315 South Shore Drive

House never flooded, including during Hurricanes Milton and Helene, and protected by a full house generator!
Lavishly embellished with Old World authenticity, this exceptional waterfront estate evokes the grandeur of a 17th century Tuscan farmhouse. Custom built by John Cannon, the home is set on what was once Ringling’s personal yacht basin, offering protected sailboat water, 180 feet of seawall, a private dock, two boat lifts, and a dedicated kayak lift platform, all framed by sweeping panoramic water views.
From the moment of arrival, the level of craftsmanship is unmistakable. Walls are finished in aged plaster, hand made terra cotta floors have been acid washed and stained to reflect centuries of wear, and authentic frescoes and ceiling beams inspired by the Renaissance period add depth and character throughout. The great room provides a dramatic setting for entertaining with soaring 22 foot ceilings, a gas fireplace, and a wet bar accented by a hammered copper sink.
The chef’s kitchen is equipped with an Italian eight burner gas range and Brazilian soapstone countertops, while the dining room features a rare brick vaulted ceiling that reinforces the home’s Mediterranean soul and creates a truly immersive dining experience. The primary suite is a romantic retreat with his and hers walk in closets and a spa like bath wrapped in rich wood and stone finishes.
Additional spaces include two to three guest bedrooms, dual offices, a bonus room, and a wine room. A true 2,500 square foot ground level garage offers tandem parking for two to four plus vehicles, making it a dream for car collectors.
Outdoor living is exceptional, with stone and wrought iron terraces, an outdoor kitchen and bar on the main level, all designed to capture natural breezes and expansive water views. The newly completed infinity edge pool and spa create a striking visual effect, with the water appearing to seamlessly spill into the bay, while two strategically placed fire pits add warmth and dramatic ambiance after sunset.
This storybook residence is ideally located near Sarasota’s beaches, dining, and cultural attractions, offering a rare blend of architectural artistry, privacy, and timeless elegance.