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$1,850,000
3 Beds ⋅ 3 Baths ⋅ A4703334 MLS
Welcome to your own slice of island paradise in the heart of Holmes Beach! Perfectly positioned on a scenic canal and just minutes from the sugar-sand shores of Anna Maria Island, this beautifully designed 3-bedroom, 3-bathroom pool home offers the ideal blend of luxury, comfort, and coastal living. Step inside to discover an open and spacious floor plan filled with natural light, thoughtfully crafted for both everyday living and effortless entertaining. The stylish interior flows seamlessly to the outdoor living area, where a private pool and tranquil canal views create the perfect setting to relax and unwind. Whether you’re searching for a full-time residence, vacation getaway, or investment opportunity, this exceptional property delivers the best of island living. Enjoy easy access to award-winning Gulf beaches, local boutiques, waterfront dining, and all the charm that makes Holmes Beach one of Florida’s most sought-after destinations. No hoa or cdd fees!

507 59th Street, Bradenton Beach
$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
$1,599,000
3 Beds ⋅ 2 Baths ⋅ A4700017 MLS
There are homes that simply exist, and there are homes that become part of an island's story. Cherished by the same family for the past 46 years and with only two owners in its history, this waterfront retreat captures the authentic charm of old Anna Maria Island. Perfectly positioned on a quiet dead-end street, this three-bedroom, two-bath home sits on a generous waterfront lot with beautiful water views from nearly every room. A deep-water canal with no fixed bridges provides direct boating access to Bimini Bay and the Gulf of Mexico, making it an ideal home for boaters, anglers, and anyone who dreams of life on the water. Thoughtfully updated while preserving its inviting island character, the home features a beautifully remodeled kitchen (2024), new ceramic tile flooring throughout, a new air conditioning system (2024), and a new water heater (2024). The private pool creates the perfect setting for relaxing after a day on the boat or enjoying Florida evenings with family and friends. Being sold fully furnished, this home is ready to enjoy from day one. Move right in and embrace the timeless island lifestyle, or use this exceptional property as the foundation for creating your own custom waterfront dream home. Opportunities like this with such history, character, and an unbeatable boating location rarely come along. Only a few blocks from the beach, offering the best of both worlds—deep-water boating from your backyard and easy access to the Gulf's white-sand shoreline. Come experience the enduring magic of old Anna Maria Island, moments from the gulf beaches and conveniently located to island dining and shopping. **Property information received from third-party sources is considered reliable but is not guaranteed. All information should be independently verified by buyers and buyer's agent.

508 83rd Street, Holmes Beach
$775,000
3 Beds ⋅ 2 Baths ⋅ A4698503 MLS
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. 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
$880,000
3 Beds ⋅ 2 Baths ⋅ A4696880 MLS ⋅ B BLDG.
Exceptional Island Investment Opportunity Just One Block 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
$1,150,000
3 Beds ⋅ 2 Baths ⋅ TB8510500 MLS
Price improvement! Welcome to this modern, yet warm and cozy, 3-bedroom, 2-bathroom home on the north end of Holmes Beach on Anna Maria Island. From the moment you arrive, the estate makes a striking first impression with its notable presence and contemporary landscaping. Updated throughout in 2026, this move-in-ready residence offers almost 1,400 square feet of stylish, single-level living designed for comfort and convenience. The bright and inviting interior features a modern kitchen with updated cabinetry and countertops, Café appliances, new interior shutters throughout, and thoughtful finishes that create a chic coastal feel. Central air conditioning and electric heat provide year-round comfort, making this home ideal as a primary residence, vacation getaway, or investment property. Situated on a generous 0.21-acre lot, the property offers a large backyard with sliding glass door access, providing plenty of space to entertain, relax, or create your dream outdoor setting. There's ample room for a pool and ADU, or additional outdoor living areas. Located on a quiet and friendly, low-traffic street, this home offers a peaceful setting with wonderful neighbors and a true sense of community. Enjoy the tranquility of island living while being just minutes from everything the north end of Anna Maria Island offers. Location truly is everything. You'll love the convenient access to sugar-sand beaches, an 8 minute walk to a public beach, island shopping, local cafes, restaurants, parks, and outdoor recreation. The golf-cart-friendly neighborhood makes it easy to explore and enjoy the island lifestyle. As an added bonus, all furnishings are included with the sale, making this a turnkey opportunity. Don't miss your chance to own an elegant home in one of Anna Maria Island's most desirable locations.

