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There is a side of island life reserved for those who demand the truly extraordinary—where the powdery white sands of the Gulf of Mexico serve as your literal backyard. Welcome to one of the most iconic and recognized beachfront estates on Anna Maria Island. Masterfully designed by the renowned architect Emily Anne Smith, this classic Coastal West Indies–inspired residence stands as a testament to timeless beauty, architectural elegance, and flawless coastal craftsmanship. Built by Whitehead Construction—one of the region’s premier custom luxury builders—every square inch of this estate reflects uncompromising quality and structural excellence. Spanning four spacious bedrooms and four bathrooms (including three luxurious ensuites), the home is perfectly positioned to capture breathtaking, unobstructed turquoise water views from nearly every vantage point. The moment you step through the door, the home’s grand sense of scale and elegant features become immediately apparent. Soaring vaulted ceilings and expansive windows invite an abundance of natural light, beautifully complementing the rich hardwood flooring and meticulous custom millwork found throughout. At the heart of the home is a chef’s dream kitchen, fully equipped for effortless entertaining. It boasts expansive quartz countertops, a large custom pantry cabinet wall, and a suite of premium professional appliances. Culinary enthusiasts will appreciate the Wolf double oven with a six-burner gas cooktop, a three appliance package by Signature Kitchen Suite including a high-capacity refrigerator, a wine cooler, and dishwasher. Additionally a bonus, premium Fisher & Paykel double-drawer dishwasher is perfect for effortless clean-up. The entire second floor is dedicated to the ultimate primary retreat. Here, you can wake up every morning to direct, panoramic views of the Gulf, completely immersed in tranquility. The outdoor living spaces are equally spectacular, designed to maximize Florida’s indoor-outdoor lifestyle. Relax on the sprawling first-level patio, or ascend to the massive rooftop viewing deck—the ultimate front-row seat for Anna Maria Island’s legendary, world-class sunsets. Anchoring the outdoor oasis is a private saltwater pool, which has been completely redesigned from the resurfacing and custom tiles to all-new, state-of-the-art pool equipment. This is a rare, once-in-a-lifetime opportunity to acquire a legendary piece of Anna Maria Island paradise. To experience this coastal masterpiece firsthand, contact listing agent Gregg Bayer to arrange your private, confidential showing. Sent from my iPhone

4 Beds ⋅ 4 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code

There is a side of island life reserved for those who demand the truly extraordinary—where the powdery white sands of the Gulf of Mexico serve as your literal backyard. Welcome to one of the most iconic and recognized beachfront estates on Anna Maria Island. Masterfully designed by the renowned architect Emily Anne Smith, this classic Coastal West Indies–inspired residence stands as a testament to timeless beauty, architectural elegance, and flawless coastal craftsmanship. Built by Whitehead Construction—one of the region’s premier custom luxury builders—every square inch of this estate reflects uncompromising quality and structural excellence. Spanning four spacious bedrooms and four bathrooms (including three luxurious ensuites), the home is perfectly positioned to capture breathtaking, unobstructed turquoise water views from nearly every vantage point. The moment you step through the door, the home’s grand sense of scale and elegant features become immediately apparent. Soaring vaulted ceilings and expansive windows invite an abundance of natural light, beautifully complementing the rich hardwood flooring and meticulous custom millwork found throughout. At the heart of the home is a chef’s dream kitchen, fully equipped for effortless entertaining. It boasts expansive quartz countertops, a large custom pantry cabinet wall, and a suite of premium professional appliances. Culinary enthusiasts will appreciate the Wolf double oven with a six-burner gas cooktop, a three appliance package by Signature Kitchen Suite including a high-capacity refrigerator, a wine cooler, and dishwasher. Additionally a bonus, premium Fisher & Paykel double-drawer dishwasher is perfect for effortless clean-up. The entire second floor is dedicated to the ultimate primary retreat. Here, you can wake up every morning to direct, panoramic views of the Gulf, completely immersed in tranquility. The outdoor living spaces are equally spectacular, designed to maximize Florida’s indoor-outdoor lifestyle. Relax on the sprawling first-level patio, or ascend to the massive rooftop viewing deck—the ultimate front-row seat for Anna Maria Island’s legendary, world-class sunsets. Anchoring the outdoor oasis is a private saltwater pool, which has been completely redesigned from the resurfacing and custom tiles to all-new, state-of-the-art pool equipment. This is a rare, once-in-a-lifetime opportunity to acquire a legendary piece of Anna Maria Island paradise. To experience this coastal masterpiece firsthand, contact listing agent Gregg Bayer to arrange your private, confidential showing. Sent from my iPhone

