Homes For Sale in Anna Maria 34216 - 87 homes

Remarks: Under contract-accepting backup offers. A rare expression of modern island luxury, this newly constructed Polynesian-inspired estate is ideally positioned on South Bay Boulevard in Anna Maria, offering privacy, architectural distinction, and sweeping bay views. Thoughtfully designed around a private, lush interior courtyard, the home centers on a resort-style pool and spa that seamlessly connect to covered outdoor living areas, creating a true indoor-outdoor lifestyle. The residence offers 5 bedrooms, 6 bathrooms, and expansive living spaces defined by clean architectural lines, warm wood accents, and walls of glass that frame tranquil water and tropical landscape views. The open main living level is ideal for entertaining at scale, anchored by a chef’s kitchen featuring custom cabinetry, a full walk-in pantry, and an oversized island, complemented by generous dining and gathering spaces that open directly to the pool courtyard. The primary suite is a private retreat, offering a custom-designed walk-in closet with a dedicated laundry area and a spa-inspired bath with a soaking tub positioned before picture windows overlooking the bay. A dramatic indoor-outdoor shower further enhances the immersive waterfront experience. Outdoor living is elevated with multiple covered terraces, a tranquil spa beneath a living green ceiling, and an expansive rooftop deck showcasing panoramic water views—perfect for sunset enjoyment and evening entertaining. Additional highlights include an elevator servicing all levels, premium finishes throughout, and thoughtfully designed spaces that balance luxury with everyday livability. Located just moments from Anna Maria’s renowned beaches, dining, and shopping, this exceptional residence presents a rare opportunity to own a newly built architectural masterpiece on the bay.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Charles Buky (941-228-6086)

Remarks: Under contract-accepting backup offers. Experience the perfect blend of modern luxury and coastal functionality in this impeccably maintained canal-front retreat. Located on the prestigious North End of Anna Maria Island, this property offers the best of both worlds: a serene, full-time sanctuary or a high-performing investment (7 nights or less). Originally transformed by a total remodel and significant additions in 2016, this elevated 3-bedroom, 2-bathroom residence offers a sophisticated island lifestyle on an expansive, oversized lot of over 10,000 square feet. The home is thoughtfully designed for both comfort and accessibility, featuring a private elevator that services the residence with ease. The interior transitions seamlessly from open-concept living areas to a unique ground-level bonus room. This versatile space is fully climate-controlled with its own bathroom, making it an ideal candidate for a private guest suite, a secluded home office, or a premier media/game room. Outside, the property is a true maritime sanctuary. Boaters will appreciate the 10,000 lb boat lift and the peace of mind provided by a newer seawall - all installed in 2012. The outdoor possibilities are as vast as the lot itself; with ample room to install a custom pool and outdoor kitchen, you can create the ultimate backyard oasis. Whether you are enjoying the breeze from the elevated decks or embarking on a sunset cruise from your backyard, 807 S Bay Blvd represents a rare opportunity to own a waterfront home built for the modern Floridian lifestyle - a true boater’s sanctuary!

Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)

Listing Agent: Lindsey Strickland (941-737-3491)

Remarks: Delightful waterfront home on the famed North end of Anna Maria Island. This 2 bedroom 2 bathroom home offers incredible opportunities for adventure. Whether it is the sand of the Gulf beaches you seek or if enjoying the water from a boat, kayak, or paddle board is your thing the choice is yours. Another incredible benefit of this location is the proximity to Pine Ave, full of fun shopping and eateries. Generously sized lot is positioned on a cul-de-sac providing privacy due to no through traffic. Concrete block paired with a metal roof creates a formidable structure. As you enter the home you will be welcomed by a sense of coziness. The kitchen features solid wood cabinetry and exquisite Taj Mahal quartzite countertops. Entertaining is aided by the in-ceiling home speaker system. Enjoy year around serene water views from the 300 square foot screened-in lanai equipped with four ceiling fans. Single car garage for all your storage needs or get creative for a possible third bedroom. The large lot leaves ample room for a pool to the front of the house. Schedule a showing today and discover if this piece of paradise if right for you.

Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)

Listing Agent: Justin Powell (941-718-0294)

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)

Remarks: Step into unparalleled luxury with this fully furnished, 6-bedroom, 7-bathroom deep-water canal-front estate, perfectly situated just two blocks from the pristine sands of Anna Maria Island. This isn’t just a home, it’s a statement, and a legacy investment all in one extraordinary package. Crafted with full concrete block construction, this residence is engineered for strength, security, and longevity, featuring hurricane impact-rated windows and doors and a Cat 5-rated roof. Every detail has been designed to provide absolute peace of mind, whether you’re seeking a lavish year-round retreat or a premium income-generating property. Inside, the home is a masterclass in modern coastal elegance. Soaring ceilings, expansive walls of glass, and curated designer lighting flood the interiors with natural light, creating an atmosphere of serene sophistication. The gourmet chef’s kitchen is a showpiece, boasting custom cabinetry, dramatic quartz countertops, a sculptural concrete range hood, a full Sub-Zero appliance suite, and a hidden walk-in Butler’s pantry, blending beauty with function flawlessly. Every space has been thoughtfully curated from the open-concept living and dining areas to multiple covered balconies and loggias that embody effortless indoor-outdoor living. The primary suite is a sanctuary, complete with a spa-inspired bathroom, walk-in closet, and private balcony overlooking the sparkling water. The rooftop deck is an entertainer’s dream and a private retreat all in one. Designed for gatherings under the stars or quiet moments of reflection, this oversized outdoor space offers panoramic views of the canal, the island, and golden Gulf sunsets, with multiple seating and lounge areas for ultimate comfort and luxury. Step outside to your private tropical oasis. The backyard features a resort-style pool and spa, lush palms, and generous lounging areas, all framing a deep-water canal with direct, bridge-free access to the Gulf of Mexico, making it perfect for boating enthusiasts. Offered fully turnkey furnished, professionally designed with luxury pieces throughout, this home allows immediate enjoyment or a high-end rental income stream. With demand for premium Anna Maria Island vacation homes at an all-time high, this property offers both an unmatched lifestyle and an exceptional investment opportunity. Words and photos only hint at the experience. To truly appreciate the craftsmanship, scale, and sheer beauty, a private tour is essential. Don’t miss your chance to claim this crown jewel of Anna Maria Island. Schedule your exclusive showing today.

Listing is courtesy of: AMI REALTY GROUP (941-794-0204)

Listing Agent: George Desear (941-725-7163)

Remarks: Under contract-accepting backup offers. Great Income Opportunity! Short-Term Rental approved on Airbnb, VRBO, etc! Over $174,000 in Yearly Rental Income with upside! Wake up every day in true island paradise at Anna Maria Chateau! Ideally positioned at the northern tip of the exclusive Anna Maria Island, just moments from the iconic Bean Point and minutes from some of the world’s most celebrated beaches, this pristine coastal retreat offers the ultimate blend of luxury, comfort, and location. From the moment you step inside, you’re welcomed by soaring ceilings and a bright, open great room floor plan designed for effortless entertaining and relaxed island living. Exceptional custom craftsmanship shines throughout, showcasing hand-scraped hickory wood floors, beautiful tongue-and-groove ceilings and walls, and thoughtful architectural details at every turn. The heart of the home is the chef-inspired kitchen, perfectly situated off the family room and equipped with stainless steel appliances, a French-style refrigerator, classic white shaker cabinetry, granite countertops, and a spacious island with breakfast bar seating ideal for gathering with family and friends. The spacious primary suite serves as a private retreat, featuring an en-suite bath with dual sinks and granite countertops. Two additional well-appointed bedrooms share a full bath, providing comfortable accommodations for guests and plenty of space for everyone to unwind. Multiple common areas throughout the home invite relaxation and connection. Step outside and experience resort-style living. Sip your morning coffee on the oversized upstairs deck, take a refreshing dip in the heated saltwater pool, or enjoy friendly competition in the expansive recreation room. The elevated first floor offers ample storage for all your water toys, bikes, and beach gear. This exceptional property offers incredible versatility perfect as a full-time residence, a private island getaway, or a highly desirable income-producing rental in one of Florida’s most sought-after destinations. Bonus: This elevated home experienced NO interior damage during the 2024 storms, providing added peace of mind. Recent updates include: brand-new water heater (2025) and new pool pump (2024). Love the island’s golf-cart-friendly lifestyle? There’s plenty of space for golf cart parking and more. Cruise by golf cart, bike, or take a leisurely walk to nearby restaurants, boutiques, and local favorites, all just blocks from your doorstep. This is your opportunity to own a true slice of paradise on one of Florida’s most beloved islands—Anna Maria Island.

Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)

Listing Agent: Mark Fazzini (727-485-9981)

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.

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)

Listing Agent: Christy Travis (941-545-5284)

Remarks: Under contract-accepting backup offers. Discover Mia Bella — a rare canal-front estate on Anna Maria Island’s coveted North End. Set on an oversized 11,000+ square-foot lot with more than 94 feet of boatable canal frontage, this exceptional property offers direct boating access to the Intracoastal Waterway, Tampa Bay, and the Gulf of Mexico, along with a private dock. Located on a quiet residential street just steps from the sandy beaches and two blocks from Pine Avenue’s shops and dining, Mia Bella delivers the ultimate island lifestyle where location truly matters. Completely restored and thoughtfully updated, this distinctive property blends Old Florida charm with modern coastal design. The estate includes a spacious single-level main house and an attached glass-wrapped villa, both positioned to capture tranquil canal and pool views framed by mangroves and passing boats. The main residence offers three bedrooms and three full bathrooms, including two ensuite suites, along with an oversized two-car garage — a rare and highly sought-after feature for an island home with plenty of space for a golf cart. Restored terrazzo floors create a light, breezy coastal feel throughout. The brand-new kitchen features classic white shaker-style cabinetry, quartz countertops, and stainless steel appliances and opens to the main living areas designed for easy indoor–outdoor flow. Hurricane-impact doors, windows, and sliders are installed throughout the main house, which is fully flood-protected with Hammerhead flood barriers and also features a new metal roof for added durability. All bathrooms have been fully updated with fiberglass showers, quartz vanity tops, and Kohler fixtures. The attached villa is a true showpiece, surrounded on three sides by floor-to-ceiling glass and highlighted by a dramatic lofted ceiling. The ground level includes a sleeping area, kitchenette, two-story living space, and a full bath, while a spiral staircase leads to a charming second-floor loft bedroom (access is outside via the 2nd floor deck) — a fun and flexible retreat for guests. Mature tropical landscaping and professional lighting provide privacy and ambiance throughout the property, creating a serene island setting. Mia Bella offers additional protection with Hammerhead flood barriers at the front entry, both garage doors, and the back sliding door. Recent improvements include impact-rated openings, new kitchen cabinets, bathroom vanities, a boat dock, redesigned decks, a resurfaced pool, new pool equipment, and a new metal roof. The list goes on and on. Offered fully furnished and operating as a successful vacation rental with strong income history and future bookings in place, Mia Bella is ideal as a luxurious second home or a high-performing investment. Oversized lot, premier North End location, boatable canal frontage with dock access, rare oversized garage, and thoughtfully designed storm and flood protection for the main house make this a truly special Anna Maria Island property. *Property information deemed reliable but not guaranteed. Buyer and Buyers agent to verify.

Listing is courtesy of: SALTY MERMAID REAL ESTATE LLC (941-224-3304)

Listing Agent: Liz Blandford (941-224-3304)

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)

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)

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)

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!

