Location: Anna Maria
Do Not Show Listings
216 GLADIOLUS ST, ANNA MARIA, FL 34216
$1,325,00041 Days on yellowkey MLS ID: A4682103
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1218 Built: 1966 Tax: $2,637 (2024)Community: Luana IslesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,637
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: Lovingly held by the same family since the 1970s, this north end Anna Maria Island bungalow presents a rare opportunity to own a cherished island property in one of the most sought-after locations on the island. Located in the City of Anna Maria, where short-term rentals are permitted with a 1–7 day minimum (subject to city registration and compliance), this home blends timeless Old Florida charm with thoughtful modern updates throughout. This single-story coastal residence features 3 bedrooms, 2 beautifully renovated bathrooms, and a versatile den/mudroom. Vaulted tongue-and-groove wood ceilings add warmth and architectural character to the open living space. The kitchen has been completely redesigned with new cabinetry, countertops, and all new appliances, creating a fresh and inviting heart of the home. New flooring flows throughout, blending classic island charm with updated coastal style. Situated on a generous 7,500 square foot lot, the property offers rare outdoor space for the north end, with mature tropical landscaping, a fenced yard, and ample room to design a custom pool or expanded outdoor living area. A current survey is available to assist with future planning. An outdoor shower, storage shed, and one-car garage add everyday convenience, complemented by ample parking rarely found in this location. A brand new AC system installed in 2025 provides added comfort and peace of mind. From this prime north end setting, enjoy walking or biking to Pine Avenue’s shops and restaurants, Bayfront Park, and the island’s beautiful beaches. Experience island living where golf carts and bicycles replace cars and every sunset feels close to home. Charming, flexible, and ideally located, this home is well suited as a full-time residence, seasonal retreat, or legacy island property. Currently among the most competitively priced 3-bedroom homes available in the City of Anna Maria. Come discover why the north end continues to capture hearts generation after generation.
Listing is courtesy of: CAPOZELLA REAL ESTATE (941-914-0802)
Listing Agent: Mara Gilmore (941-920-1267)
704 GLADIOLUS ST, ANNA MARIA, FL 34216
$2,945,000324 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)
785 JACARANDA RD, ANNA MARIA, FL 34216
$1,999,900394 Days on yellowkey MLS ID: A4644607
2 Days Off yellowkey (back on 2/25/2026)
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1500 Built: 1980 Tax: $23,744 (2024)Community: Shore Acres 1St AddSpa: YesSingle Family
Taxes:$23,744
Remarks: Under contract-accepting backup offers. OHHHH THE UPDATES!! BRAND NEW KITCHEN and flooring...and updates galore! There is so to enjoy about this great investment home! This is the perfect beach haven, just a hop, skip & a jump to the Gulf beach! Just steps to Bean Point, this elevated 3 bed/2.5 bath pool home is a great income property! Updated with beautiful coastal style, this home is designed for relaxing. Start the day sipping coffee on your screened porch or enjoy the space around your open dining table! Stretch out in the family room where the coastal comfort welcomes you with shiplap walls, large updated windows, new lighting, fresh paint and furnishings. Upstairs you will find your large bedroom with its private porch, walk in closet, updated en suite and peeks of the Gulf! Both guest rooms also enjoy an updated (2024) bathroom and the gorgeous coastal décor! Whether you're lounging at the poolside bar, relishing the breeze on the screened porches, relishing the comfort of your cozy bed, or using your back gate to pop over to the sugar sand beach, you will love the island life from every spot of this updated home! From all the UPDATED appliances, the metal roof, the luxury vinyl plank flooring, the NEW doors & door frames, the NEW paint (inside & out), the NEW lighting and the NEW fans, to all the UPDATED décor - this beach house is picture perfect! And outside you will relish the added landscaping and palm trees, lighted stair way, privacy wall, covered bar and your heated pool and spa! Enjoy a cocktail and the game while floating in the pool, and easy access to your beach toy storage space! Inside and out this island home welcomes relaxation and enjoyment! AND you will REALLY enjoy the short term rental income! It’s time for your island life to begin…
519 SOUTH DR, ANNA MARIA, FL 34216
$1,598,000116 Days on yellowkey MLS ID: A4675370
REDUCED by $97,000 (5.7%) on 04/01/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2131 Built: 1972 Tax: $26,805 (2024)Community: Wells Bay Harbor Sec ASpa: YesSingle Family
Taxes:$26,805
Remarks: “Anna Maria Oasis” is a Bimini Bay Coastal Classic, perfectly positioned on the coveted north end in the City of Anna Maria. With deep-water access directly from your backyard, no bridges to the bay or the Gulf of Mexico, and a 50’ dock with pilings already in place for lift installation, this property is truly a boater’s and fisherman’s paradise. Originally built in 1972, the home was completely transformed in a top-to-bottom remodel in 2025, blending modern luxury with timeless island charm. No detail was overlooked. Highlights include imported Filipino shell stone flooring throughout, all-new drywall, insulation, plumbing, electrical, paint, fixtures, kitchen, and fresh landscaping. The living space was thoughtfully expanded with energy-efficient mini-split systems, increasing the under-air square footage from 1,582 sq ft to approximately 2,131 sq ft, offering enhanced comfort and flexibility. Additional upgrades include a new pool (2019) and new roof (2020). Designed for effortless indoor-outdoor living, this home is ideal for entertaining, launching a sunset cruise, or unwinding while taking in tranquil water views. This one-of-a-kind island property delivers the ultimate coastal lifestyle. Don’t miss this rare opportunity to own waterfront luxury in the heart of Anna Maria—where elegant design meets laid-back island living. Currently an active vacation rental please see remarks for link to the site.
