Bailey-Dobson Homes with Beach Access Water Frontage

Welcome to Bailey-Dobson, a hidden gem nestled in the picturesque Longboat Key, Florida. This charming subdivision offers residents a unique blend of coastal living and serene tranquility, making it an ideal spot for those seeking a slice of paradise. With its stunning waterfront properties, Bailey-Dobson is renowned for its direct beach access, allowing homeowners to enjoy the sun, sand, and surf just steps from their front door.

Imagine waking up each morning to the gentle sound of waves lapping against the shore, with your morning coffee in hand as you take in the breathtaking views of the Gulf of Mexico. The homes in Bailey-Dobson are designed with coastal elegance in mind, featuring spacious layouts, modern amenities, and outdoor spaces perfect for entertaining or simply soaking in the Florida sunshine. Many of these properties boast private docks and water frontage, providing endless opportunities for boating, fishing, or kayaking right from your backyard.

In addition to the beautiful homes, the Bailey-Dobson community is conveniently located near a variety of local attractions, including upscale dining, boutique shopping, and vibrant cultural experiences. Residents enjoy a laid-back lifestyle surrounded by lush landscapes and friendly neighbors, making it the perfect place for families, retirees, or anyone looking to escape the hustle and bustle of city life.

Whether you’re searching for a permanent residence or a vacation getaway, Bailey-Dobson in Longboat Key offers an idyllic coastal lifestyle that is truly unmatched. Come and experience the beauty of waterfront living in this charming subdivision today!

Newest Bailey-Dobson Homes with Beach Access Water Frontage

$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

$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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