Real Estate 2020: The 8 hottest Connecticut towns by county

  • 9 min to read
Real Estate 2020: The 8 hottest Connecticut towns by county

In college basketball-crazy Connecticut, think of this list as the real estate version of the NCAA tournament’s Elite Eight.

Just as the NCAA tournament sets out to find out which college basketball teams are the best in the land, we wanted to find out which Connecticut communities are hottest when it comes to the real estate market. To develop our list, we looked at each of the state’s eight counties and their towns’ and cities’ annual median single-family home price for each year between 2016 and 2019. Then we determined which community in each county had the highest overall percentage increase for those years. Communities with at least 50 annual sales were eligible to be crowned the hottest in the county. (You can find data on all 169 towns here.)

The eight communities that came out on top offer a mix of urban, suburban and small-town opportunities for homebuyers. And the opportunities are not just attracting Connecticut residents, but people from neighboring New York state as well, according to some real estate agents we spoke with.

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Fairfield County: Bridgeport

Bridgeport doesn’t necessarily have the cachet of other Fairfield County communities, especially along the fabled Gold Coast, but since 2016, median sale prices for single-family homes here have outpaced the rest of the county’s other cities and towns.

“Considering the surrounding towns, like Fairfield and Trumbull, Bridgeport is much more attainable,” says Steven Lage, a sales associate with the Trumbull office of Coldwell Banker. “In the North End (of Bridgeport), there’s a lot of people buying homes for Sacred Heart [University] purposes.”

Lage says that New Yorkers have also taken notice of the Park City’s affordability. More than half the people his office sells homes to in Bridgeport are from the Empire State, he says. Another draw is the walkable seaside neighborhood of Black Rock, with its trendy shops and restaurants.

Easy access to ferry service from the city to Port Jefferson, New York, is a plus for Bridgeport home buyers, as is the new outdoor concert venue that will open this summer at the site of the former Ballpark at Harbor Yard.

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Bridgeport at a glance

Single-family home median price (2016-19): up 30.5 percent, to $196,000

Single-family home sales (2016-19): up 24.6 percent, to 724 sales

Condo median price (2016-19): up 35.3 percent, to $99,450

Condo sales (2016-19): up 20.4 percent, to 336 sales

Population: 144,900

Median household income: $45,441

You should know: Bridgeport is Connecticut’s largest city.


Hartford County: Windsor Locks

If one town in Connecticut can make a legitimate claim to being the state’s transportation hub, it’s Windsor Locks. And therein lies its appeal to home buyers.

The town is best known as home to Bradley International Airport, New England’s second-busiest airport. But transportation options don’t begin and end at the airport.

“It’s really easy to get anywhere, both within Connecticut and out of state,” says Bill Jones, sales manager of the West Hartford office of William Raveis Real Estate.

Windsor Locks is about midway between Hartford and Springfield, Massachusetts, with easy access to Interstate 91. And with a stop on the Hartford Line with its expanded commuter rail access, it’s possible to leave the car at home.

Jones says that median sale prices in Windsor Locks have benefited from a state unemployment rate that went down by 1 percent in the past 12 months as well as rising apartment rental costs around the Hartford area. He expects home values to continue to grow in the coming years, now that the state has announced it has received a $17.4 million federal grant to build a new train station in the downtown area.

“When you upgrade transportation infrastructure, real estate prices will follow,” Jones says.

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The Windsor Locks Canal State Park Trail

Windsor Locks at a glance

Single-family home median price (2016-19): up 17.5 percent, to $195,000

Single-family home sales (2016-19): up 5 percent, to 147 sales

Condo median price (2016-19): up 7.1 percent, to $142,500

Condo sales (2016-19): up 42.9 percent, to 50 sales

Population: 12,876

Median household income: $66,846

You should know: Windsor Locks is home to the New England Air Museum, whose collection of everything from early flying machines to supersonic jets celebrates the region’s role in aviation history, design and manufacturing.


Litchfield County: Woodbury

Woodbury’s just-under 10,000 residents enjoy quasi-rural living and easy access to a charming downtown area that looks like something out of a Norman Rockwell painting. But it is also close to Interstate 84, making it easy to get to Waterbury, Danbury and other points in the region.

