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866 N Shore Drive, Anna Maria
$1,750,000
4 Beds ⋅ 4 Baths ⋅ Anna Maria Beach SubDv.
Don't miss your chance to own a fully remodeled home in the City of Anna Maria. Extensively remodeled 4-bedroom, 4-bath home on North Shore Drive in the City of Anna Maria, featuring significant structural and finish upgrades throughout. This light-filled residence offers an open-concept layout with raised ceilings, refined coastal finishes, and expanded living space. Two bedrooms feature private en-suite bathrooms, with an additional two full guest bath conveniently accessible from the bedrooms and main living areas. Renovations include enclosed patio and garage areas to create an additional en-suite bedroom, expanded kitchen, dedicated laundry room, and approximately 294 square feet of added living space. Major improvements include new electrical and plumbing services; new drywall with DensGlass moisture-resistant panel; a new HVAC system with supplemental mini-split units; spray foam roof insulation; hurricane-impact windows and sliders; and new flooring throughout. The kitchen features all-new cabinetry, countertops, a large center island with breakfast bar, and Samsung appliances including: refrigerator, ice maker, wine cooler, microwave, dishwasher, and chilling drawers. Bathrooms have been fully updated with new tile and high-end plumbing fixtures. Outdoor upgrades include a private heated pool with new heater and pump, expanded paver decking, new fencing, updated landscaping, refreshed exterior stucco, and full interior and exterior paint. Ideally located just steps from the beach and close to Pine Avenue shops and dining, this is a move-in-ready island home offering modern upgrades, thoughtful design, and an unbeatable location—schedule your private showing and experience Anna Maria Island living at its best.

866 N Shore Drive, Anna Maria

771 Jacaranda Road, Anna Maria
$1,675,000
3 Beds ⋅ 2 Baths ⋅ Shore Acres Second Add SubDv.
An easy 5-minute walk to the Gulf on the coveted north end of Anna Maria Island, Limelight is a fully furnished, nightly-rental-friendly pool home offering privacy, charm, and exceptional island value. Located just a few short blocks from direct beach access, this 3-bedroom, 2-bath single-family residence is ideal as a second home, full-time residence, or income-producing investment. Inside, vaulted white wood-plank ceilings, custom millwork, and rich wood flooring create a bright, welcoming coastal atmosphere throughout the open living and dining spaces. The kitchen flows seamlessly into the main living area and features stainless steel appliances, granite countertops, a custom tile backsplash, breakfast bar seating, and a reverse osmosis drinking water system. The primary suite offers a walk-in closet and en-suite bath with a walk-in shower, while guest bedrooms feature crown molding, custom wood trim, and warm wood floors — a timeless north-end aesthetic buyers seek. Outdoor living is where Limelight truly shines. A heated freeform pool is surrounded by lush tropical landscaping for complete privacy, complemented by a covered patio, outdoor shower, and an expansive open-air ground-level living area perfect for lounging, dining, or creating a poolside bar. Electric roll-down screens and hurricane shutters allow for year-round enjoyment. Notable upgrades include a new roof 2024, impact-rated doors and windows, 2-car tandem garage with impact door, interior laundry with storage, tankless hot water heater, app-controlled HVAC with AirKnight air purification, water softener with chlorine removal, 2020 stair and railing updates, and a new 2024 TV in the cabana area. Nightly rentals are permitted, and 2025 rental history reflects just under $100,000 in gross income, despite downtime related to hurricane impacts and owner use, highlighting strong income potential alongside personal enjoyment. The home is offered fully furnished and move-in ready, making this a rare opportunity to own a private pool home within walking distance of the beach on the north end of Anna Maria Island.

