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$1,350,000
4 Beds ⋅ 4 Baths ⋅ O6384479 MLS
THE OPPORTUNITY - Everything needed is there to continue without disruption. Performs on a deliberately controlled booking schedule, math works. Consistently a favorite with high reviews and more than 1,000 stays. THE PROPERTY & LAYOUT - Proven coastal resilience and true turnkey operations on Anna Maria Island. Built to modern elevated standards, this premier duplex has successfully navigated storm seasons over the past 12 years with no insurance claims filed. Continually refreshed, fully turnkey, this mirrored multi-family property features two separate 2BR/1.5BA units in the Bradenton Beach transient rental district, allowing less-than-week-long stays. The unique back-to-back layout provides a distinct advantage over traditional side-by-side duplexes, giving each unit a private-residence feel that supports longer average stays and higher nightly rates. LOW-MAINTENANCE, RENTAL-READY FEATURES: Maximum resident privacy: Separate amenities for each unit, including individual laundry facilities, private balconies, and dedicated parking. Ample clearance and storage: Under-building parking for vehicles, boats, or golf carts, plus owner storage. Prime location: Steps to Gulf beaches, local dining, and historic Bridge Street.

2504 Avenue B, Bradenton Beach

Courtesy of BEYCOME OF FLORIDA LLC

$769,000
2 Beds ⋅ 3 Baths ⋅ A4682831 MLS
Experience the perfect blend of luxury beachfront living and strong investment potential with this rare Gulf-front condo-hotel residence on Anna Maria Island, designed in the timeless style of a charming New England coastal inn. This intimate 12-unit boutique community offers direct access to the sandy beaches of the Gulf of Mexico and delivers one of the most desirable beachfront locations in Florida. Unit #6 is ideally positioned on the second floor and accessed by both an elegant staircase and elevator, offering convenience along with privacy and elevation for enhanced views. This spacious 2-bedroom, 2.5-bath beachfront condo features beautiful original hardwood flooring, crown molding, and a bright open layout designed for coastal comfort. A rare highlight of the residence is its two private balconies, one extending from the living room and the other from the primary suite, providing panoramic Gulf views, pool views, and unforgettable sunset skies—perfect for morning coffee, evening relaxation, or listening to waves rolling onto the shore. The interior is thoughtfully appointed with built-in closets, in-unit washer and dryer, and a fully turnkey package that includes furnishings, décor, beach equipment, kayaks, and paddleboards, allowing for immediate enjoyment without additional setup. As part of a professionally managed condo-hotel investment property, owners benefit from up to 120 days of personal use a year while the on-site management team handles rentals the remainder of the time. With its prime beachfront location on Anna Maria Island, the property consistently achieves strong occupancy rates, making it an attractive income-producing vacation rental investment. Even better, ownership allows you to enjoy months of personal beachfront living annually while rental income helps offset operating costs, creating both lifestyle value and financial efficiency. Offered fully turnkey, this residence checks every box for buyers seeking a luxury beachfront condo on Anna Maria Island, a Gulf-front vacation rental investment property, or a low-maintenance coastal retreat in Florida. Simply bring your swimsuit and start enjoying beachfront living at its finest—where lifestyle, location, and long-term value all come together in one exceptional opportunity.

101 66th Street Unit 6, Holmes Beach

Courtesy of WAGNER REALTY

$1,065,000
2 Beds ⋅ 2 Baths ⋅ A4682317 MLS
Experience the peak of coastal living in this fully turnkey, elevated residence, where the rhythm of the Gulf of Mexico meets refined island design. Offered completely furnished and move-in ready, this two-bedroom, two-bathroom home allows for an immediate transition into the Bradenton Beach shoreline experience. The interior is bathed in natural light, highlighting an open-concept layout with a designer kitchen featuring granite countertops, a custom tile backsplash, and stainless steel appliances. Both bathrooms have been elegantly updated with modern stone finishes and contemporary fixtures. Outside, a sprawling wrap-around deck offers an expansive venue for sunset views and open-air relaxation. The ground level provides significant versatility with a large, covered area for secure parking and storage, alongside a private, fenced retreat featuring a personal spa. With rare commercial zoning, this property offers exceptional potential as a primary residence, a seasonal escape, or a high-performance investment. From the meticulously curated decor to the updated systems, every detail is in place for the next owner to simply arrive and enjoy.

