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The Pinnacle of Coastal Living: Prestigious Estates in Anna Maria Island

The Pinnacle of Coastal Living: Prestigious Estates in Anna Maria Island

Along the sparkling waters of the Gulf of Mexico, Anna Maria Island provides oceanfront living and laid-back tropical charm. This enchanting destination is surrounded by water, providing residents with breathtaking views and a serene atmosphere. The island's quaint streets are dotted with locally owned boutiques, adding a touch of unique character and fostering a strong sense of community.

Anna Maria Island is comprised of three picturesque villages: the city of Anna Maria, Holmes Beach in the center, and Bradenton Beach at the southern tip toward Longboat Key. Each village boasts distinctive charm, contributing to the island's overall appeal. Whether strolling through the charming shops or enjoying the tranquil ocean breeze, life on Anna Maria Island epitomizes coastal living at its finest.

Luxurious coastal retreat

110 10th St S, Bradenton Beach

This home, on the serene Mandalay Bay, is a masterpiece of luxurious coastal living for $9,495,000. This stunning estate spans 5,052 square feet and features seven bedrooms and seven baths. It is designed with an artful eye and has stylish upscale finishes. It comes turnkey furnished for immediate enjoyment or short-term rental opportunities, perfect for maximizing earnings and building generational wealth.

Thanks to its walls of glass doors and spacious balconies, the residence offers spectacular 360-degree views from the beach to the bay. The primary bedroom is a haven of tranquility, with an en-suite luxurious bath with a soaking tub, walk-in shower, and steam room. Culinary enthusiasts will appreciate the two full kitchens with beautiful cabinetry, marble countertops, and high-end appliances.

Entertainment options include:

  • A theater and game room
  • A pool table
  • An outdoor kitchen with a bar and dining table on the covered porch
The outdoor oasis includes a large heated pool, waterfall, and spa. The dock has two boat lifts and a jet ski lift. The rooftop deck provides a perfect vantage point to soak in the unparalleled views and sunsets. This high-end, well-appointed home could be your legacy for generations to come.

Coastal elegance

511 Bayview Dr, Holmes Beach

This luxury waterfront home, priced at $6,500,000, epitomizes coastal elegance. Custom-built in 2020, this exquisite residence features four bedrooms and five baths in its 3,353 square feet of living space, all situated on a 9,000-square-foot lot. The home's direct bayfront location offers breathtaking views of the Intracoastal waterway, perfectly complemented by magazine-worthy outdoor living areas.

Designed with a modern coastal architectural plan, the open living, dining, and chef's kitchen spaces provide a seamless flow for entertaining and everyday living. The grand staircase and elevator add a touch of sophistication, while the two large lanais offer an array of options for outdoor relaxation. One lanai boasts an outdoor kitchen, dining area, and generous sitting areas — all with views of the dramatic infinity pool and spa overlooking the bay's pristine waters.

The interior is adorned with engineered wood floors and vaulted ceilings, enhancing the airy, spacious feel. Lush, tropical landscaping surrounds the home, situated on a quiet cul-de-sac, ensuring privacy and tranquility. This resort-style home is a testament to luxurious waterfront living at its finest.

Beachfront bliss

915 N Shore Dr, Anna Maria

This direct beachfront gem, priced at $5,950,000, offers luxurious coastal living. The artfully designed and decorated home features four bedrooms and four baths across 2,870 square feet of stylish, upscale finishes. The turnkey furnished residence showcases walls of glass that provide breathtaking views of Tampa Bay and the iconic Sunshine Skyway Bridge.

Floor-to-ceiling glass sliders in the main living and dining areas open to a spacious bayfront balcony with serene waterfront vistas. The adjacent open kitchen is a chef's dream, featuring shaker-style cabinetry, a generous island/breakfast bar, lovely quartz countertops, and stainless-steel JennAir appliances.

