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$3,200,000

Welcome to Sea Glass Harbor, an exceptional expression of luxury coastal living in the heart of Anna Maria Island! Built in 2021, this exquisite multi-level residence offers 4 bedrooms, 5.5 baths, a private pool and spa, plus a versatile den/flex space—beautifully designed for refined island living, effortless entertaining, and unforgettable escapes. The main living level showcases an impressive open-concept kitchen, dining, and living area filled with natural light and an inviting coastal ambiance. The upscale kitchen is beautifully appointed with solid wood cabinetry, elegant quartz countertops, stainless steel appliances, and a generous center island that creates the perfect setting for entertaining family and guests. This level also offers two generously sized bedrooms, 2.5 beautifully designed baths with distinctive finishes, and a conveniently located laundry area. The upper level is home to a luxurious primary suite with a private ensuite bath, along with an additional spacious bedroom featuring its own ensuite. The bonus den/flex space provides even more options for your family to spread out and enjoy all of the areas of this stunning beach home. Designed to embrace the quintessential island lifestyle, the outdoor spaces are equally impressive. Relax beside the private pool and spa, entertain beneath multiple decks, or unwind in the lush tropical backyard. At the crown of the home, the rooftop deck delivers sweeping bay views—the perfect backdrop for sunset cocktails or quiet evenings under the stars. The unique split two-car garages provide exceptional parking and storage. Offered turnkey furnished with beautiful coastal décor, this remarkable residence is a successful vacation rental and presents a rare opportunity to own a luxurious island retreat with proven investment appeal. Ideally located in central Holmes Beach, you’re just minutes from the beach, exceptional local dining, shopping, and island entertainment. Boaters will appreciate convenient access to the community boat ramp, providing an effortless gateway to the surrounding waterways. Elegant coastal design, exceptional outdoor living, proven rental appeal, and an enviable island location—this is Anna Maria Island luxury at its finest!

4 Beds ⋅ 6 Baths ⋅ Sportsmans Harbor SubDv. ⋅ 34217 Zip Code ⋅ A4704768 MLS ⋅ Active Status

Welcome to Sea Glass Harbor, an exceptional expression of luxury coastal living in the heart of Anna Maria Island! Built in 2021, this exquisite multi-level residence offers 4 bedrooms, 5.5 baths, a private pool and spa, plus a versatile den/flex space—beautifully designed for refined island living, effortless entertaining, and unforgettable escapes. The main living level showcases an impressive open-concept kitchen, dining, and living area filled with natural light and an inviting coastal ambiance. The upscale kitchen is beautifully appointed with solid wood cabinetry, elegant quartz countertops, stainless steel appliances, and a generous center island that creates the perfect setting for entertaining family and guests. This level also offers two generously sized bedrooms, 2.5 beautifully designed baths with distinctive finishes, and a conveniently located laundry area. The upper level is home to a luxurious primary suite with a private ensuite bath, along with an additional spacious bedroom featuring its own ensuite. The bonus den/flex space provides even more options for your family to spread out and enjoy all of the areas of this stunning beach home. Designed to embrace the quintessential island lifestyle, the outdoor spaces are equally impressive. Relax beside the private pool and spa, entertain beneath multiple decks, or unwind in the lush tropical backyard. At the crown of the home, the rooftop deck delivers sweeping bay views—the perfect backdrop for sunset cocktails or quiet evenings under the stars. The unique split two-car garages provide exceptional parking and storage. Offered turnkey furnished with beautiful coastal décor, this remarkable residence is a successful vacation rental and presents a rare opportunity to own a luxurious island retreat with proven investment appeal. Ideally located in central Holmes Beach, you’re just minutes from the beach, exceptional local dining, shopping, and island entertainment. Boaters will appreciate convenient access to the community boat ramp, providing an effortless gateway to the surrounding waterways. Elegant coastal design, exceptional outdoor living, proven rental appeal, and an enviable island location—this is Anna Maria Island luxury at its finest!

