Location: Anna Maria
Keyword(s): Manatee High
Keyword(s) High School: Manatee High
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807 S BAY BLVD, ANNA MARIA, FL 34216
$2,300,00083 Days on yellowkey MLS ID: A4680500
2 Days Off yellowkey (back on 4/15/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1969 Built: 1981 Tax: $11,465 (2025)Community: Bay HarborSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$11,465
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: Under contract-accepting backup offers. Experience the perfect blend of modern luxury and coastal functionality in this impeccably maintained canal-front retreat. Located on the prestigious North End of Anna Maria Island, this property offers the best of both worlds: a serene, full-time sanctuary or a high-performing investment (7 nights or less). Originally transformed by a total remodel and significant additions in 2016, this elevated 3-bedroom, 2-bathroom residence offers a sophisticated island lifestyle on an expansive, oversized lot of over 10,000 square feet. The home is thoughtfully designed for both comfort and accessibility, featuring a private elevator that services the residence with ease. The interior transitions seamlessly from open-concept living areas to a unique ground-level bonus room. This versatile space is fully climate-controlled with its own bathroom, making it an ideal candidate for a private guest suite, a secluded home office, or a premier media/game room. Outside, the property is a true maritime sanctuary. Boaters will appreciate the 10,000 lb boat lift and the peace of mind provided by a newer seawall - all installed in 2012. The outdoor possibilities are as vast as the lot itself; with ample room to install a custom pool and outdoor kitchen, you can create the ultimate backyard oasis. Whether you are enjoying the breeze from the elevated decks or embarking on a sunset cruise from your backyard, 807 S Bay Blvd represents a rare opportunity to own a waterfront home built for the modern Floridian lifestyle - a true boater’s sanctuary!
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Lindsey Strickland (941-737-3491)
311 POINSETTIA RD, ANNA MARIA, FL 34216
$1,775,000420 Days on yellowkey MLS ID: TB8359176
Bed: 3 Bath: 2.0 Gar: 4 Liv Area Sq Ft: 1296 Built: 1988 Tax: $22,833 (2024)Community: Luana Isles 1St AddSingle Family
Taxes:$22,833
Tax Year: 2024
Remarks: 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.
Listing is courtesy of: WEICHERT REALTORS EXCLUSIVE PROPERTIES (813-426-2669)
Listing Agent: Thomas Zopf, Ii (727-366-1983)
612 FERN ST, ANNA MARIA, FL 34216
$1,795,000139 Days on yellowkey MLS ID: TB8456599
2 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1472 Built: 1991 Tax: $25,404 (2025)Community: Shore Acres Fourth AddSpa: NoSingle Family
Taxes:$25,404
Remarks: Under contract-accepting backup offers. Great Income Opportunity! Short-Term Rental approved on Airbnb, VRBO, etc! Over $174,000 in Yearly Rental Income with upside! Wake up every day in true island paradise at Anna Maria Chateau! Ideally positioned at the northern tip of the exclusive Anna Maria Island, just moments from the iconic Bean Point and minutes from some of the world’s most celebrated beaches, this pristine coastal retreat offers the ultimate blend of luxury, comfort, and location. From the moment you step inside, you’re welcomed by soaring ceilings and a bright, open great room floor plan designed for effortless entertaining and relaxed island living. Exceptional custom craftsmanship shines throughout, showcasing hand-scraped hickory wood floors, beautiful tongue-and-groove ceilings and walls, and thoughtful architectural details at every turn. The heart of the home is the chef-inspired kitchen, perfectly situated off the family room and equipped with stainless steel appliances, a French-style refrigerator, classic white shaker cabinetry, granite countertops, and a spacious island with breakfast bar seating ideal for gathering with family and friends. The spacious primary suite serves as a private retreat, featuring an en-suite bath with dual sinks and granite countertops. Two additional well-appointed bedrooms share a full bath, providing comfortable accommodations for guests and plenty of space for everyone to unwind. Multiple common areas throughout the home invite relaxation and connection. Step outside and experience resort-style living. Sip your morning coffee on the oversized upstairs deck, take a refreshing dip in the heated saltwater pool, or enjoy friendly competition in the expansive recreation room. The elevated first floor offers ample storage for all your water toys, bikes, and beach gear. This exceptional property offers incredible versatility perfect as a full-time residence, a private island getaway, or a highly desirable income-producing rental in one of Florida’s most sought-after destinations. Bonus: This elevated home experienced NO interior damage during the 2024 storms, providing added peace of mind. Recent updates include: brand-new water heater (2025) and new pool pump (2024). Love the island’s golf-cart-friendly lifestyle? There’s plenty of space for golf cart parking and more. Cruise by golf cart, bike, or take a leisurely walk to nearby restaurants, boutiques, and local favorites, all just blocks from your doorstep. This is your opportunity to own a true slice of paradise on one of Florida’s most beloved islands—Anna Maria Island.
