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530 Jessmyth Drive, Longboat Key
$5,985,000
Longboat Key Estates SubDv. ⋅ 34228 Zip Code
Currently under construction and masterfully designed for the ultimate waterfront lifestyle, this extraordinary canal-front estate in Longboat Key Estates offers an exceptional blend of luxury, comfort, and coastal elegance. Boasting 5 bedrooms, 7 bathrooms, and more than 4,500 square feet of thoughtfully crafted living space, the home features solid block construction and hurricane-impact windows, delivering both enduring quality and peace of mind. Designed to maximize seamless indoor-outdoor living, the southwest-facing pool and expansive entertaining areas capture spectacular sunset views over Sarasota Bay and toward the Gulf of Mexico. The elevated lanai is highlighted by detailed ceiling craftsmanship and a fully equipped outdoor kitchen, creating the perfect backdrop for entertaining guests year-round. For boating enthusiasts, the property includes a brand-new seawall and direct bay access, providing effortless navigation to the surrounding waterways. Residents also enjoy private beach access and exclusive HOA amenities, including a beachfront tiki hut for social gatherings and a bayside dock ideal for fishing, kayaking, swimming, or simply relaxing along the water’s edge. Nearby Bayfront Park offers additional recreational amenities including tennis courts, pickleball, walking trails, and a dog park. With construction already underway, buyers have the rare opportunity to personalize select finishes and tailor the residence to their individual style and vision. Ideally situated just minutes from St. Armands Circle, downtown Sarasota, and the world-renowned beaches of Longboat Key, this remarkable estate presents an unmatched opportunity to experience coastal living at its best.

530 Jessmyth Drive, Longboat Key
581 Rountree Drive, Longboat Key
$2,500,000
Longboat Key Estates SubDv. ⋅ 34228 Zip Code
BREAKING NEWS: LUXURY WATERFRONT LIVING • LONGBOAT KEY, FLORIDA! A Rare Opportunity to Build Your Dream Home Between Two Brand-New Mansions!! Discover an exceptional build-ready waterfront lot in Longboat Key Estates, featuring 100 feet of deep-water canal frontage and 117 feet of depth with direct boating access to Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico. Well-known John Cannon Custom Homes offers a selection of distinctive home plans designed to complement this extraordinary setting. Enjoy sunrise over the Bay and spectacular Gulf sunsets, plus PRIVATE DEEDED BEACH ACCESS with a charming Tiki Hut directly across Gulf of Mexico Drive. Just minutes from Sarasota’s world-class dining, shopping, arts and culture, championship golf, marinas, and Gulf beaches. Bayfront Park is also next door with pickleball, tennis, kayaking, fitness, and more. Boating. Beach. Bay. Gulf. Sarasota. An extraordinary location for an extraordinary home!! Longboat Key Estates is one of the only communities on Longboat Key with underground utilities! Sellers are MOTIVATED!

581 Rountree Drive, Longboat Key
617 Rountree Drive, Longboat Key
$2,150,000
3 Beds ⋅ 2 Baths ⋅ Longboat Key Estates SubDv. ⋅ 34228 Zip Code
Escape to your own waterfront haven at 617 Rountree Drive, a hidden gem nestled in the luxurious Longboat Key Estates community! Tucked away on a tranquil street, this 3-bedroom, 2-bathroom home offers an exceptional coastal lifestyle along with strong investment upside in an area surrounded by multi-million-dollar modern updates. Step directly into your backyard to take in serene canal views outside stretching toward Sarasota Bay and the Intracoastal waterway, complete with 100 feet of upgraded seawall (2022) and a 16,000-lb boat lift (2022)—saving you massive upfront capital costs and offering immediate, bridge-free water access. As a resident, you also enjoy deeded beach access to a resident-only Gulf-front beach and Tiki hut just a five-minute stroll away. Whether you choose to enjoy the existing home, customize the footprint, or build new, this generous lot provides an ideal canvas to capitalize on the neighborhood's continuing transformation. All this, just minutes from Bayfront Park's pickleball and tennis courts, kayak launches, St. Armands Circle, fine dining, downtown Sarasota, Van Wezel Performing Arts, shopping, Sarasota-Bradenton International Airport, and the wonderful Florida lifestyle!

617 Rountree Drive, Longboat Key

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