Anna Maria Real Estate

Anna Maria is a small, picturesque coastal town situated on the Florida Suncoast. It is well-known for its white sand beaches, turquoise waters, and laid-back atmosphere. The town is a popular destination for vacationers and those seeking a relaxed, beachfront lifestyle. The real estate market in Anna Maria is diverse, with a range of properties available at different price points to cater to different needs and preferences.

Anna Maria offers a range of housing options, including charming beach cottages, luxurious waterfront estates, and elegant condominiums. Many of the homes in the area offer stunning ocean views, and the town has a variety of architectural styles, from classic Floridian to contemporary. Anna Maria is an ideal location for those seeking a relaxed beach lifestyle, with plenty of outdoor recreational opportunities including fishing, kayaking, and paddleboarding.

In addition to its natural beauty, Anna Maria has a vibrant local community with a range of shops, restaurants, and attractions. The town has several parks and nature reserves, including the Anna Maria Island Historical Park, and is home to the famous Anna Maria City Pier. The pier offers stunning views of the ocean and is a popular spot for fishing and enjoying the sunset.

If you are considering buying or selling property in Anna Maria, it is important to work with a local real estate agent who is familiar with the area. An experienced agent can help you navigate the market, understand local zoning regulations, and identify properties that meet your needs and budget.

In conclusion, Anna Maria is a stunning location on the Florida Suncoast, with a range of housing options to suit different lifestyles and budgets. Its natural beauty, community feel, and laid-back atmosphere make it a popular choice for vacationers and residents alike. With its range of properties and amenities, Anna Maria is a great place to call home.

Nearby communities include Bradenton and Bradenton Beach.

Available Anna Maria Real Estate For Sale

$6,995,000
6 Beds ⋅ 7 Baths ⋅ A4704981 MLS
Introducing The Ivy — The first chapter in a new collaboration. Born from the partnership of Emily Moss Designs and Moss Builders, The Ivy marks the debut of their shared vision on Anna Maria Island — a carefully crafted waterfront residence where refined design and thoughtful construction meet. As the inaugural home in what will become a growing collection, The Ivy sets the tone for the work to come: elevated, intentional, and deeply rooted in the island’s quiet luxury. Step through the front entry — sheltered beneath a soaring tongue-and-groove wood ceiling — into a great room where large-format stone flooring, disappearing glass sliders, and a sculptural wood ceiling detail set a calm, organic tone. The chef's kitchen anchors the main level with a monumental waterfall-edge stone island, custom dark wood cabinetry, and sculptural globe pendant lighting, flowing seamlessly into a dining room defined by a dramatic wood-beamed vaulted ceiling, a statement orb chandelier, and floor-to-ceiling glass that frames water views from every seat at the table. Directly off the kitchen you’ll find a huge walk in pantry. Six bedrooms offer their own quiet retreats — from a serene primary suite with an upholstered headboard and private glass sliders, to a playful bunk room with built-in cubby storage for kids. The six and a half bathrooms are spa-like in their own right, with freestanding vessel sinks, brass fixtures, and dramatic veined stone and designer tile work throughout. Outside, The Ivy truly comes alive. A resort-style pool is anchored by an elevated spa with a cascading water feature, framed by a turfed lawn, lounge chairs, and a covered wood-ceilinged loggia built for shaded entertaining. A dramatic timber trellis staircase first leads up to the outdoor kitchen, massive TV and hanging swings. As you continue to make your way up to the crown jewel: a expansive rooftop deck with built-in bench seating, a private hot tub to enjoy sunsets, lounge chairs and seating around a fire pit. Direct canal front access completes the picture, with a brand-new dock and boat lift ready for a day on the water — all just a short, palm-lined walk to the shops and restaurants of Pine Avenue.

242 Lakeview Drive, Anna Maria

Courtesy of SATO REAL ESTATE INC.

$2,690,000
4 Beds ⋅ 3 Baths ⋅ A4704940 MLS
Under Construction. Welcome to this completely updated charming coastal home located at 259 Gladiolus St in the desirable City of Anna Maria. If you’re looking for a ground level waterfront, 4-bedrooms, 3-bathrooms, pool home on the north-end, that is close to the beach, Pine Ave shops and the bayside park, this is one to come see! The interior and exterior design offers endless charming coastal details that lean into island relaxed style. As you walk through the double glass front doors, you’ll be surprised by how much light shines into this home accentuating the high ceilings and open concept. The design selections are classic and calm, from neutrals to soft beachy blues. The home offers a split floor plan and two master ensuites plus an inside utility that takes the chore out of laundry. As you make your way to the back of the home the water views become the focal point. The home layout makes every day enjoyment of island living, including the pool and spa that has multiple water features to create relaxing sounds and set the stage for backyard fun. The waterfront setting is tranquil and a fabulous setting for dockside fishing, kayaks or even boating with two bridges to bay. The list of new items includes interior walls and open concept layout, electric, plumbing, flooring, kitchen, appliances, bathrooms, inside utility, metal roof, Therma Tru impact glass front door and PGT impact windows and sliding doors, heated pool/spa, tropical landscaping, and including low maintenance artificial turf. Whether you’re looking for your own island destination to call home or the ideal rental income property with flexible rental restrictions this is one to consider. Call today to schedule your private showing.

259 Gladiolus Street, Anna Maria

Courtesy of ISLAND DESTINATIONS

$2,395,000
3 Beds ⋅ 3 Baths ⋅ A4704186 MLS
Amazing canal front home in the heart of the city of Anna Maria with an amazing view of the canals! STUNNING! This 3 bedroom, 2.5 bath home is full of love, charm and rentals! On a quiet street at the north end of the island, Soulshine is the perfect get away for you and your family to escape the the northern weather every winter. Use it all for yourself of mix it up with some rentals. Guests will love its cozy feel, location to shops, restaurants, Pine Avenue, the City pier and the beautiful beaches that boarder the Gulf of Mexico. Not to mention the view you have from the back porch and sparkling pool and the intersection of the canals. The primary bedroom and ensuite are on the main floor and the two other bedrooms and bathroom are on the top floor. Both are spacious and give you room to spread out as well as all 3 bedrooms have balconies to enjoy the Florida air and the views of paradise. You'll have 75 feet of canal front to enjoy the wildlife in the air and in the water and not to mention...NO BRIDGES to get to the amazing open water of Tampa Bay. It's a boaters DREAM! Sit by the pool and enjoy the sunshine or park an adirondack chair on the back and throw a line in the water. This very busy vacation rental is ready for you just the way it is, but there is so much more untapped potential to this incredible home. Come live the Anna Maria Life at 322 Tarpon.

322 Tarpon Street, Anna Maria

Courtesy of ANNA MARIA LIFE REAL ESTATE

$3,300,000
5 Beds ⋅ 4 Baths ⋅ A4704769 MLS
Welcome to Spring House! Invest in one of Anna Maria Island’s most desirable locations with this exceptional 5-bedroom, 4-bath turnkey rental, just steps from Pine Avenue’s charming shops, restaurants, and the iconic Anna Maria Pier—and only a short bike ride to Bean Point. A true rental powerhouse, this property has generated well over $200,000 in gross rental income while still allowing time for owner use. One of the few properties on Anna Maria Island with Bert Harris approval for occupancy of up to 14 guests, this home offers a rare combination of income potential and flexibility. The beautifully landscaped backyard is designed for maximum guest appeal, with a heated lagoon-style pool, shallow splash area, built-in dining/bar area, Adirondack seating, and BBQ grill. A dedicated recreation room adds even more entertainment value with a flat-panel TV, foosball, ping pong, and a large sitting area. The spacious primary suite includes a king bed, private balcony access, and an ensuite bathroom with a double vanity and newly renovated walk-in shower. Four additional bedrooms and two living room areas provide flexible sleeping arrangements for large groups. Room Details: * Primary Suite – 2nd Floor: King bed, balcony access, ensuite bath. * Second Bedroom – 2nd Floor: King bed. * Third Bedroom – 2nd Floor: Twin bunk bed + twin bed + twin trundle bed. * Fourth Bedroom – 1st Floor: King bed, ensuite bath. * Fifth Bedroom – 1st Floor: Twin bunk bed + twin bed + twin trundle bed. Turnkey and rental-furnished with Wi-Fi, XBOX gaming system, and assorted beach equipment. Strong rental history, exceptional guest capacity, premier location, and an impressive resort-style outdoor space make this a standout investment opportunity on Anna Maria Island. PROVEN RENTAL INCOME • BERT HARRIS APPROVED • PRIME ANNA MARIA ISLAND LOCATION

508 Spring Avenue, Anna Maria

Courtesy of DUNCAN REAL ESTATE, INC.