111 9th Street N, Bradenton Beach

Courtesy of KELLER WILLIAMS ISLAND LIFE REAL ESTATE

$699,000
1 Beds ⋅ 1 Baths ⋅ A4682104 MLS ⋅ Peacock Hut BLDG.
One-of-a-kind Holmes Beach retreat just minutes from the sand! This completely renovated 1-bedroom, 1-bath home offers everything you need in the perfect beach getaway or income-producing property. Thoughtfully updated throughout, the home features hurricane-impact windows and doors, solid wood cabinetry, stainless steel appliances, tile flooring, and granite countertops. Offered turnkey furnished with a stylish coastal décor, it’s truly move-in or rental ready.Step outside to your private outdoor oasis featuring a large heated free-form pool, spacious patio ideal for entertaining, custom outdoor lighting, and an outdoor shower with rain head—perfect after a day at the beach. Located just two blocks from popular shops and restaurants and only a five-minute walk to the Gulf beaches, this prime island location delivers the best of Anna Maria Island living.Whether you’re seeking a personal island retreat or a strong investment opportunity, this property shines with projected rental income up to $50,000 annually. Don’t miss this rare chance to own a turnkey beach home in the heart of Holmes Beach.

205 Peacock Lane Unit A, Holmes Beach

Courtesy of BEACH HOUSE REAL ESTATE LLC

$1,372,000
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

Courtesy of COMPASS FLORIDA LLC

$4,995,000
5 Beds ⋅ 5 Baths ⋅ A4680377 MLS
There's a different side of Anna Maria Island-one where island living, privacy, and life on the water all come together. Welcome to 529 77th Street in Holmes Beach-an extraordinary British West Indies inspired waterfront residence with more than 5,000 square feet, designed for gathering, entertaining, and enjoying life on the water.  Inside you will find two luxurious primary suites, beautiful custom millwork, an elevator, media room, and a chef's kitchen with an oversized island and butler's pantry-all surrounded by expansive living spaces and multiple terraces.  Outside is where the home truly shines.  Imagine mornings overlooking Bimini Bay, afternoons by the saltwater pool and spa, and evenings entertaining family and friends from your covered lanai and outdoor kitchen.  And when the water is calling, your boat is waiting right outside.  A 70 foot dock and a 13,000 pound boat lift put you just moments from the Intracoastal. This is more than a waterfront home.  It's a place to put down roots, make memories and experience Anna Maria Island as home. Call now to schedule your private showing of this amazing island property.

529 77th Street, Holmes Beach

Courtesy of BEACH HOUSE REAL ESTATE LLC

$3,975,000
4 Beds ⋅ 5 Baths ⋅ A4681928 MLS
Sunsational is a freshly built & beautiful new home in Holmes Beach! This four bedroom, 4 and half bathroom pool home is impeccably built by Moss Construction and designed by award winning designer Emily Moss Designs. Which will be featured in Design Magazine soon, it's just THAT amazing! The facade of this incredible home feels like luxury and the minute you step inside it won't disappoint. The textures, the colors, the style of each room creates the perfect home for you to live and or continue renting as an investment home. They thought of everything and there is no lack of detail at every turn. So many things to bring to light about this gorgeous home but one of the most prominent is the back yard. It's literally a space full of beauty and fun. It's Florida outdoor living at its finest. Games, heated pool and spa as well as enough balconies for everyone. The great room creates a space large enough for everyone to come together for dining, movies or anything else the family wants to do together. Sunsation also gives you and your family or guests the ability to get away into their own spaces. With a small media room with wet bar upstairs you can spread out to in case you just can't agree on a movie. There are numerous balconies to escape to and enjoy the warm air and great views of Holmes Beach. Every bedroom is large and cozy. Three of the bedrooms are en-suites and ready for and your guests and you must see the bunk room. EVERY youngster will dive into bed and love the feel of fun in this super creative use of space. Just 2.5 blocks to the coveted sugary beaches of Anna Maria Island. Spend the morning walking the beach, collecting shells and feel the ocean breeze. Come back from the beach and spend the day at a home you literally may never want to leave. If you do decide to venture out, you are a golf cart ride or a bike ride away from it all. Hop on the free Trolley and head out to all the hubs of each cities shops and restaurants. This home is amazing and you simply must come see your new home and start living the Anna Maria Life now!

