Bailey-Dobson Real Estate

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

Bailey-Dobson is known for its picturesque streets lined with lush palm trees and beautifully manicured gardens, creating a welcoming atmosphere that feels like home the moment you arrive. The subdivision boasts a variety of stunning properties, from elegant single-family homes to luxurious waterfront estates, each offering unique architectural styles and modern amenities that cater to diverse tastes and preferences.

One of the standout features of Bailey-Dobson is its proximity to the pristine beaches of Longboat Key. Residents can easily access the soft, sandy shores and crystal-clear waters, perfect for sunbathing, swimming, or enjoying a leisurely stroll at sunset. The area is also surrounded by lush parks and nature preserves, providing ample opportunities for outdoor activities such as biking, kayaking, and birdwatching.

For those who enjoy dining and shopping, Bailey-Dobson is conveniently located near a variety of local restaurants, boutiques, and cafes, offering a delightful mix of flavors and experiences. The community is also known for its friendly neighbors and active social scene, making it easy to forge lasting friendships and connections.

Whether you’re looking for a peaceful retreat or an active lifestyle, Bailey-Dobson in Longboat Key is the perfect place to call home, where every day feels like a vacation. Come and discover the charm of this enchanting subdivision today!

Newest Listings in Bailey-Dobson

$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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