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$2,395,000
3 Beds 3 Baths Sunset Cove At Holmes Beach SubDv. 34216 Zip Code
A premier setting defines this offering. Tucked at the end of a quiet cul-de-sac in Sunset Cove—a rare enclave that prohibits weekly rentals—this elevated beach residence presents an exceptional retreat for tranquil island living. Become part of a true neighborhood community, whether in full-time residence or seasonal escape, with breathtaking Gulf vistas just a stone’s throw from the sugar-white sands of Anna Maria Island and dedicated beach access moments away. Designed by acclaimed architect H. Patterson Fletcher, this distinctive home embodies Frank Lloyd Wright–inspired principles, celebrating harmony with nature, fluid open spaces, and an abundance of natural light. Custom-built and solidly constructed, it occupies an expansive walled lot mere steps from the shoreline—offering the rare canvas to envision a private pool and bespoke outdoor sanctuary. Spanning three thoughtfully appointed levels, the 3-bedroom, 2.5-bath residence with bonus room welcomes guests through a gracious foyer, with an oversized garage below providing exceptional storage. Within, vaulted ceilings and an expansive wall of sliding glass doors bathe the living room in soft, filtered light while framing serene views of swaying palms and shimmering Gulf waters. Off the living area sliders open to a generous elevated screened lanai—an inviting setting for languid afternoons, twilight gatherings, and al fresco dining. The open-concept kitchen and living area flow together effortlessly, anchored by new appliances, a polished granite island, custom solid-wood cabinetry, and a double sized skylight that draws the sky inside. The primary suite offers a private balcony beyond its own wall of sliders, complemented by a spacious en suite bath and dual walk-in closets. The upper level is a study in versatility—an adaptable retreat featuring two distinct sleeping areas and a full bath, accommodating visiting family and friends with comfort and privacy. When not hosting, the space transforms effortlessly into a den, library, home office, or creative studio. Wraparound windows and a rooftop deck reveal sweeping water and treetop panoramas—an ideal vantage for sunrise coffee, golden-hour cocktails, and starlit evenings. While poised for cosmetic refinement, this residence's architectural provenance, enduring construction, generous grounds, and incomparable location make it an extraordinary canvas for a true luxury beach retreat.

103 Sunset Lane, Anna Maria

$3,895,000
3 Beds 3 Baths Anna Maria Beach SubDv. 34216 Zip Code
AMAZING HOME "BLUE CRUSH" ONLY 4 HOUSES TO THE BEACH!!! LOCATIONS LIKE THIS ARE RARELY AVAILABLE WEST OF GULF DRIVE! IT DOES NOT GET BETTER THAN THIS! STEPS TO BEACH AND THE WATERFRONT LIFESTYLE! This exquisite retreat offers the perfect blend of luxury, comfort, and convenience. As you step inside, you'll immediately be drawn to its enticing features. This home has been updated with no expense spared to bring it up to todays standards. Hosting gatherings becomes a delight with the updated and fully equipped kitchen, ensuring seamless meal preparation and service, especially for those poolside occasions with family and friends. The interior of this 3 bedroom, 3 bathroom haven is designed for both comfort and style. The living area, adorned with pocket sliding doors, seamlessly connects to a spacious outdoor deck, creating a harmonious indoor-outdoor living experience. Picture evenings spent watching TV, feeling the gentle breeze, and sipping drinks on the balconies. The kitchen, featuring granite countertops and stainless-steel appliances, is a chef's delight, making cooking a pleasure. An outdoor dining table on the deck provides an ideal setting for enjoying your culinary creations. The sunlit primary bedroom, with a private balcony and a luxurious ensuite bathroom, provides a dreamy retreat. Additional bedrooms include a second bedroom with balcony access and ensuite , a third bedroom with pool deck access, and an additional space could serve as a fourth bedroom, featuring bunk beds. The tropically landscaped backyard is a haven for relaxation. The stunning pool, complete with a sun shelf, invites you to bask in the Florida sun, while the expansive covered patio provides a shaded retreat for family conversations, refreshments, and games. Prime location allows for easy exploration of Pine Avenue's boutiques and culinary delights. Beach access is just a few steps away, offering warm turquoise waters and soft sand. Take a leisurely stroll to Anna Maria Island City Pier or enhance your stay with activities like chartering a fishing trip, a sunset cruise, or paddleboarding through the mangroves. Property is currently a successful rental and has forward bookings in place. Perfect for a second home or investment property. Experience the epitome of island living!

