuance: the bank still had to approve those loans. Even if you have a wealthy benefactor, the "borrower" usually needs to show the asset can cover its own weight. The fact that these were turnkey, high-income rentals likely made the underwriting possible.
Beyond the Buildings: The Business of Being Jordon Hudson
Real estate is just one wing of what Hudson is building. She’s also listed as the COO of "Belichick Productions" in various email signatures, and she’s been heavily involved in managing the optics of Belichick’s transition to the University of North Carolina.
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Her business, Trouble Cub Enterprises, isn't just for holding land. It's described as a holding company for cosmetics, media production, and "creative consultation."
She is effectively acting as a Chief of Staff and a real estate mogul simultaneously. It’s a lot for anyone, let alone someone who was competing in beauty pageants (placing 3rd in Miss Maine USA 2025) while managing 15-bedroom rental properties.
Actionable Insights for Aspiring Investors
If you’re looking at Jordon Hudson real estate as a roadmap, there are a few things to strip away from the celebrity noise.
- Focus on Multi-Family: If you want cash flow, don't buy a house; buy an apartment building. The "unit count" is what protects you from vacancy.
- Turnkey vs. Fixer-Upper: Hudson didn't buy projects. She bought properties that were "renovated to the studs." This allows for immediate high-end rental pricing without the headache of managing contractors.
- LLC Siloing: Even if you only own two properties, keep them separate. It costs a few hundred bucks in filing fees but protects your personal assets from property-specific lawsuits.
What Really Happened with Jordon Hudson is that she skipped the "beginner" phase of real estate. She went straight to the institutional-style play of buying high-density, high-rent urban units in a Tier-1 market like Boston. Whether it’s a solo flight or a co-piloted venture, the portfolio itself is a masterclass in aggressive scaling.
To get started on a similar (albeit smaller) path, your next move should be researching "house hacking" or multi-unit FHA loans, which allow you to buy up to four units with as little as 3.5% down, provided you live in one of them. It’s the closest thing to the Hudson strategy for those of us without an $8 million starting line.