Anna Maria Homes For Sale & Real Estate - 81 homes

Remarks: Positioned along the most sought-after stretch of Pine Avenue—known for its vibrant coastal charm, boutique shopping, dining, and steady pedestrian traffic, 418 Pine Avenue offers a truly rare opportunity to own a waterfront property with coveted ROR zoning. Properties like this are few and far between, especially those that combine direct water access with the ability to create both a luxury lifestyle and a dynamic income-producing asset in the heart of one of the island’s most iconic corridors. This elevated, solid concrete home features 4 bedrooms and 3 bathrooms, each bedroom offering spacious walk-in closets complete with custom closet systems. The open-concept floor plan is designed to maximize natural light and water views, seamlessly blending indoor and outdoor living. Step out onto the expansive main-level balcony or enjoy one of three additional balconies—two overlooking the water and two facing the lively energy of Pine Avenue. The ROR zoning creates exceptional flexibility for income potential. Envision renting the upper-level residence while activating the lower level as a waterfront-facing business such as a boutique retail shop, professional office, art gallery, wellness studio, café, or even a unique waterfront business concept like a paddleboard/kayak outfitter, dockside café, or marine-focused experience. The combination of visibility from Pine Avenue and direct water frontage is incredibly rare and valuable. Boating enthusiasts will appreciate having only one fixed bridge to open water, along with a private dock where marine life is frequently seen right in your backyard. The outdoor space is equally impressive, featuring a pool and ample room for entertaining, dining, and enjoying the Florida lifestyle year-round. Additional highlights include impact windows and doors throughout, plantation shutters, newer HVAC system, metal roof, and fresh interior paint. Whether you’re searching for a primary residence, a luxurious second home, or a high-performing investment with unmatched zoning advantages, this property delivers on every level. Being sold complete with professional design services to help you elevate and personalize the space.

Listing is courtesy of: KW SUNCOAST (941-792-2000)

Listing Agent: Stephanie Paxton (941-932-5509)

Remarks: 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!

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

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

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

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

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

Remarks: Unobstructed Gulf views define this true Gulf-front home on one of the most desirable stretches of Anna Maria Island. With nothing between the property and the shoreline, the balcony captures nearly three-quarters of a mile of uninterrupted beach frontage—an exceptionally rare vantage point created by the natural contour of the island to the north. Very few homes on AMI offer a view corridor this wide or this direct. Built in 2005 by Whitehead Construction, a respected builder in Manatee County, the home is well constructed and offers a layout well-suited for an immediate move-in or a next chapter renovation. The 4-bedroom, 5.5-bath design includes two Gulf-facing decks: one off the main living area and a private third-floor terrace exclusive to the primary suite. The location is one of the island’s best. Positioned at Coconut and Gulf, the home benefits from quieter traffic patterns while still offering walkable access to Pine Avenue’s coffee shops, restaurants, and boutiques. Sunset views are a nightly event, and beach access is just steps from the door. Additional features include a private pool, space for a covered outdoor kitchen, and a two-car garage with room for a golf cart and beach gear. At the time of construction, finishes were in the top tier for the island, and the home is now ready for a thoughtful update to match its premier location. Opportunities like 12106 Gulf are limited on Anna Maria Island. True Gulf-front ownership, a wide and unobstructed view corridor, and a location that delivers both privacy and walkability make this property stand out. Savvy buyers seeking the best views on the island will recognize the significance of this address.

Listing is courtesy of: REEL COASTAL PROPERTIES, LLC (941-265-3247)

Listing Agent: William Worth (214-707-6296)