111 Cedar Avenue, Anna Maria

$7,500,000
6 Beds 7 Baths Gulf View Sub SubDv. 34216 Zip Code
This turn-key custom built six bedroom six and a half bathroom luxury home on Anna Maria Island is an exceptional beach investment property offering the perfect balance of passive rental income and personal coastal living. Located on one of the most private and prestigious streets on Anna Maria Island just steps from beach access the home offers Gulf of Mexico views and a proven short term rental history grossing over $650,000 annually. Whether purchased as a primary residence, second home or vacation rental investment this newer construction property delivers strong returns and long term value. Designed as a high performing Anna Maria Island vacation rental and luxury coastal retreat the home features a resort style pool with in ground spa a rooftop deck with panoramic sunset and Gulf views and expansive open concept living spaces ideal for entertaining. The chefs kitchen includes top of the line appliances custom cabinetry an oversized island and formal dining area with seamless indoor outdoor living leading to multiple balconies and covered patios. The primary suite features a private balcony walk in shower and soaking tub while four additional king bedroom suites each include ensuite bathrooms. A custom bunk room adds a family friendly and rental optimized layout. Exclusive amenities include a private elevator, beach chairs and beach umbrellas enhancing both comfort and rental appeal. The backyard oasis includes a poolside lounge BBQ grill, ping pong table and multiple entertaining areas making it one of the most desirable luxury rental homes on Anna Maria Island. For added peace of mind the property includes a 10 year builder warranty and multiple transferable trade warranties offering low maintenance ownership and confidence for buyers seeking newer construction homes on Anna Maria Island. Perfectly located near Pine Avenue shopping and dining the Rod and Reel Pier the historic AMI City Pier and the free Anna Maria Island trolley this turnkey, fully furnished luxury vacation rental combines prime location strong rental income and the ultimate coastal lifestyle. This is a rare opportunity to own one of the best Anna Maria Island homes for sale and a premier Florida Gulf Coast real estate investment!

107 Maple Avenue, Anna Maria

$2,950,000
4 Beds 3 Baths Shore Acres SubDv. 34216 Zip Code
One or more photo(s) has been virtually staged. If you're looking for exceptional value on Anna Maria Island, this is it! Combining a prime north-end bayfront location, private pool, recent major upgrades, and breathtaking Tampa Bay views, this property represents one of the best waterfront opportunities currently available. Best-priced full bayfront pool home on the desirable north end of Anna Maria Island with breathtaking panoramic views of Tampa Bay and the Sunshine Skyway Bridge. Located on the highly sought-after north end of Anna Maria Island, this exceptional waterfront residence offers nearly 3,000 square feet of living space, 4 bedrooms, 3 bathrooms, a private bayfront pool, and valuable recent improvements including new windows and sliders installed in 2019 and both HVAC systems replaced in 2025. A charming white picket fence welcomes you into a bright, open-concept floor plan featuring soaring ceilings, light wood-look luxury vinyl flooring, and expansive 8-foot sliding glass doors that frame spectacular water views. The spacious living and dining areas flow seamlesslyan  oversized bayfront pool area, creating the perfect setting for entertaining, outdoor dining, or enjoying unforgettable sunrises over the bay. The new eat-in kitchen features quartz countertops, white shaker cabinetry, stainless steel appliances, and abundant storage. The main level includes two guest bedrooms, a full bath, and a one-car garage with room for a golf cart, beach equipment, and additional storage. Upstairs, two spacious primary suites each offer private en-suite bathrooms, and private balcony access overlooking Tampa Bay. A separate den or sitting area provides flexible living space and captures some of the home's most spectacular waterfront views. The bayfront pool, added in 2017, provides the perfect place to relax while enjoying coastal breezes and endless water vistas. Whether you're looking for a beach house, full-time island residence, second home, or short-term vacation rental investment, this property offers the ideal combination of location, space, updates, and breathtaking waterfront views. Opportunities to own a full bayfront pool home on Anna Maria Island with updated windows, newer HVAC systems, expansive outdoor living areas, private pool, and panoramic Tampa Bay views at this price point are exceptionally rare. Whether for personal enjoyment or investment potential, this is a unique opportunity to own a slice of island paradise. One or more photos have been virtually staged. Note: Property information received from third-party sources is considered reliable but is not guaranteed. All information should be independently verified by buyers and buyers' agent.

