Middletown, Conn.: Friendly and Reasonably Affordable

Tracy Degrazia and her husband, Seth Pensa, bought their townhouse in Middletown in 2019, after deciding that the central Connecticut city had more to offer than neighboring towns.

The couple, both 40, who had previously rented in the area, found that Middletown had more properties in their price range and “city vibes without the city tax rate,” said Ms. Degrazia, a G.I.S., or geographic information systems, analyst. “I really feel like the tax rate is reasonable, with all of the amenities you get.”

And because the Wesleyan University campus is downtown, “the population skews a little bit younger and hipper,” she said. “Main Street is really fun.”

The couple paid $142,000 for a 1,400-square-foot home in a complex built in the 1970s. The exterior is not particularly attractive, but that’s a reasonable trade-off for the price, Ms. Degrazia said: “Our mortgage payment is under $1,000. It’s really like a dream.”

Middletown’s broad Main Street draws residents from throughout the area.Credit…Tony Cenicola/The New York Times

Buyers who began looking in Middletown during the pandemic, however, had a different experience.

For Lauren and Matthew Croyle, who began house hunting early this year in a much hotter market, “it was absolutely horrendous,” said Ms. Croyle, 28, a graduate student in cardiovascular perfusion at Quinnipiac University, in Hamden, Conn. She and Mr. Croyle, 29, an accountant, eventually paid $327,000 — several thousand dollars over the asking price — for a three-bedroom, century-old colonial with a backyard that has plenty of romping room for their 100-pound German shepherd.

The home’s historic aesthetic is an improvement over their previous home in Ohio, Ms. Croyle said: “It was a 1970s house with wood paneling on the walls and linoleum floors. Here, we have the original hardwood floors and great architecture.”

Joseph Carusone, 33, had a similar experience when he and his partner began looking in Middletown a couple of years ago. After more than a year of searching, they finally bought a 2,800-square-foot house on almost two acres, paying $410,000 — about $30,000 over asking.

Mr. Carusone, who works in management for a V.A. hospital in West Haven, said Middletown is friendlier, more “humble” and quieter than Westport, Conn., where they previously lived. Now, he said, “we have a firepit, and we can actually see the stars and not hear horns honking all the time.”

599 CHAMBERLAIN HILL ROAD | A three bedroom, three-and-a-half-bathroom house, built in 1985 on 2.5 acres, listed for $434,900. 860-813-2275

What You’ll Find

A city of roughly 49,000 people, Middletown hugs the west bank of the Connecticut River about 16 miles south of Hartford. Once a bustling port center, it covers some 41 square miles of Middlesex County, making it one of the state’s largest municipalities by land area.

The 316-acre campus of Wesleyan University, a liberal arts institution, melds into the downtown area, its borders not easily distinguishable from city streets. Students and faculty help support the many restaurants and shops along Main Street, a wide boulevard lined with historic buildings. Fast food chains and big-box stores can be found on Route 66, the east-west route through the city.

The housing stock is relatively old — most of it built between the 1950s and the 1980s — and includes multifamily buildings, apartments and condominiums, said Jonathan Zuromski, the owner of JZ Realtors. Development is dense close to the center of the city, but spreads out near the borders of the surrounding towns.

Harbor Park is on the riverfront, with a boardwalk and a new restaurant in the works. But most of the frontage along that deep bend in the river is cut off from the city by Route 9. An ambitious, 10-plus-year plan to “reclaim” some 200 acres of the riverfront that originally fueled Middletown’s rise envisions a pedestrian bridge over the highway to reach several new districts with trails, public art, a recreation center, a winter skating rink and housing, said Ben Florsheim, the city’s mayor.

“The hope is that it will become an economic driver and a public recreation destination,” said Mr. Florsheim, whose administration is awaiting final approval of a $12 million state grant to begin remediation and site prep.

Among the city’s largest employers are Pratt & Whitney, the jet-engine manufacturer, Middlesex Health and Connecticut Valley Hospital, a public hospital for people with mental illness, which has a sprawling, hilltop campus overlooking the river.

161 TRYON STREET | A three-bedroom, two-and-a-half-bathroom house, built in 1985 on 1.34 acres, listed for $400,000. 860-385-8282

What You’ll Pay

“The market is definitely tight, in terms of listings, which is true of central Connecticut in general,” said Carl Guild, the owner/broker of Carl Guild & Associates. “New listings are down 20 percent over this time last year.”

