What Is a Serial Squatter?

The term “serial squatter” is not a formal legal classification. It is an informal term sometimes used to describe someone who repeatedly occupies properties they do not own and do not have permission to live in, often moving from one vacant or distressed property to another.

In Andrew’s experience in Jacksonville, some of the people he has encountered were not simply individuals facing a one-time housing crisis. He described people who appeared to know how to identify vulnerable vacant homes, occupy them, and then move on to another property after being removed.

That is what Andrew means when he refers to serial squatters.

They may look for homes that:

• Appear vacant or abandoned
• Have little owner or management presence
• Have broken doors, windows, or easy access points
• Are undergoing renovations
• Have recently had a tenant move out
• Are located in areas with multiple distressed or vacant properties

One of the biggest misconceptions, according to Andrew, is assuming that every unauthorized occupant fits the same stereotype.

Some may be experiencing genuine hardship. Others may repeatedly target vulnerable properties.

As Andrew put it, one person he dealt with was driving a newer GMC Denali than the truck Andrew himself was driving.

The lesson for landlords is simple:

Do not make assumptions about who is occupying your property or why. Focus on the facts, document the situation, maintain a visible presence, and follow the proper legal process for dealing with unauthorized occupants.

More Than a Handyman: How One Graystone & Property Wiz Partner Is Helping Take Back a Jacksonville Neighborhood

Today I had a conversation with Andrew, one of our trusted vendor and rehab partners for Graystone and Property Wiz in Jacksonville, and I walked away impressed.

I already knew Andrew was good at what he does.

He has helped us with properties, given us fair pricing, responded when we needed him, and become somebody we can depend on in Jacksonville.

What I didn’t fully realize was the mission he has taken on outside the four walls of the properties he’s repairing.

Andrew isn’t just fixing houses. He’s trying to improve the neighborhood around them.

And after hearing his story, I thought he deserved some recognition.

The Problem Was Bigger Than One Property

We started talking about some of the properties around Lemeing Avenue in Jacksonville.

Like many investors, when you first look at a distressed rental, you tend to focus on the property itself.

What’s wrong with the roof?

What needs to be repaired?

How much will the rehab cost?

How quickly can we get a tenant inside?

Andrew looks at things differently.

He told me:

“What’s around your property affects your property.”

That sounds obvious, but investors don’t always think about it.

You can spend thousands of dollars renovating a house, but if the vacant house across the street is attracting constant trouble, your investment is still being affected.

Your tenant sees it.

Your contractor sees it.

Your future buyer sees it.

The entire neighborhood feels it.

According to Andrew, that was part of what was happening around Lemeing Avenue.

These Weren’t Necessarily the Squatters People Imagine

Something Andrew said caught my attention.

There is a stereotype that everyone occupying a property illegally must be homeless, completely broke, or struggling with addiction.

Andrew says his experience has been much more complicated than that.

He described dealing with what he calls “serial squatters” — people who move from one vacant property to another.

Then he gave me an example I’ll probably never forget.

Andrew drives a 2014 GMC Sierra.

According to him, one of the people he helped remove from a property was driving a 2019 GMC Denali.

That immediately challenges the stereotype.

Andrew’s point wasn’t that every squatter is the same.

It was exactly the opposite.

Landlords shouldn’t assume they understand who they’re dealing with or why someone is occupying a property.

Some situations involve people in genuine hardship.

Others can involve people who repeatedly identify vulnerable vacant properties and move between them.

And those situations have to be handled properly and legally.

Sometimes the Previous Tenant Creates the Next Problem

Andrew brought up another issue investors should understand.

Sometimes a tenant is approaching eviction, becomes angry with the landlord or property manager, and allows other people into the property before leaving.

They may give someone access or even hand over keys.

Now what looked like a straightforward turnover can suddenly become a much more complicated possession issue.

That is one reason communication between the owner, property manager, maintenance team and vendors is so important.

Everyone needs to know what is happening.

Andrew’s Secret Weapon: Presence

One of Andrew’s biggest philosophies is simple:

Show up.

Don’t repair a vacant property and then disappear for three weeks.

Andrew works with multiple investors and property managers throughout Jacksonville. Even on days when he isn’t actively working at one of their properties, he regularly drives through the areas where he works.

People see his truck.

They see him checking properties.

They know somebody is paying attention.

Sometimes he’s in one vehicle. Sometimes another.

The point isn’t the vehicle.

The point is presence.

A property that looks abandoned can become an opportunity.