$5,125,000
4 Beds ⋅ 5 Baths ⋅ A4702886 MLS
A rare opportunity awaits just steps from the Gulf in this exceptional 2025 coastal residence by Eason Builders Group. Set west of Gulf Drive in one of Anna Maria Island’s most desirable locations, this four-bedroom, four-and-a-half-bath home blends refined interiors, resort-style outdoor living and the relaxed sophistication of island life. From the moment you arrive, the home makes a striking impression with crisp coastal architecture, multiple balconies, lush tropical landscaping and contemporary black-framed windows. Inside, soaring ceilings, warm wood flooring, abundant natural light and thoughtfully selected designer finishes create a refined yet relaxed atmosphere. The open-concept main living level is designed for both entertaining and everyday enjoyment. At the heart of the home, the chef’s kitchen features an oversized island with generous seating, custom cabinetry, stone countertops, premium finishes and abundant storage. The kitchen flows seamlessly into the dining area and dramatic great room, where expansive walls of glass, a sleek contemporary fireplace and oversized sliding doors connect beautifully to the outdoor spaces. A private residential elevator provides convenient access between levels, adding comfort and functionality for owners and guests alike. Each of the four bedrooms offers a beautifully appointed retreat, complemented by spa-inspired baths with sophisticated tilework, glass-enclosed showers and designer finishes. The primary suite features a luxurious bath with dual vanities, an oversized walk-in shower and freestanding soaking tub. Custom closet systems, elevated millwork and carefully considered details are found throughout. Outdoor living is at the center of the experience. The private backyard is a tropical resort with a stunning pool and elevated spa, lush landscaping and generous covered areas for lounging, dining and entertaining. Crowning the residence is an expansive rooftop deck offering panoramic island and Gulf views and an unforgettable setting for morning coffee, sunset gatherings or evenings under the stars. Multiple balconies provide even more opportunities to enjoy the Gulf breezes. Currently operating as a highly successful vacation rental, the property offers exceptional versatility as an income-producing investment, luxurious second home or full-time residence. With projected annual rental revenue of approximately $400,000, the home presents a compelling investment opportunity while delivering the lifestyle expected of a premier Anna Maria Island property. Leave the car behind and embrace island life—walk to the beach in moments, cruise the island by golf cart or bicycle, spend afternoons boating and fishing, and enjoy the boutiques, galleries, waterfront dining and acclaimed restaurants that make Anna Maria so special. Combining 2025 construction, exceptional craftsmanship, sophisticated coastal design, a private elevator, resort-style pool and spa, rooftop entertaining space, strong rental potential and an extraordinary west-of-Gulf-Drive location, this remarkable residence offers a rare opportunity to own a true luxury retreat on Anna Maria Island.

113 Palmetto Avenue, Anna Maria

Courtesy of RE/MAX ALLIANCE GROUP

$2,595,000
3 Beds ⋅ 4 Baths ⋅ A4703564 MLS
Welcome to your private coastal retreat in the highly sought-after North End of Anna Maria Island. Completely remodeled from the studs out in 2017 by Gagne Construction, this elevated 3-bedroom, 3.5-bathroom home is situated on a spacious 0.21-acre lot, just a short stroll from the island’s famous white sand beaches and only a couple of minutes on foot from Pine Avenue, the heart of Anna Maria’s shops, restaurants, and island attractions. This superb location allows you and your guests to easily experience the best of the island without ever needing to get in the car. Offering the ideal combination of luxury, comfort, and laid-back island living, this fully furnished residence is perfect as a personal getaway, second home, or investment property with excellent rental potential. Inside, the thoughtfully designed open floor plan is filled with natural light and complemented by high-end finishes throughout. Hurricane impact windows and sliding glass doors provide added protection and peace of mind, while enhancing the home’s seamless connection to its tropical surroundings. The spacious living areas flow effortlessly into the modern kitchen, which features top-of-the-line appliances and plenty of room for gathering with family and friends. Each oversized bedroom offers its own private en-suite bathroom, while elegant, spa-inspired finishes contribute to the home’s relaxed yet refined coastal atmosphere. The outdoor living space is equally impressive and has recently been refreshed with new landscaping, new exterior paint, and new outdoor furniture. Lush tropical surroundings, a heated pool, and an oversized lanai create your own private island oasis. Spend the afternoon by the pool, enjoy dinner al fresco, or unwind outdoors after a day at the beach. The seamless indoor and outdoor layout is perfectly suited for entertaining, extended stays, and creating the type of vacation experience guests will want to enjoy again and again. Offered fully furnished and move-in ready, this home makes second-home ownership effortless while also providing the flexibility to generate rental income when you are away. Anna Maria Island is celebrated for its pristine beaches, tranquil waters, fresh local seafood, and charming small-town atmosphere. With Pine Avenue just moments away, this exceptional North End location places the very best of island living right outside your door. This is a rare opportunity to own a beautifully appointed island retreat where you can vacation, relax, entertain, and invest.

315 Hammock Circle, Anna Maria

Courtesy of RIDER REAL ESTATE

$1,250,000
3 Beds ⋅ 2 Baths ⋅ A4702337 MLS
Set in the heart of Anna Maria, this elevated 3BD/2BA home holds one of the island's most enviable addresses — around the corner to the Anna Maria City Pier and steps from the bay. Celebrated dining, open water, and the island's unhurried rhythm are all right outside the door. Inside, an open living and kitchen area, generous deck space, and a two-car garage offer a solid canvas. Update it, reimagine it, or start fresh — the potential here is wide open. Better still, the home sits in a short-term rental zone, so it can earn its keep between your own stays. Then step outside, where the Anna Maria lifestyle takes over: mornings on the beach, afternoons cruising the island by bike or golf cart, evenings fishing the pier or watching the sun drop into the Gulf. Locally loved shops and restaurants sit just down the street. Location, rental potential, and a lifestyle people rearrange their lives for. Bring your vision.

524 Spring Avenue, Anna Maria

Courtesy of DUNCAN REAL ESTATE, INC.

$2,985,000
4 Beds ⋅ 3 Baths ⋅ A4700920 MLS
Back on the Market!!!!! Welcome to Tropical Paradise. Talk about Location, Location, Location. What more can you ask for in the City of Anna Maria? Four houses and 200 steps to the calm beaches at Bayfront Park. It’s an easy walk to the City Pier, the Waterfront Restaurant and all the shops of Pine Ave. It is the perfect home for any of your needs. Make it your full-time residence. Use it as a second home, turn it into a fabulous vacation rental or combine the two. This home was built in 2007. It is elevated, has hurricane strength windows and doors, and has superior hurricane protection with a metal roof. All these factors lower your insurance costs dramatically. The home has 2567 SF of air-conditioned space on two floors. It has received major updates with 2 new HVAC units and a new hot water heater. When you pull up in front of the home you are greeted by two large decks overlooking the street and from the top floor views of Tampa Bay. These decks have both been re-surfaced and weather-proofed with new wood look ceramic tiles. The stairs and deck leading to the front door were rebuilt with Trex decking. There is a large double wide car garage door opening into a massive 4 car garage that goes from the front to the back of the home. There is a direct access staircase to the living space from the garage. Go up the front stairs onto the first floor of the home. All the flooring throughout the home are re-done with weatherproof luxury vinyl planking. There is a large open-air floor plan with a comfortable great room, huge dining area and updated kitchen with granite counters, a tile back splash, breakfast bars, and stainless-steel appliances. Also on this level is one of the four bedrooms. It has an in-suite bath with a re-tiled walk-in shower and a new vanity. The kitchen and bedroom both have access to a rear porch with a spiral staircase leading down to the backyard and pool. Going up to the third floor you have three bedrooms starting with a spacious primary suite. It has two walk-in closets and a private bath suite with a walk-in shower, jacuzzi soaking tub and a new large dual vanity. There are French doors from the master bedroom opening onto the front balcony. From here, there are views of Tampa Bay and the Skyway Bridge. The two other bedrooms share a hallway bath with a new vanity, Both bedrooms have French doors with access to a rear enclosed and air-conditioned playroom. The hallway bath has a private bathtub and a new vanity. Last, there is a large laundry room with a full sized washer and dryer. On each level you will find a large storage closet. These closets are preparation for an elevator shaft, should you want or need one. The garage is big enough for all your toys. At the back of the garage are patio doors leading out to your private Astroturf back yard and heated pool. You can easily turn the back of the garage into gathering area overlooking the pool. The yard has an eight-foot rear fence for added privacy. From your front door, it is less than a 2-minute walk to the calm beaches of Bayfront Park in Tampa Bay Here there are changing rooms, showers, gazebos, and charcoal grills for a picnic on the bay. If you prefer the Gulf, it is about a 10-minute walk from the house. The free AMI trolley-stop, and Pine Ave with all its restaurants and shops are just down the street. This home is offered turn-key furnished and presently being booked in an active rental program.

