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$3,250,000
4 Beds ⋅ 4 Baths ⋅ A4697111 MLS
Unparalleled luxury, unmatched value: recently reduced by $400K! Discover the essence of island living at this premier north-end Anna Maria Island retreat, ideally positioned just moments from the sugar-sand shores of Bean Point and the tranquil waters of Tampa Bay. Following a total gut and comprehensive renovation completed in 2021, this coastal residence offers the perfect blend of modern luxury, comfort, and outdoor living. Situated on a private corner lot in one of the island's most sought-after neighborhoods, the open-concept floor plan is masterfully designed for entertaining. It features 4 bedrooms, 3.5 baths, soaring ceilings, abundant natural light, and seamless indoor-outdoor living. The chef's kitchen boasts a gas range, premium quartz countertops and opens beautifully to spacious living and dining areas, while multiple balconies and covered decks create inviting spaces to enjoy sea breezes and glimpses of the bay. The resort-style outdoor setting is truly exceptional, featuring a heated saltwater lap pool and spa, putting green, outdoor shower, lush tropical landscaping, and multiple gathering areas designed for relaxation and entertaining. Aside from being a dream personal getaway, this property is a proven investment powerhouse. It has happily welcomed guests year after year, consistently generating a fantastic rental income between $315,000 and $347,000 for each of the past four years! With a strong, established rental history and future bookings already in place, it is ready to start earning for you on day one. Detailed rental financials are available upon request. This is a rare opportunity to acquire a fully updated, income-producing luxury island home in one of Anna Maria's most desirable locations, just moments from world-famous beaches, waterfront dining, boutique shopping, and spectacular Gulf Coast sunsets.

256 Gladiolus Street, Anna Maria
$2,900,000
4 Beds ⋅ 4 Baths ⋅ A4694474 MLS
Named "A Wave From It All" by the sellers, this exceptional coastal property offers high-end finishes and a layout designed for seamless indoor/outdoor living. The outdoor pool area serves as a private tropical oasis, perfect for relaxation. The main residence features three bedrooms, each with a king bed and ensuite bathroom. The kitchen is equipped with a Sub-Zero refrigerator, a Wolf range and microwave, Bosch dishwasher and wine cooler. For ultimate privacy, the primary suite is accessed through a unique bookcase doorway. This home comes furnished and includes original artwork by renowned artists and a beautiful outdoor mural by Chad "Cheeta" Ruis. The property also includes a versatile casita featuring two Murphy beds, a half bath, an office area, a laundry room, and a convenient outdoor shower located just outside the half bath which includes both hot and cold water. A small storage garage is available on-site for bikes and beach gear. Located on the North end, the home is a short walk from Bean Point beaches, Bayfront Park, and the boutiques and dining on Pine Avenue. Additionally, the adjacent 10,600+ sq. ft. parcel at 240 Gladiolus is available for separate purchase. It is currently landscaped to enhance the estate and includes a large garage. Don't miss out on this unique opportunity and schedule your private showing today!

242 Gladiolus Street, Anna Maria
$1,750,000
3 Beds ⋅ 2 Baths ⋅ A4682093 MLS
Located just blocks from the beach, White Palms is a 3-bedroom, 2-bathroom island home situated on a large corner lot with a spacious backyard, offering excellent outdoor living close to the Gulf. The corner location provides added openness, while mature palms and established landscaping create a private coastal setting. The home features a bright, open layout designed for comfortable island living, with well-sized bedrooms and recently updated finishes throughout. The main living areas connect seamlessly to the outdoor spaces, making it ideal for both everyday living and entertaining. The backyard centers around a private pool, creating a true outdoor retreat with ample space for lounging and gathering. Whether used as a primary residence, second home, or seasonal escape, the layout offers flexibility and function. Located in Anna Maria's nightly vacation rental area, White Palms is an established rental property with documented income, offering immediate investment potential alongside its lifestyle appeal. Just a short walk to the sand, this property combines beach proximity, outdoor space, and proven rental performance in one well-located island home.

270 Gladiolus Street, Anna Maria
$1,775,000
3 Beds ⋅ 2 Baths ⋅ TB8359176 MLS
Experience the ultimate coastal retreat at 311 Poinsettia Rd in Anna Maria, FL—a home where luxury meets laid-back island living. This beautifully renovated, elevated sanctuary boasts stunning waterfront views, a sparkling pool, and your very own private boat dock with a lift, inviting endless adventures on the water. Enjoy the convenience of RV/boat parking and a generous driveway that sets the stage for memorable gatherings. Just a leisurely stroll to pristine beaches and a quick golf cart ride to lively restaurants and bars, every moment here is infused with warmth, charm, and the promise of a vibrant lifestyle. Welcome home to your dream coastal haven. This property is currently used as a NIGHTLY rental bringing in up to $25,000/month so far this year. Please do not disturb the guests.

311 Poinsettia Road, Anna Maria