A client recently asked me how I was doing on one of my slightly ridiculous real estate goals: selling a property in every corner of Vermont.
I realized I hadn’t actually counted in a while, so I finally sat down and tallied the towns and communities where I’ve represented buyers or sellers over the past nine years. I’m now approaching 35% of the state, with plenty of repeats along the way, and just this week I added two more new-to-me towns to the list.
It’s a fun goal, but somewhere along the way it became more than that. Driving thousands of miles around Vermont has fundamentally changed the way I approach real estate and, more importantly, the way I help buyers figure out where they actually want to live.
We say all the time that real estate is hyperlocal. It is. I’ve just made a very large portion of Vermont my local market.
Vermont Buyers Don’t Always Know Which Town They Want
One of the biggest shifts I’ve noticed in my business over the past several years is that many buyers aren’t actually searching for a specific Vermont town.
They think they are.
Just this week, I received a referral from another agent for buyers who were supposedly focused on one particular town. Once I started talking with them, digging into what they actually wanted and sending properties that fit those criteria, we realized something pretty quickly: they weren’t really looking for that town.
They were open to roughly a third of Vermont.
What they were searching for was a particular kind of life and property.
That’s a very different search.
A buyer may tell me they want to live in Stowe when what they really mean is that they want easy access to skiing, restaurants and outdoor recreation. Someone searching around Burlington may actually want to be within a certain drive of the city but would happily live in any number of surrounding communities. Another buyer may care far more about finding an A-frame, a historic farmhouse, acreage, lake frontage or a property that could accommodate a particular use than they do about the town printed on the mailing address.
Once you understand the why behind the location, the map can get much bigger.
Vermont Real Estate Really Is Hyperlocal
Expanding the map doesn’t mean individual Vermont markets are interchangeable.
Quite the opposite.
Drive 20 minutes in Vermont and you can encounter completely different housing stock, property values, tax considerations, school structures, zoning, road conditions, internet availability, commute patterns and access to services.
Even two neighboring towns can behave very differently from a real estate perspective.
That’s why statewide knowledge isn’t simply knowing how to get from Burlington to Bennington without GPS. It’s understanding the nuances of the communities in between.
When I’m helping someone consider a town they hadn’t originally included in their search, I want to understand what homes have actually been selling for there, what kind of inventory tends to come onto the market, how far they’ll be driving for groceries or healthcare, whether they’re going to spend significant time on dirt roads and what their everyday life might realistically look like.
Sometimes the answer is that the town is a fantastic fit.
Other times, we cross it off the list.
Both outcomes are useful because clarity is the point.
Sometimes You Need to Search for the House Before the Town
Traditional home searches often begin with geography.
Choose a town. Set a price range. Select the number of bedrooms and bathrooms. See what appears.
That works perfectly well when someone knows exactly where they need to be, but it can unnecessarily limit buyers who have more flexibility.
Sometimes I flip the process around.
What if we start with the property?
Show me the A-frames.
Show me the farms with enough acreage for what you want to do.
Show me the houses within a certain driving distance of skiing.
Show me the homes with mountain views, the historic properties, the camps, the places where you could have a barn or the unusual property that doesn’t fit neatly into a standard search.
Then we can evaluate the community surrounding the house and decide whether the entire package makes sense.
Vermont is particularly well suited to this kind of search because there are so many small communities buyers may never have heard of before they begin looking.
You don’t necessarily need to arrive knowing exactly where you want to live.
Sometimes finding the right house helps you discover the town.
Why I Keep Driving All Over Vermont
There is a practical downside to deciding the entire state is your market.
The mileage.
So much mileage.
I’ve spent an extraordinary number of hours cruising Routes 7 and 89, crossing mountain gaps, following dirt roads and discovering exactly how long it takes to get from one seemingly nearby Vermont town to another when there’s a mountain sitting between them.
Fortunately, I have audiobooks.
But all of those miles have given me something I couldn’t have learned sitting behind a desk.
