When Richard Calder laughs and says, “I don’t have trouble getting crew for Chester Race Week,” it’s not bravado, but the outcome of a successful strategy.

Racing a 40-foot J/120 with nine to 12 crew at one of the East Coast’s most prestigious sailing events means having an attractive place for the crew to stay when the sails come down. With that in mind, he created a welcoming home away from home for his loyal crew.

Richard owns jewelry retailer Charm Diamond Centres, which has stores across Canada. He began sailing his boat, Brilliance, in Chester Race Week in 2000 and purchased his first home in Chester in 2015. He still has the house, located on the town’s picturesque Back Harbour. “It’s a small place with two bedrooms and a wharf for the boat, but there’s no room for crew, family or summer guests,” says Richard. His initial solution for crew accommodation was to purchase a garage with a loft on the other side of Back Harbour, though it wasn’t on the water. This was a good temporary measure, but he had his eye on an 1,800-square-foot, three-bedroom, two-and-a-half-bath house nearby. In 2024, Richard bought what would become his yacht crew house.

Soon after, he hired designer Jonathan Legate to increase the house’s capacity and make it more beautiful and functional. There were a few caveats: Richard didn’t want to build an addition, he didn’t want to lessen the home’s summer cottage character, and it needed to be ready in less than 10 months for Race Week in August 2025. “The main floor felt awkward, we needed an extra bedroom, and I wanted to add a principal ensuite,” says Richard.

Jonathan rolled up his sleeves and got to work on the design plan. “I found square footage for an ensuite upstairs and added a bunk room using space from the stair landing,” says the designer. “Downstairs, what was once the living room became the dining room, and we widened a doorway to the kitchen and built a bar in that space, which looks through to the new living room while giving the kitchen an extra work surface.”

One of Richard’s favourite features is the stone fireplace in the living room. “It was a major budget item, but it was worth it; it’s a great focal point,” he says. And the wallpaper on the dining room and kitchen ceilings? Designer and homeowner agree that it’s part of what gives the house its exuberance and unique style.

With these tweaks to the floor plan, Jonathan created the required extra sleeping areas, as well as living space that worked better when a large crew was in residence. Along the way, the kitchen and existing bathrooms were also renovated, all windows were upgraded and the exterior got a refresh, going from taupe to white, with a sky blue–painted veranda ceiling and bright red front door.

As a youth, Jonathan spent many summer days in Chester and fondly remembers the town’s cottage style. “Many houses were seasonal and intentionally not like people’s places in the city,” he says. “They were fun, relaxed and meant to celebrate summer.” These memories guided Jonathan’s eclectic mix of colour, pattern, antiques and maritime art, as did Richard’s fondness for blue, creating a contemporary but unmistakably nautical aesthetic.

Tilework is a standout element here, which is stylish and practical. “When we were in the planning stages, Richard wondered if it might be too much tile, but it works for the house by creating interest and texture, and it’s easy to maintain,” says Jonathan.

“Painting the floors white and using neutrals like jute rugs helps ground the bolder colours,” says the designer. “And punctuations of other strong colours like red, plus the patterned wallpapers and bedding keep it all in balance.”

Race Week is about competition by day and camaraderie by night — and this house embraces that tradition wholeheartedly. It’s a party house: there’s an easy flow of spaces downstairs including the new bar, and the living areas open to the spacious wraparound veranda on three sides, plus it’s close to a barn on the property that Richard recently had rebuilt for gatherings — all reasons why this house is the premier Race Week address.

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Designer Karin Bennett designed this newly built six-bedroom Kawartha Lakes cottage to feel like a European farmhouse. Set into the woods on 150 feet of waterfront, the cottage features 10-foot ceilings, expansive glazing with views of the lake, and a beautiful kitchen with dark wood cabinets, reeded details on the island, warm-veined porcelain stone and a 48-inch La Cornue range. In the great room, a built-in bench doubles as storage, a reading nook and a game-table area, while a stone fireplace and concrete mantel anchor the room. Don’t miss the three-season room facing the lake, with a pitched ceiling, wood-burning fireplace and heated concrete floors. “We’ve been working on this space for two and a half years and our clients are so happy with the result. They plan to keep this home in the family for generations to come,” says Karin.

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