“It’s just a quaint little town with lots of good restaurants,” says Tim Drakeley, owner of Drakeley Real Estate, which has offices in Woodbury, Southbury and Bethlehem. “And it’s a great location whether you’re going to Boston or New York City.”

Woodbury is also one of the stops on Connecticut’s antiques trail, with more than two dozen stores where shoppers can peruse treasures to their hearts’ content.

The median annual income in Woodbury is $78,025, which is a little more than $27,000 higher than the median national income. And perhaps because of that, Woodbury has something many small towns don’t: a highly regarded health food store, New Morning Market.

The town also has enough prestige that, for a few years, it was the home to musician, actor and screenwriter Rob Zombie.

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Woodbury at a glance

Single-family home median price (2016-19): up 15.9 percent, to $365,000

Single-family home sales (2016-19): down 4.8 percent, to 99 sales

Condo median price (2016-19): up 1 percent, to $131,000

Condo sales (2016-19): up 54.3 percent, to 54 sales

Population: 9,537

Median household income: $78,025

You should know: Woodbury has many historic structures. Built around 1740 in the Georgian Colonial style, the Glebe House Museum features a classic English-style garden. It’s also said to be haunted.


Middlesex County: Essex

Bigger may be better when it comes to some things, but part of what makes Essex attractive to home buyers is its small-town feel. “My husband and I used to live in Simsbury and we’d come here on day trips,” says Yolanda Tine Lowe, a real estate agent who works for William Pitt Sotheby’s International Realty, which has a brokerage office on Main Street in the town. “It’s so quaint and we just fell in love with it.”

Lowe says the town has a nice mix of young and old residents who have a real sense of community. “People are always coming together to help others out,” she says.

There’s plenty to do around Essex. It is home to the Essex Steam Train & River Boat, the Ivoryton Playhouse and the Connecticut River Museum. Other nearby attractions include Gillette Castle State Park in East Haddam and Hammonasset Beach State Park in Madison.

And then there is the lure of the Connecticut River, which empties into Long Island Sound in Old Saybrook. “We get a lot of boaters here,” Lowe says.

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Essex at a glance

Single-family home median price (2016-19): up 22.1%, to $386,500

Single-family home sales (2016-19): down 3.4 percent, to 85 sales

Condo median price (2016-19): down 4.7 percent, to $205,000

Condo sales (2016-19): down 10.5 percent, to 17 sales

Population: 6,674

Median household income: $87,000

You should know: The maritime-themed Griswold Inn, “the Gris” for short, is one of the country’s oldest continuously operated inns, opening its doors in the consequential year of 1776.


New Haven County: Waterbury

Waterbury is a city on the rebound when it comes to residential real estate, and Linda Fercodini of Wolcott-based Fercodini Properties credits Mayor Neil O’Leary for the turnaround.

“It’s coming back and I credit him for that,” Fercodini says of the Democratic mayor. “He is doing a lot to attract business downtown and he’s done a great job with his anti-blight campaign. There are a lot of investors that have started to come in.”

Many of those investors are coming from New York state, she says. 

“Not only are they coming to invest, they are also coming here to live,” Fercodini says. “Taxes in Waterbury are high, but not as high as in our neighboring state. And young people today like to live in cities where they can walk to stores and entertainment.”

Two of the main attractions in downtown Waterbury are the Renaissance Revival-style Palace Theater and the Mattatuck Museum. A little farther from the city center is the highly regarded Seven Angels Theater and the newly opened Continuum Distillery.

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Waterbury at a glance

Single-family home median price (2016-19): up 33.3 percent, to $132,000

Single-family home sales (2016-19): up 8.6 percent, to 782 sales

Condo median price (2016-19): up 19.3 percent, to $65,000

Condo sales (2016-19): up 23.7 percent, to 219 sales

Population: 108,093

Median household income: $41,617

You should know: Waterbury earned its “Brass City” nickname in the first half of the 20th century by churning out more brassware than any other industrial center in the U.S. It also specialized in the production of watches and clocks.


New London County: Griswold

There’s no shortage of ways for people who live in Griswold to entertain themselves. The town is close to beaches in both Connecticut and Rhode Island, as well as our state’s two casinos and attractions in Mystic.

Perhaps that’s why the town was New London County’s top performer in terms of growth in median single-family home sale prices between 2016 and 2019.

