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517 South Drive, Anna Maria
$3,500,000
5 Beds ⋅ 5 Baths ⋅ Wells Bay Harbor SubDv. ⋅ 34216 Zip Code
EXCEPTIONAL WATERFRONT LIVING ON BEAUTIFUL ANNA MARIA ISLAND! Discover coastal luxury in this completely renovated waterfront residence offering 2,568 square feet of beautifully designed living space, featuring 5 spacious bedrooms, 4 full bathrooms, and 1 half bath. Thoughtfully updated throughout, this exceptional home blends modern elegance with the relaxed charm of island living. The inviting interior features a fireplace, an elevator for added convenience, and beautifully appointed living spaces ideal for both everyday comfort and entertaining. Step outside to your own private tropical oasis, complete with a sparkling pool, relaxing spa, and covered terraces perfect for enjoying gentle coastal breezes and Florida's year-round sunshine. Boating enthusiasts will appreciate the brand-new seawall and private boat lift, offering the ultimate waterfront lifestyle. Additional highlights include a durable metal roof and an impressive 4-car garage with ample room for vehicles, storage, and all your island essentials. Perfectly situated on Anna Maria Island, this extraordinary property places you just moments from charming boutiques, outstanding restaurants, and the island's world-famous white-sand beaches and breathtaking sunsets. Whether you're seeking a luxurious primary residence, an island retreat, or the perfect place to entertain family and friends, this beautifully remodeled waterfront home delivers the very best of Anna Maria Island living!

517 South Drive, Anna Maria
319 Tarpon Street, Anna Maria
$6,995,000
5 Beds ⋅ 6 Baths ⋅ Bimini Bay Estates SubDv. ⋅ 34216 Zip Code
Experience a striking new expression of waterfront living at 319 Tarpon Street, a fully furnished coastal residence positioned on a quiet dead-end street in the heart of Anna Maria. Set along 75 feet of saltwater canal frontage, the home was thoughtfully designed to capture sweeping, long canal views while creating an effortless connection between its indoor and outdoor spaces. Offering 3,484 square feet of air-conditioned living space and more than 7,500 total square feet, this five-bedroom, five-and-a-half-bath residence pairs refined coastal design with the comfort and resilience of new construction. A private elevator serves each level, while the three-car garage provides generous room for vehicles, a golf cart and island essentials. The main living level is centered around a beautifully appointed chef’s kitchen with custom cabinetry, stone countertops, an expansive island and ample space for entertaining. The kitchen flows naturally into the dining and great room, where a gas fireplace and wide openings to the covered waterfront lanai create an inviting setting for gatherings. Three guest suites, a den or office, laundry room and additional thoughtfully designed spaces provide flexibility for family and guests. The upper level offers a private primary retreat with a spa-inspired bath, generous walk-in closet and covered balcony overlooking the water. An additional guest suite and an expansive approximately 830-square-foot open-air terrace create an exceptional setting for morning coffee, sunset cocktails or evenings under the stars. Outdoor living is equally impressive. The resort-style heated pool and spa are framed by generous covered entertaining areas, tropical landscaping and an outdoor shower, all positioned to take full advantage of the tranquil canal setting. Seventy-five feet of concrete seawall and saltwater canal access to Bimini Bay further enhance the waterfront lifestyle. Built to current coastal standards and offered fully turnkey furnished, 319 Tarpon is equally suited as a private island retreat, full-time residence or luxury vacation property with weekly rental flexibility. Beaches, Pine Avenue shops and restaurants, the City Pier and everything that makes Anna Maria special are only a short golf-cart or bicycle ride away. This is more than a new home—it is a thoughtfully designed waterfront experience where elevated construction, relaxed luxury and the best of island living come together.

319 Tarpon Street, Anna Maria
225 Chilson Avenue, Anna Maria
$2,495,000
Bimini Bay Estates SubDv. ⋅ 34216 Zip Code
Build big. Live the dream. Welcome to Anna Maria! Oversized canal-front lots like this are rare: just a pinch shy of one-third of an acre, with a sweeping 93 feet of water frontage and direct boating access to Tampa Bay and the Gulf. Add a shared boat basin, and this is a boater’s paradise! The existing home is a teardown, and the property is being sold for land value. Bring your vision and create a show-stopping custom coastal estate or a high-performing investment in a coveted short-term rental zone. The possibilities are endless! Walk to sugar-sand Gulf beaches, then enjoy island boutiques, waterfront dining and the laid-back charm that makes Anna Maria Island legendary. Opportunities like this don’t last. Seize it!