771 Jacaranda Road, Anna Maria

213 Oak Avenue, Anna Maria
$3,100,000
4 Beds ⋅ 4 Baths ⋅ Laguna Maria SubDv.
Experience Florida coastal living at its finest in this exceptional custom-built home featured in Southern Living Magazine. Uniquely located, this house is a short walk to white sand beaches and a short cruise to the Bay and Gulf. This classic Key West styled beauty was renovated and enlarged four years ago. The lush front yard features a circular paver driveway, a gorgeous Royal Poinciana tree, an assortment of local palms and a majestic Canary Island Date Palm. The front walkway is cut from limestone slabs, replicating ocean coral. Featuring 4 bedrooms and 4 bathrooms this thoughtfully designed residence offers an open floor plan filled with abundant natural light creating a bright and welcoming atmosphere throughout with quality craftsmanship and timeless coastal style. Two screened porches and a backyard deck invite indoor-outdoor living. Inside the open floor plan features a bright spacious great room highlighted by a two-story vaulted cathedral ceiling. A stylish granite-mantled fireplace with mermaid statues beautifies this unique space. The adjoining dining room and kitchen offer granite countertops, stainless steel appliances and customized cabinets. The main suite’s spacious bedroom has well-appointed custom-built nightstands, bookshelves, and a glass and mirrored-shelved head board. There is a walk-in closet and French doors leading to the back deck with canal views. The ensuite tiled bathroom has a spa-like feel with an electric toilet, separate dual sinks, granite countertops and a combined walk-in shower and steam room. Another main floor suite has a tiled bathroom, a sit-down, walk-in Jacuzzi-styled tub, an electric toilet and granite counter top. The upstairs bedroom extends the length on the second floor with a tiled bathroom, a bathtub and shower. The backyard is a tropical oasis complete with a Tiki Hut, a midnight- blue-bottomed resort- style pool trimmed with natural stone, a waterfall, a bronze dolphin fountain, a hot tub, an enclosed hot-water outdoor shower, and old growth Coconut, King, Sable, Bismark, Foxtail, and Christmas palm and giant bird-of-paradise trees. Situated on the canal is a forty-seven foot wooden dock and boat lift, allowing direct water access via Bimini Bay and Anna Maria Sound to open waters and endless water adventures. A spacious multi-car garage provides plenty of room for stowing bikes, golf carts, and beach gear. Just a short stroll to the sugar-white sand beaches, this picturesque property is perfectly located to enjoy the beach, the bays and Gulf waters.

213 Oak Avenue, Anna Maria

807 S Bay Boulevard, Anna Maria
$2,250,000
3 Beds ⋅ 2 Baths ⋅ Bay Harbor Subdivision SubDv.
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!

807 S Bay Boulevard, Anna Maria

416 Magnolia Avenue, Anna Maria
$950,000
2 Beds ⋅ 1 Baths ⋅ Anna Maria Beach SubDv.
Located in the highly desirable Anna Maria zip code, this original 1979 two-bedroom, one-bath elevated home sits on a full, enclosed garage foundation and is positioned on an exceptionally large lot. The home is move-in ready while offering the opportunity for significant updates or customization. For buyers seeking an affordable, cost-effective structure that already meets flood elevation requirements, this property is an excellent option. With a generous 141-foot-deep lot, there is ample space to add a pool or create additional outdoor living features. Opportunities like this are becoming increasingly rare in Anna Maria—smaller homes that with a lower purchase costs, reduced taxes, insurance, and maintenance. Whether you choose to renovate the existing residence or take advantage of the expansive lot to build your dream home, this property provides multiple paths to achieve your vision.

416 Magnolia Avenue, Anna Maria

527 Magnolia Avenue, Anna Maria
$1,925,000
3 Beds ⋅ 2 Baths ⋅ Lardas Unit Three SubDv.
Tucked away along a tranquil canal in the heart of Anna Maria, this exceptional 3-bedroom, 2-bathroom waterfront retreat offers the perfect blend of coastal elegance and island convenience. Being sold turnkey with a strong rental history and bookings in place, this property is an ideal investment opportunity or full-time residence. Designed for effortless indoor-outdoor living, the spacious 1,900+ square foot interior features an open-concept layout, a fully equipped kitchen, and inviting living spaces filled with natural light. The primary suite provides a private escape with an ensuite bath, while the additional bedrooms offer plenty of space for family and guests. Step outside to your personal oasis, where a heated pool overlooks the tranquil canal, and a private dock provides easy access to Tampa Bay and the Gulf—perfect for boaters and water enthusiasts alike. A two-car garage offers ample storage for beach gear and golf carts, while the property’s zoning allows for rentals of any duration, maximizing its income potential. Just moments from white sandy beaches, Pine Avenue’s charming boutiques, and renowned dining, this is a wonderful opportunity to own a perfect little slice of island life!

527 Magnolia Avenue, Anna Maria

612 Fern Street, Anna Maria
$1,732,500
3 Beds ⋅ 2 Baths ⋅ Shore Acres SubDv.
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.

