Bailey-Dobson Homes with Anna Maria Elementary Elementary School

Welcome to Bailey-Dobson, a charming subdivision nestled in the picturesque Longboat Key, Florida! This delightful community offers a unique blend of coastal living and suburban tranquility, making it an ideal place for families, retirees, and anyone looking to enjoy the serene beauty of the Sunshine State.

Bailey-Dobson boasts a variety of beautifully designed homes that cater to diverse lifestyles and preferences. With lush landscaping and well-maintained streets, this neighborhood exudes a warm and welcoming atmosphere. Many residences feature spacious floor plans, modern amenities, and private outdoor spaces perfect for entertaining or simply soaking up the sun. The proximity to the stunning Gulf of Mexico means residents can enjoy the best of beach life, from sunbathing to water sports, just moments from their front door.

Families will appreciate the community's close-knit feel and the convenience of being served by the highly regarded Anna Maria Elementary School. Known for its dedicated staff and engaging curriculum, this school ensures that children receive a quality education in a nurturing environment. The commitment to academic excellence and character development makes it a sought-after choice for families in the area.

In addition to the educational benefits, Bailey-Dobson residents enjoy easy access to local parks, shopping, dining, and recreational activities. Whether you are strolling along the beach, exploring nearby nature trails, or indulging in fresh seafood at a local restaurant, there is always something to enjoy in and around this vibrant community.

Discover the charm of Bailey-Dobson—where coastal living meets community spirit in the heart of Longboat Key!

Newest Bailey-Dobson Homes with Anna Maria Elementary Elementary School

$695,000

A4701851 MLS

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

A4683898 MLS

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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