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$2,950,000
6 Beds ⋅ 6 Baths ⋅ A4700093 MLS
Welcome to CHIC ON THE BEACH. A six bedroom, four-full-bath, and two-half-bath luxury property built in 2020 that comes with a Massive Twist: Dual Villas. Not one, but two fully independent 3-bedroom 2.5-bath villas, each with a beautifully curated layout, and its own private, heated, resort style pool. This setup provides so many flexible options: A seamless 1031 exchange, a family compound, multi family bookings, a generational hold, dual luxury vacation rentals, or a live-in owner user enjoying one side while collecting income from the other. These two completely turnkey villas feature high-end coastal finishes and are designed to generate income from day one. Pure island perfection awaits the discerning buyer. Built in 2020 with modern construction standards, the property features hurricane impact windows, and a gentle six-step entry to the units, providing added elevation and additional hurricane protection. Premium craftsmanship and top-tier coastal details are found throughout, including wood-plank tile floors, tankless water heaters, and cutting edge lighting fixtures. Enjoy your morning coffee or evening cocktail on your covered porch overlooking your private pool oasis while taking in the relaxed Old-Florida lifestyle- slow-paced, casual, and effortlessly coastal. Ideally positioned in the heart of Holmes Beach, just a six minute walk from the Gulf beach, with excellent walkability to nearby restaurants, boutiques, coffee shops, ice cream, live music, Anna Maria island Trolley. It delivers the ultimate coastal experience, while combining personal paradise with effortless passive-income. The equity potential is incredible: two 2020-built luxury vacation Villas on Anna Maria Island for under 1.5 Million each, yet with your portfolio all under one roof.

308 57th Street Unit A & B, Bradenton Beach
$2,900,000
3 Beds ⋅ 3 Baths ⋅ A4701695 MLS
Custom-designed and meticulously maintained by its original owner, this waterfront residence offers a rare opportunity to experience the coastal lifestyle of Anna Maria Island. Positioned on a saltwater canal with direct boating access with no bridge restrictions and just a short distance from the Gulf beaches, the property combines waterfront living with convenient access to the island’s dining, shopping and recreational amenities. The home features three bedrooms, three baths, impact-rated windows, a central vacuum system serving all three levels and an elevator connecting each floor. Dual front balconies enhance the architectural character, while the ground level offers an expansive air-conditioned garage with space for multiple vehicles, a golf cart, watercraft equipment and beach gear. The main living level is designed for gathering and entertaining, featuring an open-concept great room with wet bar, dining area with built-in serving station and a spacious kitchen centered around a large island with cooktop and abundant workspace. A breakfast area opens to a balcony, while the adjoining sunroom provides additional space for dining, relaxing or working from home. An oversized guest suite on this level includes balcony access and a walk-in closet with an additional lockable storage area. The upper level is dedicated to two owner’s suites, each featuring cathedral ceilings, generous walk-in closets and access to a spa-inspired bath with dual vanities. A conveniently located laundry room completes the level. Outdoor amenities are designed to support an active waterfront lifestyle. The private dock is equipped with electricity and water, a 10,000-pound boat lift and two Jet Ski lifts. The landscaped grounds include a pergola draped in bougainvillea, mature tropical plantings and a mango tree. A spiral staircase connects the outdoor living areas, while fenced and shelled grounds provide a low-maintenance setting. Located on Anna Maria Island, residents enjoy access to waterfront restaurants, boutique shopping, fishing, community events and the free island trolley. Nearby destinations include Pine Avenue, Bridge Street, the Bradenton Historic Street Pier and many of the region’s well-known waterfront dining venues. Sarasota, Tampa and St. Petersburg are within convenient driving distance, along with cultural attractions including the John and Mable Ringling Museum of Art, Nathan Benderson Park, Mote Marine Laboratory & Aquarium and Robinson Preserve. Whether utilized as a primary residence, seasonal retreat or investment property, this thoughtfully designed waterfront home presents an exceptional opportunity to enjoy the boating and beach lifestyle of Anna Maria Island.