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Mark Fazzini (727-485-9981)
704 GLADIOLUS ST, ANNA MARIA, FL 34216
$2,945,000347 Days on yellowkey MLS ID: A4653068
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2415 Built: 2014 Tax: $34,331 (2024)Community: Shore Acres Third AddSpa: NoSingle Family
Taxes:$34,331
Remarks: PRICE CHANGE! You are just a short walk to Beach and Bay from this quality constructed 4 bed/3 bath pool home with private elevator. This ideally appointed home has TWO living rooms, large third floor porch with peeks of the water, dual zone air conditioning, open floor plan with spacious kitchen, Bosch appliances, custom lighting throughout, and covered pool deck in your private yard with mature landscaping. The quiet street in the coveted North End of Anna Maria allows short term rentals and enjoys easy access to some of your island favorites, including Pine Avenue. Storage abounds with two car garage space, ample cabinetry and custom closets. You will love the abundant features of this beautiful home, including high ceilings, plantation shutters, and 18 inch tile and plank wood flooring. Come enjoy the peace and serenity of this perfect island paradise!
Listing is courtesy of: ISLAND REAL ESTATE-ANNA MARIA (941-778-6066)
Listing Agent: Erin Leathem (941-448-5616)
50 N SHORE DR, ANNA MARIA, FL 34216
$4,850,000113 Days on yellowkey MLS ID: A4677955
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3055 Built: 2020 Tax: $44,429 (2025)Community: Bimini Bay EstatesSpa: YesSingle Family
Taxes:$44,429
Remarks: An exceptional opportunity to experience true island living where waterfront boating and beach access come together—just minutes apart—on Anna Maria Island. This beautifully designed 4-bedroom, 4.5-bath turnkey furnished coastal residence offers a rare blend of luxury, comfort, and lifestyle, ideally situated on a tranquil canal while remaining only moments from the island’s world-famous white-sand beaches. Homes offering private boating access this close to the beach are increasingly difficult to find on Anna Maria Island. From this property, enjoy the freedom of launching your boat from your own backyard, paddleboarding at sunrise, or cruising to open water—then return home and head to the beach cart in minutes. It is this seamless balance of water, sand, and island convenience that truly sets this home apart. Built in 2020 and thoughtfully designed for modern coastal living, the home features a bright, open floor plan filled with natural light and enhanced by coastal-inspired finishes and refined details throughout. The gourmet kitchen serves as the heart of the home, equipped with top-of-the-line stainless steel appliances, quartz countertops, a wine refrigerator, and generous prep and storage space—perfect for entertaining after a day on the water or hosting family and friends. Each of the four bedrooms includes a private en-suite bath, offering comfort and privacy for owners and guests alike. An elevator provides easy access to all levels, adding convenience for everyday living. Outdoor living is where this home truly shines. The private backyard retreat features a heated pool and spa with sun exposure, an expansive pool deck, lush tropical landscaping, and multiple outdoor living and dining areas designed for relaxing, entertaining, and enjoying the island breeze. Whether you’re gathering for sunset cocktails, enjoying a quiet evening under the stars, or unwinding after a beach day, this space feels like a personal resort. For boating enthusiasts, the property offers a private 16’ dock and an oversized boat slip measuring approximately 12’ x 35’, providing direct access to Tampa Bay and the Gulf. This setup is ideal for daily cruising, fishing excursions, paddleboarding, or simply enjoying the peaceful waterfront setting. Situated on an unusually large lot for Anna Maria Island with over 12,000 sq ft , the home also provides ample parking, a spacious driveway, garage, and dedicated golf cart storage—features that add meaningful convenience for both owners and guests in this sought-after location. Located in the heart of Anna Maria Island, this property places you just minutes from pristine beaches, Pine Avenue’s charming boutiques and dining, Bean Point’s legendary sunsets, local art galleries, and the island’s laid-back, walkable, golf-cart-friendly lifestyle. Known for its relaxed pace, vibrant community, and old-Florida charm, Anna Maria Island continues to be one of Florida’s most beloved coastal destinations. Whether you are searching for a full-time residence, a luxury second home, or a proven income-producing vacation rental with forward bookings already in place, this exceptional property offers unmatched versatility and long-term value. Combining waterfront access, beach proximity, turnkey luxury, and an unbeatable island location, this home represents a rare chance to own one of Anna Maria Island’s most desirable lifestyle properties.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Christy Travis (941-545-5284)