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Cindy Quinn, Pa (941-780-8000)
50 N SHORE DR, ANNA MARIA, FL 34216
$4,850,00090 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
Tax Year: 2025
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)
12106 GULF DR, ANNA MARIA, FL 34216
$6,995,00073 Days on yellowkey MLS ID: A4679008
Bed: 4 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3469 Built: 2005 Tax: $63,179 (2024)Community: Anna Maria Beach First AddSpa: NoSingle Family
Taxes:$63,179
Remarks: Unobstructed Gulf views define this true Gulf-front home on one of the most desirable stretches of Anna Maria Island. With nothing between the property and the shoreline, the balcony captures nearly three-quarters of a mile of uninterrupted beach frontage—an exceptionally rare vantage point created by the natural contour of the island to the north. Very few homes on AMI offer a view corridor this wide or this direct. Built in 2005 by Whitehead Construction, a respected builder in Manatee County, the home is well constructed and offers a layout well-suited for an immediate move-in or a next chapter renovation. The 4-bedroom, 5.5-bath design includes two Gulf-facing decks: one off the main living area and a private third-floor terrace exclusive to the primary suite. The location is one of the island’s best. Positioned at Coconut and Gulf, the home benefits from quieter traffic patterns while still offering walkable access to Pine Avenue’s coffee shops, restaurants, and boutiques. Sunset views are a nightly event, and beach access is just steps from the door. Additional features include a private pool, space for a covered outdoor kitchen, and a two-car garage with room for a golf cart and beach gear. At the time of construction, finishes were in the top tier for the island, and the home is now ready for a thoughtful update to match its premier location. Opportunities like 12106 Gulf are limited on Anna Maria Island. True Gulf-front ownership, a wide and unobstructed view corridor, and a location that delivers both privacy and walkability make this property stand out. Savvy buyers seeking the best views on the island will recognize the significance of this address.
Listing is courtesy of: REEL COASTAL PROPERTIES, LLC (941-265-3247)
Listing Agent: Sterling Worth (214-707-6296)
419 ALAMANDA RD, ANNA MARIA, FL 34216
$3,150,00025 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)
413 POINSETTIA RD, ANNA MARIA, FL 34216
$1,595,00089 Days on yellowkey MLS ID: A4677921
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1677 Built: 1972 Tax: $18,534 (2024)Community: Luana IslesSingle Family
Taxes:$18,534
Remarks: Back on the Market with a substantial price Adjustment!!!! Take another look at 413 Poinsettia Rd. Once you walk through the door you will be welcomed by the new fresh bright clean interior finishes. The wall of patio doors at the rear of the home let the sunshine into the vaulted family room and open kitchen. This Is a concrete block home, with a metal roof and impact windows throughout. Its bones were not damaged during 2024’s storms. Unfortunately, water did get into the home. However, the owners did it right. Once they were able to start, their builder immediately cleaned and remediated the damaged interior. He obtained the required permits to make the home better than before. The sellers did not stop by doing just the bare minimums. While the walls of the homes were open, they replaced the electrical panel bringing it up to today’s codes. They also replaced the old cast iron sewer pipes under the home with new PVC and installed new tile throughout the living area. The rear sliding doors were replaced with new up-to-date impact resistant panels. Once all this work was completed, the interior was renewed. All new kitchen and bathroom vanities were installed with new quartz countertops. All the appliances are new. The home was re-furnished and is now ready to move in and enjoy. All you need to do is add your own personal touches and transform this home into your own private oasis or a killer vacation rental. This home has a large, screened lanai on the rear that could be converted into a third bedroom with an ensuite bath. The room would have its own access to a secluded brick patio on the side of the house. There also appears to be room for a cozy cocktail pool at the front of the home. The property has 74 feet of deeded canal front with a 30-foot dock constructed with concrete, wood and Trex decking. This is the perfect spot to launch your kayak and maybe sail with the manatees who visit out back. (Check out the photos) The dock gives access to your boat lift, nestled in the mangroves that provide privacy from the water. Should you want to play in the sand, the Gulf Beach is about 500 steps away and the Bay Beach is about 200 steps from your door. Today’s home buyers need to be aware there are many homes on the island that were remediated after the storms with no building permits. City’s Code Enforcement is identifying them one by one. The homeowners will be required to apply for a “permit after the fact”. Do not get caught buying an unpermitted home. This could cause you problems in the future. This does not affect this home. Call to see this beautiful gem on the north end of Anna Maria. It will not last long. Note: also available for sale is the owners 2009 Scout 201 bay boat with a 150HP Yamaha outboard.
