Homelessness surges in wealthy CT: ‘I’m surrounded by millionaires, and next door this is happening’

CT Insider – Tuesday, May 20, 2025
By Alex Putterman

GREENWICH — Start in Riverside, one of the wealthiest neighborhoods in Connecticut, where the average home costs more than $2.2 million.

Drive past stately houses with expensive cars in the driveways and inground pools in the backyards. Continue by a sign discouraging panhandlers and pass quickly through Old Greenwich, another of the state’s most luxurious ZIP codes, before crossing the city line into Stamford.

Soon, you’ll hit the downtown area, where — just across from a luxury apartment complex where one-bedroom units start at $2,300 — you’ll find one of the state’s largest homeless shelters.

The shelter, called Inspirica, houses some of Connecticut’s poorest residents, while helping them find long-term homes in a market where that’s often near-impossible.

“Homelessness is very real in Fairfield County, and it’s sad, because we’re next to these wealthy neighborhoods,” said Lucy Freeman, Inspirica’s vice president of housing and program services. “We’re next to people who have $2 million, $3 million homes, and we can’t provide a simple apartment to someone.”

As of last year, an estimated 3,400 homeless people lived in Connecticut, up 13% from 2023, and other measures suggest the true number is even higher. Of that total, more than 700 lived in Fairfield County, a startling figure for one of the nation’s wealthiest enclaves. Homeless service providers in southwestern Connecticut say they served 579 households this winter alone, nearly 75% more than two years ago.

If inequality is a central fact of life in Connecticut, rarely is it starker than this: people without homes, living just miles from some of the most expensive real estate anywhere.

Advocates and homeless service providers say Connecticut’s rise in homelessness isn’t primarily about a spike in drug addiction or mental illness. It’s a matter of formerly stable residents, some of whom once lived comfortable middle-class lives, being unable to afford their rent.

“The face of homelessness has really changed.” said Rosalba Messina, Inspirica’s CEO. “We certainly deal with our fair share of mental illness and drug addiction in the homeless population, but then there are just those individuals who lost their job and have families to support.”

Or as Freeman puts it: “The line between being housed and unhoused has gotten razor thin.”

Gabriela and Courtney

On a recent Tuesday afternoon, a 32-year-old Inspirica resident named Gabriela settles into a chair at the shelter’s offices and shares her story.

She was born in New Haven but says she spent much of her childhood bouncing between foster homes across the state, some better than others. When she turned 18 she tried community college, then dropped out to become a certified nursing assistant.

She soon moved in with her boyfriend, and in 2020 the couple had their first child. They lived in a New Haven suburb for several years, until Gabriela began to fear for her safety at home and decided to take her son and leave. The two of them stayed briefly at a domestic violence shelter and spent a period sleeping in their car, before eventually landing at Inspirica.

Gabriela, who CT Insider is identifying only by her middle name out of concern for her safety, sees herself as an example of how tenuous comfort can be.

“You can be 100% stable, and then next thing you know, this is being taken away or this is changing,” she said. “And then it’s like, now I don’t know what’s to come for me.”

One night in early January, Gabriela was at Norwalk Hospital receiving treatment for a broken jaw, accompanied by her son. A stranger heard her tell a nurse she couldn’t afford a ride home and approached with an offer to help. Her name was Courtney Davis.

Davis inhabits the opposite end of Connecticut’s divide as Gabriela. She lives in Westport with her husband — a real estate developer she met years ago when she worked as a personal assistant to Jared Kushner — and their two kids. On Instagram, she shares her mostly glamorous life with more than 22,000 followers. One recent post showed her blasting 2Pac from her Mercedes.

Davis and her husband often eat out around the corner from a Westport homeless shelter, and she says she sometimes feels strange sipping an expensive cocktail so close to people who can’t afford basic essentials.

“I’m surrounded by millionaires, and right next door this is happening, where people can’t even buy any food for their family?” she said. “It’s crazy.”

And so after meeting Gabriela at the hospital and hearing her story, Davis offered to pay for an Uber to take her home, and the women exchanged contact information. Shortly after, Davis took Gabriela and her son to Target, where she bought them coats, pajamas, snacks and toys. She posted about the encounter on Instagram and started a GoFundMe for her new friend.

Months later, they still talk regularly and consider each other friends.

“That little act of kindness, it meant so much to me,” said Gabriela, who says she hopes to repay Davis one day.

Still, this isn’t one of those stories where a wealthy do-gooder shows up and every problem fades away. Gabriela and her son have continued to live at Inspirica, and her part-time work isn’t nearly enough for her to afford housing of her own in ultra-expensive Fairfield County. Even if she does find an apartment, she knows it won’t be easy to afford groceries, child care and everything else she needs to give her son a comfortable life.

Gabriela is ceaselessly optimistic, figuring that a smile and a good attitude improve almost any situation, but she wishes things were different, that there were more of a safety net to prevent people like her from struggling so much.

Davis, meanwhile, feels good about the help she’s provided Gabriela but has been forced to wonder whether she and others in her community could do more. Often, she says, well-off people would rather not think about the homelessness practically in their backyards.

“I think people around me really do care,” Davis said. “But when you have kids, it’s just so hard to focus on other people’s families.”

A statewide problem

It’s not just Fairfield County dealing with rising homelessness, of course.

In Waterbury, for example, an array of homeless service providers say they’ve never seen such dramatic need in their community.