2728 Avenue E, Holmes Beach

$4,750,000

An exceptional Sarasota Bay waterfront opportunity offering nearly 100 feet of direct bay frontage in the heart of Bradenton Beach. The existing residence is habitable and may be enjoyed as-is, while also presenting outstanding long-term redevelopment potential. The Seller has obtained City confirmation regarding the potential for two waterfront homesites following removal of the existing residence (buyer to verify all zoning, permitting, subdivision, and development requirements). The property features a 75-foot composite dock with a 4,500-pound boat lift, breathtaking open-water views, and immediate boating access. Whether enjoyed today or reimagined for the future, this is a rare opportunity to create an extraordinary waterfront legacy on Anna Maria Island.

Ilexhurst SubDv. ⋅ 34217 Zip Code

An exceptional Sarasota Bay waterfront opportunity offering nearly 100 feet of direct bay frontage in the heart of Bradenton Beach. The existing residence is habitable and may be enjoyed as-is, while also presenting outstanding long-term redevelopment potential. The Seller has obtained City confirmation regarding the potential for two waterfront homesites following removal of the existing residence (buyer to verify all zoning, permitting, subdivision, and development requirements). The property features a 75-foot composite dock with a 4,500-pound boat lift, breathtaking open-water views, and immediate boating access. Whether enjoyed today or reimagined for the future, this is a rare opportunity to create an extraordinary waterfront legacy on Anna Maria Island.

2512 Avenue A, Bradenton Beach

$1,995,000

~~~ PRICE DROP ~~~ The perfect piece of paradise ready for you to build your perfect beach house! Nestled on a very quiet street on the coveted island of Anna Maria. 9000 square feet of land for you to design everything you've ever wanted in a beach house. Build a home that will take advantage of the opportunity for sweeping views of the intercoastal waterways. Design a pool and outdoor living space to die for Just lounging for the day or entertaining family and friends. Imagine being able to walk out your back door, out onto your dock and board your boat to take an offshore fishing trip or just a leisurely ride around the islands. Have dinner at The Shore on the northern tip of longboat key via boat. You'll be close enough to the amazing beaches of the Gulf of Mexico where you can walk or take a bike ride and be there within minutes to enjoy some of the best sunsets on the planet. Spend the day at the beach and come home to cool off in your incredible custom pool. An additional opportunity exists, as the neighboring property to the south at 2308 Canasta, also a 9,000-square-foot waterfront parcel, is available from the same owner and may be purchased together. Combine both parcels for an extraordinary 18,000 square feet of prime Intracoastal waterfront—a truly rare chance to create something exceptional on Anna Maria Island.

Ilexhurst SubDv. ⋅ 34217 Zip Code

~~~ PRICE DROP ~~~ The perfect piece of paradise ready for you to build your perfect beach house! Nestled on a very quiet street on the coveted island of Anna Maria. 9000 square feet of land for you to design everything you've ever wanted in a beach house. Build a home that will take advantage of the opportunity for sweeping views of the intercoastal waterways. Design a pool and outdoor living space to die for Just lounging for the day or entertaining family and friends. Imagine being able to walk out your back door, out onto your dock and board your boat to take an offshore fishing trip or just a leisurely ride around the islands. Have dinner at The Shore on the northern tip of longboat key via boat. You'll be close enough to the amazing beaches of the Gulf of Mexico where you can walk or take a bike ride and be there within minutes to enjoy some of the best sunsets on the planet. Spend the day at the beach and come home to cool off in your incredible custom pool. An additional opportunity exists, as the neighboring property to the south at 2308 Canasta, also a 9,000-square-foot waterfront parcel, is available from the same owner and may be purchased together. Combine both parcels for an extraordinary 18,000 square feet of prime Intracoastal waterfront—a truly rare chance to create something exceptional on Anna Maria Island.