“It’s a great town,” says Denise Robillard with Continental Realty Associates. “It’s a country atmosphere with great schools. And you can get almost anywhere in Connecticut, Massachusetts and Rhode Island because Griswold is along the I-395 corridor.”

Another factor, according to Robillard, is that the town is an easy commute to some of southeastern Connecticut’s largest employers, such as Electric Boat, as well as Foxwoods and Mohegan Sun.

“Housing is still quite affordable here,” she says. “And natural gas mains are being extended here to attract more businesses to the town.”

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Griswold at a glance

Single-family home median price (2016-19): up 36.4 percent, to $191,000

Single-family home sales (2016-19): up 12.7 percent, to 80 sales

Condo median price (2016-19): up 12.7 percent, to $112,635

Condo sales (2016-19): down 33.3 percent, to 4 sales

Population: 11,591

Median household income: $62,542

You should know: Outdoor options are plentiful here, with both the Pachaug and Hopeville state forests, as well as the Pachaug and Quinebaug rivers.


Tolland County: Columbia

If you like the idea of lakeside living, Columbia has it. The town is home to a pair of large bodies of water: Columbia Lake and Mono Pond. The 281-acre Columbia Lake is maintained by the town, according to Enza Dandeneau of Dandeneau Team Real Estate, a Berkshire Hathaway affiliate in Glastonbury. In addition to the town beach, many of the homes lining the lake have private beaches of their own.

Many houses were originally built as summer homes for people who worked in Hartford and its immediate suburbs, according to Dandeneau. But as Route 2 was developed over several decades, starting in the 1950s, people began to view Columbia in a whole new light, she says. “It’s only 20 miles from downtown Hartford, which makes it a very doable commute. So people who worked at Pratt & Whitney and other major Hartford employers began taking the steps they needed to live in Columbia year around.”

Columbia is less than 10 miles away from Willimantic, home to Eastern Connecticut State University. And just 11 miles to the north is the University of Connecticut’s main campus in Storrs. “You have a lot of people who work at both schools who live in Columbia,” Dandeneau says.

Columbia at a glance

Single-family home median price (2016-19): up 22.4 percent, to $260,000

Single-family home sales (2016-19): down 11.3 percent, to 63 sales

No condo sales in 2019

Population: 5,385

Median household income: $106,604

You should know: The Mono Pond State Park Reserve, with the 113-acre Mono Pond at its core, is a popular destination for all manner of outdoor activities. It was added to the state park system in 2008. Also, Columbia was once part of neighboring Lebanon and was called Lebanon’s Crank until it broke off in 1804.


Windham County: Plainfield

Even though it’s Windham County’s third-most-populated town, Plainfield still has that small-town thing going for it. It could be one of the reasons that home-sales prices have been rising here at an impressive clip.

“It’s very affordable and is a great location right off of Interstate 395,” says Mary Collins, a real estate agent with the Woodstock office of Berkshire Hathaway. “It’s close to Rhode Island and the beaches.”

Collins says the cost of living in Plainfield is much cheaper than other parts of Connecticut and neighboring Rhode Island, which attracts a lot of Ocean State residents across the border.

One of the draws of Plainfield is that it’s part of the Last Green Valley National Heritage Corridor, which stretches from part of central Massachusetts through much of eastern Connecticut. Another natural attraction is the 96-acre Moosup Pond, where Collins says she has sold several homes within the past year.

Plainfield at a glance

Single-family home median price (2016-19): up 40.7 percent, to $189,950

Single-family home sales (2016-19): down 12.9 percent, to 108 sales

Condo median price (2016-19): up 88.5 percent, to $120,500

Condo sales (2016-19): up 200 percent, to 12 sales

Population: 15,173

Median household income: $67,551

You should know: The town was incorporated as Quinebaug in 1699, and was changed to Plainfield a year later. A Native American term meaning “long pond,” Quinebaug is the name of a village in the town of Thompson, also in Windham County.

This article appeared in the April 2020 issue of Connecticut Magazine. You can subscribe here, or find the current issue on sale hereSign up for our newsletter to get the latest and greatest content from Connecticut Magazine delivered right to your inbox. Got a question or comment? Email editor@connecticutmag.com. And follow us on Facebook and Instagram@connecticutmagazine and Twitter @connecticutmag.