Moving to Connecticut in 2027: 7 Towns About to Take Off

So you want to buy in a Connecticut town before it gets expensive — not after.

I'm Dave Jones with Dave Jones Realty, and these are seven Connecticut towns positioned to take off heading into 2027. The town at number one has already jumped 66% in four years and still comes in under $380,000.

---

How I built this list, because the method matters

I threw out every tiny town where two house sales were swinging the average. That's not a trend, that's noise. Every town here has real sales volume behind it.

And here's the whole game with a list like this. Everybody wants to buy in the hot town. The problem is that by the time a town is obviously hot — by the time it's on every list and everybody's talking about it — the deal is gone. You paid for the buzz instead of the growth.

The move is to get into a town that's already climbing but where the crowd hasn't fully arrived. That's every town below.

One caveat before we start: past appreciation doesn't predict future prices, and nobody can tell you what any town will do next year. What these numbers do show is which markets have real depth, real demand, and tight supply right now — the conditions that have historically preceded a run.

---

#7 — Southington: $421,000 median, +9.4% in a year, +34% in four

Here's the number that actually matters: 508 houses sold.

That's serious volume, and it tells you this isn't a fluke. When a town moves 508 houses in a year and the price is still climbing, that's a deep market with a lot of people wanting in. Homes sat about 17 days. In a slow town, houses sit for months.

Southington has a lot of what holds value: a real downtown with a Main Street you can walk, the Farmington Canal trail running through it, and it straddles I-84, so it's commutable in two directions — toward Hartford or toward Waterbury.

The mistake people make here is looking at Southington and thinking, "it's already discovered, I missed it." You're half right. It is discovered. But discovered and done climbing are two different things.

Here's another way to think about it: a town that sells 508 houses a year is not a town about to run out of buyers. It's a town with a deep bench. Towns with deep benches keep climbing for years, because there's always another wave of people who just found it. The towns that top out are the small ones where the buyer pool is thin. Southington's pool is enormous.

#6 — Wallingford: $395,000 median, +10.2% in a year, +41% in four

381 homes sold. 15 days on market.

Let that sit. Last year the average Wallingford house went under contract in about two weeks. That kind of speed doesn't happen in a town that's cooling off.

Wallingford gives you a lot for under $400,000: a good downtown, a station on the Hartford Line between New Haven and Hartford, a strong reputation, and a location right in the middle of the New Haven–Hartford corridor.

There's real character here too, and it's what keeps people rooted. A lot of people sell in Wallingford and buy again in Wallingford. It has one of the more walkable old main streets in the area, and it's the kind of place where people put down roots and stay.

Low turnover in a desirable town is part of why inventory stays tight. When the people living there don't want to sell and the people outside want in, prices only go one direction.

Notice this, because it becomes the theme: the towns moving fastest on this list have a train, a downtown, and a middle-of-everything location. That's not a coincidence. Write it down — it's how you spot the next one yourself.

#5 — Portland: $412,500 median, +12.2% in a year, +45% in four

Here's the number that put Portland on this list: months of supply — one.

Months supply is how long it would take to sell everything currently listed if nothing new came on the market. A balanced market is around five or six months. Portland is at one.

That means there's almost nothing for sale and plenty of buyers who want in. That's the tightest kind of market there is, and tight supply plus real demand is exactly what pushes prices up.

Portland sits across the Connecticut River from Middletown, so you get a quieter, smaller town with a bridge putting you minutes from a real city with restaurants, jobs, and a university. Quiet and access at the same time — and people are figuring that out while there's nothing on the shelf.

Portland has its own identity, too. It's not just a Middletown suburb. The old brownstone quarries here are a National Historic Landmark — Portland brownstone built a huge share of the brownstones in New York and Boston — and one of the quarries is now an adventure park with cliff jumping, zip lines, and paddleboarding right inside it.

Notice the pattern yet? Every town so far is near a city, near a highway or a train, and running low on inventory. That's the recipe, and number one is the purest version of it.

#4 — Plymouth: $344,000 median, +14.7% in a year, +53% in four

Plymouth keeps showing up on these lists for a reason.

Somebody who bought here in 2021 has watched their value climb more than half — and the median is still only $344,000. You can still get in at a price that works for most budgets.

Plymouth sits in Litchfield County and was once known as the clock town, where Eli Terry built the clocks two centuries ago that ended up in homes across the country. That history is still baked into the place.

Here's why it keeps climbing: it's affordable in a state where affordable is getting hard to find, and it's within reach of the Waterbury and Bristol job centers. When a town has already proven it can grow 53% and it's still on the cheap side, the runway is long. Cheap plus proven growth is the combination you want.

And here's what's actually happening. When the towns around a place get expensive, buyers don't leave the area — they slide one town over. Waterbury and Bristol have been climbing for a while. Plymouth is right there, cheaper, connected by the same roads. That spillover is the exact force that turns cheap towns into not-cheap towns, and it's already in motion. You can watch it in the 53%.

---

If any of this is landing and you want somebody who actually pulls these numbers — town by town, street by street — that's what my team does every day.

Call or text: 203-910-2638 | Dave@davejonesrealty.com | www.searchallcthomes.com

---

#3 — Thomaston: $338,500 median, +21.8% in a year, +48% in four

That 21.8% is the biggest single-year jump on this list, and I'll be straight with you: that means something.

Thomaston is a town I drive through, know well, and love showing houses in. It's small and it's a real Connecticut town — the Thomaston Opera House right in the middle of it, still running shows. The Naugatuck River. Trails. A genuine small-town Main Street that isn't manufactured; it's just always been there.