I’ve seen these communities in different seasons. I’ve driven the roads in winter. I’ve watched towns change, businesses open and close and neighborhoods evolve. I’ve toured homes in parts of Vermont I probably never would have explored otherwise, and I’ve developed relationships with real estate agents across the state.
Those relationships matter too.
Real estate transactions require cooperation between two sides, and after years of doing business across Vermont, there are agents in communities throughout the state whom I’ve worked with repeatedly. We’ve navigated inspections, appraisals, unusual properties, difficult negotiations and complicated closings together.
That network has become one of the most valuable parts of my business.
Real Estate Has Also Made Me a Better Vermont Road-Tripper
There is another, less serious benefit to all of this driving.
I know where to stop.
Need a sandwich halfway across the state? I probably have an opinion.
A bakery worth detouring for? Definitely.
Good coffee, a cider donut, an unexpected farmstand or a reliable bathroom on a long stretch between appointments?
This is valuable professional knowledge.
It’s also part of how my real estate career and Travel Like a Local have become so intertwined. I’m constantly moving around Vermont for work, which means I’m constantly discovering the places that make individual towns interesting.
A showing might take me somewhere I’ve never been before, and suddenly I’m pulling over because I saw an honor-system bakery or a general store I need to investigate.
Then I inevitably return with clients and tell them where they should get lunch.
I consider this part of the service.
Tracking the Numbers Changed My Business
Counting the Vermont towns I’ve worked in is fun, but I’m a big believer in tracking considerably more than that.
Clarity is power, and for me, data is where clarity starts.
I keep a goals worksheet that I look at daily. It tracks targets across my different income streams, my real estate pipeline, pending business and the other numbers that tell me whether I’m actually moving toward the goals I’ve set.
That practice has changed the way I think about growth.
Instead of vaguely feeling busy, I can see what I’m producing. Instead of waiting until the end of the year to decide whether I had a successful one, I can see where I am against my targets while there’s still time to adjust.
During one particularly strong start to the year, I looked at the numbers about 70 days in and realized I already had the same volume of pending transactions and listings taken that I’d completed during my previous best year in business.
That didn’t happen because I suddenly discovered a shortcut.
It was the accumulation of years of learning markets, building relationships, accepting referrals, driving long distances, answering my phone, tracking the business and trying to get a little better at all of it every year.
Agent Referrals Have Helped Me Explore Even More of Vermont
Some of my favorite clients have come from agents in Vermont and around the country who needed someone they trusted to help a buyer or seller here.
I don’t take those referrals lightly.
When another agent sends me a client, they’re putting their own relationship and reputation in my hands. The fact that agents continue to trust me with people they’ve worked with means an enormous amount.
Those referrals have also expanded my Vermont map.
A client might begin in one community and end up buying somewhere neither of us originally expected. Another may introduce me to a property type or corner of the state that sends me down an entirely new research rabbit hole.
Every transaction adds another layer to what I know.
And another town to my list.
The Goal Isn’t Really About Checking Off 100% of Vermont
Will I eventually sell a property in every Vermont town and community? I’m going to try.
There’s something deeply satisfying about watching the map fill in and realizing how much of the state I’ve been fortunate enough to experience through my work.
But the percentage isn’t really the point.
The goal has pushed me to become a better resource for clients who don’t fit neatly into a five-mile search radius. It’s taught me to ask better questions about what buyers actually want rather than simply accepting the first town they type into a search portal. It’s helped me build relationships with agents across Vermont and given me an increasingly nuanced understanding of how different communities function.
Most importantly, it’s allowed me to be part of an enormous number of new chapters.
The long days, weekend appointments, scheduling gymnastics and hours spent driving up and down Vermont are easy to accept when they end with one of my favorite phone calls to make: telling clients that we got the house.
I feel incredibly fortunate that the work I chose keeps giving me reasons to learn more about the state I call home.
And at this point, I’m far enough into the Vermont town challenge that I certainly can’t stop now. I’ve got a lot more driving to do. And fortunately, I know where to stop for snacks.