242 Oak Avenue

One of the MOST BEAUTIFUL HOMES on Anna Maria Island, this remarkable family estate has it all! A stunning gated waterfront location, beautiful design and quality, elevated construction.

Located on the only street on the island that directly accesses both the famous beaches of Anna Maria and the pristine boating waters of Bimini Bay, this property stands out as a true family residence. Set on a stunning triangular property with over 500 feet of water frontage, every room in this home has water views, while the spacious open plan design creates a seamless flow between indoor and outdoor Florida living. Throughout the home, imported cabinetry and Tahitian-inspired finishes reflect craftsmanship and thoughtful design. In the main house, there are two luxurious primary bedrooms, enhanced with full ensuites, while in the guest house, connected by a covered bridge, there are two additional bedrooms, a full bathroom and a kitchenette providing a private retreat for your guests or the grandkids!

Stepping out of the glass walled elevator into the huge vaulted great room, you are met with spectacular views over Bimini Bay. Twenty foot wide, hurricane safe, glass doors disappear into the outside walls, allowing a seamless flow of indoor outdoor living from the great room onto the massive covered lanai. The centrally located chef’s kitchen, with stunning bamboo finish and an illuminated glass countertop, adjoins both the inside family dining room, with seating for ten, and the 800 square foot outdoor lanai. Steps away there is a full outdoor kitchen, a Teppanyaki cooking table with seating for eight, a built in fire table, outdoor dining table, lounge seating areas and direct access to the whirlpool spa…all just off the kitchen and at the same elevated and protected level as the main floor. And all with unobstructed views of the dolphins and manatees in Bimini Bay.

One level below, next to the gym, the resort-style pool has fire and waterfall features and is set in tropical gardens that lead to a waterfront “sandy beach” fire pit, where family and guests gather beneath the stars. A 20-foot dock is ideal for launching the Kayaks or SUP, while serious boating enthusiasts will appreciate 500 feet of new concrete reinforced seawall, a 60-foot boat dock, and a 12,000 lb. boatlift, with direct access to Tampa Bay and the Gulf of Mexico.
With far too many features to list, this estate truly represents one of the island’s most distinguished offerings and has to be seen be truly appreciated. Private viewings are available exclusively by appointment. Meanwhile, you are welcome to enjoy a narrated video preview at the property’s private website, amidreamhome.com

Listed by: Michael Saunders & Company 941-896-9981. Listing information ©My Florida Regional MLS DBA Stellar MLS 2025. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale. Availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase. All other use is strictly prohibited and may violate relevant federal and state law. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Properties displayed may be listed or sold by various participants in the MLS. Data last updated on Saturday, December 6th, 2025 at 07:38:48 AM.
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