159 Crescent Drive, Anna Maria

Courtesy of SATO REAL ESTATE INC.

$1,850,000
4 Beds ⋅ 4 Baths ⋅ A4701660 MLS
An income-producing opportunity in the heart of Anna Maria Island. This 4-bedroom, 4-bathroom duplex sits on coveted North Shore — steps from the boutiques, cafés, and galleries of Pine Avenue and minutes from the Gulf's world-famous sugar-white beaches. Blue Lagoon operates as a vacation rental with a proven track record, a loyal returning guest base, and confirmed reservations already booked into 2027. The property features a large heated pool, private outdoor entertaining areas in-unit washers/dryers, and an on-site EV charger. The duplex can be rented as two separate units or opened via an interior connecting door to accommodate larger groups, maximizing both flexibility and revenue potential year-round. Bert Harris Agreement — A Significant Asset This property benefits from a Bert Harris Private Property Rights Agreement with the City of Anna Maria. When the city enacted its vacation rental ordinance limiting all short-term rentals to a maximum occupancy of 8 guests regardless of home size, many property owners successfully filed claims under Florida's Bert J. Harris Jr. Private Property Rights Protection Act, a state law that protects owners when a local government action reduces the value of their property. Through a negotiated settlement, this property secured the right to host up to 12 guests, well above the city's standard cap. This agreement transfers with the property and represents a meaningful competitive and financial advantage that cannot easily be replicated by new purchasers today. A true turnkey investment in one of Florida's most sought-after island destinations.

76 N Shore Drive, Anna Maria

Courtesy of SEA BREEZE REAL ESTATE LLC

$1,795,000
3 Beds ⋅ 3 Baths ⋅ A4699353 MLS
This amazing old Florida 1922 cottage is so quaint and cozy, you’ll never want to leave! This 3 bedroom, 3 bath island oasis is on a huge lot. With a heated pool and spa, surrounded in landscaping with a pool cabana including a TV, dining table and grill for family gatherings. Once you step through the door you will never want to leave this historic home with high end finishes and beautiful turnkey furnishings. The master suite is spacious with impact sliders on the whole wall looking out to the pool and cabana making it so private. Tile wood throughout, stainless steel appliances, beautiful countertops, there is so much this home has to offer. Living and kitchen open concept with an eat-in dining table in the kitchen. The 2nd bedroom has its own ensuite bath with a walk-in shower. 3rd bedroom is off the kitchen and uses the hallway full bath. Enjoy coffee on the back porch in the mornings listing to the birds chirp. Short walk to the shops and dining on Pine Avenue or stroll to the bay or beach as both are a short walk away. 1-7 day rentals are permitted, and bookings are in place making it easy to turn the key and it's vacation rental ready. This little island oasis is ready for you to enjoy paradise today!

504 Spring Avenue, Anna Maria

Courtesy of SATO REAL ESTATE INC.

$2,849,500
4 Beds ⋅ 5 Baths ⋅ A4699292 MLS
Welcome to the island lifestyle you've been dreaming of in the heart of beautiful Anna Maria Island! Perfectly positioned on the coveted north end of the island, this exceptional location places you just moments from the sugar-white sandy beaches of the Gulf and only a few blocks from the iconic Pine Avenue, where you'll enjoy locally owned boutiques, waterfront restaurants, charming cafés, art galleries, live music, and the beloved Anna Maria City Pier. Built in 2017, this elevated Key West-inspired POOL home offers nearly 2,200 square feet of beautifully designed living space with 4 bedrooms, 4.5 bathrooms, a private elevator, and comes completely TURNKEY. Stepping inside, you'll immediately appreciate the open concept floorplan accented by gorgeous wood-look tile flooring throughout and a stunning shiplap wood vaulted ceiling that perfectly captures the home's coastal character. The kitchen is truly the heart of the home, featuring a large center island with generous barstool seating, top-of-the-line stainless steel appliances, a wine refrigerator, custom white cabinetry, a custom vent hood, and a modern backsplash that ties the space together beautifully. The living and dining areas seamlessly flow outdoors through sliding glass doors that open onto the expansive covered balcony. Overlooking your private tropical backyard oasis, this is the perfect setting for indoor-outdoor living and entertaining. Each of the four spacious bedrooms offers its own private ensuite bathroom, providing comfort and privacy for family and guests alike, while the additional half bathroom is perfectly situated for visitors. Take the spiral staircase down to your backyard retreat where resort-style living awaits. The under-home patio features a beautiful wood plank ceiling that adds even more coastal charm, along with an expansive entertaining area complete with a bar. The freeform heated swimming pool is the true centerpiece, featuring a built-in pool tabletop with umbrella space, a relaxing spa, and lush tropical landscaping that creates a private paradise you'll never want to leave. Currently operating as a profitable vacation rental, this home offers exceptional income-producing potential while also serving as the perfect personal beach retreat. Here, golf carts and bicycles are the preferred way to get around, towering palms line the streets, and every day feels like a vacation. Spend your mornings walking the beach in search of seashells, afternoons paddleboarding or boating on crystal-clear waters, and evenings watching spectacular Gulf sunsets before grabbing fresh seafood overlooking the bay. With no high-rise buildings, Anna Maria has preserved its authentic Old Florida charm while remaining conveniently close to Bradenton, Sarasota, St. Petersburg, and Tampa. Whether you're searching for a luxurious full-time residence, an unforgettable vacation home, or a high-performing investment property, there are few places quite like Anna Maria Island. This is a rare opportunity to own a piece of paradise in one of Florida's most sought-after coastal communities, schedule your showing today!

418 Magnolia Avenue, Anna Maria

Courtesy of RIDER REAL ESTATE

$5,495,000
5 Beds ⋅ 6 Baths ⋅ A4698723 MLS
Introducing The Palm—an iconic waterfront estate where exceptional architecture, resort-inspired living, and the unmistakable charm of Anna Maria Island come together to create a remarkable home. More than a home, The Palm captures the very best of Anna Maria Island living. Thoughtfully custom built by Eason Builder Group, this newly completed waterfront residence features five bedrooms, five full baths, one half bath, and more than 3,260 square feet of beautifully designed living space where coastal elegance meets exceptional craftsmanship. Every room has been thoughtfully curated to create an effortless connection between sophisticated design and the natural beauty that surrounds it. Walls of impact glass fill the home with natural light, while tongue-and-groove cypress ceilings, custom millwork, natural stone, and carefully selected finishes create a home that feels refined and welcoming. The open floor plan was designed for effortless entertaining and everyday living, featuring spacious gathering areas, luxurious private suites, a custom bunk room, and seamless transitions between indoor and outdoor spaces. Integrated smart home technology, an elevator, premium impact-rated windows and doors, Daikin HVAC systems, tankless water heaters, composite decking, and quality craftsmanship throughout reflect the care and attention that went into every detail. Outside, the experience is every bit as impressive. A resort-style pool with a raised spa anchors the backyard, surrounded by tropical landscaping that creates beauty and privacy. The covered lanai offers multiple spaces to gather, including an outdoor kitchen, bar seating, comfortable lounge areas, and dining space designed for entertaining family and friends. A private putting green adds another element of fun. One of the home’s most memorable features is the expansive rooftop deck, designed for sunset cocktails and panoramic views stretching across Anna Maria Island. For boating enthusiasts, The Palm offers one of the island’s most desirable features—a private dock with a 16,000-pound boat lift and direct, no-bridge access to the Gulf, allowing you to leave your backyard and be on open water within minutes. Beyond the property itself lies the lifestyle that makes Anna Maria Island so special. Leave the car behind and explore the island by golf cart or bicycle. Spend your mornings browsing the boutiques, cafés, and local shops along charming Pine Avenue, your afternoons on the island’s world-famous sugar-white beaches, and your evenings enjoying waterfront dining before watching another unforgettable Gulf sunset. Here, life moves at a different pace—one defined by boating, fishing, paddleboarding, beach walks, and the timeless character that continues to make Anna Maria Island one of the Gulf Coast’s most treasured destinations. Whether you’re searching for a private waterfront retreat, a seasonal residence, or a high-end vacation rental with exceptional income potential, The Palm offers a rare opportunity to enjoy the very best of island living while owning one of Anna Maria Island’s premier waterfront homes. Beautifully designed, expertly built, and perfectly positioned, The Palm is more than a residence—it is a place where family and friends gather, memories are made, and the best of Anna Maria Island becomes part of everyday life.