It's named for Seth Thomas, the clockmaker — the same clockmaking history that runs through this whole part of the state.

And here's the fact that gets me every time. The Seth Thomas Company made the clock that hangs in Grand Central Terminal — the one over the information booth that millions of people have stood under. "Meet me under the clock." That clock came out of this little town. When the town library needed help with its debt in 1906, the money came from Andrew Carnegie. A town of about 7,500 people has its fingerprints on some genuinely famous American things.

Here's what I see that a spreadsheet doesn't. The people moving in got priced out closer to the shoreline and the cities, came inland, and found out they could get a real house with a real yard for a number that stunned them. Every one of them has the same reaction, and that word of mouth is what a 21.8% jump looks like from the inside.

When the fastest-growing town on your list is also one of the cheapest, that's the definition of early.

#2 — New Britain: $300,000 median, +11% in a year, +58% in four

I know some of you just read "New Britain" and made a face. Stay with me, because the numbers should change your mind.

Just under 400 houses sold. That's a big, deep market growing fast — and $300,000 is the lowest median on this entire list.

Here's what people get wrong about New Britain: they wrote it off years ago and never looked again.

Meanwhile it has Central Connecticut State University. It has CTfastrak, the dedicated busway straight into Hartford. It has Walnut Hill Park, designed by Frederick Law Olmsted — the same man behind Central Park. It has genuinely beautiful old housing stock at prices that don't exist anywhere near the shoreline.

And it has the New Britain Museum of American Art — the first museum in the country dedicated solely to American art. The first one anywhere, in New Britain.

The downtown has been getting real investment, and there's a whole neighborhood called Little Poland on Broad Street, one of the largest Polish communities in America, with the bakeries and restaurants to match.

This is not a town with nothing going on. It's a town a lot of people stopped paying attention to while it quietly got better.

Think about that busway for a second, because it's underrated. CTfastrak runs from New Britain into Hartford on its own dedicated road — no traffic. Somebody working in Hartford can buy here at $300,000 and have a more reliable commute than half the people paying twice as much to live closer.

58% growth in four years on a $300,000 median is not a town that's dying. That's a town that's turning. And the biggest gains almost always come from places everybody already dismissed.

#1 — Cromwell: $377,500 median, +18.5% in a year, +66% in four

The biggest four-year run of any high-volume town on this list — and 208 houses sold, so this isn't a small-sample illusion.

In plain terms: somebody who bought at Cromwell's 2021 median of $227,000 has watched it climb to $377,500. That's roughly $150,000 in four years, in a town most out-of-state buyers have never heard of.

And here's a piece of Cromwell almost nobody knows. A Swedish immigrant named Andrew Pierson started a small flower nursery here in 1870 that grew into the largest commercial rose-growing operation in America — shipping millions of roses a year out of Cromwell. They called him the rose king. The town still gets called Rose City, and the old worker houses he built are still standing in the Main Street historic district. You drive right past them and would never know.

The town itself is named for Oliver Cromwell. And a company here made one of the earliest toy cap guns in the country. For a small town, there's a remarkable amount of history packed in.

But I'll be honest with you: Cromwell is hard to buy in right now

My friend Steve has been trying to buy here, and he is not messing around. Strong offers, well over asking, waiving inspections, writing letters. He's been outbid three times. These weren't lowball offers — they were his best shot, and he still lost.

That's what a hot town looks like from the inside. That's not a number on a screen. That's somebody I know losing three houses in a row because five, six, and in one case a dozen other people wanted the same house.

So when I say Cromwell is likely to keep climbing, I'm not guessing. I'm watching it happen. And it's exactly why you don't walk into a market like this alone and unprepared. In a market this tight, the buyer who's ready — financing locked, agent who knows the town, able to move the day it lists — has a real shot. The buyer who wants to sleep on it loses every time.

Why Cromwell has all of it

Everything in this article, Cromwell has. It sits right on the Connecticut River just north of Middletown with quick I-91 access — a straight shot to Hartford, and fast down to New Haven. 1.8 months of supply, which is very tight. And a price under $400,000 in a spot that connects you to everything.

It's also got specific draws. TPC River Highlands hosts the Travelers Championship on the PGA Tour every year — that gives a town a name and an identity beyond being a place to sleep. There's riverfront and wildlife. Real shopping and dining along Route 372. Close enough to the Hartford job market to be easy, far enough south to feel like its own place.

Remember the recipe from Wallingford? Train or highway. Downtown center. Middle of everything. Tight supply. Cromwell: check, check, check, check.

That's not me finding a story to fit a number. That's the number and the story pointing in the same direction, which is exactly what you want to see.

---

All seven, side by side

Data reflects last year's closed sales. Market conditions change continuously and past appreciation does not predict future prices.

Every town on this list is under $425,000. Five of the seven are under $400,000. That's the whole point — these aren't aspirational picks, they're towns a real budget can still reach.

---

The window

If you're planning a move on any of these, do it before 2027, not after.

The numbers above are last year's numbers. By the time next year's report comes out, these towns will have moved again — and the ones that look early today will look obvious then.

Early is uncomfortable, because it feels like guessing. But early is the only time the price is still on your side. Obvious is when you overpay.

---

Call or text: 203-910-2638 Email: Dave@davejonesrealty.com Search every home in Connecticut: www.searchallcthomes.com

---

Market data reflects the most recent reporting period available at the time of writing and changes continuously. Past appreciation is not a prediction of future performance and nothing here should be treated as investment advice. Contact Dave Jones Realty for current figures on any specific town. For school information, we recommend GreatSchools.org and visiting districts directly. Buyers researching any Connecticut 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