And there tends to be considerable demand from within. “There are a lot of people who are very loyal to Middletown,” Mr. Guild said. “I have a lot of clients who, when they are ready to move, want to stay in Middletown.”

As of Nov. 11, there were just 27 active listings for single-family homes, ranging in price from $149,900 to $650,000, Mr. Zuromski said. The median sale price for the 12 months ending in mid-November was about $300,000, up from $274,000 during the previous 12 months. That median price typically buys a 1,200- to 1400-square-foot, three-bedroom home on a quarter of an acre, Mr. Zuromski said.

The median sale price for a multifamily home over the 12 months ending in mid-November was $285,000, compared with $230,000 during the previous 12 months, said Michelle Mazzotta, an agent with eXp Realty. The median price for a condominium was $160,000, she said, up from $138,000 during the previous year.

As for taxes, Middletown’s mil rate (the figure used to calculate property taxes) is $35.70, higher than that of some neighboring communities (Cromwell’s is $30.33) and on par with others (Durham’s is $35.56 and Portland’s is $35.01).

35 BROOKVIEW LANE | A three-bedroom, two-and-a-half-bathroom house, built in 1989 on 0.63 acres, listed for $369,900. 860-305-5908

The Vibe

Main Street, lined with nearly 200 businesses, buzzes with activity. Students hunch over their laptops in the downtown coffee shops. Families frequent Amato’s Toy and Hobby, a large toy store that has helped anchor the downtown since 1940. And diners from throughout the area have a wide range of restaurants to choose from, on and around Main Street, serving Italian, Chinese, Vietnamese, Mexican, Tibetan and Ethiopian food.

Residents’ politics tend to be progressive. A gay pride parade and festival first held in 2019 was one of the largest such events in the state, and is now an annual event, coordinated by Middletown Pride.

The city adopted an emergency climate resolution about two years ago, and a clean energy task force works on boosting energy efficiency, sustainability and electrification, said Anna Salo-Markowski, the chairwoman. Currently, the committee is coordinating an initiative to inform low-income residents about state efficiency programs and heat pump rebates, she said: “We have an active group here that’s interested in being as environmentally friendly as possible.”

Harrie’s Jailhouse restaurant occupies a former jail on Warwick Street that dates to the 1850s.Credit…Tony Cenicola/The New York Times

The Schools

The Middletown school district serves about 4,430 students in eight elementary schools, a middle school and a high school. The diverse school population is about 46 percent white, 22 percent Black, 16 percent Latino and 5 percent Asian, with the remainder identifying as two or more races, according to State Department of Education data.

The elementary schools all serve students in kindergarten through fifth grade. Some have a particular focus, including one, Lawrence Elementary, that was recently designated an International Baccalaureate school.

About 1,040 students attend Beman Middle School, in a new state-of-the-art building that has an innovation center equipped with a flight simulator.

Middletown High School, with about 1,375 students, has a highly regarded agricultural science and technology program, and an aerospace manufacturing education program that provides instruction on flying and fixing airplanes and drones.

“We have students who have obtained their F.A.A. license to fly a drone before they can legally drive a car,” said Jessie B. Lavorgna, the school district’s director of communications.

In 2021-22, the SAT score averages were 442 in math and 464 in reading and writing, compared with state averages of 486 and 501.

The sprawling lawns and historic architecture of the Wesleyan University campus are a few blocks from Main Street.Credit…Tony Cenicola/The New York Times

The Commute

The nearest commuter rail station is in Meriden, about a 15-minute drive. From there, commuters can catch the Hartford Line to New Haven, and then take Metro-North’s New Haven Line to Grand Central Terminal in Manhattan. The ride from New Haven to Grand Central takes an hour and 40 minutes to two hours and 10 minutes. A one-way, peak-time ticket is $23.50; a monthly pass is $450.

The 100-mile drive to Midtown Manhattan can take about three hours, depending on traffic.

The History

A five-acre tract known as the Leverett Beman Historic District, on the western edge of the Wesleyan campus, is notable as a residential subdivision laid out in 1847 by a free Black man for the benefit of Black homeowners. Leverett Beman, a shoemaker, was one of many Beman family members who were active in the antislavery movement. The district originally included 11 small house lots of less than a 10th of an acre. The neighborhood remained fairly cohesive until around 1900, when it gradually fell victim to outside investors.

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