Remarks: DIRECT BEACHFRONT - This residence generated nearly $500,000 in income for 2025!  Positioned on the pristine shores of the north end of Anna Maria Island, this extraordinary direct beachfront estate offers a rare opportunity to own a luxury coastal retreat while building lasting generational wealth through an exceptional income-producing opportunity. Offered turnkey furnished, this stunning residence seamlessly combines refined beachfront living with an impressive history of high-performing short-term rental revenue. Thoughtfully updated with numerous recent enhancements—including new upper-level sliding glass doors—this home is designed to maximize breathtaking panoramic views of Tampa Bay and the iconic Sunshine Skyway Bridge. Expansive walls of glass flood the open-concept living and dining spaces with natural light, while floor-to-ceiling sliders lead to a spacious waterfront balcony, creating the perfect setting for entertaining or simply enjoying the serenity of the Gulf Coast lifestyle. The gourmet kitchen is beautifully appointed with shaker-style cabinetry, quartz countertops, an oversized island with seating, and premium stainless-steel appliances, including a gas range. Each of the four spacious bedroom suites serves as a private retreat, complete with its own en-suite bath and private balcony surrounded by lush tropical scenery.  Additional upgrades include refreshed tropical landscaping with exterior lighting, new ground-level outdoor furnishings, and freshly painted interior and exterior spaces. The covered poolside lounge and dining area provides the ultimate waterfront experience, just steps from the sugar-sand beaches of Anna Maria Island. In the evenings, unwind as the illuminated Skyway Bridge creates a spectacular backdrop across the bay. Beyond its timeless coastal architecture and unmatched beachfront setting, this property presents a truly remarkable investment opportunity with a proven track record and substantial rental income. The residence generated nearly $500,000 in income for 2025, with $456,000 booked in 2024 and $464,000 in 2023. Future reservations for 2026--2027 are already in place, offering immediate continuity of revenue and long-term wealth-building potential. Comprehensive rental history and future booking details for 2025-2027 are available upon request.  A rare offering that blends luxury, lifestyle, and legacy investment potential—this is beachfront ownership at its finest.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)

Listing Agent: Hannah Hillyard (941-744-7358)

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: 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!

Listing is courtesy of: FRAN MAXON REAL ESTATE (941-778-2307)

Listing Agent: Stephanie Bell (941-920-5156)

Remarks: ~~~~~ 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.

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. BACKUP OFFERS BE ACCEPTED - Luxury Island Home on North End of Anna Maria Island - 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 waterfront 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!

Listing is courtesy of: WAGNER REALTY (941-383-5577)

Listing Agent: Ed Taaffe (636-346-6165)

Remarks: 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.

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

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

Remarks: Old Florida Charm – Income-Producing Property! Looking for a true Old Florida beach cottage experience with exceptional rental income? This elevated cottage on Anna Maria’s sought-after North End is just steps from the Gulf—no car needed! This fully managed, hands-off rental allows nightly stays, with all future bookings conveying for seamless income. This turnkey-furnished home blends coastal charm with modern updates, featuring a newer kitchen with Quartz counters, custom cabinetry, and new appliances, flooring and a spacious private deck. The primary suite offers a walk-in closet and updated ensuite bath, while the second bath includes double sinks and a jacuzzi tub. Located in a boutique resort with a private pool, picnic areas, and complimentary bikes, beach gear, and water toys, guests return year after year. Walk to Pine Ave’s shops or hop on the free trolley to explore the island. With pet-friendly ownership and a 6-month owner occupancy option, this turnkey investment is perfect for personal getaways and immediate passive income. Don’t miss this rare opportunity—schedule your showing today! Please note- the HOA Adjusts based on monthly income.

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

Listing Agent: Jessica Batten (941-962-3380)

Remarks: 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.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)

Listing Agent: Dee Munn (407-346-4422)

Remarks: 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!

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

Listing Agent: Kasay Gunter (941-807-1280)

Remarks: 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.

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

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

Remarks: Dreaming of Island Living? This custom-built coastal home perfectly captures the essence of luxury island living on beautiful Anna Maria Island. This exceptional six-bedrooms, six-and-a-half-baths residence spans over 3,100 square feet and was thoughtfully designed with no expense spared or detail overlooked. The open concept living & dining space includes a chef inspired kitchen which boasts solid wood cabinetry, quartz countertops, and upgraded appliances. Each serene bedroom is its own private retreat, complete with ensuite baths, custom tilework, and spa-like features. Made for entertaining with expansive spaces to enjoy RELAXING inside OR out. Your private resort style backyard is a true sanctuary with a sparkling oversized heated pool and spa surrounded by lush landscaping and durable low maintenance turf with putt-putt golf. A covered lanai and multiple balconies provide inviting spaces for relaxing, dining, and family fun. Whether you’re soaking up the sun poolside or enjoying the sunrise from the Bay AND sunset views from the Gulf from the rooftop deck, the outdoor living experience is unmatched. This coastal beauty will come completely Designer Turn-Key Furnished with upscale coastal finishes throughout. CURRENTLY A RENTAL PROPERTY WITH FORWARD BOOKINGS IN PLACE!!! This home is perfect for a full-time residence, vacation home or investment property and is ideally located on the North End of Anna Maria Island. Stroll one street over to beloved Pine Avenue and browse through the numerous shops and restaurants. The Bay and famous "almost rebuilt" Anna Maria City Pier are at the end of the street. AND the island's world-renowned Gulf beaches are a few blocks away. Hop on your bikes or golf cart to experience Anna Maria's full charm. Your ISLAND DREAM HOME AWAITS!