505 59th Street, Bradenton Beach
$775,000
3 Beds ⋅ 2 Baths ⋅ A4698503 MLS
BUY ONE OR BOTH SIDES OF THIS DUPLEX PROPERTY. STEPS TO THE BEACH AND LOCATED IN A WEEKLY RENTAL ZONE! Welcome to 202 Peacock Lane, Unit A—an elevated three-bedroom, two-bath ,2 car garage Holmes Beach property offering exceptional flexibility as a vacation home, island residence or income-producing investment. UNIT B IS ALSO AVAILABLE. The spacious interior features beautiful bamboo flooring, remodeled bathrooms, select hurricane-impact windows and a comfortable open living area. Important improvements include a newer roof, newer A/C and a 2025 water heater. The home may be purchased furnished or unfurnished, allowing the new owner to personalize it or prepare it for vacation rentals. The enclosed lower level provides valuable additional space, while the garage accommodates both a vehicle and a golf cart. The property may also offer room for a private pool, subject to buyer verification and local requirements. Enjoy an outstanding Anna Maria Island location within walking distance of the Gulf beaches, restaurants, shops, parks and everything Holmes Beach has to offer. Whether you are searching for a private island getaway, second home or short-term rental opportunity, Unit A delivers the location and potential buyers are looking for. UNIT B IS ALSO AVAILABLE, providing a rare opportunity to purchase both units and own the entire building. Live in one unit and rent the other, create a multi-generational island retreat or maximize the property’s investment potential. Unit B is offered separately under MLS #A4696880. Schedule your private showing today!

202 Peacock Lane Unit A, Holmes Beach
$5,995,000
5 Beds ⋅ 5 Baths ⋅ A4697603 MLS
Tucked along an extraordinary 225 feet of waterfront, this custom coastal retreat distills the very essence of island living—breathtaking water views, exceptional privacy, and thoughtfully designed spaces that move effortlessly between serene relaxation and spirited entertaining. A palm-lined driveway sets the tone, where timeless architecture and lush tropical landscaping leave an unforgettable first impression. This residence carries rare local significance as the very first custom home built by Ross Built Construction, masterfully designed by renowned architect Gene Aubry. It stands as a lasting testament to their craftsmanship and creativity—and their contribution to luxury coastal living on Anna Maria Island. Their influence resonates throughout: a thoughtful floor plan, an exceptional command of natural light, and a seamless connection between indoor and outdoor living. Inside, travertine tile and hand-scraped maple flooring flow through a light-filled interior crowned by soaring vaulted ceilings in the living and kitchen areas. The chef's kitchen is as functional as it is beautiful, appointed with stone countertops, copper sinks, a gas range with pot filler, premium appliances, and a generous center island that anchors the home's main gathering spaces. Five spacious ensuite bedrooms, a dedicated den/office, and an upstairs bonus room offer effortless flexibility for family and guests. The primary suite is a private sanctuary unto itself, featuring a remodeled spa-inspired bath with custom built-in shelving and elegant finishes throughout. Designed to embrace the waterfront lifestyle, expansive glass doors open to an impressive 1,400-square-foot veranda overlooking the sparkling saltwater pool and tranquil waterways beyond. Boaters will appreciate the private dock and 10,000-lb boat lift for effortless access to open water, while an oversized three-car garage, elevator, impact-rated windows and doors, Sonos sound system, mosquito misting system, rainwater cistern, and exterior irrigation system deliver convenience and lasting peace of mind. Perfectly positioned in the heart of Holmes Beach, the property is just moments from the sugar-sand beaches of the Gulf, beloved local restaurants, boutiques, and island shops—a rare pairing of private waterfront sanctuary and walkable island convenience. Whether savoring spectacular sunsets from the veranda, entertaining poolside, strolling to nearby dining, or setting out for a day on the water, this remarkable residence offers something exceedingly rare: not only an extraordinary waterfront home, but a meaningful piece of island history, where inspired architecture, enduring craftsmanship, and an unrivaled setting come together in perfect harmony.

