Bailey-Dobson Real Estate

Welcome to Bailey-Dobson, a prestigious subdivision nestled in the heart of Longboat Key, Florida. This exclusive community is located in the beautiful Manatee County, offering residents a luxurious coastal lifestyle with a touch of Southern charm.

Bailey-Dobson is renowned for its upscale homes, lush landscaping, and serene atmosphere, making it the perfect retreat for those seeking a peaceful and elegant living environment. The neighborhood features a variety of architectural styles, from modern beachfront estates to traditional Southern-inspired residences, ensuring there is a home to suit every taste.

Residents of Bailey-Dobson enjoy easy access to pristine beaches, world-class golf courses, upscale shopping, and fine dining options. The community is also in close proximity to top-rated schools, medical facilities, and recreational amenities, making it an ideal place to raise a family or enjoy retirement in style.

Whether you are looking for a permanent residence or a vacation home, Bailey-Dobson offers the perfect blend of luxury, comfort, and convenience. Come experience the best of Longboat Key living in this exclusive subdivision where every day feels like a retreat.

Newest Listings in Bailey-Dobson

$650,000

Bailey-Dobson SubDv. ⋅ 34228 Zip Code ⋅ A4683898 MLS ⋅ Active Status

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 ⋅ A4649200 MLS ⋅ Active Status

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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