Cambridge Goes Rogue Again by Keith Watts

A few months ago, I wrote that Cambridge’s new vacant-property rules looked like a sledgehammer aimed at a gnat.

Then six property owners sued.

Just the facts. On September 18, 2026, six Cambridge property owners sued the Commissioners of Cambridge in Dorchester County Circuit Court. They’re challenging two ordinances adopted March 9. Ordinance 1264 requires rentals to be registered, licensed, and inspected. Ordinance 1265 requires owners of “vacant” homes to register them and admit inspectors.

Now the part that matters: nothing has been decided.No judge has ruled. Everything below is an allegation from the filings, and the City disputes it. Both sides have even jointly asked the court to hit pause while the City drafts changes, and the City has purportedly agreed not to enforce the ordinances in the meantime.

Good. Cool heads. But the filings are a page-turner anyway, because they read like the owner’s manual for a machine nobody knows how to operate. Sound familiar?

Define “Vacant.” Go Ahead.

Ordinance 1265 calls a house vacant if nobody with a legal or equitable interest in it lives there. The plaintiffs say that sweeps in second homes, vacation homes, a house with a guest in it, and a rental between tenants.

They also say the City can’t even agree with itself. According to one affidavit, the City Manager said a rental between tenants isn’t vacant. His colleague said it is, after 90 days. Same ordinance, two definitions.

Another affidavit describes a house judged vacant because its water readings were lower than usual. Its manager says it was a rental being fixed up for a new tenant. Apparently, fixing up a house now looks like abandoning it.

Nobody alleges Cambridge used artificial intelligence. Nobody needs to. Tell a machine to “find the vacant houses,” and it will find you plenty, some of them merely quiet. The difference is that AI can’t fine you. Yet. Under 1265, it’s $500 for the first violation and $1,000 for each one after, and every day counts as a new one.

Come In. Please.

Under 1265, after 15 days’ written notice, if the owner doesn’t respond, the City “may proceed with entering and inspecting” the property. The Fourth Amendment generally requires consent or a warrant for that. You know: “home,” “castle.” The plaintiffs say the ordinance provides for neither, and that nothing in the ordinances even lets the City ask a judge for one. The City Manager reportedly said the City would get a warrant if needed. A court will have to sort that out.

Kafka Would Recognize This

Franz Kafka wrote about ordinary people trapped in bureaucracies that never explain the rules. In “The Trial”, a man is prosecuted by a court that never tells him what he did. “Kafkaesque” means a system where the rules are unknowable, every step depends on one you can’t take yet, and the exit runs through the office that caused the problem.

Here’s the rental version, as the plaintiffs describe it:

To operate a rental, you need a license under 1264. You can’t get a license until the property is inspected or self-inspected. The City planned to start inspections in May. It hasn’t. It hopes to begin in October, with about 1,300 due by June 2027, and as of the affidavit it hadn’t hired an inspector. Meanwhile, an unlicensed landlord is barred from using the landlord-tenant courts. The workaround, according to the affidavit: stop by City Hall every month for a temporary “waiver.” Bureaucracy anyone? The plaintiffs say the ordinance doesn’t mention waivers. (Self-inspection, they say, can be done by a friend or an employee.)

When the landlord remarked that the program didn’t seem to be working, the affidavit says a City employee replied that this is what happens when you have people working on a program who do not know what they are doing. That’s not my characterization. It’s apparently somebody else’s.

One more scene. A property manager swears an inspector knocked at an occupied rental, got no answer, stuck a “Condemned” sticker on the door and left. No inspection. No report. No notice. Ever.

To Be Fair. Cambridge has genuine blight, and officials are right that tenants don’t always report unsafe conditions. Nobody is against safe housing. Cambridge also tried rental inspections in 2010 and dropped them by 2011, so this isn’t its first lap around this track.

If You Own Property in Cambridge

Keep every notice, email and text. Write down dates and names. Don’t embellish, and don’t assume a City employee’s word is the law. Talk to a lawyer if you think your rights are at stake. The plaintiffs did something citizens are allowed to do: they went to court. Whether they’re right is for a judge to decide.

Open the Pod Bay Doors

In 2001: A Space Odyssey, the computer HAL 9000 locks astronaut Dave Bowman out of his own spaceship. “I’m sorry, Dave. I’m afraid I can’t do that.”

Read the filings, and you can hear the Cambridge version. “I’m sorry, property owner. I can’t issue your license without an inspection. I’m afraid I have no inspector.”

HAL at least had an excuse. It was a computer, and it took a mission to Jupiter to lock a man out of his own ship. Cambridge, allegedly, did it with a licensing loop and a monthly waiver. If so, humans have officially outdone the machines, which is the first thing about this story that qualifies as progress.

So, a modest proposal for both sides, who deserve credit for pausing the fight. Use the pause. Mediate. Owners: bring all your common sense fixes. City: hire the inspectors before you demand the inspections, and write rules a citizen can read and understand. Start by saying, in plain English, what “vacant” means.

Dave got back in by finding the manual override for the HAL 9000. Cambridge has one too. It’s a table with both sides sitting at it.

Working together in good faith. With transparency. Because with discovery and litigation, it all will eventually come out — and no one wins except the lawyers.

“Open the pod bay doors,” Cambridge. Then let’s all agree on what a “door” is.

Keith Watts is a lawyer and currently serves on Talbot County’s Short-Term Rental Review Board and is a former Chair of the Board.

Cambridge Goes Rogue Again by Keith Watts

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