526 56th Street, Holmes Beach
$880,000
3 Beds ⋅ 2 Baths ⋅ A4696880 MLS ⋅ B BLDG.
BUY ONE OR BOTH SIDES OF THIS DUPLEX PROPERTY. STEPS TO THE BEACH AND LOCATED IN A WEEKLY RENTAL ZONE! Exceptional Island Investment Opportunity Just a short walk to the Beach! Welcome to 202 Peacock Lane, Unit B, a beautifully remodeled half-duplex perfectly positioned for vacation rental investors, second-home buyers, and those seeking the ultimate Anna Maria Island lifestyle. This spacious three-bedroom, two-bath residence with an impressive three-car garage configuration offers the ideal combination of prime island location, investment potential, and coastal living. Located just one block from the sugar-sand beaches of Anna Maria Island, this property is an outstanding opportunity for those seeking a vacation home, short-term rental investment, income-producing property, or full-time beach residence. Completely renovated from top to bottom, this turnkey property features a new roof, new HVAC system, new water heater, new flooring, new walls, and a stunning designer kitchen, showcasing stainless steel appliances, abundant custom cabinetry, and upgraded countertops. The home also boasts two beautifully updated bathrooms featuring custom vanities and stylish finishes. Nearly everything in this property is new or newer, offering peace of mind and low-maintenance ownership. The spacious layout comfortably accommodates families and groups, making it highly desirable as a high-demand vacation rental property. The expansive garage area includes a two-car tandem garage plus a separate 3 car ove sized garage, lockout garage, providing exceptional space for vehicles, golf carts, beach gear, bicycles, owner's storage, and more. Plus, driveway parking for possible 4 more cars. The versatile space beneath the home (2 car tandem garage space) offers endless possibilities, including a game room, entertainment area, additional living space, or covered parking. Outside, the private fenced backyard offers room to create your own tropical oasis with potential space for a pool (buyer to verify). Location is everything, and this property delivers! Leave the car and golf cart behind you're just steps away from world famous Gulf beaches, waterfront dining, boutique shopping, local attractions, and island entertainment. Everything needed for the perfect island vacation experience is within walking distance, making this property exceptionally attractive to both guests and owners. Sold furnished with a few exclusions. Rental or move in ready! Whether you're expanding your real estate portfolio, searching for a beach investment property, looking for a turnkey vacation rental, or dreaming of owning your own piece of paradise on Anna Maria Island, this exceptional property checks every box. Rarely do island properties this close to the beach offer extensive updates, exceptional walkability, flexible living space, and outstanding rental potential.

202 Peacock Lane Unit B, Holmes Beach
$695,000
2 Beds ⋅ 2 Baths ⋅ A4696837 MLS
Welcome to your dream coastal getaway! As captured in the stunning aerial view, this charming two-bedroom, two-bathroom half duplex boasts a prime location less than two blocks from the white sands of Anna Maria and local shops. The property is purposefully elevated for peace of mind, providing the added benefit of ample ground-level storage and covered parking underneath. Zoned for weekly rentals, this home offers incredible flexibility as a versatile island retreat or a highly desirable vacation destination. Inside, the bright and airy kitchen is beautifully appointed with crisp white cabinetry, gleaming countertops, a breakfast bar with vibrant seating, and modern stainless steel appliances, including a premium gas range for effortless cooking. The coastal aesthetic continues into the restful bedrooms, highlighting a spacious setup complete with low-maintenance tile flooring and large windows that invite plenty of natural light. Whether you are looking for a personal slice of paradise or a flexible property in an unbeatable location, this beachside gem is ready to welcome you home.