411 Palm Avenue, Anna Maria

Courtesy of RE/MAX ALLIANCE GROUP

$8,995,000
5 Beds ⋅ 5 Baths ⋅ A4697213 MLS
Experience Elevated Island Living at 703 S Bay Blvd. Nestled along the tranquil Bimini Bay canal with sweeping views of Tampa Bay, this brand-new modern masterpiece by Tulia Homes offers the pinnacle of waterfront luxury on Anna Maria Island. Completely reimagined as a stunning contemporary build, this 5-bedroom, 5-bath home seamlessly blends sleek architecture with the relaxed elegance of coastal Florida living. From the moment you arrive, the home welcomes you with abundant natural light, open-concept living spaces, and thoughtfully designed interiors that flow effortlessly to the outdoors. The chef-inspired kitchen anchors the heart of the home, perfect for everything from intimate family meals to lively gatherings. A huge walk in pantry with an extra refrigerator for convenience. Generous bedroom suites provide private retreats, each finished with premium details and spa-like baths. Outside, your personal waterfront oasis awaits. Dive into the sparkling private heated pool, entertain on expansive lanai spaces and the roof top deck, or head straight to your private boat lift and dock for a day on the water. With direct canal access and breathtaking bay vistas, every day feels like a vacation in this north-facing retreat. Enjoy the private pickle ball court right in your backyard! Ideally located on coveted Anna Maria Island, this home puts you just moments from pristine beaches, charming shops, and top-rated dining, while offering easy access to boating, fishing, and all the Gulf Coast has to offer. Whether you’re seeking a primary residence, family getaway, or premium investment property, 703 S Bay Blvd delivers an unparalleled lifestyle in one of Florida’s most desirable coastal communities. Discover modern sophistication, effortless waterfront living, and island charm—all in one extraordinary home. Schedule your private tour today and make this Anna Maria dream your reality.

703 S Bay Boulevard, Anna Maria

Courtesy of SATO REAL ESTATE INC.

$2,495,000
4 Beds ⋅ 3 Baths ⋅ A4697404 MLS
Discover the ultimate island retreat just three homes from the sugar-white sands and turquoise waters of the Gulf of Mexico. Situated on an oversized 8,250-square-foot lot, this beautifully appointed 4-bedroom, 3-bath home offers nearly 1,700 square feet of coastal living and features a desirable open floor plan designed for gathering and entertaining. The thoughtfully designed layout includes two spacious ensuite bedrooms, a fun bunk room perfect for younger guests, and plenty of room to relax after a day at the beach. Step outside to your own private tropical oasis. The heated pool invites you to enjoy sunny afternoons and evening swims under the stars, while the expansive backyard offers abundant space for lounging, grilling, and making memories with family and friends. The generous lot size is a rarity on Anna Maria Island and provides a true sense of privacy and room to spread out. Along the side of the home, an outdoor game area creates the perfect setting for friendly competitions and endless entertainment after a day spent on the beach. Ideally located in the heart of Anna Maria Island, you're just a short stroll to the boutiques, restaurants, and vibrant atmosphere of Pine Avenue, as well as the island's world-famous beaches. Whether enjoying spectacular Gulf sunsets, dining at one of the island's favorite eateries, or relaxing poolside with loved ones, this home embodies the laid-back luxury of island living. With a proven history as a successful short-term rental and exceptional investment opportunity, this turnkey property offers the perfect blend of lifestyle and income potential. Rarely do homes on oversized lots this close to the Gulf become available. Experience the very best of Anna Maria Island and own your own slice of paradise, where every day feels like a vacation. Come live the Anna Maria Life!

110 Palm Avenue, Anna Maria

Courtesy of ANNA MARIA LIFE REAL ESTATE

$3,250,000
4 Beds ⋅ 4 Baths ⋅ A4697111 MLS
Unparalleled luxury, unmatched value: recently reduced by $400K! Discover the essence of island living at this premier north-end Anna Maria Island retreat, ideally positioned just moments from the sugar-sand shores of Bean Point and the tranquil waters of Tampa Bay. Following a total gut and comprehensive renovation completed in 2021, this coastal residence offers the perfect blend of modern luxury, comfort, and outdoor living. Situated on a private corner lot in one of the island's most sought-after neighborhoods, the open-concept floor plan is masterfully designed for entertaining. It features 4 bedrooms, 3.5 baths, soaring ceilings, abundant natural light, and seamless indoor-outdoor living. The chef's kitchen boasts a gas range, premium quartz countertops and opens beautifully to spacious living and dining areas, while multiple balconies and covered decks create inviting spaces to enjoy sea breezes and glimpses of the bay. The resort-style outdoor setting is truly exceptional, featuring a heated saltwater lap pool and spa, putting green, outdoor shower, lush tropical landscaping, and multiple gathering areas designed for relaxation and entertaining. Aside from being a dream personal getaway, this property is a proven investment powerhouse. It has happily welcomed guests year after year, consistently generating a fantastic rental income of approximately $225,000 - $275,000 (not including taxes or cleaning fees) for each of the past four years! With a strong, established rental history and future bookings already in place, it is ready to start earning for you on day one. Detailed rental financials are available upon request. This is a rare opportunity to acquire a fully updated, income-producing luxury island home in one of Anna Maria's most desirable locations, just moments from world-famous beaches, waterfront dining, boutique shopping, and spectacular Gulf Coast sunsets.

256 Gladiolus Street, Anna Maria

Courtesy of SATO REAL ESTATE INC.

$3,395,000
4 Beds ⋅ 5 Baths ⋅ A4695745 MLS
Don't miss this Eason Builders Group custom-built pool home located on the desirable north end of Anna Maria Island, just a short distance to the beach, Bayfront Park, Pine Avenue, City Pier, restaurants, and shopping. Built with quality and durability in mind, this four-bedroom, four-and-a-half-bath home features concrete block construction, a standing seam metal roof, impact-rated windows and doors, an elevator servicing all levels, and high-end finishes throughout. Spanning three living levels and topped by a rooftop deck, the home offers panoramic island views, sunset views, and views of the Sunshine Skyway Bridge. The open-concept floor plan features high ceilings, extensive custom trim work, a gas fireplace, built-in seating, and multiple covered balconies. The kitchen is equipped with Bosch appliances, quartz countertops, custom cabinetry, a large pantry, and an oversized island with ample seating. A separate dining area opens directly to the covered balcony, creating additional space for entertaining. All four bedrooms feature private en-suite baths. The primary suite includes a walk-in closet, soaking tub, private balcony, and views toward Tampa Bay. The outdoor living space was designed for privacy and functionality, with mature tropical landscaping surrounding the oversized heated pool, spa, and multiple gathering areas. A three-car garage and generous owner's storage provide plenty of room for beach gear, bikes, and recreational equipment. Combining quality construction, thoughtful design, rooftop views, privacy, and a prime north-end location, this property is well suited as a primary residence, second home, or island retreat.

526 Seagull Way, Anna Maria

Courtesy of SATO REAL ESTATE INC.