215 83rd Street, Holmes Beach

Courtesy of ANNA MARIA LIFE REAL ESTATE

$1,995,000
A4679981 MLS
~~~ 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

Courtesy of ANNA MARIA LIFE REAL ESTATE

$2,790,000
5 Beds ⋅ 6 Baths ⋅ A4679935 MLS
LUXURY COASTAL RETREAT with 360° WATER VIEWS just steps from Bradenton Beach!!! Just two blocks from the sugar sand shores and perfectly centered between the beach and the bay, this spectacular three-story coastal retreat offers breathtaking 360° views of both the Gulf of Mexico and Sarasota Bay. Whether you are searching for a year-round residence, seasonal escape, or high performing investment property, this one-of-a-kind home truly has it all. With 5 bedrooms, 5.5 bathrooms, and multiple indoor and outdoor living spaces, the home is designed for both luxury and comfort. The first level welcomes you with a bright sitting area featuring sliding glass doors overlooking the HEATED pool and spa, along with a separate BONUS room perfect for a home gym, owner’s storage, or beach gear room. On the second floor, you’ll find four spacious bedrooms, each with its own ENSUITE bathroom and walk-in tiled shower, plus an open loft area currently set up with extra beds that can easily become a kids’ play area, game room, or lounge space. The third floor serves as the main living area, showcasing incredible full 360° water views, an open-concept kitchen with a large island and seating, granite countertops, stainless steel appliances, and peek-through windows flanking the stove, a separate dining area for formal or casual entertaining, and a living room surrounded by STUNNING water views. Also on this level is a PRIVATE bedroom suite with balcony access and another ensuite bathroom with dual sinks, and a walk-in tiled shower, PLUS a cozy sitting area leading to a balcony overlooking the pool and a spiral staircase to the ROOFTOP DECK creating your personal PARADISE for sunset watching and stargazing over the Gulf and bay. The outdoor living space offers a beautifully tiled heated pool and spa, a large covered lanai with wood plank ceilings, pavered flooring, a fully FENCED yard, and low-maintenance TURF grass for privacy. The pool features a NEW ELECTRIC HEATER and NEW POOL PUMP, the exterior has been freshly painted, and all appliances are lightly used and in excellent condition. Located just minutes from historic Bridge Street, this home is close to colorful shops, local restaurants, vibrant nightlife, live music, a fishing pier, mini golf, and more, with Bridge Street connecting the Sarasota Bay side to the Gulf of Mexico side of the island. This is the perfect place to unwind after a long day at the beach with endless activities nearby, and it truly doesn’t get better than this...LUXURY, LOCATION, LIFESTYLE, and VIEWS all in one unforgettable coastal property.

206 Church Avenue, Bradenton Beach

Courtesy of SERHANT

$785,000
2 Beds ⋅ 2 Baths ⋅ A4679030 MLS ⋅ 5608 BLDG.
ITS TIME TO Wake up to the sound of waves and endless Gulf views in this beautifully situated two-bedroom, two-bath condo directly on the Gulf of Mexico. Step outside and onto the coveted, sugar-soft sandy beaches that make this area so sought after—perfect for morning walks, sunset strolls, and carefree beach days. Inside, the condo features a newly renovated kitchen that’s both stylish and functional, ideal for entertaining or preparing meals after a day at the beach. The thoughtfully designed layout offers comfortable living spaces and bedrooms with excellent privacy, plus the convenience of an in-unit laundry facility for effortless everyday living. Additional highlights include downstairs storage, perfect for beach chairs and gear, along with underground parking for added peace of mind. Located just minutes from shopping, restaurants, and local dining favorites, this condo perfectly balances relaxed beachfront living with easy access to all the best the area has to offer. Whether you’re seeking a full-time residence, a vacation escape, or an investment opportunity, this Gulf-front condo delivers the coastal lifestyle everyone dreams of. Come live your Anna Maria Life.

5608 Gulf Drive Unit 104, Holmes Beach

Courtesy of ANNA MARIA LIFE REAL ESTATE

$625,000
2 Beds ⋅ 2 Baths ⋅ TB8470442 MLS
**NO HOA** Find me another turnkey island property like this one that is zoned for short term rentals without an HOA... Elevated and fully updated coastal retreat on beautiful Anna Maria Island with NO HOA! Built for peace of mind with a newer metal roof, newer deck, HVAC system with brand new UV light and air scrubber, impact windows and doors with a lifetime warranty. The property has been meticulously maintained with a transferrable termite warranty, updated landscaping, outdoor shower, and covered parking for up to five vehicles. Offered fully furnished and ready for you to enjoy the option of flexible income potential with the ability to short term rent while owning a slice of island life near the Gulf beaches, dining, and laid-back charm of Holmes Beach.

4909 Gulf Drive Unit 6B, Holmes Beach

