Bailey-Dobson Real Estate

Bailey-Dobson Real Estate

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

Bailey-Dobson is renowned for its lush landscapes and beautifully maintained properties that reflect the quintessential Floridian vibe. The subdivision is characterized by its friendly community atmosphere, where neighbors become friends and gatherings are a common occurrence. With tree-lined streets and a variety of architectural styles, Bailey-Dobson boasts a warm, inviting ambiance that feels like home from the moment you arrive.

Location is everything, and Bailey-Dobson is perfectly situated to enjoy the best of Longboat Key. Residents have easy access to stunning beaches, where soft sands and crystal-clear waters await. Whether you’re looking to bask in the sun, indulge in water sports, or take leisurely strolls along the shore, this coastal paradise has it all. In addition, the nearby dining and shopping options cater to every taste, from fine dining establishments to quaint local boutiques.

For those who appreciate outdoor activities, the area is rich with parks and recreational facilities, offering opportunities for hiking, biking, and enjoying nature. The community also prides itself on its safety and excellent schools, making it a perfect choice for families.

In Bailey-Dobson, you’re not just buying a home; you’re investing in a lifestyle filled with warmth, community, and the beauty of Florida living. Come and discover the charm of Bailey-Dobson—your dream home awaits!

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

Start Your Search

Steven Koger

Customer-Focused. Knowledgeable. Experienced. Results-Driven. With over 20 years of experience representing buyers and sellers in both residential and commercial real estate, I bring a strong combination of industry knowledge, business experience, and dedication to every transaction. In addition to my real estate background, I have owned investment properties and successfully operated two small businesses, giving me valuable insight into negotiations, financial decision-making, and client service. My career and business experience have taken me from Virginia to Las Vegas and now to Florida, allowing me to work in a variety of markets and navigate many different types of transactions. No challenge is too small or too complex — I am committed to helping my clients achieve the best possible results. As a second-generation Realtor whose father owned multiple Century 21 offices, real estate has always been a part of my life. I understand the hard work, attention to detail, and dedication it takes to succeed in this industry and to help clients maximize their goals. I also hold an undergraduate degree in accounting, which gives me a strong analytical approach to evaluating real estate opportunities and managing the details of each transaction. I enjoy marketing properties, staying current with market trends, and developing strategies that help my clients succeed in today’s competitive market. I look forward to the opportunity to work together and help you achieve your real estate goals.

Learn More

Browse Bailey-Dobson Homes by Water Frontage