225 Chilson Avenue, Anna Maria
225 Chilson Avenue, Anna Maria
$2,495,000
3 Beds ⋅ 2 Baths ⋅ Bimini Bay Estates SubDv. ⋅ 34216 Zip Code
Build big. Live the dream. Welcome to Anna Maria! Oversized canal-front lots like this are rare: just a pinch shy of one-third of an acre, with a sweeping 93 feet of water frontage and direct boating access to Tampa Bay and the Gulf. Add a shared boat basin, and this is a boater’s paradise! The existing home is a teardown, and the property is being sold for land value. Bring your vision and create a show-stopping custom coastal estate or a high-performing investment in a coveted short-term rental zone. The possibilities are endless! Walk to sugar-sand Gulf beaches, then enjoy island boutiques, waterfront dining and the laid-back charm that makes Anna Maria Island legendary. Opportunities like this don’t last. Seize it!

225 Chilson Avenue, Anna Maria
607 S Bay Boulevard, Anna Maria
$2,150,000
4 Beds ⋅ 3 Baths ⋅ Wells Bay Harbor SubDv. ⋅ 34216 Zip Code
This 4 bedroom, 3 bathroom waterfront home on a canal with spectacular outdoor space with multiple decks and both bay and canal views! The home is situated at the north end of the island within an easy bike or golf cart ride to Anna Maria's Pine Avenue shops, the bayside beach, Anna Maria City Pier and gulf-side beaches! The pool is heated and the spa provides some extra warmth and relaxation at the end of a fun beach day! The home has a great backyard area with an outdoor shower and there is small private dock perfect for wetting a line or launching your kayak! The main floor is a gorgeous open concept living, dining, kitchen area. The huge kitchen island and breakfast bar has counter seating with stainless steel high-end appliances. You will be able to whip some fabulous meals at home or prep some libations for entertaining on one of the home's spacious covered balconies! There are two balconies on the first floor alone off both the front and back of the home with plenty of seating! The main floor has the master suite with closet, TV and en-suite full bathroom with tub/shower combination accessible from the living room as well. The top floor has 3 additional bedrooms. There are two additional covered decks off the front and back with bay and canal views respectively. The best of both worlds, this home has so much to offer!

607 S Bay Boulevard, Anna Maria
511 South Drive, Anna Maria
$3,700,000
3 Beds ⋅ 3 Baths ⋅ Wells Bay Harbor SubDv. ⋅ 34216 Zip Code
Tucked away at the very end of a quiet street in Anna Maria, 511 South Drive is a truly distinctive waterfront retreat offering exceptional privacy and nearly 180 feet of water frontage along Bimini Bay. Once featured in SRQ Magazine, this three-bedroom, two-and-a-half-bath residence—known as The Morris House—captures the relaxed beauty of island living, with dolphins, manatees and coastal birdlife providing an ever-changing backdrop. Originally built by Ross Built, the home is rich in British Arts and Crafts character, yet has been beautifully updated for modern living. Throughout the home, remarkable details speak to its history and craftsmanship, from a William Morris stained-glass window to a mantel sourced from a mansion in Great Britain. Since 2024, the home has undergone an extensive collection of thoughtful improvements, blending its distinctive character with beautifully updated interiors, enhanced outdoor living and important mechanical upgrades. A private courtyard surrounded by mature tropical landscaping and a charming koi pond creates a memorable sense of arrival. Step inside, and oversized windows and French doors frame the waterfront setting, immediately drawing your eye toward sweeping water views. The main level was extensively refreshed in 2025 with new wood-grain tile flooring, custom wood trim and baseboards, and built-in living room bookshelves crafted by a master carpenter. The kitchen was reimagined with new cabinetry, quartz countertops and a suite of high-end appliances including a Fulgor Milano range, ASKO dishwasher and a GE Monogram refrigerator. A Blanco undermount sink features instant ultra-filtered hot water, while the adjoining pantry received additional cabinetry and electrical upgrades. The downstairs bath was also updated with new cabinetry, quartz countertops and a new sink. Designed for both gathering and everyday living, the expansive great room opens to the waterfront setting, while a separate media room and game room offer additional spaces for entertaining. Two guest bedrooms on the main level open directly to the courtyard and share a Jack-and-Jill bath. The entire upper level is dedicated to the primary suite, creating a private retreat surrounded by spectacular water views. Windows and French doors span three sides of the bedroom, while the expansive private deck provides an idyllic setting for sunrise coffee or an evening cocktail. The primary bath features an oversized walk-in shower and a clawfoot soaking tub. Outdoor living has also been beautifully enhanced. The wraparound porch was screened in 2024, creating a wonderful extension of the interior living space overlooking the water. A new hot tub was added in 2025, followed by an outdoor shower and new pavers along the front and side of the home in 2026. A new irrigation system was also installed. Along the nearly 180 feet of waterfront, two docks invite you to embrace the boating lifestyle, including a boat lift for easy access to fishing and sunset cruises and an enclosed boathouse for fishing gear and water toys. Additional recent improvements include a new downstairs AC system, new split AC unit, new hot water heater, floor outlets, updated lighting, and more. Just minutes from the beaches, Pine Avenue's shops and restaurants and the Anna Maria City Pier, The Morris House offers a rare combination of architectural character, exceptional privacy and substantial water frontage —all within a remarkable setting in Anna Maria.