419 ALAMANDA RD, ANNA MARIA, FL 34216
$3,150,00048 Days on yellowkey MLS ID: A4686802
1 Days Off yellowkey (back on 4/8/2026)
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2185 Built: 2022 Tax: $31,509 (2025)Community: Shore Acres Fourth AddSpa: YesSingle Family
Taxes:$31,509
Middle School: None
Remarks: Under contract-accepting backup offers. Welcome to Paradise Blu, a newly built island retreat on Anna Maria Island’s highly coveted north end, just moments from the shoreline and designed for both exceptional living and strong rental performance. Featured in Travel & Leisure Magazine as a recommended vacation rental, this property offers a rare opportunity to own a home with proven appeal on a national level. This thoughtfully designed 4-bedroom residence features ensuite baths in every bedroom plus an additional half bath, offering comfort and privacy for owners and guests alike. Soaring ceilings and an open, light-filled layout create a refined yet relaxed coastal atmosphere, ideal for effortless island living. Step outside to your private tropical oasis, where a resort-style pool and spa are surrounded by lush landscaping, creating the perfect setting for entertaining or unwinding after a day on the water. Amazing panoramic views of the bay and the gulf from the roof top deck. Enjoy coffee for sunrise or your favorite cocktail at sunset. Ideally located just a one-minute walk to Tampa Bay and only two blocks from the world-renowned Bean Point, the home captures the essence of Anna Maria Island’s most sought-after lifestyle. Whether you are seeking a refined second home, a full-time residence, or a high-performing vacation rental, Paradise Blu delivers a rare combination of location, design, and investment potential on the north end of Anna Maria Island. Schedule your private showing and experience firsthand what makes Paradise Blu one of the most compelling opportunities on Anna Maria Island today.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Kathy Harman (941-900-9828)
306 S BAY BLVD, ANNA MARIA, FL 34216
$3,295,00058 Days on yellowkey MLS ID: A4684377
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1752 Built: 1967 Tax: $34,126 (2024)Community: Wells Bay Harbor Sec ASingle Family
Taxes:$34,126
Remarks: Welcome to AMI Swedish Beach House, a beautiful 3-bedroom, 2-bath Bayfront home perfectly positioned on the tranquil shores of Tampa Bay on the renowned Island of Anna Maria. This charming single-story home offers breathtaking water views and the relaxed island lifestyle that makes this area so special. Step outside onto the spacious back patio overlooking some of the most beautiful waters in the world. The perfect spot to enjoy your morning coffee, watch boats glide by, watch the aqua life play or unwind in the evening with the coastal breeze and amazing view of the Sunshine Skyway all lit up. Outdoor living is effortless here with an outdoor shower, gas grill, and dining space for six, ideal for entertaining family and friends. Inside, the home comfortably accommodates guests with two bedrooms featuring king beds—one with sliding door access to the deck and a view to die for as you wake up—and a third bedroom with two full beds. The home is designed for comfort and convenience. With an amazing kitchen with no detail left untouched. A 10 foot island that seats 6+ so everyone can get involved with the chef cooking up the catch of the day. Located just a few blocks from the sugar-white sands and turquoise waters of Tampa Bay, this property offers the best of both worlds—peaceful Bayfront views and easy beach access. You’ll also love being within easy walking distance of Pine Avenue’s shops and restaurants, as well as the free island trolley that travels the entire 7-mile length of Anna Maria Island, making it simple to explore beaches, dining, and local attractions. This home has an unbeatable island location. Discover the charm, beauty, and laid-back luxury of Anna Maria Island living in this exceptional Bayfront getaway.