893 N Shore Drive, Anna Maria

$3,950,000
5 Beds 5 Baths Bimini Bay Estates SubDv. 34216 Zip Code
STUNNING RENOVATED 5 BEDROOM POOL HOME ON A DEEP WATER CANAL ONLY STEPS FROM THE BEACH!!! Nestled on the highly coveted north end of Anna Maria Island, this beautifully renovated and turnkey furnished 5-bedroom, 5-bathroom home spans 3,844 sq. ft. of luxurious living space. Perfectly situated on a deep-water canal with direct Gulf of Mexico access, this home is a dream for boating enthusiasts while also being just moments from the island’s pristine beaches. Upon entering, you’ll be greeted by a flood of natural light, creating a bright and airy atmosphere that welcomes you into this thoughtfully designed home. The living room offers ample seating and flows seamlessly into the adjacent dining room, where elegance meets functionality. With light flooring and coastal tones throughout, the home exudes a relaxed yet sophisticated vibe. The dining room opens easily to the kitchen and outdoor pool area, making it an ideal space for entertaining. The gourmet kitchen is a chef's delight, featuring quartz countertops, custom cabinetry, stainless steel appliances, and a cozy breakfast bar. From the living room, large sliding glass doors provide effortless access to the pool, creating a perfect blend of indoor and outdoor living. The first floor hosts three spacious bedrooms, each with excellent closet space, and three beautifully updated bathrooms, all exuding modern elegance. The expansive game room and laundry area combine fun and practicality, equipped with two washers and dryers, a second refrigerator, ample cabinetry, and a ping-pong table. Whether you’re hosting family or friends, this well-designed layout provides comfort for all. Upstairs you will find an additional two bedrooms and two bathrooms with an outdoor deck overlooking the canal. Renovated in 2023 and 2025, this home boasts an array of high-end upgrades including new appliances, new flooring, remodeled bathrooms, new lighting and fans, an outdoor kitchen, a new electric fireplace, freshly painted interiors and exteriors, new patio sliders, new putting green, a new front entrance door, and updated back doors. Step outside into the breathtaking backyard, and you'll instantly be transported to your own private tropical retreat. The heated salt water pool and spa invite relaxation, while the outdoor kitchen, covered cabana with a dining area, tiki hut, and hammock offer multiple options for entertaining or unwinding. The putting green and dock complete this outdoor haven, where you can fish, relax, or simply enjoy the island lifestyle. Deep water canal with no bridges to the Bay, ICW and Gulf of Mexico. This home is an exceptional investment opportunity, benefiting from a transferable BERT HARRIS ACT RIGHT, ALLOWING SHORT-TERM RENTALS FOR UP TO 12 GUEST--a rare and valuable advantage. With a proven rental history, this property appeals equally to investors and those seeking a tranquil personal retreat. Every detail has been meticulously curated to create the perfect island home. Ideally located, this home is just a short stroll to the Anna Maria City Pier and the charming shops and restaurants along Pine Avenue. Whether you're looking for the ultimate vacation getaway or an income-generating property, this is truly a slice of paradise on Anna Maria Island.