511 South Drive, Anna Maria
515 Loquat Drive, Anna Maria
$4,995,000
4 Beds ⋅ 5 Baths ⋅ Lacios Sub SubDv. ⋅ 34216 Zip Code
Welcome to 515 Loquat Drive. This exceptional waterfront residence on Anna Maria Island offers a refined blend of coastal elegance, thoughtful design, and effortless island living. Set along a peaceful canal, this impressive 4-bedroom, 4.5-bathroom home features a private dock, elevator, rooftop deck, and beautiful bay views, with Pine Avenue, local dining, and the free island trolley just a short walk away. Currently operating as a successful vacation rental, this property offers an excellent opportunity for both personal enjoyment and investment. Inside, the bright, open layout is designed for both everyday comfort and entertaining. The spacious living area flows seamlessly into a gourmet kitchen with high-end appliances and a generous island, while a wet bar and dedicated office add convenience and versatility. Each of the four well-appointed bedrooms features its own ensuite bathroom, with three offering king beds and the fourth including two twin-over-full bunk beds. The primary suite provides a private retreat with a soaking tub and walk-in shower. Outdoor living is equally impressive, with a private heated pool, oversized spa, and multiple lounging and dining areas. Enjoy morning coffee by the water, gather around the pool, or take in spectacular sunsets from the rooftop deck. The private dock offers convenient waterfront access, while the home's elevated design and island location create an exceptional setting for enjoying the best of Anna Maria Island. With its desirable waterfront setting, generous living spaces, impressive indoor-outdoor amenities, and successful vacation rental history, 515 Loquat Drive presents a rare opportunity to own a beautifully appointed island home in one of Florida's most sought-after coastal destinations.

515 Loquat Drive, Anna Maria
109 Gull Drive, Anna Maria
$1,175,000
Luana Isles SubDv. ⋅ 34216 Zip Code
Rare opportunity to own a canal-front lot in the heart of Anna Maria Island. Take your clean slate to design and build the coastal dream home you've been waiting for. Located on a quiet cul-de-sac street with access to the Bay and the Gulf of Mexico, boats to be able to fit under the 2 bridges. Anna Maria offers a laid-back, old-Florida lifestyle — walkable access to the island's white-sand beaches, local restaurants, and shops on Pine Ave. Whether you're envisioning a modern coastal retreat or a classic Florida cottage on stilts, this lot gives you the location and the water access to make it happen. Zoning allows for 1-7 day vacation rentals.

109 Gull Drive, Anna Maria
109 Gull Drive, Anna Maria
$1,175,000
2 Beds ⋅ 2 Baths ⋅ Luana Isles SubDv. ⋅ 34216 Zip Code
Rare opportunity to own a canal-front lot in the heart of Anna Maria Island. Take your clean slate to design and build the coastal dream home you've been waiting for. Located on a quiet cul-de-sac street with access to the Bay and the Gulf of Mexico, boats to be able to fit under the 2 bridges. Anna Maria offers a laid-back, old-Florida lifestyle — walkable access to the island's white-sand beaches, local restaurants, and shops on Pine Ave. Whether you're envisioning a modern coastal retreat or a classic Florida cottage on stilts, this lot gives you the location and the water access to make it happen. Zoning allows for 1-7 day vacation rentals.

