So you're thinking about moving to Connecticut.
Good. Let me give you the good, the bad, and the ugly — and let me not sugarcoat any of it.
I'm Dave Jones, and I help people move here from all over the country and, honestly, from all over the world. New Jersey, New York, California, Chicago. I've worked with buyers relocating from the Czech Republic and from Ireland. And there's one thing almost every single one of them says to me a few months after they close.
"I can't believe we waited this long."
I'll get to that reason at the end. But first, let's do the hard part, because you deserve the honest version before anybody sells you on the pretty one.
The 5 Cons of Living in Connecticut
Con #1: The taxes — and the mill rate trap nobody warns you about
I'm starting with the one nobody wants to hear, because it's the main reason people leave Connecticut.
Connecticut is not cheap. I'm not going to sit here and pretend otherwise. Property taxes can be genuinely expensive.
But here's the part that actually gets people, and it's not the number itself — it's how wildly it swings from town to town.
Connecticut taxes property using a mill rate. One mill equals one dollar of tax per $1,000 of a property's assessed value, and in Connecticut a property is assessed at 70% of its appraised value. So on a $500,000 home, you're taxed on a $350,000 assessment.
Now here's the kicker: mill rates aren't remotely uniform. You can have neighboring towns where one is nearly double the other. Waterbury and Prospect sit right next to each other and are not remotely close on this. You can drive fifteen minutes down the road, buy essentially the same house, and pay thousands of dollars more — or thousands less — every single year, forever, purely because of which town line you landed on.
And here's where people mess it up, and I see it constantly. They find a house they love. They fall head over heels for the kitchen, the backyard, the whole thing. And they never once look up the mill rate. They sign. They move in. Six months later that tax bill lands in the mailbox and they feel physically sick.
I had a buyer come up from New Jersey completely dead set on one specific house. Beautiful property, no argument from me. I sat him down and showed him that a town one exit further up the highway had a nearly identical house for thousands of dollars less in annual taxes. He almost didn't believe me until we ran it side by side.
The town you pick matters as much as the house you pick. Sometimes more. Write that down.
Con #2: The winters are real
I'm not going to tell you Connecticut is sunshine year-round, because it isn't. We get four real seasons, and winter is emphatically one of them. Full disclosure — the winters are a big part of why I'm building a place in Florida.
You will see snow. You will shovel snow. There will be a stretch in February where the sky is gray for what feels like a solid month and you find yourself standing at the window doing some genuine soul-searching.
If you're coming from Florida, Arizona, or Southern California — anywhere you've never owned a snow shovel — this is a real adjustment, and I'd rather you hear it from me now. You will probably end up buying a roof rake. That's a real product and you will own one.
The first winter is the hardest. Everybody tells me that. It's the test.
But hold that thought, because I'm circling back to it, and the flip side of this con is one of the best things about living here.
Con #3: There's no big-city energy inside the state
We do not have a New York City sitting inside Connecticut. Our biggest cities are nothing like Manhattan. And we don't have an NFL, MLB, NBA, or NHL franchise to call our own — the closest thing we've had is the WNBA's Connecticut Sun at Mohegan Sun, and that franchise is relocating after this season. What we do have is real minor-league life: the Hartford Yard Goats, the Hartford Wolf Pack, Hartford Athletic. Great nights out, but it isn't the big-league experience.
If you're the kind of person who needs a rooftop bar, a 2 a.m. slice, and a brand-new restaurant every night within walking distance, Connecticut is going to feel too quiet for you. I'd genuinely rather tell you that right now than sell you a house and have you calling me in three months asking me to list it.
But here's the flip. You're roughly an hour and a half to New York City — two hours tops — and a couple of hours from Boston. So you can grab the big-city day whenever you want one. Dinner, a show, a game. I'm a season ticket holder to a New York team; I make that trip regularly and it's completely manageable.
For most of the people I work with, that's the entire point. They wanted out of the chaos without losing access to it. You just have to be honest with yourself about which kind of person you actually are.
Con #4: The traffic, and two words — I-95
If you've spent any time along the Connecticut shoreline you already know. I-95 can turn into a parking lot, especially heading toward New York.
If your plan is to commute into the city regularly, you have to be brutally honest with yourself about that drive or that train ride before you lock into a town. Because here's the truth: the commute is the thing people underestimate most, and it's the thing that wears them down fastest. Nobody quits a town because the house was too nice. They quit because the drive broke them.
So let me ask you something. Have you actually mapped your commute? Not guessed at it — mapped it. Have you looked at what it takes to get where you need to go on a random Tuesday morning, or a Thursday at rush hour?
Because that one exercise changes which towns you should even be looking at.
There are towns sitting right on Metro-North where you're on a train with your laptop open and a coffee in hand, rolling into Grand Central without ever touching a steering wheel. And there are towns twenty minutes inland that turn that same trip into an hour in the car just to reach the station.
Same county. Completely different life on a Tuesday morning.
I run that math with clients before we ever step foot inside a house, because the right town can hand you back an hour of your day, twice a day. That's not a small thing. That's your life.
Con #5: Some of these towns are genuinely sleepy
This one's softer, but it's real.
Connecticut has these absolutely gorgeous small towns — stone walls, town greens, little coffee shops, a hardware store that's been on the same corner for a hundred years. It's the real New England thing and it's beautiful.
But if you're 28, single, and you want nightlife, some of these towns are going to feel like you moved into a retirement postcard.
There is a town up here for every single type of person. You just have to get matched with the right one. That's genuinely what we do at Dave Jones Realty — we're matchmakers between people and towns. The town that's perfect for a family of five can be miserable for a young couple. The spot that young couple loves might be the exact town a retiree can't stand.
