Bailey-Dobson Homes with Boatable Water Water Frontage

Welcome to the enchanting Bailey-Dobson subdivision, nestled in the heart of Longboat Key, Florida, within the picturesque Manatee County. This idyllic community offers a unique blend of coastal charm and modern luxury, making it a coveted destination for those seeking the ultimate waterfront lifestyle.

Bailey-Dobson is renowned for its stunning homes that boast boatable water frontage, providing residents with direct access to the shimmering waters of the Gulf of Mexico and the serene canals that weave through the area. Imagine stepping out of your backyard and onto your private dock, ready to embark on a day of fishing, boating, or simply soaking up the sun on your vessel. With the gentle sound of waves lapping against the shore and breathtaking sunsets painting the sky, every day in Bailey-Dobson feels like a vacation.

The subdivision is characterized by beautifully designed homes that reflect the coastal aesthetic, featuring open floor plans, expansive windows, and outdoor living spaces perfect for entertaining. Surrounded by lush tropical landscaping, residents enjoy a serene environment that fosters relaxation and tranquility.

In addition to its stunning waterfront properties, Bailey-Dobson is conveniently located near the vibrant amenities of Longboat Key, including exquisite dining, boutique shopping, and pristine beaches. Whether you're looking for a peaceful retreat or an active lifestyle filled with water sports and community events, Bailey-Dobson offers the perfect blend of both.

Come explore the charm of Bailey-Dobson, where your dream of waterfront living awaits!

Newest Bailey-Dobson Homes with Boatable Water Water Frontage

$695,000

Bailey-Dobson SubDv. ⋅ 34228 Zip Code

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. ⋅ 34228 Zip Code

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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