Bailey-Dobson Homes with Bay Front Water Frontage

Welcome to Bailey-Dobson, a hidden gem nestled in the heart of Longboat Key, Florida. This picturesque subdivision offers an idyllic coastal lifestyle, where the serene beauty of bay-front living meets the charm of a close-knit community. Imagine waking up each morning to the gentle sound of waves lapping against your private dock, with stunning water views that stretch as far as the eye can see.

Bailey-Dobson is renowned for its exquisite homes, many of which boast direct bay-front waterfrontage. These properties are designed to maximize the breathtaking vistas and provide residents with a seamless blend of indoor and outdoor living. Picture yourself enjoying sunset dinners on your spacious deck, or hosting lively gatherings with friends and family while the sun dips below the horizon, painting the sky in vibrant hues.

The subdivision is not just about stunning homes; it’s also about a lifestyle. Residents of Bailey-Dobson enjoy easy access to the pristine beaches of Longboat Key, where sun-soaked days can be spent swimming, paddleboarding, or simply relaxing on the shore. The area is also home to a variety of boutique shops, gourmet restaurants, and cultural attractions, ensuring that there’s always something new to explore.

Whether you’re looking for a permanent residence or a vacation retreat, Bailey-Dobson offers the perfect blend of luxury, comfort, and coastal charm. Discover the magic of bay-front living in Longboat Key, where your dream home awaits amidst the tranquility of Florida’s stunning waterways. Come, experience the allure of Bailey-Dobson and make it your own slice of 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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