Picking Connecticut is the easy part. Picking your Connecticut town is the part that actually decides whether you like it here.
The 5 Pros of Living in Connecticut
Okay. That was the honest bad, and I didn't dress any of it up. Now let me flip the whole thing over, because this is exactly where Connecticut starts winning people over — and it wins them over fast.
Pro #1: The location is close to unmatched
Think about where you're actually sitting. You're tucked between two of the largest cities in the country — Boston to the north, New York City to the south. You've got Long Island Sound and real shoreline towns to the south. You've got rolling hills, farms, and genuine mountains up in the northwest corner.
World-class everything within a short drive, and you don't have to live stacked on top of your neighbors to get it.
Want a beach day? Forty-five minutes. Want to hike? Twenty. Want a Broadway show or a ballgame? Hour and a half. A real night out in the city, then back in your own quiet driveway by midnight. Apple picking and leaf peeping at a working farm on a Saturday morning is just a normal weekend around here.
Most places make you choose — the city, the quiet, the beach, or the mountains. Connecticut hands you the whole menu and tells you to take your time.
Pro #2: The seasons (yes, the same ones I listed as a con)
Here's the trade you're actually making.
Fall in Connecticut is unreal. The leaves turn and the entire state lights up orange, gold, and red. You will be driving down some random country road and physically have to pull over to take a picture.
Summers on the shoreline, on Bantam Lake, on Candlewood Lake — the beaches, the boats, the whole thing. It's excellent.
Spring shows up and the entire place comes roaring back to life.
And winter gives you the cozy New England Christmas card that people fly in from around the world and pay good money to experience for a single weekend. Walk the shops around the Litchfield green after the first real snowfall and tell me you don't feel like you wandered onto a movie set.
Four real seasons is a feature, not a bug — as long as you walk in with your eyes open.
Pro #3: Education is a genuine draw
I want to be careful here, because I never rank schools. That information changes year to year and every family's needs are different — you should always do your own research at GreatSchools.org and visit districts in person before you make a decision.
But I'll give it to you straight: Connecticut has a serious national reputation for education, and a large share of the families who relocate here are moving specifically for it. We also have some of the most respected prep schools in the country.
A lot of the buyers I work with are coming from somewhere they felt like they were constantly fighting the system, and they want a town where the schools are a selling point instead of a problem. That reason alone drives a real percentage of the relocations I handle.
Pro #4: The community feel sneaks up on people
This one blindsides buyers, in the best way.
There's something about a Connecticut small town that you can't manufacture. The guy behind the deli counter knows your name — and your kids' names, and that they ride their bikes down to the town green. He sees you at the fall festival, at the tree lighting in December, at the Little League games where the whole town shows up and it somehow feels like the World Series. The barber knows your family. The woman at the farm stand saves the good corn for you.
For buyers coming from somewhere busier and more anonymous — where you can live next to someone for five years and never learn their name — this is the thing that hits completely out of nowhere. They didn't even know they were missing it until they had it.
They move here for the house. They stay for the community. I've watched it happen more times than I can count.
Pro #5: Space — and the #1 reason people say they'd never go back
Here's what happens when you come from New York or New Jersey. Your entire idea of what a house is has been shrunk down on you.
You've been trained to believe a yard is a luxury. That a two-car garage is a fantasy. That having a basement and an office and a guest room in the same house is something only wealthy people get. You made peace with small, because small is all anybody ever showed you.
And then you come to Connecticut and look at what's actually sitting there in your price range, and your jaw hits the floor.
Which brings me to the thing I promised you at the top.
The number one reason people move to Connecticut and tell me they'd never go back is the value. It's how much more life your money actually buys here.
I watch this exact moment happen on practically every tour I do. A family comes up from the city with a budget of $400,000, $500,000, $600,000 — a number that back home buys a cramped box, if it buys anything at all. Up here, that same money buys a real house. A yard you can actually run around in. A driveway. A two-car garage. A room that can genuinely be an office. Room to breathe.
They walk out into the backyard, they go quiet, and then they turn around and look at me and say, "Wait — this is really in our budget?"
Yes. It really is.
That's the moment. Every time. And it isn't any one feature — it's the feeling of finally having room to spare. That's the thing people can't believe they waited so long for, and it's what makes every con on that list shrink down to nothing.
Before you book a plane ticket, do this first
Here's where I'll be honest about what I actually do for a living.
If you're seriously considering a move — not someday, but actually considering it — this is what Dave Jones Realty does every single day. We help buyers figure out which part of Connecticut fits their lifestyle, their budget, and their commute reality, before they burn a weekend and a plane ticket wandering around blindly.
Book a free Zoom relocation call with us. We'll sit down screen to screen and map the whole thing out together. And I promise you this: we'll tell you the truth, even when the truth is "that's not the right town for you."
That's the whole job. It's the only way we do it.
Call or text: 203-910-2638 Email: Dave@davejonesrealty.com Search every home in Connecticut: www.searchallcthomes.com
Connecticut isn't perfect, and I hope this post proved I'm not going to pretend it is. But for the right person in the right town, it's the move people tell me they wish they'd made five years earlier.
Let's find out if you're that person.
Market and tax information changes regularly; contact Dave Jones Realty for current figures on any specific Connecticut town. For school information, we recommend GreatSchools.org and visiting districts directly. Buyers researching any community should conduct their own independent due diligence on all factors relevant to their decision.
Dave Jones Realty LLC | Serving New Haven, Hartford, and Litchfield Counties