$1,595,000
3 Beds ⋅ 3 Baths ⋅ A4695399 MLS
FINANCING FELL THROUGH BACK ON THE MARKET!!! Welcome to your dream getaway, an adorable bungalow located on the north end of Anna Maria Island, directly across from the beach and a lovely park. This charming 3-bedroom, 3-bathroom home is perfect for a full-time residence, an income-generating rental, or a part-time retreat—all in an unbeatable location. Step inside to discover a welcoming living room with beautiful hardwood floors and delightful beach views, seamlessly connecting to the dining area for an open and inviting layout. The kitchen features wood cabinets, sleek quartz countertops, and stainless steel appliances, along with convenient countertop seating. The spacious primary bedroom includes a cozy sitting area and French doors that frame stunning beach views, complemented by an updated en-suite bathroom with a stylish glass shower. The second bedroom also boasts its own en-suite, providing comfort and privacy for guests. Outside, enjoy your private deck, ideal for sunbathing and grilling, complete with an outdoor shower for rinsing off after a day at the beach. The heated pool offers a refreshing retreat on warm days, while the covered, screened front porch is the perfect spot to relax with morning coffee and take in the serene blue waters. Located close to Pine Avenue’s boutique shops, delightful restaurants, and the picturesque Bean Point, this property features a durable metal roof, hardy board siding, and newer windows, enhancing its appeal and longevity. Don’t miss the chance to make this charming bungalow your own—schedule your showing today and embrace the island lifestyle!

317 N Bay Boulevard, Anna Maria

Courtesy of DUNCAN REAL ESTATE, INC.

$2,175,000
3 Beds ⋅ 2 Baths ⋅ A4694221 MLS
Spring Avenue. One of Anna Maria Island's most coveted addresses and this elevated pool home does it justice. Located on an island named one of America's prettiest cities by Forbes, this is the kind of home that turns heads before you even walk through the door. Four-car garage plus additional off-street parking front and back means no compromises, whether you're hosting a full house or storing all the toys that come with island life. The open, airy layout with vaulted ceilings and warm wood accents gives you that treehouse-in-the-palms feeling the moment you arrive. Two bedrooms open directly to a private back deck. The pool is your backyard centerpiece. Stroll to Pine Avenue for coffee, dinner, and boutique shopping. Catch the free island trolley at the corner. The Gulf and the Bay are both within easy reach and you are centered between them. No HOA. Weekly rentals permitted. Turnkey furnished. Whether this becomes your primary island escape or a high-performing vacation rental, the bones, the location, and the lifestyle are already here waiting.

315 Spring Avenue, Anna Maria

Courtesy of WHITE SANDS REALTY GROUP FL

$2,000,000
A4694634 MLS
Located on the north end of Anna Maria Island, this 10,600+ square foot parcel is just a short walk from Bean Point beaches, Bayfront Park, and the boutiques and dining on Pine Avenue. The property is beautifully landscaped and includes a large garage, offering a fantastic opportunity to build a custom home with ample space. If you are not interested in building, the adjacent home at 242 Gladiolus is also available for purchase. Both properties are owned by the same sellers, who currently use this parcel for additional privacy and the existing garage. Purchasing both parcels would provide a rare 18,175 square feet of land on Anna Maria Island.

240 Gladiolus Street, Anna Maria

Courtesy of FRAN MAXON REAL ESTATE

$2,900,000
4 Beds ⋅ 4 Baths ⋅ A4694474 MLS
Named "A Wave From It All" by the sellers, this exceptional coastal property offers high-end finishes and a layout designed for seamless indoor/outdoor living. The outdoor pool area serves as a private tropical oasis, perfect for relaxation. The main residence features three bedrooms, each with a king bed and ensuite bathroom. The kitchen is equipped with a Sub-Zero refrigerator, a Wolf range and microwave, Bosch dishwasher and wine cooler. For ultimate privacy, the primary suite is accessed through a unique bookcase doorway. This home comes furnished and includes original artwork by renowned artists and a beautiful outdoor mural by Chad "Cheeta" Ruis. The property also includes a versatile casita featuring two Murphy beds, a half bath, an office area, a laundry room, and a convenient outdoor shower located just outside the half bath which includes both hot and cold water. A small storage garage is available on-site for bikes and beach gear. Located on the North end, the home is a short walk from Bean Point beaches, Bayfront Park, and the boutiques and dining on Pine Avenue. Additionally, the adjacent 10,600+ sq. ft. parcel at 240 Gladiolus is available for separate purchase. It is currently landscaped to enhance the estate and includes a large garage. Don't miss out on this unique opportunity and schedule your private showing today!

242 Gladiolus Street, Anna Maria

Courtesy of FRAN MAXON REAL ESTATE

$1,525,000
3 Beds ⋅ 3 Baths ⋅ A4693882 MLS
LOCATION! NEW STEEL ROOF! .19 ACRE LOT! RARE ARTISAN WELL! MOTHER-IN-LAW SUITE! Opportunity is knocking on one of the most desirable streets on Anna Maria! This rare opportunity offers incredible potential in an unbeatable location. Just moments from the beach, the bay, the community center, and the shops and restaurants of Pine Avenue. This 3 bedroom, 3 bathroom home sits on an oversized .19-ACRE LOT in the heart of Anna Maria. The property features a NEW STEEL ROOF installed in MAY 2024 with a TRANSFERABLE 50-YEAR WARRANTY, providing a major upgrade already completed for the next owner. One of the bedrooms functions as a private mother-in-law suite with its own separate entrance, full bathroom, and existing hookups for a kitchenette - ideal for guests, extended family, or added rental flexibility. A unique highlight of the property is the separately deeded ARTISAN WELL, which supplies irrigation water to the community center as well as neighboring properties. This creates both community value and potential tax benefits! WEEKLY RENTALS are allowed, making this an outstanding opportunity for investors, builders, or buyers looking to create their dream island home. The property experienced flooding and will require renovation/gutting, but the location, lot size, and valuable existing features make this a truly exceptional investment opportunity on Anna Maria Island!

306 Palm Avenue, Anna Maria

Courtesy of DUNCAN REAL ESTATE, INC.

$4,495,000
4 Beds ⋅ 4 Baths ⋅ A4691979 MLS
Welcome to The Beachwood! Discover coastal elegance in this brand-new constructed home with elevator on the coveted North End of Anna Maria Island. This exceptional 4-bedroom, 4-bathroom home offers the ultimate island lifestyle with contemporary elegance and breathtaking views. Boasting a private heated saltwater pool & spa surrounded by tropical palms, multiple spacious balconies, and a ooftop deck with spectacular views of the Gulf, this home is designed for effortless entertaining and unforgettable sunsets. Inside you will find a spacious open living area with a chef’s kitchen including high end Thermador appliances, bar with a wine and beverage fridge, and cozy fireplace to relax. Tastefully furnished and decorated with calming colors and natural materials, this open design also allows for plenty of natural light and inviting views of the mature tropical landscape. Enjoy the beauty of the custom wood features in the home like the live edge teak mantel, and the upstairs coffee and beverage bar cut out of Brazilian hardwood. You can read and study in the privacy of the office with built-in bookshelves or relax outside the office on the balcony. Either side of the home features custom IPE wood and metal gated fences for luxuriousness and ultimate privacy. There’s a large two-car garage with plenty of storage space. The home is secured with impact and hurricane sliders and windows. Perfectly situated between the beautiful beaches of Bean Point and Pine Avenue, you’re just steps away from serene bayfront beaches, restaurants, boutique shopping, and waterfront recreation. Whether you’re relaxing in the spa after a day at the beach or hosting friends on the rooftop with panoramic vistas of Tampa Bay and the Skyway Bridge, every detail invites you to unwind in paradise. Schedule your private showing today!

513 N Bay Boulevard, Anna Maria

Courtesy of SATO REAL ESTATE INC.

$6,950,000
9 Beds ⋅ 9 Baths ⋅ A4691620 MLS
Located on picturesque Anna Maria Island, this exceptional 9-bedroom, 8.5-bathroom coastal retreat offers 4,244 sq ft of heated living space with luxurious amenities throughout. The open-concept interior features an oversized kitchen with a spacious quartz island, upgraded appliances, and a wet bar for entertaining. Enjoy the multiple balconies or the rooftop deck, showcasing Gulf of Mexico views and unforgettable sunsets. Just a 3 MINUTE WALK TO THE BEACH! The private backyard oasis includes a custom styled pool with a hot tub, a game area, and plenty of space for lounging. The primary suite, located on the third floor, includes a king bed, private balcony, and a spa-like ensuite with an enclosed shower and tub. 5 additional king bedrooms feature ensuite bathrooms, some with balcony access, while 2 king bedrooms share a hallway bathroom. The ninth bedroom offers a full-over-full bunk bed and an ensuite bath. ALL FURNISHINGS INCLUDED. Additional highlights include an elevator, game room, and parking for up to FIVE cars. This ideal beach retreat combines modern elegance with relaxed island charm- GREAT RENTAL OPPORTUNITY.

