Bailey-Dobson Real Estate

Bailey-Dobson Real Estate

Welcome to Bailey-Dobson, a hidden gem nestled in the picturesque surroundings of Longboat Key, Florida. This charming subdivision offers an idyllic lifestyle where the sun-kissed beaches meet tranquil living, making it the perfect retreat for those seeking a slice of paradise.

Bailey-Dobson is renowned for its serene atmosphere and close-knit community, providing residents with a sense of belonging. The homes here are beautifully designed, reflecting the coastal aesthetic that Longboat Key is famous for. With a variety of architectural styles, ranging from modern beach houses to elegant Mediterranean villas, there’s a perfect residence for every taste.

One of the standout features of Bailey-Dobson is its proximity to some of the finest beaches in Florida. Just a short stroll away, residents can enjoy the soft sands and crystal-clear waters of the Gulf of Mexico. Whether you're looking to bask in the sun, take a leisurely swim, or indulge in water sports, the beach is right at your doorstep.

In addition to its natural beauty, Bailey-Dobson is conveniently located near a variety of shopping, dining, and entertainment options. Explore the vibrant local scene, where you can savor fresh seafood at waterfront restaurants, shop at boutique stores, or enjoy cultural events throughout the year.

For families, the subdivision is served by excellent schools and community amenities, making it a wonderful place to raise children. With its perfect blend of relaxation and recreation, Bailey-Dobson truly captures the essence of coastal living. Come discover your dream home in this enchanting subdivision where every day feels like a vacation!

Newest Listings in Bailey-Dobson

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

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

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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Sasha Volosevych

Sasha Volosevych is a dedicated Florida Realtor proudly serving Sarasota and Florida's beautiful Gulf Coast communities. In just the past three years, she has established herself as one of the area's top-performing agents, consistently ranking among the Top 5 agents in her company while closing more than $100 million in sales and helping over 200 buyers and sellers achieve their real estate goals. Known for her in-depth market knowledge, strategic negotiation skills, and personalized approach, Sasha is committed to making every transaction as smooth and successful as possible. Whether you're buying your first home, selling a luxury waterfront property, building a new construction home, or expanding your investment portfolio, she provides the expertise, communication, and guidance needed to make confident decisions. Sasha specializes in luxury homes, waterfront properties, new construction, resale homes, and investment opportunities throughout Sarasota and Florida's Gulf Coast. She takes pride in delivering exceptional service, honest advice, and results-driven representation tailored to each client's unique needs. For Sasha, real estate is about much more than buying or selling a home—it's about building lasting relationships, earning trust, and helping her clients achieve their dreams. Her goal is to provide a seamless, stress-free experience while helping every client confidently move into their next chapter.

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