Bailey-Dobson Homes with Bay Front Water Frontage

Welcome to Bailey-Dobson, a hidden gem nestled in the picturesque Longboat Key, Florida. This idyllic subdivision offers a unique blend of coastal charm and luxurious living, making it a sought-after destination for those looking to embrace the serene beauty of the Gulf Coast.

Bailey-Dobson is renowned for its spectacular bay front properties, where every day feels like a vacation. Imagine waking up to the gentle sound of waves lapping against the shore, with stunning waterfront views right from your backyard. These homes boast expansive outdoor spaces perfect for entertaining or simply enjoying the breathtaking sunsets that Longboat Key is famous for. With direct access to the bay, residents can indulge in a variety of water activities, from kayaking to fishing, all within steps of their front door.

The community is designed for those who appreciate the finer things in life, with elegant homes featuring modern amenities and timeless architecture. Whether you’re seeking a cozy retreat or a grand estate, Bailey-Dobson has something to suit every taste. The lush landscaping and well-maintained surroundings create an inviting atmosphere, perfect for families or those looking to enjoy a peaceful lifestyle.

Located just a short drive from the vibrant cultural scene of Sarasota, you can enjoy the best of both worlds—tranquility at home and excitement nearby. With pristine beaches and a welcoming community, Bailey-Dobson is not just a place to live; it’s a lifestyle. Discover your dream home in this enchanting subdivision and start creating unforgettable memories in paradise!

Newest Bailey-Dobson Homes with Bay Front Water Frontage

$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

$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

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