Courtesy of EXP REALTY LLC

$6,245,000
A4680465 MLS
Very rare opportunity to own one of the most coveted addresses on Anna Maria Island—Sunset Lane. This estate-sized, over ½-acre beachfront parcel offers 80’ of direct Gulf frontage with an impressive 470’ depth. DEP state permit in hand allows for up to 6,558 sq ft of living space (Ground: 74’ x 58.6’, First Living: 74’ x 58’, Second Living: 67’ x 48.6’). Design and build your dream coastal estate with unobstructed sunset views from every room.

102 Sunset Lane, Holmes Beach

Courtesy of COLDWELL BANKER REALTY

$2,185,000
4 Beds ⋅ 3 Baths ⋅ A4680135 MLS
Start your island getaway here at our newly refreshed coastal home in a charming neighborhood of Holmes Beach! This gorgeous, modern four bedroom, three bath retreat is a short walk to the glistening sandy beaches of the Gulf! An open layout with chic-boho furnishings, serene hues, a private pool, and state of the art appliances throughout. You’ll love the proximity to local restaurants, boutiques, and how bike friendly the island is. Cruise the bike paths or rent a golf cart to explore the island. Venture over to the North End by the free AMI Trolley, where you have the infamous Pine Ave, that has one of a kind shops and cafes. Island living at its finest! Nothing feels more tropical than arriving to a home where the streets are dotted with beautiful swaying palm trees. Step inside to the immaculate space that has all the cozy comforts to make your tropical dreams come true. The living room features plush sofas and modern chairs where you can kick back and watch a show on the mounted flat screen. The chef’s kitchen is complete with quartz counters, custom cabinets, stainless steel appliances, and a dining table to enjoy a home cooked meal with the family. The four bedrooms provide pure comfort with luxury bedding and natural wood elements that enhance the calm ambiance. The master suite features a king bed with an ensuite bathroom that has a freestanding soaking tub, glass walled step-in shower with wood flooring, and dual quartz vanities for a spa-like experience. In the other 3 dreamy bedrooms you have king beds in two of the rooms and your last bedroom highlights a full over full bunk bed that is popular for the younger crew in tow.

305 73rd Street, Holmes Beach

Courtesy of STARZ REAL ESTATE, LLC

$990,000
2 Beds ⋅ 2 Baths ⋅ A4679951 MLS
This stunning completely renovated 2-bedroom, 2-bathroom home offers 1,500 square feet of bright, open-concept living space designed for effortless island lifestyle. Step inside to find a seamless flow between the gourmet kitchen, dining area, and spacious living room—perfect for relaxing with friends, family gatherings, or simply soaking in the Florida sunshine that pours through large windows. The thoughtful renovation shines through with contemporary finishes, high-quality fixtures, and a fresh, inviting palette that feels brand new yet timeless. Both bedrooms provide comfortable retreats, while the well-appointed bathrooms add a touch of luxury. Situated on a prime lot in desirable Holmes Beach, you'll enjoy generous outdoor space—ideal for morning coffee, evening barbecues, or creating your own tropical oasis. Just moments from the sands of Manatee Public Beach and the calm Gulf waters, this home puts you in the center of Anna Maria Island's relaxed charm: pristine beaches, boutique shops, waterfront dining, and easy access to everything the island offers.

510 69th Street, Holmes Beach

Courtesy of LPT REALTY, LLC

$4,900,000
3 Beds ⋅ 3 Baths ⋅ A4678416 MLS
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

Courtesy of CENTURY 21 INTEGRA

$3,300,000
4 Beds ⋅ 6 Baths ⋅ A4679359 MLS
Nestled along a serene canal and embraced by a curtain of mature tropical palms, this custom-remodeled residence unfolds as a private coastal estate, an intimate sanctuary where luxury, tranquility, and effortless island living exist in perfect harmony. Masterfully re-imagined by Eason Builder Group, the home was completely gutted and rebuilt just four years ago, and last year the entire first level was once again fully renovated, resulting in a residence that feels both newly crafted and timelessly refined. From the moment you arrive, a sense of seclusion and calm sets in. As you walk up to the home, an old-growth Gumbo Limbo greets you. Sunlight filters through new hurricane-impact windows, illuminating interiors designed to feel open yet intimate, grand yet soothing. The main living space becomes a natural gathering place, anchored by a custom-built-in entertainment center and a coffee station. An elegant touch that invites slow mornings, refined evenings, and effortless entertaining. Sonos surround sound flows throughout the home, creating an ambient soundtrack for daily life, while a fully integrated security and camera system offers peace of mind and quiet confidence. Complementing the home's HURRICANE-IMPACT WINDOWS, professionally INSTALLED