239 S Harbor Drive, Holmes Beach

$3,400,000

Experience elevated coastal living in this brand-new, designer-finished 4BR/4.5BA luxury home located just a 5-minute walk to the pristine beaches of Anna Maria Island. Thoughtfully crafted with high-end finishes and a bright, open-concept layout, this residence blends modern elegance with relaxed island charm. Currently utilized as a successful short term vacation rental with proven rental revenue. 4 spacious ensuite bedrooms, including three king suites with walk-in showers Gorgeous open living area with abundant natural light and upscale coastal décor Chef’s kitchen featuring modern cabinetry, stone counters, and stainless appliances Private heated pool with in-ground spa, surrounded by lush tropical landscaping Expansive rooftop deck offering panoramic views and unforgettable sunsets Fully furnished with professionally curated interiors Designed for relaxation and entertaining, the outdoor oasis includes a sparkling pool, spa, covered lounging areas, multiple decks including a rooftop deck ideal for sunrise coffee or sunset cocktails. The fenced yard provides privacy while maintaining a breezy, coastal feel. Situated in the heart of Holmes Beach, this home offers walkable access to sugar-sand beaches, local dining, boutiques, and the island’s free trolley. Enjoy the perfect blend of tranquility and convenience in one of Florida’s most desirable beach communities. This unique property can be utilized as primary residence, second home, or high-performing vacation rental investment property. This property delivers luxury, comfort, and strong rental appeal in a premier island location.

4 Beds ⋅ 5 Baths ⋅ Sportsmans Harbor SubDv. ⋅ 34217 Zip Code ⋅ A4684262 MLS ⋅ Active Status

Experience elevated coastal living in this brand-new, designer-finished 4BR/4.5BA luxury home located just a 5-minute walk to the pristine beaches of Anna Maria Island. Thoughtfully crafted with high-end finishes and a bright, open-concept layout, this residence blends modern elegance with relaxed island charm. Currently utilized as a successful short term vacation rental with proven rental revenue. 4 spacious ensuite bedrooms, including three king suites with walk-in showers Gorgeous open living area with abundant natural light and upscale coastal décor Chef’s kitchen featuring modern cabinetry, stone counters, and stainless appliances Private heated pool with in-ground spa, surrounded by lush tropical landscaping Expansive rooftop deck offering panoramic views and unforgettable sunsets Fully furnished with professionally curated interiors Designed for relaxation and entertaining, the outdoor oasis includes a sparkling pool, spa, covered lounging areas, multiple decks including a rooftop deck ideal for sunrise coffee or sunset cocktails. The fenced yard provides privacy while maintaining a breezy, coastal feel. Situated in the heart of Holmes Beach, this home offers walkable access to sugar-sand beaches, local dining, boutiques, and the island’s free trolley. Enjoy the perfect blend of tranquility and convenience in one of Florida’s most desirable beach communities. This unique property can be utilized as primary residence, second home, or high-performing vacation rental investment property. This property delivers luxury, comfort, and strong rental appeal in a premier island location.

227 S Harbor Drive, Holmes Beach

$2,995,000

A rare waterfront opportunity just became irresistible!!! Luxury 5 Bedroom Waterfront + Dock | 3-Min Walk to Beach -Exceptional waterfront retreat perfectly positioned in the heart of Anna Maria Island. Just a three-minute stroll to the soft sugar sands of Manatee Beach, this stunning five-bedroom, three-and-a-half-bath residence delivers coastal luxury at every turn—complete with a private dock with ladder where manatees often glide by, a heated pool and spa, and a show-stopping rooftop deck with Gulf and Bay views. Designed for unforgettable gatherings, Coral Castle seamlessly blends upscale comfort with relaxed island charm! Outdoor Living at Its Finest, the rooftop deck is the crown jewel of Coral Castle—offering breathtaking sunrise and sunset views over both the Gulf and Bay. Start your mornings with coffee and ocean breezes or unwind in the evening with a cocktail as the sky glows in brilliant island hues. The tropical backyard is a private sanctuary featuring a heated pool, spa, lounge seating, and outdoor grill, perfect for post-beach relaxation or entertaining under the stars. From the private dock, enjoy peaceful water views—and keep watch for friendly manatees passing by, an unforgettable hallmark of island living. Stylish Interiors Made for Comfort-Step inside to a bright, open-concept living space filled with natural light and coastal elegance. The living room offers plush seating, a flat-screen TV, and sliding glass doors that open directly to the outdoor patio—blurring the line between indoor and outdoor living. The chef-inspired kitchen is fully equipped with stainless steel appliances, generous counter space, and a wine fridge, making meal prep effortless. Gather inside at the dining table or dine alfresco beneath the covered patio for a true island experience. Sleep in Luxury- Primary Suite: King bed, private balcony, vaulted shiplap ceiling, walk-in closet, spa-style ensuite with soaking tub and walk-in shower; Second Bedroom: King bed, Jack-and-Jill bathroom with walk-in shower; Third Bedroom: King bed, Jack-and-Jill bathroom with walk-in shower; Fourth Bedroom: Full bed, Jack-and-Jill bathroom with shower/tub combo; and Fifth Bedroom: Full bed, Jack-and-Jill bathroom with shower/tub combo. Prime Island Location- Enjoy peaceful mornings fishing from the dock or take a short drive to Pine Avenue and Bridge Street, where you’ll discover charming boutiques, local dining, and island favorites. Whether your days are spent boating, lounging by the pool, or soaking in rooftop views, Coral Castle delivers the perfect balance of relaxation and adventure. Every detail is designed to create lasting memories—from manatee sightings to sunset cocktails on the rooftop. This is more than a stay—it’s a true Anna Maria Island experience. Currently operating as a vacation rental with solid history and a strong start to 2026—ideal personal-use + income opportunity.