612 Fern Street, Anna Maria

903 N Shore Drive Unit B, Anna Maria
$5,500,000
4 Beds ⋅ 5 Baths ⋅ Shore Acres SubDv.
Welcome to this stunning show stopping property on the North End of Anna Maria Island very well known as Beachfront Bliss. Enjoying panoramic views of the bay will captivate you while also having your own private beach! This 4 bedroom, 4.5 bathroom home is one of the highest producing rental properties on the north end of the island. The rental income on this property is outstanding with 2026 having $455,251 on the books thus far! The location doesn't get any better as it’s located directly on the bay, steps from Bean Point and a short stroll to the heart of Anna Maria, Pine Ave where all the boutiques and restaurants are. Unwind in the open living space, where an abundance of natural light and breathtaking views creates a tranquil atmosphere. Enjoy viewing dolphins and manatees from the plush furniture without even leaving the home! The primary bedroom has a private balcony to capture the picturesque sunrises and breathtaking views of the illuminated Sunshine Skyway Bridge colors at Night. While the additional three bedrooms has its own ensuite bathroom and walk-in closet, ensuring a comfortable and private retreat. Kids (and adults!) LOVE the game room featuring classic video games to family board games and puzzles, the game room is the perfect spot for lively entertainment. Golden Tee Golf and a variety of classic games provide hours of enjoyment for the whole family. Step outside into an expansive outdoor space designed for leisure and recreation. Lounge on the sandy beach, take a dip in the heated pool or oversized hot tub, or play a round on the putting green. The outdoor living area features a wet bar and a large Weber Genesis gas grill, perfect for alfresco dining. Enjoy the tropical oasis with outdoor Sonos speakers, an aquarium selfie wall, and various beach gear and toys. Large 2 car garage and an elevator for convenience. Being its first time on the market, this opportunity to own this unique piece of property won’t last long!

903 N Shore Drive Unit B, Anna Maria

116 Hammock Road, Anna Maria
$2,200,000
4 Beds ⋅ 4 Baths ⋅ Island Cedars SubDv.
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.

116 Hammock Road, Anna Maria

108 Magnolia Avenue, Anna Maria
$3,830,000
4 Beds ⋅ 4 Baths ⋅ Anna Maria Beach SubDv.
Welcome to your dream coastal retreat at 108 Magnolia Ave on the north end of Anna Maria! This stunning 4 bedroom, 4 bathroom home is just three houses away from the pristine Gulf of Mexico beach, offering the perfect blend of luxury and island living. Located on a sought after street, west of gulf drive and being one of the unique VERY deep lots is one of the many reasons why you don’t want to pass up this opportunity! Step inside to discover high-end finishes throughout, showcasing impeccable craftsmanship and style. The open-concept living spaces flow seamlessly for an indoor/outdoor living and entertaining experience. The kitchen has a large island, 2 sinks, high end stainless steel appliances including thermador 6 burner stove. Additionally, there is a wet bar including a subzero fridge and wine cooler which holds 65 bottles of wine! There are multiple balconies, 3 of which have awesome partial Gulf of Mexico views! Step outside to your private oasis featuring a large heated pool and spa, ideal for relaxing or entertaining. Enjoy lounging on the balconies under the string lights and gulf breeze. Hang out back at the outdoor bar, play some put put golf in the turfed side area or a game of ping pong! New pool pump and pool heater. 2 car epoxied garage but have fit 8 cars total in garages and driveway! Elevator, wood like ceramic tile through out, office area, and more! With the Sandbar restaurant and Captain Anthony’s being your backyard neighbors, it is fun and convenient for all! Spacious and beautifully designed, this home is your gateway to the ultimate beach lifestyle on Anna Maria Island. Paradise awaits!

