Bailey-Dobson Homes with Bayshore High High school

Welcome to Bailey-Dobson, a hidden gem nestled in the picturesque Longboat Key, Florida. This charming subdivision offers a unique blend of coastal living and suburban tranquility, making it an ideal destination for families, retirees, and anyone seeking a serene escape by the water.

Bailey-Dobson is characterized by its beautifully landscaped streets, where palm trees sway gently in the ocean breeze and neighbors greet each other with a warm smile. The community is known for its spacious homes that boast modern amenities, stylish designs, and stunning views of the nearby bay. Each residence is thoughtfully crafted to provide comfort and elegance, perfect for creating lasting memories with family and friends.

One of the standout features of Bailey-Dobson is its proximity to Bayshore High School, which is highly regarded within the community. Families with school-aged children will appreciate the convenience of having quality education just a stone's throw away. The school’s commitment to academic excellence and extracurricular activities ensures that students receive a well-rounded experience, preparing them for future success.

Living in Bailey-Dobson means embracing the Longboat Key lifestyle, where pristine beaches, gourmet dining, and vibrant cultural experiences are just minutes away. Residents can enjoy a day soaking up the sun on the soft sands, exploring local boutiques, or indulging in fresh seafood at waterfront restaurants.

Discover the charm of Bailey-Dobson and experience the perfect blend of coastal living and community spirit. Your dream home awaits in this idyllic Florida subdivision!

Newest Bailey-Dobson Homes with Bayshore High High school

$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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