3303 6th Avenue Unit B, Holmes Beach
$994,000
2 Beds ⋅ 2 Baths ⋅ A4694707 MLS
This home is a renovated 2-bedroom, 2-bathroom with a private den. The home has an open concept with the kitchen, dining area and living room. The primary suite has an en-suite bathroom. It has a private backyard and a heated and chilled pool. There is an upper deck and a lower covered outdoor living and dining area. It is in a weekly rental zone and has good history and 5-star reviews. This lovely property is convenient to the beach and in a very quiet Holmes Beach residential neighborhood. It has one shared wall with the unit next door that was double insulated during renovation to reduce noise. It's just a short walk to the many shops and restaurants of downtown Holmes Beach, as well as the Island’s only dog park. There is a storage room that includes a ping pong table, a beach cart, beach toys and lots of beach equipment and a propane grill and outdoor propane fire pit ready to enjoy.

308 60th Street Unit A, Holmes Beach
$3,450,000
4 Beds ⋅ 6 Baths ⋅ A4688761 MLS
Virtually Staged. Imagine arriving at a private estate tucked along the shimmering waters of Tampa Bay on Anna Maria Island, where 235 feet of pristine waterfront create a rare sense of space, privacy and uninterrupted views. This four-bedroom, six-bath coastal residence in Holmes Beach is designed to capture the beauty of the bay from nearly every angle. Expansive walls of glass and sliding doors frame panoramic water vistas, filling the home with natural light and bringing the outdoors in, a hallmark of luxury waterfront homes in this area. Inside, the home blends refined elegance with relaxed island living. A grand open-concept layout connects the living room, dining area and a chef’s kitchen outfitted with high-end appliances, custom cabinetry and generous entertaining space. Multiple living areas, often found in premier Anna Maria Island homes, offer flexibility for hosting guests or enjoying quiet retreats. Each of the four bedrooms is generously sized, while the six total baths provide a resort-style convenience ideal for family and guests. The primary suite is typically a sanctuary of its own, featuring water views, private balcony access and a spa-inspired bath. Outside, the property becomes exceptional. A resort-style pool and spa overlook the bay, surrounded by lush tropical landscaping and expansive outdoor living areas designed for entertaining or unwinding in the coastal breeze. Waterfront homes here often emphasize seamless indoor-outdoor flow, creating an island lifestyle experience. With 235 feet of frontage, the property offers a private dock and boat lift, ideal for direct access to the open waters of Tampa Bay and the Gulf beyond. Whether you’re setting out for a sunset cruise, fishing at dawn or simply watching dolphins and manatees pass by, the water becomes an extension of daily life. Set on one of the desirable stretches of Anna Maria Island, this home combines rare waterfront scale, luxury amenities and effortless boating access, a showcase of elevated coastal living.

518 58th Street, Holmes Beach
$985,000
2 Beds ⋅ 2 Baths ⋅ A4693773 MLS
DEEDED BOAT SLIP and ROOM FOR A POOL! Discover the best of island living in beautiful Holmes Beach. Nestled on a quiet street in a peaceful neighborhood, you’ll love the combination of boating access and close proximity to the beach this home has to offer. Elevated with impact windows, this 2-bedroom, 2-bathroom home is turnkey furnished and includes a deeded, unimproved boat slip at the end of 85th Street, perfect for boating enthusiasts and those seeking the ultimate coastal lifestyle. NEW ROOF installed in August 2025. The downstairs area has been professionally remediated and renovated, while the upstairs living area remained untouched by hurricanes in 2024. Situated on an expansive 9,000sqft lot, there is ample space to add a pool and create your own private oasis. Whether you’re seeking a primary residence or a tropical getaway, this property is ideal for enjoying Anna Maria Island living. Book your showing today!

221 85th Street, Holmes Beach
$879,000
2 Beds ⋅ 3 Baths ⋅ A4691196 MLS
Experience the ultimate Florida beach lifestyle in this elevated 2-bedroom, 2-bathroom coastal retreat situated just steps from the pristine white sands of the Gulf. This home exudes classic island charm with modern peace of mind, featuring full impact-rated windows and doors along with durable Hardie siding designed for long-lasting beauty and protection. The exterior is anchored by a sprawling paver driveway and professional tropical landscaping, leading to a versatile covered under-house area perfect for shaded relaxation or gear storage after a day on the water. The property also boasts ample garage space that offers incredible flexibility, with plenty of room that could easily be converted into a game room or additional lounge area. Inside, the open-concept living space is bathed in natural light and anchored by rich wood flooring that flows throughout the main areas. The chef-inspired kitchen is well-appointed with warm wood cabinetry, granite countertops, and a suite of stainless steel appliances, all centered around a large breakfast bar that overlooks the dining and living zones. Offered fully furnished for the buyer’s convenience, this home is truly move-in ready and designed for immediate enjoyment. Step through elegant French doors to the expansive covered porch, an ideal setting for al fresco dining and morning coffee in the coastal breeze. Whether you are looking for a primary residence or a seasonal getaway, this turnkey coastal gem offers the rare opportunity to live life just minutes from the water’s edge.

