How to Choose a Real Estate Agent in Boston: 7 Questions You Need to Ask

Buying or selling a home in Boston isn't unlike anywhere else. Between the historic neighborhoods, the brutal competition, and the maze of local regulations, you need someone who actually knows what they're doing.

The problem? From the outside, most agents look the same. They've all got professional headshots, they all promise they'll work hard for you, and they're all perfectly nice people (a little too nice). But when you're about to make one of the biggest financial decisions of your life, "nice" doesn't cut it. Here's what does: asking the right questions before you sign anything.

1. How Long Have You Worked in This Specific Neighborhood?

Notice I didn't ask "How long have you been an agent?" That's because an agent who's spent ten years working Brookline doesn't know jack about Jamaica Plain, and vice versa. Boston neighborhoods might as well be different planets.

What you're really asking is: Do you know which South End blocks are mostly owner-occupied versus investor-owned? Can you tell me which streets in Dorchester are three minutes from great schools and which streets are fifteen? Do you know why that condo in Charlestown is priced $50K under market?

A good agent will get specific. They'll mention actual streets, actual buildings, actual problems they've helped clients navigate. If they start talking about "the greater Boston area," run.

2. How Many Transactions Did You Close Last Year?

This question separates the full-timers from the side-hustlers. You want someone who does this for a living, not someone who sells two houses a year while working their "real job."

Industry standard for a productive agent is around 12-15 transactions annually. Below that and they might not have the negotiation experience you really need. Way above that (30+) and you have to wonder: are they actually going to return your calls, or are you going to be one of forty clients fighting for attention?

The sweet spot? 15-25 deals a year. Enough experience to know what they're doing, focused enough to actually help you.

3. What's Your Communication Style?

This sounds touchy-feely, but it matters. Some agents text you at 10 PM because a new listing just dropped. Some prefer scheduled weekly check-ins. Some will call you after every showing. Some expect you to reach out.

None of these approaches are wrong—they're just different. What matters is whether their style matches what you need. If you want hand-holding through every step, say that. If you want someone to find properties and leave you alone until you're ready to make an offer, say that too.

A good agent will be honest about how they work. A bad agent will tell you whatever you want to hear.

4. Do You Work with [My Situation]?

Not all agents work with all buyers. Some focus exclusively on first-time buyers. Some only do luxury properties. Some specialize in multi-family investments. Some work primarily with sellers.

If you're a first-time buyer using an FHA loan, you don't want an agent who usually works with cash investors—they won't know the ins and outs of your financing, and they might not have patience for the questions you need answered.

Be specific: "Do you regularly work with VA buyers?" or "Have you closed deals with people using down payment assistance programs?" Their answer will tell you if you're a good fit.

5. What's Your Negotiation Strategy in Multiple Offer Situations?

In Boston, you're almost guaranteed to face multiple offers. The question isn't if you'll need to compete—it's whether your agent knows how to win.

Some agents escalate offers aggressively. Some write personal letters. Some waive contingencies (careful with this one). Some have relationships with listing agents that help. Some know exactly which terms sellers actually care about beyond price.

Ask them: "Walk me through how you handled the last multiple offer situation." If they don't have a clear strategy, or if their strategy is just "bid higher," keep looking.

6. Can You Provide Recent Client References?

Not reviews on their website. Not testimonials written three years ago. Recent clients who closed deals in the last six months, in the neighborhood you're looking at.

Then actually call those references. Ask them: "What was the hardest part of working with this agent?" and "If you were doing it over, would you use them again?"

Good agents will hand over references without hesitation. Mediocre agents will stall or give you their two favorite clients from 2019.

7. How Do You Handle Bad News?

This is the most important question, and almost nobody asks it.

Some agents will sugarcoat everything. "Oh, that inspection report isn't that bad." "I'm sure the seller will come down on price." "Don't worry about the foundation issue."

Others will be straight with you: "This is a terrible deal and we should walk away" or "You're not going to get this house at that price" or "I don't think you're ready to buy yet."

You want the second type. The one who'll tell you when you're about to make a mistake, even if it means they don't get paid this month.

Finding Agents Who Can Answer These Questions

The hardest part isn't asking these questions—it's finding agents worth asking in the first place.

Random listings on the big sites like Zillow or Realtor.com aren't going to help, but they have the largest directory of agents so you probably can't ignore them.

Thing is, it's usually pay to play on those platforms so it's hard to trust the results. Agents pay Zillow in order to be a "featured agent" or come up at the top of search results in certain area codes. You're getting the highest bidder, not necessarily the "best" or most experienced agents.

Same with Googling "real estate agent near me." It gives you whoever spent the most on Google Ads. Asking your cousin's friend who "just got their license" is a gamble too so please don't go that route.

Another way to find the right agent is by looking for experienced local real estate agents with a proven track record. These directories highlight agents who have verified experience, years of local knowledge, successfully closed deals, and strong client reviews. Focusing on measurable results and community expertise helps you connect with agents who truly understand the market and can guide you confidently, without raising any compliance concerns.

It's basically quality over quantity. You're starting from a pool of people who've already cleared a baseline of competence. From there, you interview two or three, ask these seven questions, and pick whoever gives you the best answers.

 

Published 1/2/26