Owning a vacation home in Florida was never this Connecticut couple’s wish—at least, as far as the wife was concerned. “My husband, on the other hand, was always sold on having a second residence here,” she notes. But one trip to visit a family friend quickly changed her mind. “As soon as we drove into the neighborhood, I thought, ‘Oh my, this is lovely,’ ” she recalls. Embarking on a house hunt soon thereafter, the pair found a listing that intrigued them: a 20-year-old British Colonial-style residence with an Asian influence, an interior courtyard, a guest suite and a cabana adjacent to the pool. “Once we virtually toured it, we knew this was the home we wanted,” she remembers. “Forty-eight hours later, we owned it.”

Because the Windsor property had great bones and a generous layout, the owners felt the need for only a minor renovation that included revamping the bathrooms and kitchen, adding a second cabana and tending to the landscaping. So they assembled a formidable team with their longtime designer, Melissa Lindsay; the original architect, Clemens Bruns Schaub; landscape architect Neil Sickterman; and builder Kenny Nolen, whose firm constructed the house.

Having worked closely with the couple on their primary residence, Lindsay knew their preferences well. “The wife loves pattern, color and interesting mixes of both,” the designer says. “She didn’t want your classic beach house with blue and white—or a preppy or coastal vibe.” Lindsay began by tackling the most challenging space: the living room, a long, rectangular area that has sight lines to the dining room and into the kitchen. The starting point turned out to be an oversize brass floor lamp with a botanical shape that the designer and the wife instinctively discovered together during a sourcing excursion. “We both ran to it,” the client recalls with a laugh. “It was bought before we even had a furniture arrangement in mind.” Centering the lengthy room, the lamp serves as a focal point while simultaneously separating and connecting two seating areas. One end, which contains the television, features linear upholstered furnishings, while the other responds with sculptural forms, including a rounded coffee table, a crescent-shaped sofa and armless rattan chairs. “The curved pieces work well with the shape of the lamp, invite you in and counteract the box-like space,” Lindsay explains. “I love mixing unexpected styles. It creates design tension in a room and gives it soul.”

Variations of cream, teal and salmon establish the living room’s color palette and flow into the adjoining dining room, which the designer wrapped in a hand-painted floral wallpaper. “The pattern gives it a whimsical feel,” she says, “and I could pull from its colors.” A warm pink, for instance, backs the dining chairs, and teal brightens the room’s new pantry, formerly a closet.

While mindful of creating harmony in the main house, Lindsay viewed the property’s freestanding outbuildings as opportunities for presenting a different aesthetic. “Because you’re entering a whole new space,” she says, “it allowed me to be creative in a way in which I could shift the energy.” She shrouded the guest suite in an exuberant palm pattern, offering a flair that is more edgy than tropical. In the two cabanas, she then crafted distinct atmospheres— the original lined with a bold teal grass cloth for a “masculine, Havana vibe,” Lindsay describes, and the new one a sunny retreat with touches of yellow. “They’re just steps from the pool,” she adds, “and it feels like you’re in the lush greenery surrounding them.”

These structures augment the property’s outdoor-focused sensibility, says Schaub, whose original plans for the home carefully considered orientation to the shade, sunlight and breeze. “The inside supports the outside, rather than the other way around,” he explains, citing the open galleries and main living pavilion that overlooks the pool. “All of that remained with the new owners. They embraced the spirit of the house nicely.” This is evident upon opening the front door, which reveals not an interior as expected but rather a verdant courtyard. “I call it ‘the Alice in Wonderland experience,’” Schaub muses. “You think you’re going inside a home, but you’re in a garden.” Taking cues from the architecture, particularly the Asian-influenced rooflines, Sickterman introduced plantings such as traveler’s palms, bougainvillea, yellow Tabebuia and short hedges. “I imagined the courtyard being a Singapore-style garden, with a timeless, historic appearance to it,” he says.

Although spending time in the Sunshine State was never part of the wife’s plan, a change of heart came easily thanks to a sense of familiar surroundings. “We’re amazed at how immediately comfortable this house felt,” she says. “It feels like home.”