108 Magnolia Avenue, Anna Maria

522 Pine Avenue Unit 7D, Anna Maria
$525,000
2 Beds ⋅ 1 Baths ⋅ Bayou Condominium SubDv.
“Sittin’ on the dock of the Bay…” Welcome to an effortless island retreat designed for relaxed second-home living on Anna Maria Island. This elevated 2-bedroom, 1-bath waterfront condo is being offered turnkey furnished and includes its own deeded boat slip, providing direct access to Tampa Bay and quick passage to open water. Set along a peaceful canal, the home invites you to slow down and unwind. Enjoy morning coffee or evening breezes from your private back patio as manatees glide by and seabirds fill the air. When you are ready to explore, you are perfectly positioned on iconic Pine Avenue, just steps from local shops, dining, and island favorites, with the historic City Pier nearing completion nearby. Inside, the condo offers a clean, comfortable layout with two generously sized bedrooms and a full bath. The space is move-in ready as is, while also offering future flexibility. Many owners in the Bayou Condo Complex have enhanced their units by opening the kitchen to the living area, adding interior laundry, or converting the walk-in closet into an additional bath, creating exciting options to personalize over time. This residence has been lovingly used as a second home and also allows twice-monthly rentals, offering optional income when you are away. The well-maintained Bayou Condo community recently completed new metal roofs in 2025 and features low condo fees, a designated parking space, and ample guest parking. Whether you envision weekend escapes, seasonal stays, or boating adventures right outside your door, this waterfront condo delivers the ultimate lock-and-leave island lifestyle. Schedule your private showing and discover how easy owning a second home on Anna Maria Island can be.

522 Pine Avenue Unit 7D, Anna Maria

57 N Shore Drive, Anna Maria
$1,750,000
3 Beds ⋅ 3 Baths ⋅ Anna Maria Beach SubDv.
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.

57 N Shore Drive, Anna Maria

419 Alamanda Road, Anna Maria
$3,100,000
4 Beds ⋅ 5 Baths ⋅ Shore Acres SubDv.
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.

419 Alamanda Road, Anna Maria

821 S Bay Boulevard, Anna Maria
$7,850,000
5 Beds ⋅ 6 Baths ⋅ South Bay Subdivision SubDv.
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.

821 S Bay Boulevard, Anna Maria

412 Alamanda Road, Anna Maria
$1,575,000
2 Beds ⋅ 2 Baths ⋅ Shore Acres SubDv.
This stunning and private retreat is perfect for those who enjoy indoor/outdoor living, floating in a pool or lounging at your very own tiki bar. Light and bright open concept floor plan and impact sliders that open up to the pool and backyard oasis. This home is offered turnkey furnished and ready to move in or ready to be a great vacation rental. Zoned for 1-7 days. The primary bedroom is spacious and comfortable with your own private bathroom and access directly to the pool area. The other bedroom uses the hallway bathroom. Enjoy the large yard, tiki bar, tropical landscaping, turf put-put golf and more! Plenty of yard for kids to run around and dogs to play and plenty of parking too! Nestled in Anna Maria's quiet north end, it's steps away from sunrise on Tampa Bay and a short walk to sunset at the exclusive Bean Point beach. Quaint shops and restaurants of Anna Maria are just blocks away and close to Pine Avenue. This unique home is the perfect combination of a modern cottage set in a serene tropical environment with a quiet sense of luxury and simple detail. Schedule your private showing today!

412 Alamanda Road, Anna Maria

526 Loquat Drive, Anna Maria
$2,050,000
3 Beds ⋅ 3 Baths ⋅ Lacios Sub SubDv.
You have to see this home to appreciate the efficient layout and spacious living spaces. This property comes turnkey furnished, making it a seamless transition for the fortunate new owners. Meticulously maintained and never rented, the home exudes a sense of care and pride. For those considering short-term rentals, this residence presents an attractive opportunity. Featuring three bedrooms, including two master suites, and three bathrooms, the open floor plan enhances the spacious and airy ambiance, creating an inviting atmosphere for residents and guests alike. Nestled along a serene saltwater canal, this home caters to boating and fishing enthusiasts with a 12,000lb boat lift and a fish cleaning station. This deepwater canal has no fixed bridges to get to open water, both sailboats and power boats are welcome. The covered back porch overlooks the canal, providing a tranquil setting for relaxation and entertainment. Immerse yourself in the refreshing saltwater pool. The pool is heated with an electric heat pump and comes with a pool sweep and fitted cover. Inside, the residence boasts high-end finishes, including granite countertops, crown molding, Hunter Douglas window dressing and hardwood floors throughout, with tile accents in the bathrooms. Practical features of this elevated home include a new metal roof and a completely enclosed lower level that boasts a 2-car garage, ample storage space under the entire home on a generous lot with 75' on the canal, ensuring privacy and room for outdoor activities. A short seven-block stroll or bike ride takes you to the beautiful Gulf beaches that Anna Maria Island is renowned for. And Tampa Bay water access is literally half a block away, across South Bay Blvd. Again, turnkey furnished and ready to move in. And as an extra bonus a meticulously maintained 2006 Shearwater Z2400 power boat is included. Don't miss this opportunity!!!

