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On a crisp autumn morning, Jane Smith strolls to her favorite café in downtown Hartford – a routine that would have been unthinkable a year ago, when she still lived in the four-bedroom Suffield colonial where she raised her kids. Now in her mid-60s, Jane and her husband have sold their longtime suburban home and moved into a modern apartment overlooking Bushnell Park¹.

They’ve joined a growing cohort of Connecticut baby boomers trading big yards for city skylines. Marguerite Rose did the same, relocating from West Hartford to a condominium high-rise downtown¹. Both women say they don’t miss the mowing and maintenance – instead, they relish having restaurants, theaters, and hospitals within walking distance.

Urban Downsizing: A New Chapter in City Life

Their parents may have spent retirement in age-restricted suburban communities, but “more and more, baby boomers are deciding that’s definitely not for them,” a Connecticut Public Radio report noted¹. Instead of secluded 55-plus developments, today’s boomers increasingly seek “walkable, vibrant neighborhoods where there’s a mix of young and old, lots of dining options, and plenty of culture.”¹

In fact, one survey found 8 in 10 boomers who live in cities want to remain urban even into their 80s¹. For empty nesters like Jane and Marguerite, that has meant selling the oversized house where they raised their children and embracing downtown living.

“We may not have a backyard garden, but we don’t have to shovel snow either,” Jane laughs, noting that in a condo, someone else clears the sidewalks and she never worries about losing power in storms. The appeal of city life – with its energy and convenience – is a big draw for many boomers rewriting the script on retirement.

Suburban Downsizing: Small Homes, Big Competition

Small house in Connecticut — Shutterstock

Not every Connecticut boomer is moving downtown. Many are downsizing in place or closer to home – opting for smaller houses or condos in suburban towns where they’ve long lived, or relocating to be nearer to children and grandchildren.

After decades in one house, the motivation is often to reduce upkeep and expenses. “They [older homeowners] have been in their house 20, 30, 40 years, and they’re moving to lower-cost properties as they’re downsizing,” explains Bryan Tunney, a Fairfield County real estate executive².

The Starter Home Squeeze

But there’s a catch: those “lower-cost” homes are often the same starter homes that young first-time buyers are desperate to purchase. In today’s tight market, downsizing boomers are directly competing with millennials for starter houses².

“There’s a severe lack of starter homes in Connecticut,” agents warn, and older buyers swooping in with built-up equity only add to the crunch². With more wealth and often the ability to make all-cash offers, boomers frequently win bidding wars against younger buyers².

“It’s mayhem,” says Tammy Felenstein, a Fairfield County Realtor, describing how limited inventory and multiple offers have become the norm – especially for modest-sized homes that appeal to downsizers and first-timers alike². The result? Millennials are sometimes pushed back into renting for longer, even as boomers secure the cozy capes and ranches that were once considered starter homes.

A Generation Staying Put – For Now

While some boomers are downsizing, many others are not budging from the houses where they raised their families. The stereotypical Florida retirement isn’t as common as people think – most older Americans actually prefer to stay in their own homes if they can³.

The Numbers Tell the Story

Connecticut data reflects this aging-in-place trend. Baby boomer “empty nesters” continue to occupy a large share of family-sized houses across the state. In 2022, boomers in one- or two-person households (around age 58–76) owned roughly 26–29% of all single-family homes with three or more bedrooms in Connecticut’s major metro areas, whereas millennials with children owned only about 12–15%⁴.

This gap is even wider than the national average – nationwide, older empty-nesters hold about 28% of large homes, versus 14% for young families⁴ – and represents a striking change from a decade ago, when the two groups owned a similar share of big homes⁴. In other words, many of those spacious suburban houses are still in boomer hands.

Why Boomers Are Staying Put

What’s behind this stay-put tendency? For one, baby boomers are healthier and more independent than previous generations at the same age, so fewer are moving in with adult children or to nursing facilities. Unlike their parents or grandparents, boomers aren’t rushing to downsize to a little condo or senior home – they’re often choosing to grow old in their own houses⁵.

Mark Abraham, a Connecticut data analyst, points out that a wave of boomers who settled in CT in the 1980s is now reaching retirement, contributing to a fast-growing over-65 population in the state³. Many are happy where they are, using those extra empty bedrooms for hobbies or hosting the grandkids on holidays.

“The thing I always hear is, ‘We need room for when the kids and grandkids come to visit for Thanksgiving,’ even though that’s only two weeks [out of the year],” observes Carl Lantz, president of the Connecticut Association of Realtors⁴. Some boomers, now freed from paying college tuition or other child-rearing costs, have even upsized into dream homes or renovations they couldn’t afford before⁴.

Financial Factors Keep Boomers in Place

And crucially, many have little financial incentive to move. More than half of boomer homeowners in the U.S. own their homes outright with no mortgage, and many others refinanced to rock-bottom interest rates in the 2010s⁶.