Listing Agent: John Damato, Ii (941-737-3354)
155 CRESCENT DR, ANNA MARIA, FL 34216
$2,200,00034 Days on yellowkey MLS ID: A4684535
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1512 Built: 1963 Tax: $24,963 (2024)Community: Lake La Vista RepSingle Family
Taxes:$24,963
Remarks: Your private island retreat awaits in this exquisitely renovated coastal cottage, situated on an oversized lot North of Pine Avenue in the city of Anna Maria. This solid concrete block, ground level residence offers 3 bedrooms and 2 bathrooms with a bright, open layout design that embodies refined island living. Inside, elegant ceramic tile flooring, hurricane impact windows, and expansive living spaces create an inviting yet sophisticated atmosphere. The spacious living room flows seamlessly into the great room, offering the perfect setting for both relaxed coastal living and stylish entertaining. The designer chef’s kitchen features beautifully refinished cabinetry, a classic subway tile backsplash, stainless steel appliances, and a chic breakfast bar for casual dining. The serene primary suite offers a private en-suite bath, while two additional guest bedrooms provide comfortable accommodations for family and visitors. An oversized two car garage adds both convenience and storage. Step outside to your secluded backyard sanctuary, where lush tropical landscaping surrounds a sparkling pool and private cabana. Artificial turf and thoughtfully placed LED landscape lighting create an ambiance perfect for evening gatherings or peaceful island nights. This exceptional property is part of a voluntary HOA providing access to six community boat docks with direct entry to the sparkling waters of Tampa Bay and the Gulf of Mexico. Just a short stroll away, you’ll find the pristine white sands of Bean Point, the boutiques and dining along Pine Avenue, the City Pier, the local farmer’s market, and the convenient island trolley. Experience the very best of Anna Maria Island living and schedule your showing today to claim your slice of paradise.