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-778-7777)

Listing Agent: Sabrina Ullmann (203-300-8181)

Remarks: Grandfathered to accommodate up to 12 guests—a rare and increasingly valuable advantage on Anna Maria Island—505 S Bay Boulevard offers an exceptional opportunity for investors seeking one of the island's highest-performing vacation rental properties. Unlike many homes subject to today's stricter occupancy regulations, this property retains its coveted higher occupancy allowance, creating significantly greater rental flexibility and income potential. The results speak for themselves: the property has already generated more than $163,000 in gross rental income by the end of June and is currently projected to exceed $210,000 in gross rental revenue by year-end, making this an incredible opportunity to own a luxury waterfront home with proven, substantial income-producing performance. Let the island breeze guide you home to 505 S Bay Boulevard, a waterfront haven where the world slows down and coastal living feels like poetry. Tucked along the tranquil north end of Anna Maria Island, this elevated five-bedroom, five-bath home invites you to experience a lifestyle wrapped in beauty, comfort, and pure island magic. Step inside and discover more than 3,200 square feet of thoughtfully designed living space, filled with natural light and framed by sweeping water views. The open-concept floor plan flows seamlessly, anchored by a gourmet kitchen featuring dual islands, high-end finishes, and a gas cooktop—perfect for everyday living and effortless entertaining. Multiple ensuite bedrooms, a versatile top-floor loft, and separate living areas provide privacy and flexibility for family, guests, or long-term stays. Four balconies extend the indoor living spaces outdoors, offering uninterrupted views of spectacular sunrises over the bay and peaceful evenings overlooking the water. Luxury amenities continue throughout the property, including a heated saltwater pool, private boat dock and lift on the canal, an eco-friendly rainwater cistern system, two tankless water heaters, an R38-rated metal roof with spray-foam insulated walls for exceptional energy efficiency, and a transferable 25-year termite warranty for added peace of mind. For boating enthusiasts, the home's 32 feet of saltwater canal frontage, deeded boat slip, and private lift provide direct access to the Intracoastal Waterway and the Gulf of Mexico. Durable coastal construction, impact-resistant features, and low-maintenance materials ensure lasting value while embracing the waterfront lifestyle. Beyond the home, Anna Maria Island offers one of Florida's most celebrated coastal experiences. A short stroll or bike ride leads to the charming boutiques, cafés, and galleries along Pine Avenue, while world-famous sugar-sand beaches and crystal-clear Gulf waters provide endless opportunities for boating, paddleboarding, fishing, shelling, and unforgettable sunsets. At 505 S Bay Boulevard, you're not simply purchasing a luxury waterfront residence—you're acquiring one of Anna Maria Island's rare investment opportunities, combining grandfathered high occupancy, exceptional proven rental performance, premier boating access, and the timeless island lifestyle that continues to make this one of Florida's most sought-after coastal destinations.

Listing is courtesy of: KELLER WILLIAMS SOUTH TAMPA (813-875-3700)

Listing Agent: Brenda Wade (813-655-5333)

Remarks: 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.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)

Listing Agent: Dee Munn (407-346-4422)

Remarks: 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, an 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!

Listing is courtesy of: RIDER REAL ESTATE (404-368-8072)

Listing Agent: William Gryboski (404-368-8072)

Remarks: 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.

Listing is courtesy of: O'STEEN GROUP INC (941-527-4227)

Listing Agent: Clay Osteen (941-704-7038)

Remarks: Under contract-accepting backup offers. Under Construction. Welcome to your dream home in the heart of Anna Maria. Currently under construction and thoughtfully designed for elevated island living, this exceptional coastal retreat offers 4 spacious bedrooms, 4 full bathrooms, and a powder bath, blending sophisticated design with modern comfort. One of the home's most captivating features is the expansive rooftop deck, where breathtaking island views, stunning sunsets, and refreshing Gulf breezes create the perfect setting for entertaining or simply unwinding at the end of the day. Designed for effortless enjoyment, the residence will be offered fully furnished, including elegant décor and curated artwork by Inside Eye Design, allowing you to move right in and begin enjoying the Anna Maria lifestyle from day one. Step outside to your private tropical oasis, featuring a sparkling resort-style pool surrounded by lush landscaping that provides both privacy and tranquility. Whether hosting family and friends or enjoying a quiet afternoon in the sun, the outdoor living spaces are designed to embrace the best of Florida living. This is a rare opportunity to own a brand-new luxury home in one of Anna Maria's most sought-after locations. Move in, relax, and start living the beach life you've always imagined at 764 Jacaranda Road.

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

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