FLOOD PANELS provide an additional safeguard, reflecting the thoughtful attention to both luxury and long-term resilience found throughout the property. The kitchen stands as a statement of both beauty and performance, where quartz countertops, solid-wood glass-front cabinetry, a sculptural range hood, designer pendant lighting, and stainless-steel Bosch appliances come together in a space crafted for culinary artistry and connection. It opens seamlessly to the dining area, where a wood-burning travertine stone fireplace adds warmth and architectural presence, setting the stage for candlelit dinners and lingering conversations. Two luxurious primary suites, one on each level offers the rare indulgence of privacy and flexibility. Each is finished with shiplap walls, porcelain tile, recessed lighting, and abundant natural light. The upper-level retreat opens to a private balcony overlooking the pool and tropical grounds, a serene perch for sunrise reflections and evening breezes. Its spa-inspired ensuite features a quartz walk-in shower, while the first-floor primary bath is appointed with a solid-wood double vanity, continuing the home’s narrative of tailored craftsmanship and understated elegance. Completing the residence are two additional bedrooms with a shared bath and an upstairs bonus room ideal for recreation, fitness, or creative pursuits. Beyond the interiors, the estate reveals its most captivating chapter. The backyard unfolds as a secluded resort, where a glistening pool and spa are framed by layered, well-established tropical landscaping that has matured into a living wall of privacy. Covered and open-air lounges invite both sun-drenched afternoons and starlit evenings, while a turf-lined grilling and gathering area provides an elevated setting for alfresco dining. Just beyond the palms, the canal stretches quietly behind the property, creating the illusion that the waterway is an extension of your own grounds and inviting a lifestyle of boating, paddleboarding, and sunset cruises from your private dock. When you venture beyond this sanctuary, the unmistakable charm of Holmes Beach awaits.

506 58th Street, Holmes Beach

Courtesy of KW SUNCOAST

$749,900
2 Beds ⋅ 2 Baths ⋅ A4678332 MLS ⋅ Playa Encantada BLDG.
Set within the beachfront enclave of Playa Encantada, this beautifully maintained two-bedroom, two-bath residence offers an effortless coastal lifestyle just steps from the sand and the island trolley — placing the area's finest shops, restaurants, and attractions within easy reach. Inside, an open and light-filled layout creates an inviting sense of space. The kitchen is appointed with granite countertops, stainless steel appliances, and generous cabinetry, while the living and dining areas flow seamlessly onto a private balcony overlooking the heated pool — an ideal setting to take in the Gulf breezes and glimpses of the water beyond. Both bedrooms are generously sized, with the primary suite featuring a private en-suite bath. Residents enjoy a thoughtful collection of resort-style amenities, including a heated pool, tennis courts, shuffleboard, and private beach access. A flexible two-week minimum rental policy further enhances its appeal, offering an exceptional opportunity as a seasonal retreat or income-producing investment.

6006 Gulf Drive Unit 214, Holmes Beach

Courtesy of DUNCAN REAL ESTATE, INC.

$1,350,000
4 Beds ⋅ 2 Baths ⋅ A4679453 MLS
OVER 150K INCOME OVER LAST 12 MONTHS!!! Embrace the pinnacle of island luxury with this impeccably designed, turnkey Holmes Beach duplex—operating as a successful Airbnb and ready for seamless ownership transition. Each side features two spacious bedrooms and one bath, complete with gleaming marble countertops, white shaker cabinetry, elegant, natural-flow tile backsplashes and breathtaking remodeled bathrooms. With fresh paint, brand-new flooring, and a 2022 roof, the home is both stunning and secure. Every door and window is hurricane-rated and newly installed—offering peace of mind in every detail. Outdoors, one side boasts a heated pool with newly installed heater and a gorgeous waterfall feature, while the other side offers a soothing hot tub just installed in 2025 as well. Two outdoor showers add to the coastal experience, surrounded by lush, meticulously maintained landscaping. With five parking spots and separate entrances, you can host larger groups as a whole or individual parties in each unit and your guests will fall in love with this location when they find out public beach access is less than a block away! This duplex is uniquely positioned for maximum rental flexibility. Weekly rentals are fully allowed, making this a prime investment. High-end furnishings down to the last detail—silverware, plates, bedding, towels—ensure a seamless guest experience. Just steps from the vibrant charm of historic Bridge Street—known for its waterfront dining, boutique shops, and lively atmosphere—and minutes from the serene Bean Point, this property is at the heart of one of Florida’s top destinations. This is more than a home; it’s a fully operational, luxurious escape. Whether you’re continuing its rental success or claiming it for yourself, this is an unparalleled opportunity for coastal living and investment combined.