109 Gull Drive, Anna Maria
242 Lakeview Drive, Anna Maria
$6,995,000
6 Beds ⋅ 7 Baths ⋅ Lake La Vista Sub SubDv. ⋅ 34216 Zip Code
Introducing The Ivy — The first chapter in a new collaboration. Born from the partnership of Emily Moss Designs and Moss Builders, The Ivy marks the debut of their shared vision on Anna Maria Island — a carefully crafted waterfront residence where refined design and thoughtful construction meet. As the inaugural home in what will become a growing collection, The Ivy sets the tone for the work to come: elevated, intentional, and deeply rooted in the island’s quiet luxury. Step through the front entry — sheltered beneath a soaring tongue-and-groove wood ceiling — into a great room where large-format stone flooring, disappearing glass sliders, and a sculptural wood ceiling detail set a calm, organic tone. The chef's kitchen anchors the main level with a monumental waterfall-edge stone island, custom dark wood cabinetry, and sculptural globe pendant lighting, flowing seamlessly into a dining room defined by a dramatic wood-beamed vaulted ceiling, a statement orb chandelier, and floor-to-ceiling glass that frames water views from every seat at the table. Directly off the kitchen you’ll find a huge walk in pantry. Six bedrooms offer their own quiet retreats — from a serene primary suite with an upholstered headboard and private glass sliders, to a playful bunk room with built-in cubby storage for kids. The six and a half bathrooms are spa-like in their own right, with freestanding vessel sinks, brass fixtures, and dramatic veined stone and designer tile work throughout. Outside, The Ivy truly comes alive. A resort-style pool is anchored by an elevated spa with a cascading water feature, framed by a turfed lawn, lounge chairs, and a covered wood-ceilinged loggia built for shaded entertaining. A dramatic timber trellis staircase first leads up to the outdoor kitchen, massive TV and hanging swings. As you continue to make your way up to the crown jewel: a expansive rooftop deck with built-in bench seating, a private hot tub to enjoy sunsets, lounge chairs and seating around a fire pit. Direct canal front access completes the picture, with a brand-new dock and boat lift ready for a day on the water — all just a short, palm-lined walk to the shops and restaurants of Pine Avenue.

242 Lakeview Drive, Anna Maria
259 Gladiolus Street, Anna Maria
$2,690,000
4 Beds ⋅ 3 Baths ⋅ Luana Isles SubDv. ⋅ 34216 Zip Code
Under Construction. Why buy before December 31, 2026? Review recently passed Florida Amendment 3 with your CPA/tax advisor for potential tax advantages! Welcome to this completely updated charming coastal home located at 259 Gladiolus St in the desirable City of Anna Maria. If you’re looking for a ground level waterfront, 4-bedrooms, 3-bathrooms, pool home on the north-end, that is close to the beach, Pine Ave shops and the bayside park, this is one to come see! The interior and exterior design offers endless charming coastal details that lean into island relaxed style. As you walk through the double glass front doors, you’ll be surprised by how much light shines into this home accentuating the high ceilings and open concept. The design selections are classic and calm, from neutrals to soft beachy blues. The home offers a split floor plan and two master ensuites plus an inside utility that takes the chore out of laundry. As you make your way to the back of the home the water views become the focal point. The home layout makes every day enjoyment of island living, including the pool and spa that has multiple water features to create relaxing sounds and set the stage for backyard fun. The waterfront setting is tranquil and a fabulous setting for dockside fishing, kayaks or even boating with two bridges to bay. The list of new items includes interior walls and open concept layout, electric, plumbing, flooring, kitchen, appliances, bathrooms, inside utility, metal roof, Therma Tru impact glass front door and PGT impact windows and sliding doors, heated pool/spa, tropical landscaping, and including low maintenance artificial turf. Whether you’re looking for your own island destination to call home or the ideal rental income property with flexible rental restrictions this is one to consider. Call today to schedule your private showing.