5 Beds ⋅ 4 Baths ⋅ Sportsmans Harbor SubDv. ⋅ 34217 Zip Code ⋅ A4678835 MLS ⋅ Active Status

A rare waterfront opportunity just became irresistible!!! Luxury 5 Bedroom Waterfront + Dock | 3-Min Walk to Beach -Exceptional waterfront retreat perfectly positioned in the heart of Anna Maria Island. Just a three-minute stroll to the soft sugar sands of Manatee Beach, this stunning five-bedroom, three-and-a-half-bath residence delivers coastal luxury at every turn—complete with a private dock with ladder where manatees often glide by, a heated pool and spa, and a show-stopping rooftop deck with Gulf and Bay views. Designed for unforgettable gatherings, Coral Castle seamlessly blends upscale comfort with relaxed island charm! Outdoor Living at Its Finest, the rooftop deck is the crown jewel of Coral Castle—offering breathtaking sunrise and sunset views over both the Gulf and Bay. Start your mornings with coffee and ocean breezes or unwind in the evening with a cocktail as the sky glows in brilliant island hues. The tropical backyard is a private sanctuary featuring a heated pool, spa, lounge seating, and outdoor grill, perfect for post-beach relaxation or entertaining under the stars. From the private dock, enjoy peaceful water views—and keep watch for friendly manatees passing by, an unforgettable hallmark of island living. Stylish Interiors Made for Comfort-Step inside to a bright, open-concept living space filled with natural light and coastal elegance. The living room offers plush seating, a flat-screen TV, and sliding glass doors that open directly to the outdoor patio—blurring the line between indoor and outdoor living. The chef-inspired kitchen is fully equipped with stainless steel appliances, generous counter space, and a wine fridge, making meal prep effortless. Gather inside at the dining table or dine alfresco beneath the covered patio for a true island experience. Sleep in Luxury- Primary Suite: King bed, private balcony, vaulted shiplap ceiling, walk-in closet, spa-style ensuite with soaking tub and walk-in shower; Second Bedroom: King bed, Jack-and-Jill bathroom with walk-in shower; Third Bedroom: King bed, Jack-and-Jill bathroom with walk-in shower; Fourth Bedroom: Full bed, Jack-and-Jill bathroom with shower/tub combo; and Fifth Bedroom: Full bed, Jack-and-Jill bathroom with shower/tub combo. Prime Island Location- Enjoy peaceful mornings fishing from the dock or take a short drive to Pine Avenue and Bridge Street, where you’ll discover charming boutiques, local dining, and island favorites. Whether your days are spent boating, lounging by the pool, or soaking in rooftop views, Coral Castle delivers the perfect balance of relaxation and adventure. Every detail is designed to create lasting memories—from manatee sightings to sunset cocktails on the rooftop. This is more than a stay—it’s a true Anna Maria Island experience. Currently operating as a vacation rental with solid history and a strong start to 2026—ideal personal-use + income opportunity.

203 N Harbor Drive, Holmes Beach