3604 Gulf Drive Unit A and B, Holmes Beach

Courtesy of PREFERRED SHORE LLC

$2,399,000
6 Beds ⋅ 6 Baths ⋅ A4679284 MLS
Welcome to Sands of Time, a recently updated six-bedroom, four-and-a-half-bathroom coastal retreat located less than two blocks from the white-sand beaches in the heart of Holmes Beach on Anna Maria Island. Thoughtfully designed and professionally decorated, this home blends relaxed beach style with upscale comfort, making it ideal as a primary residence, second home, or high-performing investment property. Inside, the spacious layout comfortably accommodates family and guests, with multiple living areas and a fully equipped kitchen designed for entertaining and everyday living alike. High-capacity laundry is conveniently located on the main floor, perfect after long days at the beach. Four private balconies invite you to enjoy morning coffee or evening breezes, while the home’s open flow creates a welcoming atmosphere throughout. The outdoor living space is a true highlight. A private heated pool and spa with a waterslide anchor a beautifully updated backyard featuring a bar with seating, lounge chairs, a large outdoor dining area, an outdoor shower, and a stainless-steel grill. A covered lanai beside the pool offers ample seating and an outdoor television, making it an ideal gathering place day or night. As evening falls, the backyard transforms into a tropical oasis with illuminated palms and ambient lighting. Entertainment continues indoors and in the oversized garage, which has been converted into a game space complete with a ping pong table, foosball table, and arcade game. When it’s time to unwind, the home offers six well-appointed bedrooms, each with a flat-screen television. Four bedrooms feature king beds, including three with en suite bathrooms and private balconies. One bedroom includes two twin beds, while another offers two sets of bunk beds, creating a perfect space for kids or guests. A half bath is located on the main floor, with an additional full bathroom upstairs. Situated on a quiet stretch of Holmes Boulevard, the property offers both privacy and convenience. Shops, restaurants, and island favorites along Pine Avenue are just minutes away, and the free island trolley stops nearby, providing easy access to all seven miles of Anna Maria Island. From boutique shopping and dining to fishing, boating, kayaking through mangroves, dolphin tours, and unforgettable sunsets, everything the island is known for is within easy reach. Sands of Time delivers the best of island living with space, style, and an unbeatable location in the heart of Holmes Beach. Schedule your private showing today!

6908 Holmes Boulevard, Holmes Beach

Courtesy of BEACH HOUSE REAL ESTATE LLC

$1,425,000
A4679240 MLS
BUILD YOUR BAYFRONT DREAM HOME...Gorgeous views of the bay & Intracoastal Waterway from this property on a quiet, serene street. Home was remediated after the hurricanes of 2024 and is now a blank slate for a new owner to create their forever home on the water. This 2/2 home has good bones, vaulted ceilings and a nice floor plan to reinvent OR raze current structure to build a magnificent bayfront home on Anna Maria Island. Ideally situated right on the bay and just a short stroll to the beach with easy access... Waterfront parcel, PI#74413.0010/9 will convey with this sale.

2316 Canasta Drive, Bradenton Beach

Courtesy of MIKE NORMAN REALTY INC.

$1,425,000
2 Beds ⋅ 2 Baths ⋅ A4679231 MLS
BUILD YOUR BAYFRONT DREAM HOME... Gorgeous views of the bay & Intracoastal Waterway from this property on a quiet, serene street. Home was remediated after the hurricanes of 2024 and is now a blank slate for a new owner to create their forever home on the water. This 2/2 home has good bones, vaulted ceilings and a nice floor plan to reinvent OR raze current structure to build a magnificent bayfront home on Anna Maria Island. Ideally situated right on the bay and just a short stroll to the beach with easy access... Waterfront parcel, PI#74413.0010/9 will convey with this sale.

2316 Canasta Drive, Bradenton Beach

Courtesy of MIKE NORMAN REALTY INC.

$2,995,000
5 Beds ⋅ 4 Baths ⋅ A4678835 MLS
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

Courtesy of BLUESRQ REAL ESTATE INC

$698,000
2 Beds ⋅ 2 Baths ⋅ A4678364 MLS ⋅ 26 BLDG.