Listing is courtesy of: ANNA MARIA LIFE REAL ESTATE (941-567-6253)
Listing Agent: Billi Gartman (941-545-8877)
303 S BAY BLVD, ANNA MARIA, FL 34216
$4,795,00058 Days on yellowkey MLS ID: A4684390
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2657 Built: 2015 Tax: $62,179 (2024)Community: Wells Bay Harbor Sec ASpa: YesSingle Family
Taxes:$62,179
Remarks: ~~~ MUST SEE FLY THROUGH VIDEO ATTACHED ~~~ Experience elevated island living in Anna Maria's Best; this custom three-level, five-bedroom, three-and-a-half-bath AND 5 DECKS! This island home offers stunning views and exceptional indoor-outdoor living. Designed for both comfort and entertaining, the main living level features a spacious open-concept layout with a large living area, dining space for ten, and a gourmet kitchen highlighted by an impressive 10-foot island—perfect for gathering with family and friends. A large laundry room and convenient half bath are also located on this level. Professionally designed with color, comfort and perfection in mind. Just off the living room step outside to enjoy an expansive balcony a with full views of Tampa Bay and it's sparkling water. If you need your own balcony, there are more! Enjoy the cozy balcony overlooking the private pool, hot tub, and putting green, creating the ultimate outdoor retreat. The primary suite is located on the second floor, offering privacy along with a spacious en-suite bath. Wake up to the amazing view and step straight out to the balcony for breakfast and coffee. There are two additional bedrooms to provide ample accommodations for family and guests. Take a ride in the elevator, that starts in the garage and goes all the way to the top, up to the third level features two additional bedrooms, a full bath, and an inviting media room complete with an 80" TV, beverage cooler, and bar, making it the perfect space for relaxing or entertaining. Open up the large sliders while you watch the game and the let the ocean breeze create the vibe. With yet another large covered balcony for over flow or just chilling with a cocktail as you take in one of the MANY stunning sunsets of the year. If the pool is your scene, Anna Maria's Best has a large pool, hot tub and tons of seating so you can catch some rays, read a book in the shade or take on the team in on the putt putt green. When you return from the beach, you can rinse off in the fully enclosed outdoor shower. At the top, a rooftop deck delivers breathtaking 360-degree views of the island and spectacular vistas of Tampa Bay, providing an unforgettable place to watch sunrises, sunsets, and everything in between. Additional highlights include a 4+ car garage and a prime island location just minutes from shops, restaurants, piers, and a quick golf cart ride to the beautiful beaches of the Gulf of Mexico. This exceptional home offers the perfect blend of luxury, views, and island convenience. Come live your Anna Maria Life in Anna Maria's Best NOW!