526 Loquat Drive, Anna Maria

101 Sunset Lane, Anna Maria
$2,900,000
4 Beds ⋅ 4 Baths ⋅ Sunset Cove At Holmes Beach SubDv.
Built in 2002 by respected Whitehead Construction, this elevated coastal residence is ideally positioned just a short walk from the Gulf of Mexico, offering a relaxed island lifestyle paired with thoughtful updates and versatile living spaces. Set on a lush, quarter-acre lot in the desirable Sunset Cove area of Anna Maria Island, the home is surrounded by mature tropical landscaping that creates privacy and a true sense of retreat—while keeping the beach within easy walking distance. Outdoor spaces are a highlight of the property. The organic-shaped tropical swimming pool is surrounded by a custom Florida sandstone deck, creating a private setting for relaxing or entertaining. Lush foliage enhances seclusion, while a hot-water outdoor shower makes returning from the beach effortless. Deeded beach access is just a short stroll away, allowing you to enjoy sunrise walks, sunset views, and spontaneous days along the Gulf’s sugar-sand shoreline. Designed with a “fun” coastal aesthetic, the residence features a lifestyle-driven floor plan that blends indoor comfort with exceptional outdoor living. High ceilings with tray and tongue-and-groove detailing, crown molding, and custom built-ins add architectural interest and warmth throughout the main living areas. The open layout connects seamlessly to the kitchen, which is appointed with custom solid-wood cabinetry, granite countertops, a breakfast bar, glass tile backsplash, Viking gas range, built-in oven and microwave, pantry storage, and newer appliances—including refrigerator, dishwasher, and washer (approximately two years old). Recent improvements enhance both comfort and efficiency, including a new air-conditioning system for the main house (installed November 2025), blown-in insulation to improve cooling on the west exposure, fresh exterior paint, and updated outdoor lighting. A pre-framed elevator shaft provides the option for future installation, offering flexibility for long-term enjoyment. The oversized, ground-level, under-building garage offers exceptional functionality with space for multiple vehicles, recreational equipment, and storage. Insulated garage doors were installed with classic car storage in mind, and the generous footprint supports a wide range of coastal living needs. Located close to island dining, waterfront restaurants, boating, and everyday conveniences, this residence also offers easy access to Sarasota’s cultural attractions, shopping, and entertainment just across the bridge. Whether used as a full-time residence or a refined beach getaway, this well-maintained coastal home delivers walk-to-the-beach living, privacy, and flexibility in one of Anna Maria Island’s most appealing setting

101 Sunset Lane, Anna Maria

120 White Avenue, Anna Maria
$3,300,000
5 Beds ⋅ 4 Baths ⋅ Gulf View Sub SubDv.
Nestled on Anna Maria Island’s most famous street, this beautifully renovated coastal retreat boasts five spacious bedrooms and four luxurious bathrooms, offering the perfect blend of comfort and style. Designed for seamless indoor-outdoor living, it features multiple porches where you can bask in the island breeze. Expansive sliding doors open to a generous deck, creating a natural flow between the elegant interiors and the lush tropical surroundings. Step down to the heated pool and spa, enveloped by vibrant landscaping, providing a secluded sanctuary for relaxation and entertainment. A private elevator enhances convenience, providing effortless access to all levels of the home and ensuring a seamless living experience. While the home’s prime location places you just steps from the beach, renowned as the best surfing spot on the island, it offers an ideal setting for surfers drawn to its incredible waves. With premier shopping and dining just minutes away, you’ll have the best of island living right at your fingertips.