2306 Canasta Drive, Bradenton Beach

$4,750,000

CONFIRMED POTENTIAL FOR TWO BUILDABLE WATERFRONT LOTS creates one of the most compelling redevelopment opportunities on Anna Maria Island with nearly 100 feet of direct Sarasota Bay frontage. Privately owned by the same family for decades, this exceptional bayfront property offers expansive open-water views, a coveted location in the heart of Bradenton Beach, and the opportunity to create two luxury waterfront residences or an extraordinary private estate. The City of Bradenton Beach has confirmed the property's potential for two buildable waterfront lots, presenting a rare opportunity for builders, developers, investors, or those seeking to create a legacy property. The existing property features a 75-foot composite dock and 4,500-pound boat lift, providing immediate boating access to Sarasota Bay and beyond while future plans take shape. Waterfront parcels of this size, width, and potential are becoming increasingly scarce on Anna Maria Island. Whether your vision is two exceptional custom homes, a multi-generational family retreat, or a landmark bayfront estate, this is an opportunity to secure one of the island's most remarkable waterfront offerings.

3 Beds ⋅ 3 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code

CONFIRMED POTENTIAL FOR TWO BUILDABLE WATERFRONT LOTS creates one of the most compelling redevelopment opportunities on Anna Maria Island with nearly 100 feet of direct Sarasota Bay frontage. Privately owned by the same family for decades, this exceptional bayfront property offers expansive open-water views, a coveted location in the heart of Bradenton Beach, and the opportunity to create two luxury waterfront residences or an extraordinary private estate. The City of Bradenton Beach has confirmed the property's potential for two buildable waterfront lots, presenting a rare opportunity for builders, developers, investors, or those seeking to create a legacy property. The existing property features a 75-foot composite dock and 4,500-pound boat lift, providing immediate boating access to Sarasota Bay and beyond while future plans take shape. Waterfront parcels of this size, width, and potential are becoming increasingly scarce on Anna Maria Island. Whether your vision is two exceptional custom homes, a multi-generational family retreat, or a landmark bayfront estate, this is an opportunity to secure one of the island's most remarkable waterfront offerings.

2512 Avenue A, Bradenton Beach

$5,900,000

This exquisite waterfront home is perfectly situated just 3 blocks away from the island's seven miles of sandy beaches!! This luxury property features 8 spacious bedrooms, 8.5 bathrooms, and nautical-themed decor throughout. The home offers a private oversized heated pool and spa, a rooftop deck with stunning 360-degree views of both the beach and bay, and a screened lanai for enjoying beautiful sunrises. The property includes a two-car garage, parking for four cars, a fishing pier, and a 10,000 lb boat lift. The large kitchen and dining area offers ample seating and includes quartz countertops, JennAir appliances and a laundry room with two sets of washer and dryer. 7 of the 8 bedrooms feature king beds, with one room equipped with bunk beds. The third floor also has access to the rooftop deck with views of both the gulf and the bay! This prime location, between the two bridges of Anna Maria Island, offers easy access to the island’s best attractions while providing a serene and luxurious retreat.

8 Beds ⋅ 9 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code

This exquisite waterfront home is perfectly situated just 3 blocks away from the island's seven miles of sandy beaches!! This luxury property features 8 spacious bedrooms, 8.5 bathrooms, and nautical-themed decor throughout. The home offers a private oversized heated pool and spa, a rooftop deck with stunning 360-degree views of both the beach and bay, and a screened lanai for enjoying beautiful sunrises. The property includes a two-car garage, parking for four cars, a fishing pier, and a 10,000 lb boat lift. The large kitchen and dining area offers ample seating and includes quartz countertops, JennAir appliances and a laundry room with two sets of washer and dryer. 7 of the 8 bedrooms feature king beds, with one room equipped with bunk beds. The third floor also has access to the rooftop deck with views of both the gulf and the bay! This prime location, between the two bridges of Anna Maria Island, offers easy access to the island’s best attractions while providing a serene and luxurious retreat.

2516 Avenue A, Bradenton Beach

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