A property that clearly has someone checking on it sends a completely different message.

From Code Enforcement Problems to a Seven-Day Turnaround

Andrew also told me about dealing with code issues around several of the properties.

His philosophy is another one I really respect.

If code enforcement gives him 30 days to resolve something, he doesn’t ask:

“How long can I wait?”

He asks:

“How quickly can I fix it?”

Andrew said that on one group of properties, the team was able to make substantial improvements across five properties in roughly seven days.

There can sometimes be a temptation in real estate to say:

“We’ll just pay the code fine.”

Andrew sees that completely differently.

The fine isn’t the real problem.

The condition creating the fine is the problem.

Paying a fine costs the investor money and leaves the neighborhood with the same problem.

Fixing the property protects the investment and improves the community.

That’s the mindset we want at both Graystone and Property Wiz.

When City Officials Start Noticing

What impressed me even more was hearing that the improvements weren’t going unnoticed.

Andrew has developed working relationships with local code enforcement personnel and law enforcement through years of consistently responding when issues arise.

According to Andrew, one city inspector has jokingly referred to him as the “Mayor of the West Side” because of how involved he has become in the area.

Andrew also described elected representatives and city personnel visiting the neighborhood and taking notice of the turnaround occurring around the properties.

That’s powerful.

It is one thing for the property owner to say:

“Look at what we fixed.”

It is something different when people who work throughout the city begin noticing that a previously troubled area looks different.

For me, that’s when this stopped being a story about a handyman.

It became a story about somebody who takes ownership of his community.

He Started Looking Across the Street

Andrew eventually realized that one of the biggest problems wasn’t even on the properties he had been hired to repair.

It was across the street.

He described it with an analogy I thought was perfect:

You can keep treating a wound, but if bacteria keeps getting into it, the wound will continue getting infected.

Andrew and his wife started researching what was happening with a neighboring problem property.

According to Andrew, they learned the recorded owner had passed away and uncovered additional information that helped them determine which agencies needed to become involved.

Instead of saying:

“That’s not our property, so that’s not our problem,”

he looked at the bigger picture.

Because if activity across the street is threatening your tenants, contractors and investment, ignoring it doesn’t make the problem disappear.

From 71 Calls to 18

One of the most striking statistics Andrew shared with me concerned calls for law enforcement service in the area.

According to information Andrew received, there had been approximately 71 JSO calls during one month associated with the street.

After the concentrated cleanup efforts and increased presence, Andrew says that number fell to approximately 18 calls during a later month.

That number needs to be put into perspective.

Eighteen calls is still eighteen too many.

Andrew will be the first person to tell you the work isn’t finished.

But going from approximately 71 to 18 illustrates something important:

Consistent action can change a block.

It doesn’t happen overnight.

And one contractor doesn’t do it alone.

It takes property owners, residents, police, code enforcement, contractors, property managers and other people in the community doing their part.

Why Andrew Earned My Respect

I’ve been investing in real estate for a long time.

One thing I’ve learned is that the best people on your team aren’t necessarily the people with the fanciest title.

Sometimes it’s the person in the truck who sees something wrong and says:

“I’m not going to ignore that.”

Andrew could simply complete the work order, collect his money and leave.

Instead, he watches the surrounding properties.

He communicates with our team.

He deals with code issues quickly.

He builds relationships within the community.

He keeps showing up.

And most importantly, he cares about what happens after the invoice gets paid.

That’s why I wanted to recognize him.

At Graystone and Property Wiz, we talk a lot about helping investors protect and improve their properties.

People like Andrew are the ones on the ground helping make that promise real.

Thank you, Andrew. Keep being the “Mayor of the West Side.”

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10 Things Landlords Should Do When They Discover Squatters

Andrew’s experience also reinforced several lessons every landlord and real estate investor should know.

1. Don’t Confront Occupants Yourself

Your rental property is not worth somebody getting hurt.

Avoid escalating a potentially dangerous situation. If you discover unauthorized occupants, document what you see from a safe location and involve the appropriate authorities.

2. Determine Whether You’re Actually Dealing With a Squatter

This matters legally.

A former tenant, current tenant, unauthorized guest, transient occupant and person who unlawfully entered a vacant home may be treated differently under Florida law.

Don’t assume that everybody without your permission can simply be removed the same way.

3. Contact Law Enforcement and Follow the Legal Process

Florida has a specific procedure that can allow a property owner or authorized agent to request a sheriff’s immediate removal of certain unauthorized occupants from residential property when statutory requirements are satisfied.