212 Oak Avenue, Anna Maria

$6,375,000
5 Beds 5 Baths Anna Maria Beach SubDv. 34216 Zip Code
Here is your chance to own a 5 bed/4.5 bath custom waterfront residence on one of the most coveted streets in the City of Anna Maria. Enjoy the rare luxury of having direct boat access in your backyard while just a short walk to the pristine shores of the Gulf. This home offers the best of both waterfront lifestyles. Thoughtfully designed with a modern coastal aesthetic, the home features high-end appliances, custom trim details throughout, and smart home integration for effortless convenience. Each bedroom offers a private en-suite bath. A custom built-in bunk room maximizes space (sleeping up to 5) with craftsmanship that speaks to intentional design, adding versatility for guests or family. Privately tucked away on the third floor, you have the expansive primary suite that offers a serene and secluded retreat, featuring a large walk-in shower and soaking tub. Open the sliding glass doors and you are greeted with a generous private balcony that invites quiet moments of relaxation. Anchored by an oversized island, the kitchen is a chef and entertainer’s dream, featuring a gas range by Wolf, a Sub-Zero refrigerator, and a 24-bottle wine fridge. The main living level balcony is outfitted with built-in outdoor cabinetry and a premium ceramic grill, creating a fully functional alfresco cooking space just steps from the kitchen. The kitchen is the centerpiece of this well-designed floor plan that allows for the living and dining spaces to come together effortlessly. Built-in storage in the living room offers seamless organization without disrupting the clean aesthetic, while a dedicated coffee bar adds a touch of everyday luxury and convenience. Another major convenience is the elevator that gives you access to all levels of the home. These subtle yet meaningful touches are found throughout the home, reflecting a level of care and quality rarely seen. On the ground level you have a beautifully constructed cabana space that blurs the line between indoors and out, overlooking a meticulously turfed lawn and an expansive pebble finish pool that shimmers like cut glass. On rainy days, the pool cabana offers a theater like movie experience equipped with a large tv that includes a Sonos surround system and plenty of space for indoor gaming. Lime rock landscape adds geological gravitas, while an outdoor shower and a tucked-away kayak rack offer an unexpected delight. For the nautical connoisseur, the composite dock with an elevator lift provides open-water access with ease. The garage offers ample space for 2 cars, a golf cart, and all your beach toys. This meticulously maintained home has never been a vacation rental, but this could be a wonderful investment property that allows for short-term stays. Come schedule your private showing today!

229 Willow Avenue, Anna Maria

$2,945,000
4 Beds 3 Baths Shore Acres Third Add SubDv. 34216 Zip Code
Relish the quiet neighborhood of this North End beauty! Just a hop, skip and a jump to Beach and Bay from this 4 bed/3 bath pool home with private elevator. This ideally appointed home has an open floor plan with TWO living rooms, a large third floor porch with peeks of the water, dual zone air conditioning, and a fabulous, spacious kitchen with Bosch appliances, custom lighting throughout, and covered pool deck in your private tropical oasis with mature landscaping. This ideal location in the city of Anna Maria allows short term rentals and enjoys easy access to some of your island favorites, including the shops and eateries of Pine Avenue. Storage abounds with ample cabinetry and custom closets. You will love the abundant features of this beautiful home, including high ceilings, plantation shutters, 18 inch tile and plank wood flooring. Come enjoy the peace and serenity of this perfect island paradise!

