Bailey-Dobson Real Estate

Bailey-Dobson Real Estate

Welcome to Bailey-Dobson, a hidden gem nestled in the picturesque Longboat Key, Florida. This charming subdivision offers a unique blend of serene coastal living and vibrant community spirit, making it an ideal destination for those seeking a tranquil yet engaging lifestyle.

Bailey-Dobson is characterized by its lush landscapes and stunning waterfront views, providing residents with a daily dose of Florida's natural beauty. The area features a variety of beautiful homes, each designed to complement the surrounding environment, with many properties boasting private docks and easy access to the sparkling waters of the Gulf of Mexico. Whether you’re looking for a cozy beach cottage or a luxurious waterfront estate, Bailey-Dobson has something to suit every taste.

Living in this delightful community means enjoying the best of both worlds: the peace and quiet of a residential neighborhood combined with the vibrant culture of Longboat Key. Residents can indulge in an array of outdoor activities, from sunbathing on pristine beaches to boating and fishing in the nearby waters. The area is also home to exquisite dining options, boutique shopping, and lush golf courses, ensuring that there’s always something to do.

With its friendly atmosphere and close-knit community, Bailey-Dobson is more than just a place to live; it’s a lifestyle. Discover the charm of this beautiful subdivision and experience the warmth of Longboat Key living. Whether you’re looking for a permanent residence or a seasonal retreat, Bailey-Dobson is waiting to welcome you home.

Newest Listings in Bailey-Dobson

561 Gulf Bay Road, Longboat Key
$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
681 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
560 Gulf Bay Road, Longboat Key
$1,270,000
Bailey-Dobson SubDv. ⋅ 34228 Zip Code
Back on the Market! RARE DOUBLE-SIZED ESTATE LOT ON LONGBOAT KEY – 18,000 SQ FT OF ISLAND LUXURY READY FOR YOUR VISION. Opportunities like this are few and far between. Nestled in one of the most coveted areas of Longboat Key, this expansive 18,000-square-foot estate lot at 560 Gulf Bay Road offers a blank canvas for your dream coastal retreat—just steps from the sugar-white sands of the Gulf of Mexico. Perfectly situated between the charm of Anna Maria Island and the upscale allure of St. Armands Circle, this oversized lot provides unparalleled space, privacy, and freedom—with no HOA and no deed restrictions limiting your design. Bordering the award-winning Joan Durante Park, you'll enjoy direct access to peaceful nature trails, scenic bayfront views, and regular visits from local wildlife including ospreys, eagles, and herons. Plus, enjoy private deeded beach access to a tranquil stretch of the Gulf, and walkable access to beloved Longboat Key staples like Euphemia Haye, Harry’s Continental Kitchen, and charming neighborhood shops. Whether you're building a serene getaway or a luxury showpiece, this one-of-a-kind homesite blends natural beauty, prime location, and limitless potential—a rare find on Florida’s Gulf Coast. Schedule your private showing today to walk the property and begin planning your Longboat Key dream build. Representative photos added, all information provided is deemed reliable but not guaranteed. The Buyer/Buyer's Agent should independently verify all information provided.,

560 Gulf Bay Road, Longboat Key
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