9407 Gulf Dr, Anna Maria

Courtesy of BEACH HOUSE REAL ESTATE LLC

$1,845,000
3 Beds ⋅ 2 Baths ⋅ A4690821 MLS
Anna Maria Island Income-Producing Beach Retreat | 3BR/2BA | Oversized Pool + Spa Exceptional opportunity to own an elevated 3-bedroom, 2-bath home on Anna Maria Island, just a short walk to the beach. Whether you’re looking for a personal island getaway, full-time residence, or a successful vacation rental investment, this property offers the perfect combination of lifestyle and income potential. Designed for coastal living, the home features a bright and open floor plan with spacious living and dining areas, ideal for entertaining guests or relaxing after a day in the sun. The elevated design offers added peace of mind and classic island charm. Step outside to your own private tropical oasis featuring an oversized heated pool and spa, with plenty of room for lounging, outdoor dining, and enjoying the Florida sunshine year-round. This outdoor space is a major highlight for both homeowners and vacation renters. Located in one of the most desirable areas on the North end Anna Maria Island, the home is within easy walking distance to the beach, shops, dining, and everything that makes island living so special. Property Highlights: • 3 bedrooms, 2 bathrooms • Elevated home • Oversized private pool with spa • Short walk to beach access • Proven vacation rental / income-producing property • Excellent investment potential

228 Gladiolus Street, Anna Maria

Courtesy of PINEYWOODS REALTY LLC

$5,895,000
4 Beds ⋅ 5 Baths ⋅ A4689780 MLS
Welcome to a rare offering on the coveted north end of Anna Maria Island — a brand-new coastal sanctuary where architectural sophistication meets the timeless charm of Old Florida. Ideally positioned just steps from the sugar-white sands of the Gulf and moments from the boutique shops, galleries, and countless dining options of historic Pine Avenue and the surrounding area, this exceptional 4-bedroom, 4.5-bath residence captures the essence of elevated island living — and sits within one of the island’s most desirable short-term rental zones. Designed with a refined, light-filled aesthetic, the home welcomes you with wide-plank hardwood flooring and a seamless flow between spaces that feel at once elegant and effortless. At the heart of the main level, a designer kitchen serves as the showpiece — outfitted with custom cabinetry, a generous island with seating, premium appliances, a dedicated wet bar, and a fully appointed butler’s pantry that makes entertaining feel second nature. Multiple gathering areas, including a secondary upstairs family room, offer a thoughtful balance of togetherness and retreat. The primary suite is a private sanctuary of understated luxury, anchored by a spa-inspired bath with a sculptural soaking tub, oversized walk-in shower, and bespoke designer finishes. Three of the four bedrooms enjoy their own private ensuites, and every bedroom features a walk-in closet — a refined blend of privacy and comfort for family and guests alike. Step outside to a fully screened ground-level living area that functions as a true extension of the home, complete grilling area and lounge designed for year-round enjoyment. Beyond, a private tropical oasis unfolds around a sparkling pool with integrated spa and a gas firepit framed by lush landscaping and a vinyl privacy fence that creates a secluded, resort-caliber setting for gathering or quiet escape. Every detail has been considered for ease and longevity, including Lutron lighting controls, three-zone climate systems, a metal roof, outdoor shower, and a three-car garage. Offered fully furnished, the property is delivered as a true move in ready opportunity. Beyond the walls of the home lies the magic of the north end — the most coveted and character-rich stretch of Anna Maria Island, known for its pristine beaches, the legendary white sands of Bean Point where the Gulf meets Tampa Bay and the walkable, tree-lined corridor of Pine Avenue with its celebrated restaurants, cottage shops, and cafés. Days begin with sunrise strolls along the shore and end with sunset dinners just minutes from your front door. With short-term rentals permitted, unmatched walkability to both the beach and Pine Avenue, and a rare combination of design, location, and lifestyle, this residence represents one of the most compelling offerings on Anna Maria Island — a legacy property with exceptional income potential in Florida’s most storied coastal village.

215 Sycamore Avenue, Anna Maria

Courtesy of DUNCAN REAL ESTATE, INC.

$1,500,000
2 Beds ⋅ 2 Baths ⋅ A4689815 MLS
One or more photo(s) has been virtually staged. MAJOR PRICE REDUCTION $100,000...Allowing You Endless Possibilities for Improvements. Welcome to the highly sought after North end of Anna Maria Island. Just steps away from the Morning Sunrise or Evening Sunsets, Take your Pick. This 2 Bed / 2 Bath Island Home Features an Open Floor Plan, Spacious Kitchen, Front & Back Balconies, Large Fenced Back Yard and Ample Parking Both Under House and Extended Driveway. Use your creativity to convert the large open 1st floor workshop into your Personal Space, Home Office, or Outdoor Entertaining Venue. The large backyard can easily accommodate a Pool, Putting Green, Bocci Ball Court, or whatever suites your fancy. Excellent vacation rental income opportunity as well. A perfect combination of Island comfort. A short walk to the Anna Maria City Beach and the bustling offering of shops & dining venues on Pine Avenue. Not to mention the soon to be completed, (October 2026), Anna Maria Island City Pier. "PIERADISE" will feature an Open-Air Neighborhood Bar & Grill, Bait & Tackle Shop and Open Dock Fishing. Island Living at its Best with Great Rental Income Potential Option. This one is definitely worth a visit. Call today to schedule your private showing.

517 Spring Avenue, Anna Maria

Courtesy of O'STEEN GROUP INC

$5,350,000
5 Beds ⋅ 5 Baths ⋅ A4689581 MLS
LUXURY COASTAL LIVING AT IT’S FINEST! This one-of-a-kind residence, designed by Emily Anne Smith, stands on one of the most sought-after streets in Anna Maria, just one home from the Gulf and a short walk to the charm of Pine Avenue. The location offers an exceptional combination of beach proximity, walkability, and privacy. Thoughtfully designed for both entertaining and multi-generational living, the home offers over 4,500 square feet of curated living space with distinct gathering areas throughout. The main living room opens to a front verandah and features a fireplace, with an additional fireplace located in the primary suite. The kitchen, designed for both function and presentation, featuring marble countertops and backsplash, custom cabinetry, a butler’s pantry, and dual sinks is well-suited for both everyday use and larger gatherings. Emily Anne Smith is known for her mindful and timeless coastal design, and this home reflects that level of craftsmanship throughout. The property includes a main residence and a separate cottage, providing flexibility and privacy with a total of 5 bedrooms and 4.5 bathrooms. Additional features include multiple verandahs, two dedicated study spaces, and a well-designed outdoor living area with a pool, shower, and lounge space. The private guest quarters with separate entrance offers an ideal setup for extended family, guests, or private accommodation. This is a rare opportunity to own a thoughtfully designed home in a premier Anna Maria location, with Gulf views and exceptional sunset exposure.

103 Park Avenue, Anna Maria

Courtesy of MICHAEL SAUNDERS & COMPANY

$4,200,000
3 Beds ⋅ 3 Baths ⋅ A4688600 MLS
This Bayfront home is calling your name! Perfectly positioned directly on the bay, this 3-bedroom, 2.5-bathroom residence offers breathtaking water views from almost every window, inviting the serene beauty of Tampa Bay inside. Step into an open, light-filled layout designed for relaxation and entertaining. The spacious interiors flow effortlessly, with generous living areas that frame panoramic bay vistas. Multiple balconies provide the ideal spots to savor morning coffee, sunrise, or the gentle bay breeze while watching dolphins play and boats glide by. Long, private driveway and attached garage offering ample parking for family and guests. Whether you’re hosting a weekend getaway or enjoying everyday island life, there’s plenty of room for boats, cars, and more. Just minutes from Anna Maria’s world-famous white-sand beaches, Pine Avenue’s charming shops and restaurants, this home combines privacy and convenience in one of the island’s most desirable north-end locations. Experience true Florida waterfront living—where every day feels like a vacation. Don’t miss this rare opportunity to own a slice of paradise on Anna Maria Island!

889 N Shore Drive, Anna Maria

Courtesy of SATO REAL ESTATE INC.