“It’s the worst it’s been in the four years that I’ve been here,” said Gavin Titus, an outreach worker with Brian Gibbons Homeless Outreach, a small organization serving the city’s neediest residents. “We’re getting an influx of clients left and right.”

Titus and Joshua Royer, the organization’s executive director, spoke on a chilly January morning from the parking lot of a building that houses, among other things, offices of Connecticut’s Department of Social Services.

In the small wooded area behind them — literally in the state government’s backyard — stood tents where homeless people spend the night. The encampment used to be much larger, Royer and Titus explained, until the company that owns the woods cleared it last year.

Royer and Titus do what they can for their homeless clients, checking on them, bringing them blankets and food and connecting them with services whenever possible. Ultimately, though, they’re only two people, and they can only do so much.

“It’s hard sometimes to go home knowing that there are families outside, there are kids that are outside, living in cars,” Royer said.

Elsewhere in the city, the story is similar. Megan Santiago, who directs St. Vincent DePaul Mission of Waterbury, the state’s largest homeless shelter, said the facility’s 108 beds are almost always full these days.

“We always had beds open when I started back in 2018,” Santiago said. “We don’t have beds open now.”

Advocates say it’s the same statewide, with far more homeless people than there are services to help them. Jessica Kubicki, chief initiative officer at the Housing Collective, a Bridgeport-based non-profit, says Connecticut has seen an increase in elderly people without homes, as well as a rise in homeless families, many of whom simply can’t afford life in the state.

Providers recently asked the state for more than $33 million in additional funding for the homeless response system.

Titus grew up in New Milford, and he says he didn’t think much about homelessness until he started as an outreach worker.

“It really opened my eyes to what really goes on in the day to day of any city, any town,” he said. “There are people struggling no matter where you go.”

Staff strained

Startlingly, it’s not only the clients at shelters and food pantries who find themselves grasping for a stable life. It’s often the employees there as well.

“We live paycheck to paycheck some weeks, and some weeks we don’t,” said Santiago, who lives with her husband, an exterminator, and their kids.

Regina Suggs, head cook at the Greater Waterbury Interfaith-Ministries soup kitchen, said she’s had to become increasingly frugal over recent years as the cost of groceries has risen.

“When I go to the grocery store, I put stuff back,” Suggs said. “If it’s not essential, I don’t buy it.”

In some cases, employees find themselves seeking the same services they help others access: food stamps, housing assistance, Medicaid coverage and more.

It’s not uncommon, providers say, for people who work in homeless services to face homelessness themselves. According to the Housing Collective, 22.5% of frontline homelessness response workers in Fairfield County say they were at risk of losing their housing in 2023 or 2024.

Kubicki said she knows one homeless worker who holds jobs with three different agencies but can’t afford a car. Freeman spoke of a current Inspirica staff member who has to leave her current housing in April and has nowhere else to go.

“When she calls me, she’s literally crying,” Freeman said. “And I wish I could just fix it for her, and I can’t.”

Jared Bruzas, chief impact officer at the United Way of Greater Waterbury, said the organization has a hard time retaining employees, as people seek better-paying jobs. Much of his time, he says, is spent training new hires who he knows aren’t likely to stay long.

“All of them are severely underpaid,” Bruzas said. “Turnover rate is extremely high in the homeless response world, just because we can’t keep folks.”

No place to go

Matthew Edmond has seen Connecticut from several vantage points.

As a teenager, he experienced what he calls a “nice suburban upbringing” in the middle-class town of Beacon Falls, where he played football on back-to-back state championship teams. His stepfather was a police officer, and his mother studied to become a nurse.

At some point, though, he was prescribed an opioid painkiller, and he soon became addicted. He was diagnosed with bipolar disorder. As his problems compounded, he spent four years homeless.

Today, just a few towns over where he spent his teenage years, Edmond, 36, experiences another Connecticut. He lives in a tiny apartment in Waterbury, which he’s grateful to have. He picks up groceries from a local non-profit and weekly meals from a church across the street. He works odd jobs, often under the table.

Edmond, who was born in Michigan, says he loves Connecticut and appreciates the support he’s gotten amid his struggles. But he also wishes more people who passed him on the street would understand what his life is like.

“I like to try to show people the other side,” he said. “Not everybody out there is trying to just get couple dollars for drugs and take off. Some people are really trying to turn this s— around and make something out of their life.”

Back at Inspirica, the staff seek to help people like Edmond but find it increasingly difficult to do so. As affordable housing becomes more and more scarce, they’re often forced to manage expectations.

“There was a time when you could be a little more hopeful, and now the most important thing is to be realistic,” Freeman said. “When you have to say to people, ‘You have to opt for something maybe not as great as you want it to be,’ that’s a hard conversation to have with people.”

Freeman and Messina, Inspirica’s CEO, said they’d like to see the state do more to create and preserve affordable housing, whether by making it easier to build homes for low-income people or by implementing rent control measures.

They also say they and other shelters could use more state funding to match the growing need.

Freeman doesn’t blame the wealthy surrounding towns for the struggles of Inspirica’s residents. In fact, she says, the shelter gets a small amount of funding from the city of Greenwich, for which she’s grateful.

But she would love if more people, in Fairfield County and elsewhere, saw and acknowledged the side of Connecticut that her staff experiences every day.

“I just wish people recognized that you have families that don’t have a place to go,” she said.

Editor’s note: This is part two in a five-part series examining inequality in Connecticut.

Part 1: Two Connecticuts: How gaps between rich and poor define life in CT

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