Two lawyers teamed up to buy a cottage with million-dollar views

The stunning property doubles as a vacation home and a long-term investment
Lindsay Charles and Nick Todorovic inside their cottage on Wolfe Lake looking out large living room windows

Lindsay Charles and Nick Todorovic pulled into the driveway of a three-bedroom cottage on Wolfe Lake, which is located about an hour’s drive north of Kingston, full of excitement. The real estate listing had showcased an impressive country retreat, and the pair couldn’t wait to see it with their own eyes. Once they stepped out of the car, the tranquil atmosphere, the picture-perfect view and the cottage’s high ceilings lived up to their loftiest hopes. In an instant, both Charles and Todorovic had the same thought: Yep, this is the one. 

Lindsay Charles and Nick Todorovic, colleagues at McLeish Orlando, stand outside their cottage on Wolfe Lake

The owners: Lindsay Charles and Nick Todorovic 

Charles’s role: Partner at McLeish Orlando LLP 

Todorovic’s role: Partner at McLeish Orlando LLP 

Years of call: 2014 (Charles) and 2016 (Todorovic) 

Location: South Frontenac 

Cottage profile: Three bedrooms plus a loft, 2,700 square feet 

That moment took place in March of 2021. At least a year earlier, Charles and Todorovic, long-time friends and colleagues at the personal-injury law firm McLeish Orlando LLP, had started to talk about the benefits of buying an investment property and renting it out. “We’re both fairly captivated by the real estate market,” says Charles. “We knew that this would be a smart financial decision.” 

The duo decided to pool their cash and purchase a property together. From the beginning, the idea was to buy a cottage outside the city. The lawyers planned to list it on short-term rental websites like Cottages in Canada for most of the year and use that revenue to afford the maintenance costs and any other expenses that might arise. Because rental websites let users take properties off the market at any moment, the pair would be able to use the cottage as a part-time vacation home. Not a bad perk. 

After Charles and Todorovic visited the cottage on Wolfe Lake, they made an offer. And, after a brief bidding war, it was accepted. “We were pretty excited,” says Todorovic. “Then the hard work started.” 

With the summer fast approaching and the demand for cottage rentals about to spike, the lawyers were eager to list the property online. To get it ready for the season, Charles and Todorovic bought a full complement of furniture from IKEA and took time off work to transport the items to the cottage in jam-packed rental trucks. At the same time, they hired contractors to apply a fresh coat of paint to the walls and construct a set of stairs going down to the dock. “Cottages are a lot of work,” says Charles. “So it’s nice to have someone that you can trust wholeheartedly to help with managing it all.” 

After a fully booked summer that generated rave reviews, Charles and Todorovic were thrilled with the purchase. Looking ahead, they’re hoping to acquire a series of rental cottages that will add up to a robust real estate portfolio. 

By the fall, both lawyers had started to enjoy the cottage themselves, both as a quiet place to work remotely and as a getaway spot with friends and family. “Lindsay and I keep telling each other we can’t believe we got this place,” says Todorovic. “It’s kind of like winning the lottery.” 

Vintage map of Wolfe Lake
Minimally decorated bedroom in the cottage of Lindsay Charles and Nick Todorovic

Home decor
While the house is minimally decorated for a modern, hotel-like vibe, Charles and Todorovic have hung up a selection of vintage maps of their favourite places — including Copenhagen, Toronto and Wolfe Lake itself — to add some subtle personality to the space.

Person in an outdoor hot tub overlooking the frozen Wolfe Lake

Lake effect
The shores of Wolfe Lake are home to a mix of farms, cottages and fishing camps. The area is remarkably quiet. “A small fishing boat might come up first thing in the morning and cast a couple of lines,” says Todorovic. “But that’s pretty much it.”

Lindsay Charles and Nick Todorovic inside their cottage on Wolfe Lake looking out large living room windows
Setting the table with black dish ware on a light wood table

Entertainment value
When Charles spends time at the cottage, she often invites friends and family to tag along. On those occasions, the open-concept kitchen and living area is an ideal hangout spot. “It’s nice that people can be in the living room and you can be cooking dinner,” she says. “You still feel like you’re part of the same environment.”

Large windows in the living space of Lindsay Charles and Nick Todorovic's cottage overlooking Wolfe Lake

Cottage life
The large windows that overlook the lake are the cottage’s defining feature. “It’s up at the top of a hill,” explains Charles, “so it has a spectacular view.” 

This story is from our Spring 2022 Issue.

Photography by Johnny C.Y. Lam.