Bailey-Dobson Real Estate

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

Bailey-Dobson is characterized by its lush landscapes, well-maintained homes, and a friendly community atmosphere. Residents enjoy spacious lots adorned with tropical foliage, creating a vibrant and inviting environment. The architecture here is a delightful mix of modern elegance and classic Floridian charm, ensuring that every home feels like a unique retreat.

Living in Bailey-Dobson means embracing the best of Longboat Key’s stunning natural beauty. Just a short stroll away, you’ll find pristine sandy beaches with crystal-clear waters, perfect for sunbathing, swimming, or leisurely walks at sunset. The area is also renowned for its abundant outdoor activities, including kayaking, paddleboarding, and world-class fishing.

For those who appreciate fine dining and shopping, the nearby St. Armands Circle offers an array of boutique shops and gourmet restaurants, ensuring that you’re never far from a delightful culinary experience. Plus, with easy access to the vibrant city of Sarasota, cultural attractions, art galleries, and entertainment options are just a short drive away.

Bailey-Dobson is more than just a place to live; it’s a community where neighbors become friends and memories are made. Discover the charm of this beautiful subdivision and experience the quintessential Florida lifestyle in Longboat Key!

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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