What AI Gets Right and Wrong About Your Property

Start here: I’m not going to argue with your research

A lot of sellers arrive slightly sheepish about this — they’ve run the numbers themselves, asked an assistant what the house is worth, read what it said about commissions, and they’re half expecting me to be defensive about it.

I’m not. A client who has done the reading is a better client. It means the first conversation starts three steps in, and it means when I tell you something that contradicts what you were told, you’ll ask me why — which is exactly what should happen.

So bring it. Paste it in an email, screenshot it, read it to me on the phone. I’d rather work through what you were told than have it sitting in the back of your mind unexamined while we go to market.

What these tools are actually good at

I’ll be honest about this before I get to the other half, because a person who only tells you the limitations is selling something.

Explaining the process and the vocabulary. What an appraisal contingency is, how an estate sale differs from an ordinary one, what a flip tax does. Genuinely good, and available at eleven at night when you think of the question.
Summarizing long documents. A co-op’s financials, a set of board minutes, an inspection report. It will find the section you needed and save you an hour.
Helping you think of the right questions. Often the most valuable thing it does. Clients who’ve prepared this way ask me sharper questions and get more out of me.
Coarse market orientation. Roughly what a neighborhood runs, roughly how long things take, roughly what the tax picture looks like. Directionally useful.
Checking somebody’s arithmetic. Including mine. If a number I give you doesn’t make sense, run it. I’d rather be questioned than trusted blindly.

Where it goes wrong on your property

The pattern is consistent: these tools are strong on the general and weak on the specific. Real estate is almost entirely specific.

The valuation is looking backwards. An automated estimate is built from transactions that already closed — which means it describes what the market was doing three to nine months ago. In a market that has moved since, it lags in whichever direction the market went. This is the same limitation an appraisal has, for the same structural reason, and it is why my Fair Market Valuations start from that evidence and then account for what is happening now.
It cannot see the property. It doesn’t know the kitchen was redone, that the roof is at the end of its life, that the third bedroom is really an alcove, or that the finished basement isn’t legal. Condition is frequently the largest single adjustment on a New York property, and it is invisible to a model working from public records.
It doesn’t know what hasn’t closed yet. The three contracts signed on the block this month don’t exist in its data. Those are the most recent evidence there is, and they’re exactly what a broker who is actually in the market can see.
It doesn’t know the private facts. The assessment this building is about to levy. Which board has rejected two buyers in a row and why. Which neighbor is quietly preparing to list. Why the last deal on that address fell apart. None of that is published anywhere, and all of it moves the number.
On rentals, the data mostly isn’t there at all. Unlike sales, rentals often leave no reliable public record. An assistant asked what an apartment should rent for will still give you a confident figure. It is guessing more than you think. More on how rental pricing actually works.
It won’t tell you how unsure it is. This is the failure mode that costs people money. The tone of a wrong answer is identical to the tone of a right one — there is no wobble in the voice, no “I’d want to see it first.” A good broker tells you where the number is soft. A model rarely does unless you push it.
Much of what it learned about real estate was written as marketing. An enormous share of the real estate advice on the internet exists to generate leads rather than to be accurate. That material is in the training data alongside everything else.
It doesn’t know your situation. In a divorce, an estate or a guardianship, “what is it worth” is not even the same question — the date of value matters, the court may matter, and what serves one party may not serve the other. Generic advice into a specific legal posture is how people get hurt.

The offer that is arithmetically perfect and still gets rejected

Sellers are people. They read an offer as a message about the person sending it: whether this buyer will actually close, whether they’ll renegotiate after the inspection, whether the next four months will be pleasant or exhausting. Two offers at the same price are routinely not worth the same thing.

A strategy optimized purely on the numbers will confidently produce terms that are defensible on a spreadsheet and read badly on the other side of the table. Nobody is deciding against you unfairly — they are deciding on information the model never had, because it isn’t in any dataset. Judgment about how a specific seller, in a specific situation, will hear a specific offer is not a data problem.