214 85th 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
$1,500,000
3 Beds ⋅ 3 Baths ⋅ A4690200 MLS ⋅ 2 BLDG.
Newly updated with fresh paint throughout, brand new stainless steel appliances, quartz countertops on kitchen and bathrooms and so much more!! Nestled near the north end of Anna Maria Island, 215 81st Street is a three-bedroom, two and a half bath home boasting over 2,000 square feet of living space—an Airbnb gem zoned for weekly rentals. Just two blocks from some of the island’s most pristine beaches, this property offers a true tropical paradise out back. The fully fenced oasis features a gorgeous pool with a built-in hot tub, while the expansive paver-lined lounge area creates a true island escape. The elevated design includes a two-car garage and a game room—currently set up with a ping pong table, connect 4, and Tic Tac Toe but offering ample space to add additional attractions for guests. The second floor invites you into a bright, open living, dining, and kitchen area featuring a brand new LG stainless steel appliance package and gorgeous quartz countertops. This floor also features a half bath, complemented by a massive, screened-in balcony deck (freshly screened in less then a year ago) overlooking the pool oasis below—perfect for soaking in the tropical ambiance. You will also find a dedicated interior laundry room with full size washer and dryer on this floor as well. On the third floor, you’ll find three spacious bedrooms and two full baths, with the primary suite offering not only luxury but also absolutely gorgeous views from every angle—a panoramic reminder of the beauty that surrounds you on Anna Maria Island. This home is packed with recent updates: a 2022 roof, 2019 AC, and a brand-new water heater. The exterior shines with hardie board siding installed less than a year ago and fresh paint. Beyond the home, you’re a stone’s throw from Pine Avenue’s charm and all that Anna Maria offers—laid-back vibes, local eateries, and coastal culture. Fully furnished and turnkey, this is both a thriving investment and an island escape waiting for you.

215 81st Street Unit 2, Holmes Beach
$4,295,000
4 Beds ⋅ 3 Baths ⋅ A4685020 MLS
One or more photo(s) has been virtually staged. Spectacular Waterfront Key West-Style Home on Bimini Bay!! This beautifully maintained 4 bedroom, 3 bathroom single-family home, offering 2,775 sq ft of living space on a spacious 9,400 sq ft lot. Meticulously crafted with thoughtful architecture, interiors and landscaping by legendary award-winning architect, Emily Anne Smith. As you step in, you’ll notice the double height ceilings, unique, blue glass chandelier in the entry that leads into the spacious open floor plan. Large slider impact doors that create natural light and provide stunning views of Bimini bay. The living room is warmed by a modern linear fireplace complemented by a wall of custom illuminated floating shelves and built-in cabinetry with an exquisite backlit blue agate Antolini countertop. A chef's dream, the kitchen is equipped with Monogram Professional Series appliances, quartz countertops and a thoughtful layout. Abutting the kitchen is the large laundry room leading to an oversized two car garage. A first floor primary suite has privacy and features an oversized en suite bathroom with double marble vanity. In addition, the first floor has a full bathroom with a frameless glass shower, custom blue glass waterfall sink and two generously sized bedrooms. The entire second level luxurious main suite features breathtaking water views, cathedral ceilings, dual custom walk-in closets, a large spa-like bathroom with a freestanding jetted tub surrounded by backlit quarzite counters, Bisazza tile, modern crystal chandelier, dual Carrara marble vanities, and spacious modern reclaimed wood porcelain tile walk-in shower. An expansive rooftop terrace and gazebo, not to be missed, offers a stunning 360-degree view of Anna Maria Island. Step outside to entertain on the expansive pool deck with a large pool, or retreat to the private upper deck for quiet sunsets and bay breezes. Resort style outdoor area includes an outdoor kitchen and bar, outdoor shower, covered fishing station, dual lift and dock area for jet skis and ample space to accommodate a large yacht, fishing or sport boat, making indoor/outdoor living and entertaining flawless. Brand new Interior and exterior paint throughout! Enjoy deep-water frontage with no bridges to the Gulf of Mexico and your own 9,000 lb boat lift — perfect for boating enthusiasts who want effortless Gulf access and quick runs to the open water. The home is just a short golf cart ride gorgeous sand beaches, making it ideal for beach lovers, families, or those seeking the ultimate Florida island lifestyle.

8321 Marina Drive, Holmes Beach
$2,150,000
5 Beds ⋅ 4 Baths ⋅ A4675614 MLS
Discover a versatile two-unit property in Holmes Beach offering the flexibility many buyers seek on Anna Maria Island. With a combined total of 5 bedrooms and 4 bathrooms, this property includes two fully turnkey residences: Pool Party South, a 3-bedroom, 2-bath main home, and Pool Party North, a 2-bedroom, 2-bath secondary unit. This configuration is well suited for those looking for a two-unit island home, a vacation property with short-term rental potential, or a second home that can help offset expenses when not in use. Both units feature coastal-inspired updates, including modern tile flooring, granite countertops, stainless steel appliances, newer roofs, and comfortable furnishings. Offered turnkey, the property is ready for immediate enjoyment or rental use. Weekly rentals are permitted, providing owners the flexibility to enjoy the island on their own schedule while generating income when away—an important consideration for buyers seeking short-term rental options on Anna Maria Island. The outdoor living area enhances the relaxed Florida lifestyle with a heated pool and spa, outdoor bar with sink, and multiple areas for dining and lounging. The oversized lot adds a sense of privacy, creating an inviting retreat for both owners and guests. This layout appeals to a variety of uses, including a multi-residence setup, a dual-unit investment property, or a home offering separation between living space and guest accommodations while maintaining rental flexibility. Located just a short walk to the Gulf beaches, as well as nearby dining, shopping, and island amenities, this property captures the ease and charm of Holmes Beach living. For buyers searching for an updated two-unit home with a pool, walkable beach access, and strong rental potential, Pool Party South and Pool Party North provide a compelling blend of lifestyle and opportunity on Anna Maria Island.

314 61st Street, Holmes Beach