Bring your yacht. This is Sarasota waterfront living at its most refined. First time on the market, this custom-built John Cannon estate is perfectly positioned within Southbay Yacht and Racquet Club—one of Sarasota's most exclusive waterfront communities offering a true private yacht club lifestyle within the neighborhood. With a deep-water marina reserved for residents, accommodating vessels up to fifty-five feet, and direct access to the Intracoastal Waterway and Gulf of Mexico, this is a setting designed for those who expect seamless access to life on the water. Privately situated on a homesite surrounded by water on two sides, the property offers a rare level of exposure and presence. From your outdoor living spaces, the backdrop is ever-changing—boats moving through the marina, dolphins just beyond your dock, and unobstructed sunsets that define the end of each day. Inside, the residence is a study in craftsmanship and comfort, where rich wood detailing carries throughout—from the staircase to the ceilings in the main living areas and extending into the outdoor spaces—creating a warm architectural continuity rarely seen. Walls of impact-rated windows and doors bring in natural light while offering peace of mind, while expansive sliders pocket away completely—creating a perfect expression of Florida living with seamless indoor-outdoor flow and unobstructed sunset views across the bay. The kitchen is both striking and highly functional, appointed with Wolf and Miele appliances, dual Sub-Zero refrigerators, a warming drawer, two sinks, and a concealed pantry—all complemented by generous storage and oversized closets throughout the home. A fireplace anchors the main living space adding warmth and ambiance. Designed for real life as beautifully as it is for entertaining, the home also features a thoughtfully designed mudroom off the garage entry creating an organized and functional transition into the home. Outdoor living is equally elevated and designed for year-round enjoyment. Electronic roll-down screens allow you to fully enjoy the outdoor kitchen complete with a propane grill and hood sink along with composite cabinetry. Just beyond, a propane-fed fire pit creates the perfect setting for evenings by the pool. The separate air-conditioned poolside cabana offers stunning bayfront views and is equipped with its own refrigerator and ice maker—ideal for entertaining or creating a private retreat for guests. The floor plan is thoughtfully designed offering four bedrooms four-and-a-half bathrooms—a private office upstairs lounge—and expansive laundry room—balancing everyday livability with elevated design. For collectors and enthusiasts—the five-car garage with nine thousand-pound lift provides exceptional capacity while being accompanied by one hundred ten-foot private dock with jet ski lift delivering an unprecedented level of waterfront utility that is increasingly rare.Southbay Yacht & Racquet Club offers curated lifestyle featuring private marina clubhouse fitness center heated pool tennis courts pickleball courts along walking trails—all within minutes of Casey Key where pristine beaches waterfront dining relaxed coastal elegance define surrounding area.This property stands apart compare it to anything else on market value clear priced sell motivated seller