120 White Avenue, Anna Maria

803 Gladiolus Street, Anna Maria
$3,200,000
5 Beds ⋅ 5 Baths ⋅ Shore Acres SubDv.
Welcome to 803 Gladiolus St, a serene retreat located in the highly desirable Bean Point area of Anna Maria Island. Often referred to as A Bean Point Paradise, this exceptional property features one of the largest private pools on the island, surrounded by lush tropical landscaping and a relaxing spa. This versatile home is ideal as a primary residence, second home, or vacation rental. A Burt Harris Settlement Agreement allows occupancy for up to 12 guests, offering rare flexibility and strong rental potential. Property Details Bedrooms: 5 Bathrooms: 4.5 Parking: Accommodates up to 6 vehicles with oversized parking and space for a boat trailer — a rare feature compared to most homes on Anna Maria Island Location: Approximately a five-minute walk to the Gulf beaches at Bean Point Exterior Features Enjoy a private tropical backyard designed for entertaining, complete with an expansive pool and spa. Outdoor amenities include a BBQ grill and poolside refrigerator, perfect for al fresco dining. Conveniently located near beaches, shopping, and local restaurants. Interior Features The home offers an open and inviting living area with ample seating, a chef’s kitchen with stainless steel appliances, a large island, and a formal dining area. Multiple indoor and outdoor dining options enhance the home’s flexibility for both everyday living and entertaining. Floor Plan Second Floor: Three bedrooms Third Floor: Primary suite plus one additional bedroom Den: Queen sleeper sofa for additional guest accommodations Balconies: Off the living room and primary bedroom Additional Features The converted garage has been transformed into a dedicated game room, complete with a ping-pong table, foosball, seating, and a TV—creating a fun and functional space for guests of all ages while enhancing the home’s rental appeal. Remarks 803 Gladiolus St offers a rare combination of generous parking, a resort-style backyard, a prime Bean Point location, and a bonus game room rarely found on Anna Maria Island. A unique opportunity to own a well-appointed island property with exceptional lifestyle and income potential.

803 Gladiolus Street, Anna Maria

785 Jacaranda Road, Anna Maria
$1,850,000
3 Beds ⋅ 3 Baths ⋅ Shore Acres SubDv.
OHHHH THE UPDATES!! BRAND NEW KITCHEN and flooring...and updates galore! There is so to enjoy about this great investment home! This is the perfect beach haven, just a hop, skip & a jump to the Gulf beach! Just steps to Bean Point, this elevated 3 bed/2.5 bath pool home is a great income property! Updated with beautiful coastal style, this home is designed for relaxing. Start the day sipping coffee on your screened porch or enjoy the space around your open dining table! Stretch out in the family room where the coastal comfort welcomes you with shiplap walls, large updated windows, new lighting, fresh paint and furnishings. Upstairs you will find your large bedroom with its private porch, walk in closet, updated en suite and peeks of the Gulf! Both guest rooms also enjoy an updated (2024) bathroom and the gorgeous coastal décor! Whether you're lounging at the poolside bar, relishing the breeze on the screened porches, relishing the comfort of your cozy bed, or using your back gate to pop over to the sugar sand beach, you will love the island life from every spot of this updated home! From all the UPDATED appliances, the metal roof, the luxury vinyl plank flooring, the NEW doors & door frames, the NEW paint (inside & out), the NEW lighting and the NEW fans, to all the UPDATED décor - this beach house is picture perfect! And outside you will relish the added landscaping and palm trees, lighted stair way, privacy wall, covered bar and your heated pool and spa! Enjoy a cocktail and the game while floating in the pool, and easy access to your beach toy storage space! Inside and out this island home welcomes relaxation and enjoyment! AND you will REALLY enjoy the short term rental income! It’s time for your island life to begin…

785 Jacaranda Road, Anna Maria

329 Tarpon Street, Anna Maria
$5,500,000
4 Beds ⋅ 5 Baths ⋅ Bimini Bay Estates SubDv.
Experience the charm of Anna Maria Island with this NEWLY COMPLETED CONSTRUCTION. This luxurious home boasts four bedrooms and four and a half baths, offering STUNNING VIEWS. Features include an elevator, a three-car garage, and 3,751 square feet of air-conditioned space, and 7,893 square feet overall. Enjoy premium appliances, elegant wood floors throughout, and an open floor plan that is designed for effortless entertaining. Outside, the property features multiple covered patios perfect for relaxation and entertainment. Whether you're enjoying the pool, spa, or sitting on the dock, the views are unparalleled, all from the comfort of your own backyard. Conveniently located near shopping, restaurants, and the most beautiful white sandy beaches, this slice of paradise could be your new home.