704 Gladiolus Street, Anna Maria

$4,800,000
4 Beds 6 Baths Anna Maria Beach SubDv. 34216 Zip Code
Welcome to SeaLuxe, where luxury meets the beach! Located on one of the most desirable streets on Anna Maria Island. SeaLuxe is a home thats perfectly positioned to put you just a short walk away from a world-renowned beach or to Pine Ave where you can find locally owned shops and restaurants. This coastal retreat features 3,265 sqft of indoor living space, 4-bedrooms all with ensuite bathrooms, and 2 powder baths. Once inside, you are welcomed by an open concept living space bathed in natural light, featuring high ceilings and a seamless flow between spaces. The gourmet kitchen is a chef’s dream with form and function, equipped with premium stainless-steel appliances, walk in pantry, quartz countertops, solid wood cabinetry, and a large island with seating. The spacious primary bedroom offers a serene retreat with a luxurious ensuite bath featuring a soaking tub, walk-in shower, and a generous walk-in closet. Take the elevator to the top floor where you will find an inviting movie room equipped with a wet bar and beverage fridge, a powder bath, and one of the four bedrooms. On the ground level of this luxurious property, you have an area that is designed for ultimate relaxation and entertainment, featuring a stylish entertainment room with a pool table for indoor fun. Step outside to a resort-style outdoor space complete with a gorgeous pool, spa, and sun shelf, all surrounded by lush landscaping and a beautifully turfed area. An expansive covered patio offers the perfect setting for al fresco dining and grilling, making it easy to unwind or entertain in true island style. SeaLuxe perfectly blends sophisticated coastal design with exceptional comfort, offering not just a luxurious escape but a highly successful, turnkey vacation rental investment with future reservations in place. Schedule your private showing today and see why so many guests fall in love with this home!

222 Willow Avenue, Anna Maria

$1,775,000
3 Beds 2 Baths Luana Isles SubDv. 34216 Zip Code
Experience the ultimate coastal retreat at 311 Poinsettia Rd in Anna Maria, FL—a home where luxury meets laid-back island living. This beautifully renovated, elevated sanctuary boasts stunning waterfront views, a sparkling pool, and your very own private boat dock with a lift, inviting endless adventures on the water. Enjoy the convenience of RV/boat parking and a generous driveway that sets the stage for memorable gatherings. Just a leisurely stroll to pristine beaches and a quick golf cart ride to lively restaurants and bars, every moment here is infused with warmth, charm, and the promise of a vibrant lifestyle. Welcome home to your dream coastal haven. This property is currently used as a NIGHTLY rental bringing in up to $25,000/month so far this year. Please do not disturb the guests.

311 Poinsettia Road, Anna Maria

$8,000,000
9 Beds 9 Baths Bimini Bay Estates SubDv. 34216 Zip Code
This stunning 9-bedroom, 8.5-bathroom beachfront property offers 3,983 sq ft of heated interior space and comes FULLY FURNISHED with luxurious details throughout. The home boasts an open-concept layout with vibrant living areas, a well-appointed chef’s kitchen, and multiple decks for enjoying ocean views. This home completed in 2020, has a custom private pool with a lazy river-inspired style, a putting green, and a rooftop deck offering 360 water views. Each of the 7 king-sized bedrooms features chic designs, ensuite baths, with many including private balconies. The primary suite includes a large tub, step-in shower, and a private ocean-view balcony. Additional amenities include a convenient elevator, laundry room, and a bar area with a wine fridge. The property’s modern coastal elegance blends perfectly with functional design, creating a space ideal for everyday living or hosting guests- GREAT RENTAL OPPORTUNITY. Located on Anna Maria Island, this home offers beach access and endless opportunities to enjoy the sun and sand. Experience the ultimate blend of luxury and comfort in this meticulously designed coastal haven.