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Andrea Miller (860-541-1050)
612 FERN ST, ANNA MARIA, FL 34216
$1,795,000116 Days on yellowkey MLS ID: TB8456599
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: 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)
107 TUNA ST, ANNA MARIA, FL 34216
$7,750,00024 Days on yellowkey MLS ID: A4686563
Bed: 6 Bath: 5.5 Gar: 6 Liv Area Sq Ft: 4345 Built: 2026 Tax: $5,729 (2025)Community: Anna MariaSpa: YesSingle Family
Taxes:$5,729
Remarks: Under Construction. Blending modern coastal construction with Old Florida charm, 107 Tuna Street offers a level of design, scale, and positioning that is seldom found on Anna Maria. Just 50 feet from sugar-white sand and set on an oversized corner lot along the coveted North End, this residence enjoys a peaceful setting away from the activity of the public beaches, offering a more private, “locals’ luxury” experience just steps from the Gulf’s iconic turquoise waters. The residence’s Key West–inspired architecture sets the tone with deep balconies, porch brackets, generous openings, and a layout that favors natural light and easy indoor-outdoor living. Built with full concrete block construction and engineered to 2026 Florida hurricane standards, the residence offers exceptional durability and peace of mind inherent to premier coastal living. Upper floors are thoughtfully oriented to catch optimal light and frame coastal views, so the home feels bright and connected to its setting throughout the day, even before you step onto the balconies to watch sunsets that stop everything. Inside, vaulted and cathedral ceilings create volume throughout the open-concept living spaces. The main-level primary suite offers both convenience and privacy, complemented by accessible design features including wider doorways, a full bath, and thoughtful flow for long-term livability. A three-stop elevator connects all levels with ease. The kitchen, with its custom wood cabinetry, is designed as both a showpiece and a workspace, anchored by a full Thermador appliance suite, including a 7-burner range, integrated refrigeration, and dishwasher. Adjacent living and dining areas extend effortlessly outdoors, where 3,000+ square feet of covered and open-air living space transforms the home into a true coastal retreat. Here, the outdoor environment is an extension of your everyday living space. A fully integrated alfresco kitchen anchors the space, complemented by three distinct dining areas designed for everything from casual mornings to large-scale entertaining. The expansive 48’ x 25’ free-form pool and spa create a resort-style centerpiece, surrounded by three lounging areas near a private volleyball court. Positioned just a 120-second stroll from one of Anna Maria Island’s most serene stretches of powdery white sand, the home offers immediate access to the Gulf without sacrificing privacy. Just moments from the charm of Pine Avenue with boutique shopping, cafés, and local favorites like Dips and The Donut Experiment, plus local or even waterfront dining at the Sandbar, The Porch, and The Waterfront, all just blocks away, making everyday living feel like a vacation. With projected strong rental income potential, a six-car garage, and a delivery timeline of Summer 2026, 107 Tuna Street represents a compelling opportunity to secure a newly built, design-forward residence in one of Anna Maria Island’s most desirable and tightly held enclaves. Nearby marinas, boating access, and waterfront parks enhance the island lifestyle, while the cultural amenities of downtown Sarasota, St. Armands Circle, and Longboat Key are all within easy reach. SRQ International Airport is approximately 40 minutes away, offering convenient access. This is a setting that balances seclusion and accessibility, where everyday feels like a vacation, and everything you need is effortlessly within reach. Live on Anna Maria Island, ranked by U.S. News & World Report as the #2 Best Family Beach Vacation in the U.S.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: John Forberger (305-905-1842)
311 POINSETTIA RD, ANNA MARIA, FL 34216
$1,775,000397 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
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)
306 S BAY BLVD, ANNA MARIA, FL 34216
$3,295,00035 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
$4,795,00035 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!
111 PALMETTO AVE, ANNA MARIA, FL 34216
$5,125,00053 Days on yellowkey MLS ID: A4682245
REDUCED by $125,000 (2.4%) on 04/07/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 2677 Built: 2025 Tax: $16,293 (2025)Community: Anna Maria BeachSpa: YesSingle Family
Taxes:$16,293
Elementary School: None
High School: None
Remarks: Experience elevated island living in this exceptional brand-new custom four bedroom four and a half bath coastal retreat by Eason Builders Group Construction, ideally positioned west of Gulf Drive on Anna Maria Island just moments from the sugar-white sands and turquoise waters of the Gulf. Thoughtfully designed to capture both refined personal enjoyment and outstanding vacation rental performance, this architecturally striking residence blends sophisticated design, superior craftsmanship, and effortless indoor-outdoor living in one of the island’s most coveted locations. From the moment you enter, soaring ceilings with rich wood detail and expansive walls of impact-rated glass create a dramatic yet relaxed coastal ambiance filled with natural light. The open-concept floor plan is ideal for entertaining, seamlessly connecting the main living areas while maintaining an intimate, luxurious feel. The chef’s kitchen serves as the heart of the home, featuring an oversized quartz island with ample seating, custom cabinetry, premium appliances, designer lighting, and abundant storage. The kitchen flows effortlessly into the spacious great room, highlighted by a sleek modern fireplace and dramatic sliding glass doors that open to covered terraces, creating the ultimate setting for indoor-outdoor gatherings. The private elevator offers convenience & accessibility. Step outside to your private resort-style backyard oasis where a stunning heated pool with elevated spa takes center stage. Generous covered lounge areas, outdoor dining space, and lush tropical landscaping provide both privacy and year-round enjoyment, offering owners & guests a true boutique resort experience. Whether hosting sunset cocktails or enjoying a quiet afternoon poolside, this outdoor environment is designed for relaxation and entertainment. Each beautifully appointed bedroom offers a tranquil retreat, while spa-inspired bathrooms elevate daily living with freestanding soaking tubs, glass-enclosed showers, dual vanities, & upscale designer finishes. A thoughtfully designed custom bunk room enhances flexibility & maximizes short-term rental occupancy, making the home especially appealing for larger groups & multi-generational stays. Crowning the residence is an expansive rooftop deck delivering sweeping Gulf views. This spectacular vantage point creates an unforgettable setting for sunset gatherings, morning coffee, or evening stargazing—one of the most desirable features for both homeowners & vacation guests alike. Beyond the property itself, embrace the quintessential island lifestyle. Leave the car behind & explore by golf cart or bicycle, cruising to the charming boutiques, art galleries, & acclaimed restaurants along Pine Avenue. Enjoy morning beach walks, afternoons on the water, and evenings filled with breathtaking Gulf sunsets just steps from your door. Built with impact windows and doors, high-end designer finishes, and meticulous attention to detail throughout, this residence offers both peace of mind and enduring quality. With projected annual rental revenue of approximately $400,000, the home presents a compelling investment opportunity while delivering an unparalleled luxury lifestyle. Combining prime west-of-Gulf Drive positioning, exceptional craftsmanship, resort-style amenities, and strong income potential, this remarkable property represents the very best of Anna Maria Island living.