$6,795,000
6 Beds ⋅ 8 Baths ⋅ A4688392 MLS
Discover coastal luxury at 209 Willow in the heart of Anna Maria Island on a very sought out quiet street. This stunning canal-front home offers the perfect blend of relaxed island living and high-end amenities, just 10 houses from the pristine sugar-sand beaches of the Gulf while situated on a canal, you get the best of both worlds! Step inside to this 6 bedroom, 6 bathroom, 2 half bath, thoughtfully designed home. This home has never been a rental, it is very well taken care of. The interior has just about every feature you can think of, natural light, soaring ceiling, impact slider doors/windows, wet bar, very large wine cooler, whole house generator for peace of mind, a water filtration system/softener, and a pressure booster. Each bedroom is spacious and has its own private en-suite bathroom ensuring your family and guests have their own privacy. Current owners are using the 6th bedroom as an office, or you can turn it into a bedroom. Kids will love the fun built-in bunk bed room, while still plenty of space to play too. If desired, an upstairs closet has washer/dryer hookups if you wanted an additional set on upper level. Relax on the rooftop deck with breathtaking views or unwind on the lower deck complete with comfortable loungers. The highlight is the resort-style backyard: a heated pool and spa with a beautiful Shellcrete bar accented by shimmering sea glass. Includes a refrigerator and grill. A screened-in covered downstairs area provides shaded comfort, while boaters will appreciate the private dock and lift right on the canal—perfect for quick access to the Intracoastal and Gulf waters. The epoxy-finished 3-car garage adds durability and style to your storage space. Big outdoor shower so you can rinse off after the sandy beach. Located on a quiet canal yet incredibly convenient, this home sits in one of Anna Maria’s most desirable spots. Enjoy easy access to world-class beaches, charming island dining, and everything the Florida Gulf Coast has to offer. Whether you’re seeking a primary residence, a vacation retreat, or an exceptional investment property, 209 Willow Avenue delivers island elegance with every modern comfort.

209 Willow Avenue, Anna Maria

Courtesy of SATO REAL ESTATE INC.

$7,750,000
6 Beds ⋅ 6 Baths ⋅ A4686563 MLS
Virtually Staged. Under Construction. Under construction on an oversized corner lot along Anna Maria Island’s North End, just 50 feet from sugar-white sand beaches and the turquoise waters of the Gulf of Mexico, this three-level luxury coastal home combines scale, outdoor living, and modern new construction in one of the island’s most sought-after locations. Built with full concrete block construction and engineered to 2026 Florida hurricane standards, the residence is designed for durability, low-maintenance ownership, and peace of mind. What truly sets this approximately 4,345-square-foot residence apart is the way it lives outdoors. More than 3,000 square feet of covered outdoor living space transforms the property into a private resort designed for entertaining and everyday Florida beach living alike. A fully integrated outdoor kitchen anchors the backyard experience, complemented by three separate dining areas, multiple covered lounging spaces spanning approximately 1,582 square feet, and a 48’ x 25’ resort-style pool and spa that create a seamless indoor-outdoor lifestyle. A private volleyball court further elevates the property, creating a setting equally suited for quiet mornings, sunset gatherings, or hosting family and friends on Anna Maria Island. Daily living is thoughtfully centered on the main level above the six-car garage, where the primary suite, two guest bedrooms, den, laundry room, and an approximately 800-square-foot-plus combined kitchen and living area offer comfort and convenience. Wider doorways and a spacious full bath add flexibility for long-term livability, while a three-stop elevator services all floors. Designed for both entertaining and functionality, the kitchen features custom wood cabinetry, a wine cabinet display wall and a full Thermador appliance suite, including a 7-burner gas range, refrigerator, and dishwasher. Vaulted ceilings add volume throughout the open-concept living spaces, while upper levels capture natural light and Gulf views. All levels open onto expansive covered balconies, including a 1,200-square-foot upper balcony steps from the kitchen. Whether envisioned as a luxury vacation home, income-producing rental, or 1031 exchange opportunity, this property offers exceptional flexibility in one of Anna Maria Island’s most exclusive neighborhoods. Just moments from Pine Avenue, waterfront dining, boutique shopping, marinas, boating access, and some of Florida’s most beautiful beaches, this is a rare opportunity to own brand-new construction on Anna Maria Island at an impressive scale in one of the Gulf Coast’s most tightly held enclaves.

107 Tuna Street, Anna Maria

Courtesy of DOUGLAS ELLIMAN

$3,250,000
5 Beds ⋅ 4 Baths ⋅ A4683945 MLS
Exceptional island retreat located on beautiful Anna Maria Island, just one block from the beach and a short stroll to the charming shops and restaurants along Pine Avenue. This custom-built 2,000 sq. ft. home offers the perfect blend of coastal luxury and investment potential. Designed with an open-concept floor plan, the residence features 5 bedrooms, 3 1/2 baths, providing ample space for family and guests. The newly remodeled kitchen showcases high-end finishes and flows seamlessly into the main living areas, ideal for entertaining. Step outside to your private resort-style oasis featuring a luxury heated pool and spa with generous poolside seating, perfect for relaxing after a day at the beach. Additional highlights include a dedicated game room and a rooftop deck offering the perfect space to enjoy island sunsets and coastal breezes. Whether you are seeking a private second home or a strong income-producing investment property, this home delivers. With short term rentals allowed, a 12-person occupancy, and a proven rental history, it offers excellent income potential. Being sold turnkey, this island property is ready for immediate enjoyment or continued rental success.

117 Willow Avenue, Anna Maria

Courtesy of BEACH HOUSE REAL ESTATE LLC

$7,295,000
4 Beds ⋅ 6 Baths ⋅ A4680603 MLS
Homes of this architectural caliber are rarely offered for sale - and even more rarely as a fully curated estate. Every furnishing, antique, original artwork, lighting fixture, textile, and accessory has been thoughtfully selected specifically for this residence, including the linens and towels. Bespoke furnishings, fine antiques, original art, and an extraordinary collection of antique Persian rugs create a truly turnkey estate where architecture and interiors exist in perfect harmony. Nestled within the private enclave of Villa Rosa, this custom-built coastal property offers exceptional craftsmanship, privacy, and a lifestyle reserved for Anna Maria Island's finest properties. Inspired by timeless European architecture, the home showcases reclaimed wood beams, marble flooring, handcrafted millwork, and designer finishes throughout. At the heart of the home, the chef's kitchen features a statement Lacanche range, Sub-Zero refrigeration, custom cabinetry, and a large island designed for gathering and entertaining. Outdoor living is equally impressive, with a fully equipped Lynx kitchen, built-in pizza oven, covered lounge with a wood-burning fireplace, and multiple terraces for relaxation and entertaining. The rooftop observation terrace offers panoramic island views and breathtaking Gulf sunsets, while lush tropical landscaping surrounds a private heated and cooled pool, creating a secluded coastal retreat. Situated on a protected deep-water canal with direct, bridge-free access to Tampa Bay and the Gulf of Mexico, the property includes a private dock and 10,000-pound boat lift, making waterfront living effortless. Villa Rosa is among Anna Maria Island's most coveted residential communities, where rental restrictions help preserve a quiet neighborhood atmosphere. Just moments away are world-famous beaches, waterfront dining, boutique shopping along Pine Avenue, and the laid-back coastal lifestyle that defines the island. More than a waterfront home, this is a fully realized estate - an extraordinary blend of design, craftsmanship, and a curated collection offered as one exceptional property.

513 Villa Rosa Way, Anna Maria

Courtesy of COLDWELL BANKER REALTY

$5,450,000
4 Beds ⋅ 4 Baths ⋅ A4683902 MLS
Welcome to 103 Palm Avenue on Anna Maria Island, home to some of the best beaches in Florida. This exceptional beachfront property features not one, but two direct Gulf-front residences, offering a rare opportunity for multi-generational living, rental income, or a private coastal compound. The property includes 4 bedrooms and 4 bathrooms and was completely remodeled in 2020, with a brand-new roof installed in 2025. An elevator provides convenient access between levels, enhancing both comfort and accessibility. Enjoy breathtaking beach views, unforgettable sunsets, and the relaxed island lifestyle Anna Maria Island is known for. Ideally located close to shopping, dining, and local attractions, this is true beachfront living at its finest.