329 Tarpon Street, Anna Maria

316 Hammock Circle, Anna Maria
$2,770,000
3 Beds ⋅ 3 Baths ⋅ Coconut Bayou SubDv.
Welcome to Manatee Manor, a life where every evening ends in a watercolor sunset, manatees swim in your backyard, and every morning begins with the quiet ripple of wide open canal waters just beyond your dock. Perfectly positioned on a peaceful cul-de-sac in the heart of Anna Maria, Manatee Manor is more than a home — it’s a daily invitation to slow down and savor island living. This elevated 3-bedroom, 3-bath residence has been lovingly owner-occupied and meticulously maintained — never rented — offering a level of care and quality that’s immediately felt. Designed for relaxed coastal living, this home captures breathtaking sunset views with a seamless indoor-outdoor flow. Recent renovations include kitchen and bathroom remodels, designer GE Cafe appliances, all impact doors and sliders, water filtration system, landscaping and more! Ready to enjoy the Florida sunshine? Step outside to your private backyard retreat and enjoy your putting green, heated pool (28x18), spa, artificial turf, sitting areas, and an outdoor kitchen — ideal for sunset dinners and weekend gatherings. The 100' canal-front setting includes a dock (36x22), making it effortless to launch a kayak, hop on a paddleboard, or head out for a day on the Gulf. Unique to this area, the protected sanctuary across the water provides a peaceful quiet oasis to you and your guests. Life here means: Morning walks to the sugary white sands of the Gulf beaches, Strolling to the boutiques and dining along Pine Avenue, Quiet evenings in a friendly, tucked-away cul-de-sac, and Manatees passing by as you lounge waterside. Whether you’re entertaining poolside, cruising the waterways, or biking to nearby shops and restaurants, this address delivers the ultimate North End island lifestyle. Manatee Manor isn’t just a waterfront property — it’s where sunsets become rituals and every day feels like vacation. Call today for your private showing!

316 Hammock Circle, Anna Maria

301 Palm Avenue, Anna Maria
$1,040,000
2 Beds ⋅ 2 Baths ⋅ Bimini Bay Colony Club Sub SubDv.
One or more photo(s) has been virtually staged. Come feast your eyes on 301 Palm Avenue. First, let’s talk about Location, Location, Location. The property is about 120 steps to the gorgeous silky sand of the City of Anna Maria’s gulf front park at Palm Ave. There are public benches under magnificent Australian Pines offering shade throughout the day. Should you rather lounge around the house you can do so in your private heated in-ground pool. The yard faces southwest, providing sun all day. However, it is screened from road by lush mature palms. The property is also a short walk to the shops and restaurants on Gulf Dr and Pine Ave. Make sure you catch sunset from the Sandbar Restaurant. You can walk there on the beach. Now, let’s talk about the home. It is a two-bedroom 2 bath half a of duplex, totally renovated in 2025. It is not a land condo so there are no HOA fees, and you own the land on your half of the building. Nothing was over looked in its transformation. There are new kitchen cabinets and countertops, vanities, plumbing fixtures, appliances, HVAC, and hot water heater. All the work was done by permit and inspected by the City of Anna Maria. It is a clean blank canvas waiting for you to transform it into personal island oasis. The home was used primarily by the owner’s parents and was never a vacation rental. In front of the home is a carport to keep your car out of the sun with a brick paver driveway. Should you choose to use the home as a vacation rental, it can accommodate up to six guests by city ordinances. Should you choose to use it personally there are no occupancy limits for you and your family. This is the lowest-priced, renovated and ready-to-furnish home in the City of Anna Maria. Do not let this one get away!!!

301 Palm Avenue, Anna Maria

513 Bayview Place, Anna Maria
$3,600,000
4 Beds ⋅ 6 Baths ⋅ Wells Bay Harbor SubDv.
This Bayview Palace is a One of a kind, there’s nothing quite like this on Anna Maria Island!! Discover paradise in this 4 bedroom, 4 full bathrooms and 2 half baths, stunningly renovated home nestled in the heart of Anna Maria Island. Situated on two spacious lots, this exquisite property offers rare space, privacy, and direct access to the sparkling waters of Tampa Bay. Complete with TWO private 20,000 lb boat lifts, floating dock and can fit up to a 42 ft boat, and has 50 amp! The absolute ultimate boating lifestyle! This beautifully updated residence blends modern elegance with bohemian island charm. The open-concept living space dazzles with soaring ceilings, abundant natural light, high end brand name kitchen appliances and a separate bar with sub zero ice maker! The gourmet kitchen is a chef’s dream with a very spacious island perfect for gatherings, custom cabinetry and porcelain travertine floors throughout! Each of the four generously sized bedrooms boasts its own en-suite bathroom. The master suite is a serene oasis, complete with custom closets and a huge walk in shower spa-inspired bathroom. Right off the master suite is the private spa hot tub for relaxing under the stars. Outside, the expansive double lot provides endless possibilities—enjoy lush tropical landscaping, a sparkling pool, pool bath, screen in porch and tiki bar / game room. Just a short stroll to Pine Avenue’s boutique shops, restaurants, and the Gulf, this home offers the ultimate island lifestyle. Detached 3 car garage includes an upstairs storage room/ play room. Other features include a well, generator, outdoor shower and more! Don’t miss this unique opportunity to own a fully renovated masterpiece on two lots in one of Florida’s most charming coastal communities. Schedule your private tour today!