In Jacksonville, JSO specifically provides guidance for owners dealing with unauthorized occupants.

Never resort to self-help tactics without first knowing whether they are legally permitted.

4. Document Everything

Take photographs and video when safely possible.

Keep:

• Dates and times
• Police report or incident numbers
• Photos of entrances and damage
• Communication with occupants
• Contractor observations
• Neighbor reports
• Utility information
• Prior lease documentation

Documentation can become extremely important if the situation turns into a legal dispute.

5. Secure the Property Immediately After Lawful Possession Is Restored

Once you legally regain possession:

Change the locks. Secure windows. Repair broken doors. Remove obvious entry points. Check fencing and exterior lighting.

Don’t leave yesterday’s entry point available for tomorrow’s occupant.

6. Maintain a Visible Presence

This may be Andrew’s biggest lesson.

Don’t let a vacant rental look abandoned.

Have somebody inspect it regularly.

Maintain the lawn.

Remove trash.

Pick up mail and flyers.

Complete repairs quickly.

A maintained property communicates:

Someone is watching this house.

Jacksonville’s code-compliance program also treats issues such as high grass, trash, debris and unsecured vacant structures as property-maintenance concerns.

7. Know Your Code Enforcement Officers and Local Resources

This doesn’t mean asking for favors.

It means being a responsible property owner.

Respond when the city contacts you.

Correct legitimate violations quickly.

Know how to report dangerous structures, nuisance properties and neighborhood problems.

When officials know that you take problems seriously and follow through, everyone works more efficiently.

8. Look Beyond Your Property Line

Walk the block.

What’s happening next door?

Across the street?

Behind the property?

A neighboring abandoned property may not belong to you, but it can still affect:

tenant safety, rental demand, vandalism, property values, contractor safety and your ability to stabilize your own investment.

You can’t take matters into your own hands on somebody else’s property, but you can report legitimate concerns through the appropriate channels.

9. Screen Your Next Tenant Carefully

Don’t respond to a difficult neighborhood by lowering every standard.

Andrew made an excellent point:

A struggling neighborhood doesn’t automatically require a struggling tenant.

Putting responsible tenants into well-maintained homes is one of the ways rental owners can contribute to stabilizing a neighborhood.

10. Build a Local Team That Actually Cares

This may be the biggest lesson I’ve taken from Andrew.

An out-of-town investor cannot see everything.

You need good people on the ground:

Property management. Maintenance. Rehab contractors. Neighbors. Local vendors.

You want people who don’t simply say:

“That’s not on my work order.”

You want people who notice something wrong and communicate it.

That’s what Andrew has done for us in Jacksonville.

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Final Thought

Real estate investing is usually presented as numbers.

Purchase price.

ARV.

Rent.

Cap rate.

Cash flow.

Rehab.

But there’s another side to owning hundreds of properties that doesn’t fit neatly into a spreadsheet.

We own pieces of communities.

When we improve those properties, choose better tenants, respond to code issues, work with local authorities and surround ourselves with people like Andrew who genuinely care about the neighborhood, we’re doing more than protecting an investment.

We’re helping improve the block where that investment sits.

And sometimes that starts with one guy in a truck who refuses to drive past a problem and pretend he didn’t see it.

Editor’s note: Specific incidents, call volumes and comments attributed to Andrew in this article reflect his account and should be independently verified before publication. Property owners should consult appropriate legal counsel or local authorities regarding their specific circumstances.

Related Reading

Self-Managing Rental Property in Florida
https://graystoneig.com/articles/self-managing-rental-property-in-florida
A practical guide to the legal and operational responsibilities Florida landlords take on when managing their own rentals.

What Self-Managing Landlords Don’t See Coming
https://graystoneig.com/articles/everythings-fine-until-its-not-what-self-managing-landlords-dont-see-coming
Why rental property problems can escalate quickly without strong systems, local oversight, and professional management.

Tenant Screening 101: Avoid the Nightmare Scenarios
https://graystoneig.com/articles/tenant-screening-101-avoid-the-nightmare-scenarios
Why strong tenant screening is one of the most important tools for reducing risk, evictions, and costly problems.

Jacksonville Sheriff’s Office – Unauthorized Occupants (Squatters)
https://www.jaxsheriff.org/Resources/Squatters.aspx
Official Jacksonville Sheriff’s Office information for property owners dealing with unauthorized occupants.

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