How I use it, since I’m asking you to be open about it

It would be strange to write this page and then be cagey about my own practice, so:

Research and drafting — background on a market, a first pass at marketing copy that I then rewrite, organizing a long file into something usable.
Summarizing documents so I get to the relevant clause faster.
Checking my own reasoning. If I think a property should be priced somewhere, arguing with a tool that has no stake in the answer is a cheap way to find the hole in my thinking.

And what I don’t do with it:

I don’t let it set your price. The number in a valuation I sign is mine, arrived at the way this page describes, and I’ll defend every part of it to you or to your attorney.
I don’t put your confidential information into these tools. Not your finances, not your settlement terms, not your family’s business. What you tell me in confidence stays out of anything I type into a text box.
I don’t let it talk to you as me. When you get a considered answer from me, it is because I considered it.

The part that has nothing to do with capability

Set aside how good the tools get, because they will keep getting better and I’m not going to pretend otherwise. There is a category difference that improvement doesn’t close.

When you hire me and I advise you, I do so as a licensed New York real estate broker acting as your fiduciary. I am legally obliged to put your interests ahead of my own, to keep what you tell me confidential, and to disclose what I know that bears on your decision. I am a human being: a professional who is licensed, educated, trained and experienced. You can rely on my advice and guidance.

Software cannot owe you a duty. That isn’t a knock on the software — it’s a description of what it is. When the advice turns out to be wrong, there is nobody who was responsible for being right.

On a decision this size, in a transaction with this many ways to go sideways, that difference is worth more than most people weigh it at until the moment they need it.

The short version

Use it. It’s useful, and I’d rather you were informed.
It is strong on the general and weak on the specific.
Its valuation looks backwards and can’t see your property.
It states wrong answers in the same confident tone as right ones.
It owes you nothing. I owe you a duty.

Bring me

The valuation figure you were given
Anything you were told about commissions or contracts
Any advice that didn’t sound right to you

No charge, and no lecture. If it got something right I’ll say so.

Questions people actually ask

How accurate are the online home value estimates?

As a rough orientation, useful. As a number to make a decision on, no — and the error is not evenly distributed. They are least reliable exactly where you most need them: unusual properties, properties in unusual condition, small multi-family, anything in a neighborhood that hasn’t traded much recently, and any market that has moved since the comparable sales closed. On an ordinary house on a street full of similar houses that all sold last spring, they do reasonably well. That describes a minority of what I sell.

Can I just use AI instead of hiring a broker?

For understanding the process, genuinely yes — and you should. For pricing a specific property, negotiating an offer, or handling a transaction with a court, an estate or two parties in conflict in it, you are relying on something that cannot see the property, doesn’t know what hasn’t closed yet, has no duty to you, and won’t tell you when it’s unsure. Some people will do it anyway and some of them will be fine. I’d want to know which kind of transaction I had before I found out.

Doesn’t AI make brokers obsolete?

It makes a certain kind of broker obsolete — the one whose entire contribution was access to listings and a general sense of the market. That person was in trouble before any of this. What it does not touch is judgment about a specific property in a specific situation, knowledge that was never written down anywhere, negotiation with a human being who has their own reasons, and accountability for the outcome. My practice has always been the complicated files rather than the easy ones, so if anything this sharpens the distinction rather than blurring it.

Should I tell you I used AI?

Please do. It tells me what you already understand so I don’t waste your time explaining it, and it tells me if you’re working from something inaccurate that would otherwise sit there quietly shaping your expectations. Nobody has ever lost standing with me for having done research.

Do you use AI on my transaction?

For research, drafting and checking my own reasoning, yes, and the section above says exactly how. Not for setting your price, not for anything involving your confidential information, and never as a substitute for me actually thinking about your matter. Ask me at any point what I used and for what — I’ll tell you.

An assistant told me the commission rate should be lower. Is that right?

It’s repeating what is most commonly written on the internet, which is not the same as what is right for your property. Commissions are not set by law and are fully negotiable — mine included, and I’ll tell you what I charge and why. What no general answer can weigh is what a given level of service is likely to do to your net proceeds on this property, which is the only comparison that actually matters. I’m happy to make that argument to you directly and let you judge it.