For this cottage country brokerage, 50% of sales start with a free vacation

An $11-million eight-bed, eight-bath luxury home on Lake Joseph that’s currently listed for sale by CV Real Estate (photo: supplied by the brokerage). 

Most of the clients who walk through the doors of CV Real Estate don’t arrive as buyers or sellers, but as vacationers. 

Jay Katzeff and Tyler DaCosta launched the brokerage in 2022, building it around the established Ontario-based vacation rental company they had already acquired, Cottage Vacations. 

“We kept doing deals in between both the renter and owner profile,” said Katzeff, company president. “We were like, ‘We’re doing this enough that I think it warrants opening our own brokerage.’” 

Co-founders Jay Katzeff and Tyler DaCosta and their newest partner, Josh Chisvin.

Under their ownership, the vacation rental business has expanded its managed rental portfolio from about 140 cottages to roughly 400. The brokerage, which serves Muskoka, Parry Sound, Haliburton, Simcoe County and the Kawarthas, now has 30 agents and, according to Katzeff, is on pace to complete about 150 transactions this year, up from roughly 40 in 2025.

Katzeff, whose background is in commercial real estate, said he met DaCosta through mutual connections in Muskoka while searching for both a business partner and a broker of record.

The leadership team expanded again this year with the addition of Josh Chisvin as a third partner, whom Katzeff said has helped support the brokerage’s continued expansion.

From vacation to ownership

The brokerage’s growth has been driven not only by referrals, but by people who have already experienced cottage life through the rental business. 

“Most of our renters become buyers, and our owners are sellers,” Katzeff said. “The amount of people that come into our ecosystem is significant.”

A significant portion of the brokerage’s transactions now originate from Cottage Vacations-generated leads, with atleast 50 per cent of buyers participating in what they call a “try before you buy” program. 

Prospective buyers can rent one of the cottages managed through Cottage Vacations and, if they later purchase a property through one of the brokerage’s agents, receive a refund worth up to the full cost of their vacations.

The strategy allows potential buyers to experience the lifestyle before committing to a purchase.

“Why don’t you rent three different cottages, do your research, see what you like the most,” he said. “If you end up buying with us, we’ll refund those vacation dollars back to you.”

“So you really get a free vacation if you end up buying it.”

For many buyers, Katzeff said, choosing the right lake, community and lifestyle is just as important as choosing the cottage itself.

Growing beyond cottage country

Katzeff said about 75 per cent of Cottage Vacations’ rental database comes from the Greater Toronto Area, while about one-quarter consists of international visitors from markets including the United States, Germany, the United Kingdom and China.

“The international crowd is growing,” he said, noting that Muskoka continues to gain recognition beyond Canada.

Toronto-area buyers, however, remain the market’s core clientele.

“The core buyer for cottages in general are typically high-net-worth individuals out of Toronto,” he said.

As the market has normalized from the rapid pace seen during the pandemic, Katzeff said success increasingly depends on setting realistic expectations.

“If you’re on a good lake with good waterfront and a good property, and you’re priced correctly, things are selling,” he said.

At the same time, he said, buyers have become more selective.

“Nobody is overpaying in this market,” Katzeff said. “But if it’s good real estate and it’s priced appropriately, things are moving.”

Rather than chasing ambitious asking prices, he said, the brokerage encourages sellers to price properties in line with current market conditions.

“We’re not looking to just put listings up at crazy prices and watch them collect days on market.”

A listing that came full circle

The listing is described as an “entertainer’s dream,” both indoors and outdoors.

One of the brokerage’s current listings demonstrates how its rental and real estate businesses often overlap.

The approximately $11-million Lake Joseph property had been one of Cottage Vacations’ strongest-performing rentals before the owner decided it was time to sell.

“So we were renting out this cottage,” Katzeff said. “It’s one of our top performers.”

According to Katzeff, the property generated about $500,000 in annual rental income before the owner approached the company about listing it.

“He was trusting us already to rent it,” Katzeff said. “He was like, ‘Hey, if you guys want to list it, happy to work with you.'”

Katzeff said that’s not unusual among owners of luxury recreational properties. Many use their cottages only part of the year and want the option of generating income while they’re away.

A winterized 1-bed/1-bath bunkie that expands the property’s potential for hosting.

“A lot of people buy cottages and are very invested in cottage country, and then they kind of feel guilty not being at the cottage,” he said.

The brokerage’s rental business allows owners to offset some of their carrying costs while maintaining the flexibility to use the property themselves.

“If you’re gonna do that trip, you might as well let it pay for itself,” Katzeff said, adding that comparable luxury waterfront properties can command weekly rental rates of between $60,000 and $70,000.

A different approach to growth

For Katzeff, the brokerage’s business model is built around relationships that often begin years before a client is ready to buy or sell.

Someone who first books a summer rental may later purchase a cottage through the brokerage. Years afterward, that same owner may place the property into the rental program or eventually return to sell it.

Rather than treating those as separate transactions, Katzeff said the company sees them as different stages of cottage ownership.

As the brokerage continues expanding across Ontario cottage country, he believes understanding those long-term relationships—and the unique dynamics of the recreational property market—will remain its competitive advantage.

Even in the luxury segment, he said, patience remains essential.

“At the $10 million-plus category, things don’t move in three days,” Katzeff said. “It’s going to take a little bit of time, especially unique assets.”

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