103 Palm Avenue, Anna Maria

Courtesy of COLDWELL BANKER REALTY

$2,299,900
4 Beds ⋅ 3 Baths ⋅ A4682522 MLS
END OF SUMMER SALE- GREAT PRICE for this Luxury Island Home on North End of Anna Maria Island - Direct Bay Views & Skyway Bridge Views - Pool - Excellent Rental Income - Being Sold Turnkey - Welcome to exceptional island living on the highly sought-after north end of Anna Maria Island, where homes like this rarely become available.This beautifully maintained turnkey 4-bedroom, 3-bathroom coastal residence offers stunning sunrise views over the bay, an unbeatable location just steps from Bayfront Park, and easy access to a sandy beach and calm waterfront waters. This property is now one of the Best Priced investment or vaction home opportunites on Anna Maria Island. Enjoy your own fenced-in tropical backyard retreat, featuring: Private swimming pool with in-pool umbrellas, Lush, mature landscaping, Outdoor lounging and entertaining areas, Seamless indoor-outdoor island living.This Anna Maria Island luxury home features a bright, open-concept floor plan designed for entertaining and relaxed coastal living: Spacious living and dining areas, Large chef-style kitchen ideal for gatherings, and Wrap-around porches on multiple levels for bay breezes and water views, including nightly views of the lite-up Skyway Bridge. Two upstairs bedrooms open directly to the expansive second-floor porch, offering panoramic bay views and unforgettable sunrise beach views over the Bay. The oversized primary suite includes a spa-inspired ensuite bathroom with: Dual vanities, Large private soaking tub, Walk-in shower, and Luxury finishes throughout This Premier Island Location provides access to Walk, Bike, or Golf Cart Everywhere. Perfectly positioned near: Boutique shops, cafes, and ice cream parlors, waterfront dining and local restaurants, and the historic charm of the north-end of the island. Just minutes from the iconic Anna Maria City Pier, and easily accessible to Gulf beaches by golf cart or bicycle, this location defines true Florida island lifestyle living. This property is also a high-performing opportunity for investors:, Daily rentals permitted, Strong short-term rental demand on Anna Maria Island, and Ideal for luxury vacation rental income or second home use. Whether you are searching for a luxury waterview home on Anna Maria Island, a high-income vacation rental property, or a private coastal retreat, this home delivers unmatched location, lifestyle, and value. Pack your bags and start living the Island Dream - Don't Worry - Bay Happy!

403 N Bay Boulevard, Anna Maria

Courtesy of WAGNER REALTY

$1,700,000
4 Beds ⋅ 2 Baths ⋅ TB8476324 MLS
BEAUTIFUL WATER VIEWS. This four-bedroom, two-bath stilt home with a two-car garage offers magnificent, expansive views of Tampa Bay from every level. Designed to capture the beauty of its surroundings, the home features impact-rated windows and sliding glass doors throughout, complemented by stylish plantation shutters. Tile floors flow throughout both living levels and bedrooms. The first level boasts a spacious living and dining room combination alongside an open kitchen complete with granite countertops, stainless steel appliances, wood cabinetry, and an island cooktop—perfect for entertaining. This level also includes a guest bedroom and a full bathroom with a walk-in shower. On the second level, the primary suite offers a large walk-in closet and an en suite bath with a walk-in shower. Two additional bedrooms are located down the hall, along with a convenient inside laundry closet housing the washer and dryer. Both guest bedrooms enjoy stunning blue water views of Tampa Bay. The true money shot awaits on the third-level rooftop deck, where panoramic views stretch all the way around Anna Maria —the perfect setting for sunrise coffee or sunset gatherings. The spacious backyard provides ample room for a pool, and with some updating, this property could truly shine and reach its full potential.

872 North Shore Drive, Anna Maria

Courtesy of RE/MAX ACTION FIRST OF FLORIDA

$1,700,000
3 Beds ⋅ 2 Baths ⋅ A4682093 MLS
Located just blocks from the beach, White Palms is a 3-bedroom, 2-bathroom island home situated on a large corner lot with a spacious backyard, offering excellent outdoor living close to the Gulf. The corner location provides added openness, while mature palms and established landscaping create a private coastal setting. The home features a bright, open layout designed for comfortable island living, with well-sized bedrooms and recently updated finishes throughout. The main living areas connect seamlessly to the outdoor spaces, making it ideal for both everyday living and entertaining. The backyard centers around a private pool, creating a true outdoor retreat with ample space for lounging and gathering. Whether used as a primary residence, second home, or seasonal escape, the layout offers flexibility and function. Located in Anna Maria's nightly vacation rental area, White Palms is an established rental property with documented income, offering immediate investment potential alongside its lifestyle appeal. Just a short walk to the sand, this property combines beach proximity, outdoor space, and proven rental performance in one well-located island home.

270 Gladiolus Street, Anna Maria

Courtesy of MICHAEL SAUNDERS & COMPANY

$4,500,000
A4670910 MLS
OVER A 1/2 ACRE ON THE BEACH... “Go the extra beach mile” and build on this cleared lot directly on the Bay at the tip of Bean Point ready for you to design the ultimate beach retreat, your new home! Morning coffee with the manatees, birds and dolphins and evening sunsets with the sandy beach within steps from your door. Loggerhead Turtles like to nest on the Island and you get a front row seat to this amazing event and then you get to watch and count the hatchlings as they swim away to return again in the future! Now is the time to plan for your new home on Anna Maria Island so you can walk to the future ROD & REEL Pier! Survey available 2/19/2016 Specific Purpose (fence) 25,200 SF Lot

831 North Shore Drive, Anna Maria

Courtesy of MIKE NORMAN REALTY INC.

$1,995,000
3 Beds ⋅ 3 Baths ⋅ A4679433 MLS
~~~~~ PRICE DROP ~~~~~ Come take a look at this amazing Anna Maria home ready for you and your family to come live in paradise. Villa Maria is ready for you! An amazing 3 bedroom, 2 bathroom and a half bath just 2.5 blocks away from some of the most coveted beaches in the country. This popular vacation rental is perfectly nestled in the city of Anna Maria. Walking distance, a bike ride or short golf cart ride to the beautiful beaches of the Gulf of Mexico where you can bask in the sunshine all day. Or take in one of the most amazing sunsets in the world. Villa Maria is also close to all the happenings on Pine Avenue. Take in the shopping and grab a bite at one of the delicious restaurants. Villa Maria has been beautifully remodeled with the upmost attention to detail and beauty. As soon as the home comes into view, you will feel its character and beach vibe. Walk through the carport, just past the outdoor ping pong table and you'll enter the home. With a clean bright fully equipped kitchen, a dining table that seats 6, and a cozy living room ready for family night. Along with an additional family so the kids can have all the space they need for fun. The beautiful primary bedroom and bathroom are up stairs and away from the all the action. You will feel as if you entered a spa and be able to escape and chill out whenever you need. The other two bedrooms are beautifully decorated and ready for the rest of the family and or friends. Enjoy dining in the sun soaked dining area inside or you can take the fresh catch outside to the outdoor dining area just off the incredible pool. With lush landscaping and the feel of privacy, you'll want to spend the day by the pool. Villa Maria is a very popular vacation rental and could be your ticket to Anna Maria Life. It’s beautiful, full of fun and close to it all.

307 Spring Avenue, Anna Maria

Courtesy of ANNA MARIA LIFE REAL ESTATE

$4,490,000
4 Beds ⋅ 5 Baths ⋅ A4677955 MLS
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.

50 N Shore Drive, Anna Maria

Courtesy of RE/MAX ALLIANCE GROUP

$3,895,000
4 Beds ⋅ 5 Baths ⋅ A4678140 MLS
LOCATION!!!! North Shore Drive, one of the most popular streets in Anna Maria! This is a gorgeous custom built home with panoramic views of the Bay. 4 bedroom, 4 and a half baths enjoy the spacious layout with high ceilings and views of the Bay from almost ever window! Enjoy the expansive balconies on each floor, looking out onto the beautiful water where you’ll see dolphins playing and jumping. At night, directly across the way you’ll see the Skyway Bridge light up with all different color lights. Elevator and 2 car garage with plenty of parking out front as well. The backyard will be where you spend all your time. Relax on the bay beach or hang in the heated pool and spa surrounded by lush landscaping and very private. Ideal location so close to Pine Ave, just a short stroll away. Schedule your private showing today!

870 N Shore Drive, Anna Maria

Courtesy of SATO REAL ESTATE INC.

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