When Benn Haitsma and his family were looking for homes in the town of New Preston in 2019, they initially considered renting. But rent prices were rising. Instead, they bought a historic bed and breakfast.
They invested in some home projects to modernize the late 1800s-era property while maintaining its unique features and historic charm. Surrounded by farm houses, their New Preston property stands out with its high ceilings, a large staircase in the center of the home, a formal gentleman's room, a formal sitting room and dramatic windows.
Just a year after buying the property, Haitsma said their real estate agent started calling them. People were inquiring: Would they consider renting it out?
"The numbers were significantly more than we thought we would get, and so we were like, 'OK, let's do this,'" Haitsma said.
As soon as they started renting — for tens of thousands of dollars a month in the peak summer months — high-end clientele began booking the house for months in advance, he said. Families who stayed there would immediately ask to rebook for the next year.
Renting instead of buying is becoming more popular for Connecticut's wealthy, according to data from the U.S. Census Bureau. In 2023, more than 9% of Connecticut households with an income of $750,000 or more were renting. That's up from 2018, when just about 7% of Connecticut households in that income group chose to rent rather than buy.
Matt McElhone, a sales associate at William Pitt Sotheby's International Realty and Haitsma's realtor, works with high-end clients primarily in Litchfield County. He said he sees clients renting for a few reasons: to familiarize themselves with the area before committing to a down payment, to have a weekend place or to look for rentals for an academic year for their children.
Loading...
The growth in the high-profile rental market comes as housing inventory has strained Connecticut residents from every tax bracket. Buyer demand continues to outpace the limited supply of listings, a trend that has shaped the housing market in the state and nation over the past few years. Just 0.3% of homes and 2.9% of rental units in the state were vacant in 2024, according to the Federal Reserve Bank of St. Louis. Those are some of the worst rates in the country.
There were 5,000 active single-family, condo or townhome listings in the state in July 2025, according to the Federal Reserve Bank of St. Louis, down from nearly 18,000 listings in July 2019.
And on top of all that, the market is becoming more saturated with millionaires. Between 2022 and 2023, lower Fairfield County gained at least 500 millionaires. The towns of Greenwich and Darien had 12,500 millionaires in their combined populations as of 2023.
When a good house in a good location comes on the market, it's often there for just a few days, said Andrew Whiteley, a broker for Harris Brown Stevens who works primarily in Fairfield County. Some of his clients have had the highest bid on a house multiple times, but still weren't able to secure their dream home. The experience drove them to rent for the time being.
"Some of those people just say, 'Look, you know what? This is too much. I can't keep coming out every weekend and losing out on homes. Let me just rent something. Take a deep breath, and we'll figure it out,'" Whiteley said.
When the squeeze of the historically low housing inventory impacts wealthy shoppers, they have more flexibility to be patient with the housing market. Luxury rentals can provide flexibility for those looking for their perfect Connecticut home, Whiteley said.
A recent client of his was looking for houses in the town of Southport, though they weren't very familiar with the area. Rather than buy, they rented — for $55,000 a month.
"The house was on the market for $12 million, so they don't necessarily want to buy a $12 million house and decide they hate it. It didn't sit well with them," said Whiteley, who described it as a kind of trial run.
Litchfield County specifically is becoming an increasingly popular market for rentals, explained Kitty McBride, who with her husband rents out their West Cornwall home to high-end clientele. They call their home, a hillside residence set back from the road and surrounded by trees and picturesque hillside, Olive Farm, "which is so obnoxious," McBride said.
"We don't grow anything and there's no animals," she said. "Everything is painted green ... and it's like a little retreat."
After buying the house in December 2023 with the intention of it becoming an investment property, she said they've had many people test out the area through their rental.
For McBride, the constant demand hasn't just been an additional stream of income, it's been a delight. She's gotten to meet many wonderful people, some who have even turned into friends, she said.
The Haitsma family at first felt a pull to keep their New Preston home to themselves, but when they found themselves lucky enough to be in a position to cash in on the luxury housing market, the decision practically made itself.
"You have to ask yourself the question, 'would I pay this to be in my house for that period?'" Haitsma said. "And the answer is usually no."