Lender paid 1-0 Buydown Interest Rate by using our preferred lender! Tranquil waterfront canal townhome on Anna Maria Island in Holmes Beach! Welcome to this beautifully and completely updated TURNKEY FURNISHED 2-bedroom, 2-bath townhome tucked away on a quiet cul-de-sac. Designed with an open floor plan, the home features tile floors throughout, a stylish plank ceiling, and a light-filled living area where charming jalousie windows frame serene canal views. The kitchen is thoughtfully upgraded with stainless steel appliances, a micro hood, custom tile backsplash, and elegant gold accents, making it both functional and eye-catching. Both bedrooms offer private en-suite baths with dual sinks and glass-enclosed showers, while the primary suite enjoys peaceful water views. A dedicated laundry room provides additional storage, and low association fees add to the home’s appeal. Outdoors, a large open lanai and deck create the perfect setting for entertaining. Newer dock with ladder access for a 24" boat, fishing from your back yard or simply relaxing, with easy access to launch your kayak and explore the Anna Maria waterways or Palma Sola Bay. Ideally located on highly sought after Anna Maria Island and close to the Holmes Beach boat ramp, shopping, dining, tennis and basketball courts, baseball fields, dog park, and playground, this canal-front retreat offers the best of coastal living.

26 Seaside Court, Holmes Beach

Courtesy of KW COASTAL LIVING III

$1,100,000
2 Beds ⋅ 2 Baths ⋅ A4678032 MLS
Welcome to "Captains Quarters" this luxury duplex is recently renovated and centrally located on Anna Maria Island with over $140k in projected rental revenue for 2026. This property underwent a full renovation in 2023 with full permits for new windows, electric, ac, and plumbing. This island retreat features a brand new heated saltwater pool and spa nestled among the palm trees with a secluded beach alley access. Each side features it's own kitchen, living and dining area. The gourmet kitchen in both units features quartz countertops, new shaker cabinets and stainless steel appliances. This home is being sold turn-key furnished. Property is currently being used as a vacation rental. Call today for your private showing!

3016 Gulf Drive, Holmes Beach

Courtesy of PINEYWOODS REALTY LLC

$1,420,000
3 Beds ⋅ 2 Baths ⋅ A4678590 MLS
Welcome to LivinGood, a thoughtfully redesigned beach home where effortless indoor-outdoor living shines. Slide open the glass doors and step directly into your private pool and entertainment area, keeping family and guests seamlessly connected without the need to climb a single set of stairs. This completely remodeled 3-bedroom, 2-bath pool home is offered turnkey furnished and blends modern luxury with laid-back beachside charm, with beach access just minutes away. Inside, impeccable craftsmanship is highlighted by restored terrazzo floors, a gourmet kitchen with quartz countertops, all-wood custom cabinetry, and a high-end gas range, a split floor plan for added privacy, and fully updated bathrooms with modern finishes. The home is equipped with a tankless water heater, two mini-split units, a top-of-the-line Trane A/C system, and an EV charger for comfort and efficiency. Outdoors, enjoy a custom high-end pool built by one of the top pool builders on AMI, a screened-in lanai, lush low-maintenance turf, a putting green, built-in closets, ample storage, and close proximity to the island’s best dining and shopping. Everything has been thoughtfully designed with the end user in mind. Schedule your private showing today!

306 66th Street, Holmes Beach

Courtesy of DUNCAN REAL ESTATE, INC.

$1,125,000
2 Beds ⋅ 2 Baths ⋅ A4678029 MLS
Welcome to "Pineapple Paradise" this luxury duplex is recently renovated and centrally located on Anna Maria Island with over $140k in rental revenue projected for 2026. This property underwent a full renovation in 2023 with full permits for new windows, electric, ac, and plumbing. This island retreat features a brand new heated saltwater pool and spa nestled among the palm trees with a secluded beach alley access. Each side features it's own kitchen, living and dining area. The gourmet kitchen in both units features quartz countertops, new shaker cabinets and stainless steel appliances. This home is being sold turn-key furnished. Property is currently being used as a vacation rental. Call today for your private showing!

3014 Gulf Drive, Holmes Beach

Courtesy of PINEYWOODS REALTY LLC

$5,950,000
A4676896 MLS
Rich in history and ripe with potential on one of the area’s most desirable coastal locations—formerly home to the iconic Queens Gate Resort, the property has been cleared following storm damage and now stands ready for its next chapter. This expansive assemblage of three contiguous parcels and a fourth adjacent parcel offers a clean slate for your vision, whether you’re imagining a boutique lodging experience, a landmark residential development, or a custom dream estate. Zoned R-3, the property presents immense possibilities in a prime location that visionaries will immediately recognize. This is more than a vacant piece of land—it’s your legacy project.

1101 Gulf Drive N, Bradenton Beach

Courtesy of DUNCAN REAL ESTATE, INC.

$3,495,000
7 Beds ⋅ 8 Baths ⋅ A4678136 MLS