Each of the four en-suite bedrooms is separated for privacy and offers generous bathrooms and gracious balconies with tropical vistas. Outdoor living is equally impressive, with covered poolside dining and seating areas just a few steps from the beach. With a rental history available upon request, this home is an excellent investment opportunity.

Island oasis

116 50th St, Holmes Beach

This unique, oversized island home, priced at $4,999,000, is designed for luxurious short-term weekly rentals. The custom-built residence, completed in 2015, features six bedrooms and seven baths within its expansive 4,332 square feet, set on a generous 12,400 square foot lot. Fully furnished and boasting an established book of business with future rental bookings secured for 2025, this property is an exceptional investment opportunity.

The home includes three large master suites, two additional en-suite bedrooms, and a charming bunkroom area. The dream kitchen has a retro gas range, a Sub-Zero side-by-side refrigerator, a U-Line under-counter fridge, a wine cooler, and a spacious butler's pantry. Just steps from beach access, the outdoor spaces are equally impressive, featuring a lagoon-style pool with a waterfall, waterslide, hot tub, and therapeutic cold plunge tub.

The home has ample outdoor living areas designed for entertaining, multiple screened-in porches, and an outdoor shower with hot and cold water. A detached separate cabana includes a seating area with a TV and a gas fireplace. Additional highlights include a front porch with a swing, a rooftop deck with 360-degree views of the Gulf and the Bay, lush tropical landscaping, and unique ceiling angles.

Inside, you'll find a built-in bunk bed area, a large theater room with reclining chairs, an office area, and a game table. Two showers are steam showers, and there's also a convenient pool bath. This one-of-a-kind island home is ready to welcome guests for unforgettable stays.

Coastal charm

116 White Ave, Holmes Beach

This beautiful home priced at $2,950,000 features four bedrooms and three baths within its spacious 3,275 square feet, situated on a generous 12,576 square-foot lot with direct beach access. The light-filled, open floorplan creates an inviting atmosphere, with the kitchen, dining room, and great room boasting impressive 10-foot ceilings. Sliding doors extend the living space outdoors to a refreshing pool and covered cabana surrounded by lush tropical landscaping. A rooftop balcony and hot tub provide additional outdoor relaxation and entertainment options.

Inside, the home includes a second kitchen in the study, impact windows, and a cozy wood-burning fireplace. Solar panels heat the pool, adding an eco-friendly touch to this luxurious property. With its prime location and thoughtfully designed features, this home is a dream come true for those seeking the ultimate coastal lifestyle.

Tranquil retreat

216 Palm Ave, Anna Maria

This charming coastal home, priced at $2,899,500, is just two blocks from the beach. It is an ideal short-term rental vacation property, recognized by Travel + Leisure as one of the World's 50 Best Places to Travel in 2024. The open floor plan combines the kitchen, dining, and great room, centered around a cozy fireplace. French doors extend the living space to a large, covered balcony with steps leading to a refreshing pool, which was beautifully renovated in 2020.

The oversized primary suite includes a private sitting room, two additional guest bedrooms, and a spacious fourth bedroom. The backyard features lush tropical landscaping and a covered sitting area. With its prime location and thoughtful design, this home is a lucrative investment in one of the most sought-after coastal destinations.

Secure your dream home

The Hannah Hillyard Group is a top producer with a devoted following of satisfied customers. A Certified Luxury Home Marketing Specialist (CLHMS) and a proud member of the Million Dollar Guild, Hannah Hillyard brings a wealth of experience and a keen eye for luxury properties. Whether you're seeking a personal beachfront retreat or an investment property, the Hannah Hillyard Group will help you secure the home of your dreams.

Hannah Hillyard

About the Author

Hannah Hillyard

An Anna Maria Island resident since 2001, Hannah is known as an extraordinary force in luxury real estate, with a remarkable record of selling world-class properties.

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Hannah’s integrity and discretion, along with her attention to detail, marketing savvy, and refined negotiating skills, consistently deliver impressive real estate results for buyers and sellers.