120 MAPLE AVE, ANNA MARIA, FL 34216
$1,575,00069 Days on yellowkey MLS ID: A4680151
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1506 Built: 1973 Tax: $16,951 (2024)Community: Gulf View Sub Of Anna Maria KeySingle Family
Taxes:$16,951
Remarks: Prime Beachside Retreat – Steps to the Sand on Anna Maria Island! Discover coastal living at its finest in this beautifully remodeled and updated 3-bedroom, 2-bathroom single-family home, perfectly positioned west of Gulf Drive in the heart of Anna Maria. Just a short stroll (literally steps away) from the pristine, sugar sandy beaches of the Gulf of Mexico, this residence offers effortless access to turquoise waters, breathtaking sunsets, and the relaxed island vibe that makes Anna Maria a sought-after paradise. The home boasts modern upgrades throughout, including fresh finishes, an open and inviting floor plan, and thoughtful touches that blend comfort with contemporary style. The spacious layout is ideal for families, weekend getaways, or as a high-demand vacation rental investment. One of the standout features? Ample room to add your dream pool—imagine lazy days by your private oasis, just moments from the beach! West of Gulf Drive means no busy roads to cross for beach access, putting you in the most desirable pocket of the island. Enjoy peaceful mornings with the sound of waves, evening walks along the shore, and the charm of nearby Pine Avenue’s shops, restaurants, and cafes—all while owning a piece of true Anna Maria magic. Whether you’re seeking a primary residence, second home, or lucrative rental property, this beachside gem delivers the ultimate in Florida coastal sophistication and easy island living. Don’t miss your chance to own steps from the Gulf—schedule your private showing today!
Listing Agent: James Wilson (727-331-4353)
57 N SHORE DR, ANNA MARIA, FL 34216
$1,890,000109 Days on yellowkey MLS ID: A4676196
1 Days Off yellowkey (back on 4/7/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1240 Built: 1980 Tax: $21,447 (2024)Community: The ArroyoSpa: YesSingle Family
Taxes:$21,447
Remarks: Under contract-accepting backup offers. 57 North Shore Drive: The Art of Island Living Discover the perfect balance of classic Anna Maria charm and contemporary coastal elegance. Tucked away at the corner of North Shore Drive and Palmetto Avenue, this serene retreat sits just two short blocks from the Gulf’s velvet sands. Here, the best of the island is at your doorstep—from the quiet beauty of the shore to the morning coffee spots and hidden gems along Pine Avenue. Thoughtfully Reimagined Freshly renovated with a keen eye for detail, this home is a turnkey sanctuary designed for modern peace of mind. Every inch has been updated to marry style with resilience, featuring: A Bright, Airy Kitchen: The heart of the home, featuring brand-new finishes and high-end stainless steel appliances. Seamless Upgrades: New hurricane-impact windows and a Garrison Aluminum flood protection system ensure your piece of paradise is as secure as it is beautiful. Modern Essentials: From the new HVAC and LED lighting to the redesigned bathrooms, every system has been refreshed for effortless living. Your Private Tropical Escape The outdoor space is a true island oasis, set on an oversized, lushly landscaped lot. Spend your afternoons lounging by the custom saltwater lap pool or unwinding in the spa, all framed by swaying palms and tropical greenery. The screened lanai serves as a shaded sanctuary, perfect for hosting casual sunset dinners or simply listening to the breeze after a day in the surf. Sun-Soaked & Effortless Inside, the single-level layout flows with natural light, capturing that coveted "barefoot luxury" feel. The Living Quarters: Three comfortable bedrooms and three bathrooms are complemented by fresh, coastal-inspired décor. The Bonus Space: An air-conditioned garage provides a versatile extra layer of living, complete with a full bath and laundry area. Ready for You: Sold with its new, meticulously chosen furnishings, the home invites you to move right in and start living the island dream from day one. A Premier Opportunity Whether you envision a permanent change of pace, a family getaway, or a sophisticated investment, 57 N Shore Drive delivers. Currently a successful vacation rental, this property offers the rare chance to own a piece of Anna Maria’s most sought-after lifestyle—where every day feels like a Saturday. * Note: Property Information received from third-party sources is considered reliable but not guaranteed. All information should be independently verified by buyers and buyers agent.