9403 Gulf Dr, Anna Maria

$2,785,000
4 Beds 3 Baths Anna Maria Beach SubDv. 34216 Zip Code
BEAUTIFUL COASTAL HOME ONLY STEPS AWAY FROM THE PRISTINE BEACHES ON BEAN POINT. THIS 4 BEDROOM 2.5 BATH HAS QUALITY FINISHES THROUGHOUT INCLUDING SOLID GRANITE SURFACES, SOLID WOOD CABINETS, HARDWOOD FLOORS, VOLUME CEILINGS, NEW S/S APPLIANCES, ELEVATOR, AND COMES TURNKEY FURNISHED WITH A COASTAL DECOR. OUTSIDE IT HAS A METAL ROOF, IMPACT WINDOWS AND DOORS, HARDI SIDING, AND TROPICAL LANDSCAPING. THERE IS A COVERED ENTERTAINING AREA RIGHT OFF THE MAINJ LIVING AREA GREAT FOR ENJOYING THOSE COOL GULF BREEZES. IT ALSO COMES COMPLETE WITH AN OUTDOOR KITCHEN, AND PERGOLA COVERED PATIO FOR LOUNGING BY THE HEATED POOL. JUST INSIDE THE FRENCH DOORS BY THE POOL IS A CUSTOM GAME ROOM PERFECT FOR ENTERTAINING THE WHOLE FAMILY.

796 Jacaranda Road, Anna Maria

$4,995,000
3 Beds 3 Baths Anna Maria Beach SubDv. 34216 Zip Code
Beachfront Oasis is elegant European design luxury home that has been professionally decorated and has spectacular beach views from every room. Floor to ceiling glass allows full views of the beach and aqua tropical gulf waters. The clean lines of the homes upscale design allow you to just sit back, relax and enjoy the stunning open beach view on any of the four beachfront decks. Indulge in the home’s high-end finishes from the moment you walk in the door including a private elevator to all floors. Once you’re on the main level you’re welcomed by breathtaking views, the high-end kitchen and open concept living and dining areas that are perfect for entertaining. The high-end kitchen offers stainless steel appliances, induction stove top and built-in oven. The kitchen island provides the perfect spot for entertaining as you prepare a gourmet meal or simple treats. On the top level there are two separate master suites, both with king beds, their own private baths and private beach front balconies. On the main level, off the living room, is another bedroom with a queen bed and another private balcony. The outdoor area features a private pool and beach area with outdoor lounge chairs plus a table and chairs to enjoy poolside refreshments. Beachfront Oasis is ideally located on the quiet north-end of Anna Maria Island. It is one block from the charming Pine Ave shops, restaurants and attractions. On the bayside of Pine Ave is the Anna Maria City Pier and Waterfront Restaurant.

107 Elm Avenue, Anna Maria

$5,487,000
5 Beds 6 Baths Anna Maria Beach SubDv. 34216 Zip Code
This recently constructed home on Anna Maria Island overlooking a stunning canal is just one block from the pristine Gulf of Mexico beaches and a short walk to the restaurants and boutiques on Pine Ave. This luxurious 5-bedroom, 5.5 bath retreat offers a spectacular backyard with a private pool and swim up bar, in-ground spa, a covered shellcrete patio with seating, a ping pong table, and a BBQ grill. The coastal home features two garages and a private drive accommodating four vehicles. The main living floor has an open layout with bright natural lighting, a plush living area with sofas and a TV. The kitchen is equipped with upgraded stainless steel Bosch appliances and quartz countertops. There are many dining areas including the cozy kitchen nook, kitchen island, formal dining room, or on the balcony overlooking the canal. The 5 beautifully designed bedrooms feature elegant decor, chic furnishings, bedside lighting, and ensuite bathrooms. The second floor houses 3 bedrooms with king beds and full baths, a half bathroom for guest use, and a walk-in laundry room with a washer and dryer. The third floor includes a seating area with a table and chairs, a TV area, a wet bar, and two primary suites accessible by elevator or stairs. These suites feature king beds, private terraces, walk-in closets, and ensuite bathrooms with large glass-walled showers. Additionally, the rooftop deck provides an ideal spot for relaxation and taking in the views. This home offers a blend of luxury, comfort, and convenience, making it an exceptional choice for your Anna Maria Island life!!

404 North Shore Dr, Anna Maria