Listing is courtesy of: ANNA MARIA LIFE REAL ESTATE (941-567-6253)

Listing Agent: Billi Gartman (941-545-8877)

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)

Remarks: Welcome to your dream getaway on Anna Maria Island! THIS HOME HAS A BRAND NEW ROOF! Nestled in a prime location midway between the enchanting Tampa Bay and the pristine Gulf of Mexico waters, this meticulously maintained home offers the perfect blend of convenience and relaxation. Unbeatable location that allows you to stroll effortlessly to Anna Maria's hotspots, from Ginny's to the iconic Sandbar, Two Scoops, the charming Donut Shop, and a plethora of other shops and restaurants. The local trolley system, easily accessible, lets you explore the entire seven-mile-long island with ease. This thoughtfully designed home boasts three bedrooms for guests, two well-appointed bathrooms, and a spacious open living, dining, and kitchen area with a cathedral ceiling. The kitchen is a chef's delight, featuring updated cabinets and granite countertops and a center island with breakfast bar. An indoor laundry room adds valuable convenience, a highly desirable feature for both guest and owners. After a day of sun-soaked adventures, return to your private tropical oasis and indulge in a refreshing dip in the generously sized heated pool and spa. The sprawling backyard provides the ideal setting for relaxation and unwinding. Offered turnkey furnished, this home is not only a delightful retreat but also a savvy investment opportunity. With a proven track record of income generation and repeat bookings in place, it's a seamless transition into the vibrant vacation rental market. The location offers exceptional accessibility, with easy drives to Tampa, Sarasota and multiple airports, making travel convenient for both weekend visitors and longer stays. Nearby shopping, dining and entertainment options further enhance the appeal. Pack your bathing suits and immerse yourself in the laid-back luxury of Anna Maria Island – your slice of paradise awaits!

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)

Listing Agent: Christy Travis (941-545-5284)

Remarks: Incredible, spacious home with a private heated pool - close to the beach!! This 3 bedroom, 2.5 bathroom elevated home is located in a desirable area of Anna Maria Island, you're only a one-and-a-half-block walk from Bean Point Beach to the north and a short distance to Pine Avenue's shops and restaurants to the south. Colorful, fun lighting and art throughout gives it that beachy feel. Enjoy so many great features like high wooden ceilings, large windows, natural light, and a wrap-around screened balcony. The balcony overlooks the private heated pool and outdoor dining area below. Inside, use the kitchen's stainless steel appliances and granite countertops to whip up a delicious meal. Schedule a showing today!

Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)

Listing Agent: Jason Sato (941-778-7200)

Remarks: 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.

Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)

Listing Agent: Jason Sato (941-778-7200)

Remarks: 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!

Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)

Listing Agent: Jason Sato (941-778-7200)

Remarks: Under Construction. Luxury residence coming soon in the heart of Anna Maria! This 4 bedroom, 4.5 bathroom + den home is just a short stroll to the sparkling Gulf waters and situated on a lagoon. The main floor has high ceilings and natural light with an open concept living area. With multiple spacious balconies and a rooftop deck, you have many choices to relax, dine and enjoy the outdoors. The views from the rooftop deck are stunning! The kitchen, a chef’s dream with high-end appliances. Additional features include custom cabinetry, quartz counters, elevator that goes to all levels, impact windows and doors and so much more. 3 car garage for plenty of parking space and beach toys. The backyard oasis has living and dining areas, heated pool and spa, perfect for entertaining. It's perfect for year-round living, an island getaway or vacation rental as 1-7 day rentals are permitted. Located on the North End of Anna Maria Island, you are just a short walk to all the boutiques and dining on and off Pine Avenue.

Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)

Listing Agent: Jason Sato (941-778-7200)

Remarks: Charming coastal retreat located at 165 Crescent Dr in the heart of Anna Maria! This beautifully maintained 3-bedroom, 2-bath home offers the perfect blend of comfort and island living. Featuring a private pool and spa, this property is ideal for relaxing or entertaining guests. The outdoor space is a true highlight, complete with a built-in grill and outdoor shower—perfect after a day at the beach. Currently operating as a successful vacation rental, this home presents an excellent investment opportunity or a personal getaway. Inside, the home offers a bright and inviting layout with plenty of natural light and a functional floor plan. Whether you're looking for a turnkey rental property or your own slice of paradise, this home delivers. Just a short distance to the beach, local shops, and dining, this property captures the essence of Anna Maria Island living. Don’t miss this opportunity to own a piece of paradise!

Listing is courtesy of: ISLAND REAL ESTATE-ANNA MARIA (941-778-6066)

Listing Agent: Ryan Sheck (863-581-4005)

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

Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)

Listing Agent: Joey Hutchinson (941-518-5585)