Bailey-Dobson Homes with Boatable Water Water Frontage

Welcome to Bailey-Dobson, a picturesque subdivision nestled in the heart of Longboat Key, Florida. Known for its serene coastal charm and stunning waterfront views, Bailey-Dobson offers an idyllic retreat for those seeking a blend of luxury and tranquility. This exclusive community is characterized by its beautifully designed homes that boast boatable water frontage, making it a paradise for boating enthusiasts and water lovers alike.

Imagine waking up to the gentle sound of waves lapping against your private dock, with the sun casting a golden glow over the shimmering waters. Each residence in Bailey-Dobson is thoughtfully crafted to maximize the breathtaking views and provide easy access to the sparkling Gulf of Mexico. Whether you are an avid sailor or simply enjoy leisurely afternoons on the water, this subdivision offers unparalleled opportunities for recreation and relaxation.

In addition to its stunning waterfront properties, Bailey-Dobson is conveniently located near a variety of local amenities. Residents can enjoy world-class dining, boutique shopping, and vibrant cultural attractions, all just a short drive away. The community is also surrounded by lush parks and pristine beaches, perfect for outdoor activities and family outings.

With its unique blend of natural beauty, luxurious homes, and a welcoming community atmosphere, Bailey-Dobson is not just a place to live—it's a lifestyle. Whether you are looking to invest in a vacation home or seeking a permanent residence, this enchanting subdivision promises a life of comfort and adventure in one of Florida's most sought-after locations. Embrace the possibilities that await you in Bailey-Dobson!

Newest Bailey-Dobson Homes with Boatable Water Water Frontage

$695,000

Bailey-Dobson SubDv.

Create your custom coastal retreat or bring the seller’s thoughtfully prepared plans to life at 561 Gulf Bay Road. This rare 9,990-square-foot vacant homesite is ideally located in the heart of Longboat Key, between the charm of Anna Maria Island and the sophistication of St. Armands Circle. Bordering the 32-acre Joan M. Durante Community Park, the property offers exceptional privacy, peaceful natural surroundings, and convenient access to scenic walking trails, a picnic pavilion, and picturesque views of Sarasota Bay and the Sarasota skyline. Imagine watching eagles, ospreys, and other native wildlife from your future home or backyard. With no HOA or deed restrictions, you have the flexibility to personalize the available plans or design a custom residence that reflects your vision and lifestyle. The property also includes deeded beach access to a quiet stretch of white sand along the Gulf of Mexico, allowing you to enjoy the best of both Gulf and bay living. Nearby destinations include Euphemia Haye, Harry’s Continental Kitchens, boutique shopping, and a neighborhood deli, with additional dining, recreation, shopping, and entertainment available throughout Longboat Key, Anna Maria Island, and Sarasota. Underground utility improvements throughout the area are complete. Previously prepared plans for a custom single-family residence and an elevation study are available upon request, providing an excellent starting point for your future island home. Buyers should independently verify current building requirements and property suitability. This is a special opportunity to build in one of Longboat Key’s most naturally beautiful and desirable locations. Schedule your private showing and begin planning your Florida coastal lifestyle. Representative Photos Added to listing showcase preliminary renderings showcasing Conditioned Square Footage of 4,936 and Unconditioned Square Footage of 4,053.

561 Gulf Bay Road, Longboat Key

$650,000

Bailey-Dobson SubDv.

Tucked along one of Longboat Key’s most peaceful and naturally beautiful streets is 681 Gulf Bay Road, a 9,000-square-foot homesite. Positioned just moments from Sarasota Bay and the Gulf of Mexico, this prime island lot offers the rare opportunity to design and build a custom coastal home in a location where nature, privacy, and convenience coexist effortlessly. Set on a quiet residential street bordered by the 32-acre Joan M. Durante Park, this property offers immediate access to shaded walking trails, mangrove boardwalks, bayfront docks, and daily wildlife sightings. With deeded access to both the beach and the bay, you are within easy reach of Longboat Key’s white sand beaches and tranquil bay waters. At the entrance to the street, iconic island favorites like Euphemia Haye and The Haye Loft make impromptu dinners and sunset cocktails delightfully effortless. The lot provides flexibility for a thoughtfully designed primary residence or second home, with space for elevated construction, a private pool, outdoor entertaining areas, and lush tropical landscaping. Located between Anna Maria Island and St. Armands Circle, you’ll enjoy the perfect balance of quiet island living and access to shopping, dining, boating, and cultural attractions in Sarasota.

681 Gulf Bay Road, Longboat Key

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