Trading a paid-off house (or a 3% mortgage) for a new 7% loan on a downsized home can feel like a bad deal. “You don’t want to be economically stupid,” says Sherry Murray, 73, who considered selling her four-bedroom home but realized downsizing would actually cost her more.

With today’s high prices and rates, “it just is a dumb economic decision to spend that much extra money for getting so much less,” she concluded⁶. This “mortgage lock-in” effect, as economists call it, discourages seniors from moving when it means forfeiting a historically low interest rate⁶.

The Housing Mismatch Problem

There are also practical reasons some boomers hesitate to downsize. “You’ve got a pure housing mismatch for older homeowners,” says Gary Engelhardt, a Syracuse University economist who studies aging and housing⁶.

Many boomers live in multi-story houses with big yards that can become burdensome – even hazardous – as they age. Climbing steep stairs or shoveling driveways in winter can pose serious health risks over time (falls, for example, are a major concern in later life)⁶.

Ideally, Engelhardt notes, seniors would be “matched with their housing in a much better way than we currently have.”⁶ But finding that “better match” isn’t easy in Connecticut’s housing landscape.

Then and Now: Shifting Trends Over Five Years

The past five years (2020–2025) have brought these conflicting forces into focus. In the late 2010s (2015–2020), experts and realtors were already puzzling over why boomers weren’t selling their big houses as expected. The housing market was softer then, and many boomers were still working or had mortgages they were comfortable carrying, so downsizing could wait.

The Pandemic Housing Boom

Fast forward to the 2020s: the pandemic-era real estate boom gave older homeowners unprecedented equity to work with – yet also made smaller homes more expensive to buy. This dual reality has produced a mixed trend.

On one hand, more boomers are finally making a move. In 2022, for the first time since 2014, baby boomers surpassed millennials as the largest share of homebuyers in America, accounting for 39% of all home purchases (up from 29% the year before)⁷.

Armed with cash from years of home appreciation, they’ve been able to “trade later in life” and relocate to homes that better suit their retirement dreams. “Baby boomers have the upper hand in the homebuying market,” says Jessica Lautz, deputy chief economist at the National Association of Realtors.

“The majority of them are repeat buyers who have housing equity to propel them into their dream home – be it a place to enjoy retirement or a home near friends and family. They are living healthier and longer and making housing trades later in life.”⁷ This marks a clear shift from the previous five-year period, when millennials dominated homebuying and many boomers stayed put.

The Supply Bottleneck

On the other hand, a large portion of boomers still haven’t downsized, even as they enter their 70s. Nationwide and in Connecticut, thousands of family-sized homes remain occupied by one or two older adults, tightening the real estate supply for younger families.

Abraham, the Connecticut data expert, cautions that if “older residents aren’t vacating their homes,” the state’s housing shortage will only worsen³. Fewer big homes turning over means fewer opportunities for growing families, especially given Connecticut’s chronically low rate of new home construction³.

It’s a dynamic that didn’t trouble prior decades as much, because earlier generations were more apt to downsize or move in with relatives by their late 60s. Boomers, by contrast, are breaking that pattern – a historical context that underscores how unique this generation is in housing behavior.

The Road Ahead: Balancing Act

Connecticut’s real estate professionals are watching these trends closely, and many are encouraging boomers to right-size their housing – for their own sake and the market’s. “It’s absolutely a fantastic time for those older folks to downsize,” Realtor Carl Lantz says, citing the high demand and prices their large homes can fetch⁴.

Selling now allows boomers to cash out equity at a peak and potentially find a home that will be easier to manage as they age (all on one level, for instance). Some have heeded this advice, while others remain unconvinced.

Finding New Housing Solutions

Enticing more boomers to downsize may require new solutions. Engelhardt suggests policy makers could encourage the construction of more senior-friendly housing – think single-story homes, condos with elevators, or walkable “village” developments with universal design features⁶.

Incentives like tax credits for developers to build such homes (analogous to those for affordable housing) might expand the options available to an aging population⁶. The hope is that if attractive, reasonably priced downsizing options exist, more seniors will make the leap – freeing up larger houses for the next generation of families.

Diverse Paths Forward

Meanwhile, personal decisions will continue to vary. For some, like Jane Smith, swapping suburbia for city life has brought newfound joy and convenience. For others, the attachment to a longtime home – or the arithmetic of the current market – may keep them in place a while longer.

Connecticut’s baby boomers are charting diverse paths in their housing journeys, from urban condos to cozy bungalows to staying put in the old homestead. Their choices are already reshaping neighborhoods and market dynamics across the state.

In the coming years, these trends will bear close watching, as a generation known for doing things its own way navigates the classic question of retirement living: stay or go? The answer, it seems, is a little bit of both – with profound implications for Connecticut’s housing landscape.⁴