Architectural Gems: Unique High-End Homes in Longboat Key

Stretching a little over 10 miles from north to south and no more than a mile from east to west at its widest point, Longboat Key is not unlike other barrier islands you'll find up and down Florida's celebrated Gulf Coast—a spot bathed in sun, sand, and the shimmering turquoise waters of the Gulf of Mexico and Sarasota Bay. But a leisurely drive along the Gulf of Mexico Drive reveals a treasure trove of architectural wonder. Venture further into any of the island's canal-laden waterfront neighborhoods, and the sheer magnitude of Longboat's architectural significance becomes clear.

As a showcase of high-end, residential brilliance, luxury homes reflect the elegance, history, and innovation of coastal living; it's challenging to pick a starting point from which to appreciate the depth of Longboat Key's architectural diversity. It's a living museum of residential design that includes mid-century moderns, Old Florida-inspired homes and Key West-style retreats, European-inspired estates including canal-influenced Venetian homes and Mediterranean-styled palazzos, and a proliferation of sleek Modern statement-making estates.

Of course, even in a collection as extensive as what's found on Longboat Key, certain homes rise above the rest and claim genuine one-of-a-kind property status. Below, we explore the timeless and trendsetting residences that redefine the already lofty standards of high-end architectural artistry.

The first home on our list of architectural gems is Serenissima, a grand Venetian-inspired estate in Longboat Key Club's Regent Court. Completed in 2005 after five years of construction, the home earned notoriety in 2017 when it hit the market with a listing of $26.5 million—at the time, the loftiest single-family listing ever in Sarasota. The 1.18-acre property boasts nearly 20,000 square feet of living space with six bedrooms, six full baths, and two half-baths.

Notable features include an opulent gilded birdcage elevator, a marble-clad main hall with a glass sky dome, hand-painted dining room murals, a grand salon for 100 guests, a master chef's kitchen, and a Byzantine-styled rear loggia with archways and columns standing sentry over an infinity pool overlooking the Gulf of Mexico.

Ohana, one of Longboat Key's most extraordinary properties, is a sprawling estate that blends tropical resort-style luxury with high-end craftsmanship. Constructed with teak, clear Douglas fir, Philippine shell stone, and Sipo African mahogany, the home embodies a seamless connection between architecture and nature. The estate features multiple pavilions—a series of immersive experiences—including a 5,300-square-foot Gulf-facing main living and dining area with an open kitchen, media room, laundry, and primary suite with an exercise room.

A separate 1,200-square-foot suite sits to the south, while the original ground-level beach house was transformed into a guesthouse with three-bedroom suites. There's also a tennis court, a pool, a spa, and a thatched-roof hut for open-air lounging. Despite architectural accolades, Ohana has drawn attention for a seawall, that protrudes onto the beach's natural shoreline. While opinions vary on that bold territorial claim, the property's boundless allure is undeniable.

The 10,000-square-foot beachfront estate at 3105 Gulf of Mexico Drive is a striking blend of elegant luxury and whimsical entertainment. Most notably, it features a waterslide that extends from the third-story rooftop deck down to the beachfront pool. The five-bedroom residence offers breathtaking Gulf views and a host of high-end amenities, not the least of which includes a saltwater infinity pool complemented by an outdoor kitchen with custom cabinetry, creating an ideal space for indoor-outdoor entertaining.

Making the most of every square inch of the property, the home's air-conditioned seven-car garage spans the ground floor, while the rooftop deck serves as a private retreat, complete with a twisting waterslide. Interiors are awash in marble, glass, and wood textures, creating a resort-style vibe in one of the region's most unique residences.

Considered small by Longboat Key standards, this 2,500-square-foot two-bedroom, three-bath home overlooking Sarasota Bay casts an endearing footprint on the island's design landscape. Designed by architect Jerry Sparkman, the property, which was purpose-built as a winter retreat, is efficient and extravagant. Contemporary boldness is expressed in the home's swooping roofline, which envelopes a massive wall of glass—a modernist take on the classic, all-caps mountainside A-frame cabin, repurposing it as a near-cursive, lowercase-A canal home.

The property's artistic expression doesn't stop at the exterior, boasting a whitewashed facade, cantilevered secondary structure, and geometric roof inserts. The interior counters with warm tones and freestanding art niches, which counter the lack of non-glass-clad wall space. The overall design further helps manage South Florida's abundance of heat and light without sacrificing the enjoyment that both bring.

Indeed, a number of celebrities own homes up and down the Sarasota coast, but rarely do they show up and create a custom retreat from the ground up. Not so with fashion designer and Project Runway star Michael Kors. After purchasing twin lots totaling 2.25 acres with Gulf frontage along the northern end of Longboat Key, Kors commissioned Stelle Lomont Rouhani Architects to create a dreamy beach estate featuring eight bedrooms, 10 bathrooms, and spanning 6,300 square feet. A modern retreat that evokes visions of mid-century Florida resorts, construction included primarily teak, concrete, and glass.

There's no shortage of amenities, and attention-to-detail design touches in this sleek coastal architecture that effortlessly blends into its seaside setting. Crafted for both cozy private moments and lavish entertaining, one finds private and communal decks that gaze out upon a 70-foot by 20-foot pool, a 55-foot planter, and a lush tropical landscape that includes fishtail and sabal palms, and sea grape and jasmine foliage.

Finally, while more recently built canalside estates and Gulf-frontage compounds are the most celebrated homes on Longboat Key, the island's architectural heritage extends more than 100 years into the past. One of these rare gems is in Longboat Village, an original settlement at the island's northernmost point. The century-old beach cottage at 680 Broadway is a testament to timeless, Old Florida charm. Built using masonry blocks in the late 1920s, this home has weathered many storms, both natural and of the human variety. Yet, it effortlessly retains vintage appeal while sporting all the modern comforts one expects from a 21st-century home.

One of only about ten original homes left from the pre-war era, the small main cottage and second-floor guest house both live big. Typical of homes of this age, several design touches enhance its appeal, including a wood-burning fireplace, screened-in porch with swing, original shiplap walls, and freestanding clawfoot tub.

This exclusive island, renowned for its elegance and luxury, 12 miles of uninterrupted beach, and panoramic waterfront views, also boasts some of the unique high-end residences in Southwest Florida. For visitors and residents alike, Longboat Key's architectural landscape is a rare find where each home tells a unique story, and the breadth of design is at the heart of every plot. If you're interested in learning more and ready to find your Longboat Key architectural gem, or looking to capitalize through selling one of the island's notable properties, contact The Kepecz-Hays Team today to begin your Longboat Key real estate journey.