513 Bayview Place, Anna Maria

129 Hammock Road, Anna Maria
$2,550,000
4 Beds ⋅ 3 Baths ⋅ Anna Maria Beach SubDv.
Welcome to 129 Hammock Road, where island dreams meet modern luxury. This 4-bedroom, 3-bath canal front pool home has been completely transformed for the buyer who wants more than a property they want a lifestyle. Whether you’re searching for a full time residence, a second home to escape to, or an investment with strong rental potential on Anna Maria Island, this home delivers it all with ease. Nightly rental allowed. From the moment you step inside, the home feels calm, elevated, and intentional. Sunlight pours through new impact slider doors, highlighting new hardwood floors, designer fixtures, and refined coastal details. The remodeled kitchen and bathrooms feature new tiling, quartz surfaces, and stylish finishes that feel both current and timeless perfect for hosting guests, family, or future renters. Out back, your private oasis awaits. The heated saltwater pool sits on a travertine patio framed by tropical landscaping, creating a space that feels like a boutique resort. Enjoy morning coffee by the water, afternoons floating in the sun, and evenings watching the sky fade behind the canal. The newly replaced dock with new pilings and composite decking opens the door to adventure—kayaking, paddleboarding, boating, or simply taking in the peaceful waterfront. Pool features a raised equipment platform, new pool pump and heater, and even a built in basketball hoop make the outdoor space as practical as it is fun. The rare 4 car garage with screening and double garage doors provides room for vehicles, golf carts, beach gear, and storage, an essential feature for both full time living and high performing vacation rentals. With new pavers, a newer zoned air conditioner, and thoughtful updates throughout, the home feels move-in ready from day one. Here, you’re not just buying a home you’re stepping into the Anna Maria Island lifestyle. The Gulf beaches, Pine Avenue boutiques, waterfront dining, sunsets, salt air, golf carts, boat days, and barefoot weekends… they’re all just minutes away. For the buyer who wants income opportunity, but also wants somewhere they’ll be proud to call home. For the buyer looking to settle in, invest smart, and finally live the island life they’ve been dreaming of—this is it.

129 Hammock Road, Anna Maria

522 Pine Avenue Unit 6A, Anna Maria
$445,000
2 Beds ⋅ 1 Baths ⋅ Bayou Condominium SubDv.
Life’s better on island time—especially when you can own a waterfront condo in the coveted city of Anna Maria at a price this rare! Dreaming of island life? This is your chance. Tucked away on the water just steps from the sugar-sand beaches, local shops, and breezy restaurants of Anna Maria Island, this 2-bedroom, 1-bath condo is the kind of opportunity that doesn’t come around often. Wake up to gentle water views, grab your paddleboard or kayak, and set off right from your private dock into Tampa Bay. Even better, the private dock is big enough for boats up to 24 ft. Whether you’re boating to the bay, fishing at sunset, or simply sipping a drink with your feet dangling over the water, your dock is your front-row seat to island living at its core. In the evenings, walk out your front door to the Waterfront restaurant, stroll down Pine Ave, or catch the sunset on the Gulf. This condo puts you at the heart of the island lifestyle. The space is fully remediated. It is a blank canvas waiting for you to make it your perfect island getaway. Want help bringing your vision to life? We can connect you with local contractors who’ve already worked magic on the island. New HVAC (2022). New metal roofs (2025). Dedicated parking + guest spaces. Affordable, flexible, and full of potential. Perfect as a cozy getaway, smart investment, or future full-time home. Anna Maria Island waterfront living, at a price point rarely seen. This is more than a condo—it’s your gateway to the island lifestyle you’ve been dreaming about.

522 Pine Avenue Unit 6A, Anna Maria

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