306 MAGNOLIA AVE, ANNA MARIA, FL 34216
$1,249,900109 Days on yellowkey MLS ID: A4678747
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 806 Built: 1963 Tax: $1,938 (2024)Community: Anna Maria BeachSingle Family
Taxes:$1,938
Remarks: Great Beach Cottage completely renovated after last year's storms by Kerns & Gilner. Everything is new & the Terrazzo floors have been beautifully restored. Large lot (50X139) with plenty of room for additions or building a new large home down the road. Great Location in Anna Maria City! Only 2 blocks to the Gulf & 2 blocks to Pine Ave.
Listing is courtesy of: GREEN R E OF ANNA MARIA (941-778-0455)
Listing Agent: Kenneth Jackson (941-778-0455)
519 VILLA ROSA WAY, ANNA MARIA, FL 34216
$5,000,000173 Days on yellowkey MLS ID: A4671485
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 3385 Built: 2017Monthly Fee: $100 Tax: $23,649 (2024)Community: Villa RosaSingle Family
Taxes:$23,649
Remarks: This stunning property, situated on the premier private street of Anna Maria, was designed for the perfect blend of island indoor living and outdoor entertaining. Completed in 2017, this 3385sq ft open-plan luxury home has over 2000 SQ FT OF EXTERIOR PORCHES (6 porches). The ROOFTOP LOOKOUT DECK has expansive views extending from Tampa Bay to the Gulf of Mexico beaches. The outdoor movie deck, with the wonderful backdrop of the Skyway Bridge, makes a family movie-night an event to remember. This home has extensive access to a navigable canal with direct entry (no bridges) to Tampa Bay and the Gulf, via beautiful Bimini Bay, where the local dolphins love to gather. The main dock has a modern seawall, a 15,000LB CANTILEVERED BOAT LIFT and composite decking, including lights, electric pedestal, and fresh water. Alongside is a matching 18 ft floating dock for ease of use with kayaks or wave runners. Whether you enjoy fishing, boating, or just sitting along the waters edge in the evening this property blends your onshore life with the endless water possiblities. The rear garden area is extensively landscaped for privacy. The large pool has a tanning ledge that can accommodate lounge chairs and umbrellas . There is a matching hot tub incorporated into the elegant outdoor layout that is located in the shade. When you’ve finished with swimming and sunbathing, why not continue the fun on the 3-HOLE PUTTING GREEN. Adults will enjoy the TIKI BAR and outdoor entertaining area. There is a boating/fishing storeroom, a full bathroom, and a laundry room so wet towels, swimming suits and fishing clothes will not be hauled into the main home. The interior boasts an open floor plan that provides for abundant natural light. Whether you're hosting a family get-together, cocktail party, or just relaxing in this coastal paradise, you can enjoy the tranquillity of the layout. All levels are served by an elevator for ease of access. Most of the rooms enjoy decks or porches, with attractive views of the waterfront or of the quiet neighbourhood. The main living floor is comprised of a gourmet chef's kitchen, outfitted with professional-grade appliances, extensive countertops and custom cabinetry. Adjacent to the kitchen, there is a butlers pantry laundry room and prep kitchen. Walls of high-impact sliding glass doors blur the lines between indoors and out, framing breathtaking panoramic views. The thoughtful design and natural textures—from the luxury flooring to the elegant finishes—ensure a comfortable space where every detail is in tune with the island lifestyle. Separate from the living area is a large den that can serve as an office workspace with access to a relaxing porch. The floor plan on the middle level is completed by two large bedrooms. On the upper-level is the expansive master suite, where you can retreat to your own personal sanctuary and private porch area. There is a generous walk-in closet and a luxurious master bathroom. The front-facing guest suite is spacious with a walk-in closet and a modern stylish bathroom. It also has its own private sitting porch. There is a double and a single garage with epoxy flooring. The home was designed with the environment in mind with an economical geothermal heating and cooling system for both the living spaces and the pool/ spa. There are fast electric car charges in the driveway and in the garages on seperate electric circuits. For your saftey, the whole house has Hurricane Impact window and doors.
Listing is courtesy of: WAGNER REALTY (941-383-5577)
Listing Agent: Ed Taaffe (636-346-6165)
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