Listing is courtesy of: SALTY MERMAID REAL ESTATE LLC (941-224-3304)
Listing Agent: Liz Blandford (941-224-3304)
108 PELICAN DR, ANNA MARIA, FL 34216
$2,295,00052 Days on yellowkey MLS ID: A4680808
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1472 Built: 1994 Tax: $10,106 (2024)Community: Luana IslesSingle Family
Taxes:$10,106
Remarks: Located on the north end of Anna Maria, this elevated canal-front home is a true boater’s paradise with direct water access and a private dock. This 4-bedroom property underwent an extensive interior remodel, showcasing modern upgrades and coastal living at its finest. The open-concept layout is filled with natural light and offers comfortable living spaces ideal for both everyday living and vacation enjoyment. Step outside to an expansive back deck overlooking the peaceful canal — the perfect setting for relaxing or entertaining. Outdoors, a new pool and refreshed entertaining area further enhance the Florida lifestyle. Ideally situated near beaches, dining, and shopping, this home captures the very best of Anna Maria Island waterfront living and is perfectly suited as a full-time residence or a short-term rental investment.
Listing Agent: Jessica Batten (941-962-3380)
866 N SHORE DR, ANNA MARIA, FL 34216
$1,949,00058 Days on yellowkey MLS ID: A4680714
REDUCED by $50,000 (2.5%) on 03/31/2026
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 1904 Built: 1951 Tax: $16,227 (2024)Community: Shore Acres ResubdividedSpa: YesSingle Family
Taxes:$16,227
Remarks: Don't miss your chance to own a fully remodeled home in the City of Anna Maria. Extensively remodeled 4-bedroom, 4-bath home on North Shore Drive in the City of Anna Maria, featuring significant structural and finish upgrades throughout. This light-filled residence offers an open-concept layout with raised ceilings, refined coastal finishes, and expanded living space. Two bedrooms feature private en-suite bathrooms, with an additional two full guest bath conveniently accessible from the bedrooms and main living areas. Renovations include enclosed patio and garage areas to create an additional en-suite bedroom, expanded kitchen, dedicated laundry room, and approximately 294 square feet of added living space. Major improvements include new electrical and plumbing services; new drywall with DensGlass moisture-resistant panel; a new HVAC system with supplemental mini-split units; spray foam roof insulation; hurricane-impact windows and sliders; and new flooring throughout. The kitchen features all-new cabinetry, countertops, a large center island with breakfast bar, and Samsung appliances including: refrigerator, ice maker, wine cooler, microwave, dishwasher, and chilling drawers. Bathrooms have been fully updated with new tile and high-end plumbing fixtures. Outdoor upgrades include a private heated pool with new heater and pump, expanded paver decking, new fencing, updated landscaping, refreshed exterior stucco, and full interior and exterior paint. Ideally located just steps from the beach and close to Pine Avenue shops and dining, this is a move-in-ready island home offering modern upgrades, thoughtful design, and an unbeatable location—schedule your private showing and experience Anna Maria Island living at its best.
107 ELM AVE, ANNA MARIA, FL 34216
$5,145,000642 Days on yellowkey MLS ID: A4615677
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2432 Built: 2012 Tax: $56,527 (2023)Community: Anna Maria Beach Sub First AddSpa: NoSingle Family
Taxes:$56,527
Tax Year: 2023
Remarks: 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.
Listing is courtesy of: ANNA MARIA ISLAND BEACHES RE (941-567-5234)
Listing Agent: Gregg Bayer (941-799-9096)
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