2811 Gulf Drive, Holmes Beach
$3,490,000
4 Beds ⋅ 4 Baths ⋅ A4683981 MLS
Beachfront Bliss – Gulf Views from Every Angle! Just one house from the beach, this 4-bedroom, 4-bath coastal stunner delivers postcard-perfect Gulf views straight from the kitchen sink—yes, you’ll actually smile while scrubbing plates! Natural light throughout, high ceilings, 2 sided fireplace, wet bar in the living room, open living area that flows into a chef’s kitchen. Stainless steel appliances, gas stove, double ovens and more! The coastal chic blue countertops and tile throughout for easy beach sand clean up! Step outside to your wrap around balcony to dine and enjoy the gulf breeze. Backyard features your private heated pool that includes a sun shelf. All the bedrooms are spacious and have their own privacy. The primary suite is upstairs with even better views of the Gulf to wake up to. Enjoy your private balcony AND a spiral staircase leading up to the roof top deck, ideal to watch sunsets and dolphins jump in the water. Master bathroom has a huge walk-in shower, soak in tub, dual sinks and a large walk-in closet that includes a safe. The location is central to the island, close to everything and very convenient. 30 day minimum rental period. One house away from the Gulf, this may be the island’s best-kept secret!

105 49th Street, Holmes Beach
$1,376,000
2 Beds ⋅ 2 Baths ⋅ A4682162 MLS
Pre-Construction. To be built. Why buy old when you can get new for the same price? Green Street Builders brings 35+ years of experience, and refreshing coastal elegance at an unbeatable $900/sqft price point. The plans speak for themselves. 4 defined sleeping areas per side (including an open air loft), high-functionality, and open concept design with vaulted ceilings. Quartz waterfall counters, modern sleek cabinets, a lot of glass, built to latest hurricane codes; everything you would want in a new construction at a more obtainable price point. Zoned for weekly rentals, it's a lush, tropical, vacation themed setting for you to enjoy... or for your guests to come back to year after year. 45% down, 10% at drywall, the rest not due until Certificate of Occupancy. Nearby comparable sales at least $125,000-$175,000 higher. Call to chat, do your own research or ask for a list of recent comparables, no obligations.

311 59th Street Unit B, Holmes Beach
$3,495,000
4 Beds ⋅ 6 Baths ⋅ A4676665 MLS
Striking modern luxury meets investment potential at The Black Pearl, a four-bedroom, five-and-a-half-bath residence located just a short walk from the beaches of Holmes Beach, downtown shopping and dining, and the island trolley. This architecturally distinctive black-and-white home features a private black-bottom infinity-edge pool, resort-style outdoor living, and a rooftop deck with panoramic Gulf views. Designed for both lifestyle and performance, the home offers a bright open-concept interior, gourmet kitchen with island seating, and four king bedroom suites—each with a private ensuite bath—plus a bonus den with additional sleeping flexibility. Outdoor amenities include a full outdoor kitchen, multiple lounge and dining areas, outdoor shower, and ample on-site parking. Currently part of the Exclusive Vacations luxury rental program, the property offers immediate access to a professionally managed, high-end short-term rental platform focused on premium positioning, elevated guest experience, and revenue optimization. A rare opportunity to own a visually iconic, walkable luxury home with proven short-term rental appeal on Anna Maria Island.

5612 Guava Street, Holmes Beach