2206 Avenue A, Bradenton Beach, FL 34217 Luxury Investment Meets Coastal Perfection A premier 7-bedroom, 7.5-bath luxury retreat just a 5-minute walk from Bradenton Beach. This 2022-built coastal haven combines elegant design, proven rental performance, and exceptional guest appeal—making it an ideal rental investment on coveted Anna Maria Island. Designed for large groups and multi-family stays, this property offers an unbeatable combination of scale, amenities, and location—features that drive consistent high occupancy and premium nightly rates. Investment Highlights: Prime location — 5-minute walk to Bradenton Beach and close to Pine Avenue shops & dining High-income layout — 7 bedrooms / 7.5 bathrooms (sleeps large groups comfortably) Premium amenities — rooftop deck with panoramic Gulf & Bay views, private heated pool & spa, BBQ area, and outdoor lounge Turnkey luxury — sold fully furnished and professionally designed with coastal chic interiors Proven rental appeal — ideal for reunions, retreats, and vacation groups seeking a luxury experience Strong ROI potential — similar homes on Anna Maria Island generate six-figure annual rental revenue Inside, guests are greeted by an airy open-concept living space filled with natural light, a fully equipped chef’s kitchen with quartz counters and stainless appliances, and seamless indoor–outdoor flow through sliding glass doors. Every bedroom includes a private ensuite, ensuring comfort and privacy for guests. From sunrise coffee on the balcony to sunset cocktails on the rooftop deck, Beachly Beloved offers an unforgettable guest experience—one that translates to repeat bookings and sustained income for savvy investors. Your opportunity: A rare, income-producing coastal asset in one of Florida’s strongest luxury rental markets.

2206 Avenue A, Bradenton Beach

Courtesy of COLDWELL BANKER REALTY

$8,400,000
10 Beds ⋅ 12 Baths ⋅ A4678111 MLS
Welcome to 2175 Avenue A, Bradenton Beach, Florida A Luxury Island Estate Designed for Generational Memories & Investment Returns Step into the pinnacle of coastal elegance with this magnificent 10-bedroom, 12-bath luxury estate, nestled just steps from Bradenton Beach on coveted Anna Maria Island. Built in 2022, this turnkey coastal compound offers the perfect blend of refined relaxation and high-end amenities, making it ideal for luxury vacation rentals, multi-family getaways, or premium short-term rental investment. With sleeping space for 23 guests, new designer furnishings, and resort-style features, this stunning property checks every box for the discerning investor seeking both lifestyle and ROI. An established rental estate with a return clientele and a healthy ROI for any seasoned investor, this is a proven performer in one of Florida’s most desirable coastal markets. Investor Highlights: 3-minute walk to Bradenton Beach – Prime proximity to one of Florida’s most beloved beaches 10 spacious bedrooms | 12 modern bathrooms Sleeps up to 23 guests – Ideal for large family reunions or group rentals 8 king suites, 2 twin beds, and a full/full bunk – All with ensuite bathrooms Heated private pool & spa + outdoor bar, grill, and patio dining Rooftop deck with panoramic Gulf & Bay views – Ideal for sunsets and evening gatherings Game-ready backyard with putting green, ping pong, and foosball Steps to Bridge Street, dining, shopping, and marina – all walkable or bikeable Property Features: Every detail in this estate has been thoughtfully curated for upscale beach living: Bright, multi-level layout with expansive balconies and water views Open-concept great room, oversized TV, and seating for groups Gourmet kitchen with quartz island, premium appliances, and plenty of space for entertaining 11 spa-inspired bathrooms with sleek finishes, walk-in showers, and designer details Private suites throughout ensure comfort and privacy for every guest Outdoor Living at Its Finest: The tropical backyard is a private oasis: Heated pool with spillover spa Outdoor dining, grill, and lounge area Custom putting green and games for all ages Rooftop deck with 360° views of Gulf waters and the island skyline Why Investors Love 2175 Avenue A: High rental income potential in a top-tier vacation rental market Established rental estate with proven performance and return clientele New construction = minimal maintenance Ideal for 1031 exchange buyers, portfolio diversification, or luxury Airbnb investor Located in one of Florida’s strongest coastal markets, with year-round demand Zoned and designed for maximum occupancy and revenue optimization 2175 Avenue A isn't just a home—it's a rare investment opportunity on Anna Maria Island, combining luxurious design, unbeatable location, and outstanding rental appeal. Whether you're looking to expand your luxury rental portfolio, secure a premium vacation home with income potential, or enter Florida’s elite coastal market, this estate delivers on all fronts.

2175 Avenue A, Bradenton Beach

Courtesy of COLDWELL BANKER REALTY

$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

Courtesy of DUNCAN REAL ESTATE, INC.

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