259 Gladiolus Street, Anna Maria
411 Palm Avenue, Anna Maria
$5,395,000
5 Beds ⋅ 6 Baths ⋅ Bimini Bay Estates SubDv. ⋅ 34216 Zip Code
Introducing The Palm—an iconic waterfront estate where exceptional architecture, resort-inspired living, and the unmistakable charm of Anna Maria Island come together to create a remarkable home. More than a home, The Palm captures the very best of Anna Maria Island living. Thoughtfully custom built by Eason Builder Group, this newly completed waterfront residence features five bedrooms, five full baths, one half bath, and more than 3,260 square feet of beautifully designed living space where coastal elegance meets exceptional craftsmanship. Every room has been thoughtfully curated to create an effortless connection between sophisticated design and the natural beauty that surrounds it. Walls of impact glass fill the home with natural light, while tongue-and-groove cypress ceilings, custom millwork, natural stone, and carefully selected finishes create a home that feels refined and welcoming. The open floor plan was designed for effortless entertaining and everyday living, featuring spacious gathering areas, luxurious private suites, a custom bunk room, and seamless transitions between indoor and outdoor spaces. Integrated smart home technology, an elevator, premium impact-rated windows and doors, Daikin HVAC systems, tankless water heaters, composite decking, and quality craftsmanship throughout reflect the care and attention that went into every detail. Outside, the experience is every bit as impressive. A resort-style pool with a raised spa anchors the backyard, surrounded by tropical landscaping that creates beauty and privacy. The covered lanai offers multiple spaces to gather, including an outdoor kitchen, bar seating, comfortable lounge areas, and dining space designed for entertaining family and friends. A private putting green adds another element of fun. One of the home’s most memorable features is the expansive rooftop deck, designed for sunset cocktails and panoramic views stretching across Anna Maria Island. For boating enthusiasts, The Palm offers one of the island’s most desirable features—a private dock with a 16,000-pound boat lift and direct, no-bridge access to the Gulf, allowing you to leave your backyard and be on open water within minutes. Beyond the property itself lies the lifestyle that makes Anna Maria Island so special. Leave the car behind and explore the island by golf cart or bicycle. Spend your mornings browsing the boutiques, cafés, and local shops along charming Pine Avenue, your afternoons on the island’s world-famous sugar-white beaches, and your evenings enjoying waterfront dining before watching another unforgettable Gulf sunset. Here, life moves at a different pace—one defined by boating, fishing, paddleboarding, beach walks, and the timeless character that continues to make Anna Maria Island one of the Gulf Coast’s most treasured destinations. Whether you’re searching for a private waterfront retreat, a seasonal residence, or a high-end vacation rental with exceptional income potential, The Palm offers a rare opportunity to enjoy the very best of island living while owning one of Anna Maria Island’s premier waterfront homes. Beautifully designed, expertly built, and perfectly positioned, The Palm is more than a residence—it is a place where family and friends gather, memories are made, and the best of Anna Maria Island becomes part of everyday life.

411 Palm Avenue, Anna Maria
703 S Bay Boulevard, Anna Maria
$8,995,000
5 Beds ⋅ 5 Baths ⋅ Wells Bay Harbor SubDv. ⋅ 34216 Zip Code
Experience Elevated Island Living at 703 S Bay Blvd. Nestled along the tranquil Bimini Bay canal with sweeping views of Tampa Bay, this brand-new modern masterpiece by Tulia Homes offers the pinnacle of waterfront luxury on Anna Maria Island. Completely reimagined as a stunning contemporary build, this 5-bedroom, 5-bath home seamlessly blends sleek architecture with the relaxed elegance of coastal Florida living. From the moment you arrive, the home welcomes you with abundant natural light, open-concept living spaces, and thoughtfully designed interiors that flow effortlessly to the outdoors. The chef-inspired kitchen anchors the heart of the home, perfect for everything from intimate family meals to lively gatherings. A huge walk in pantry with an extra refrigerator for convenience. Generous bedroom suites provide private retreats, each finished with premium details and spa-like baths. Outside, your personal waterfront oasis awaits. Dive into the sparkling private heated pool, entertain on expansive lanai spaces and the roof top deck, or head straight to your private boat lift and dock for a day on the water. With direct canal access and breathtaking bay vistas, every day feels like a vacation in this north-facing retreat. Enjoy the private pickle ball court right in your backyard! Ideally located on coveted Anna Maria Island, this home puts you just moments from pristine beaches, charming shops, and top-rated dining, while offering easy access to boating, fishing, and all the Gulf Coast has to offer. Whether you’re seeking a primary residence, family getaway, or premium investment property, 703 S Bay Blvd delivers an unparalleled lifestyle in one of Florida’s most desirable coastal communities. Discover modern sophistication, effortless waterfront living, and island charm—all in one extraordinary home. Schedule your private tour today and make this Anna Maria dream your reality.

703 S Bay Boulevard, Anna Maria
240 Gladiolus Street, Anna Maria
$2,000,000
Luana Isles SubDv. ⋅ 34216 Zip Code
Located on the north end of Anna Maria Island, this 10,600+ square foot parcel is just a short walk from Bean Point beaches, Bayfront Park, and the boutiques and dining on Pine Avenue. The property is beautifully landscaped and includes a large garage, offering a fantastic opportunity to build a custom home with ample space. If you are not interested in building, the adjacent home at 242 Gladiolus is also available for purchase. Both properties are owned by the same sellers, who currently use this parcel for additional privacy and the existing garage. Purchasing both parcels would provide a rare 18,175 square feet of land on Anna Maria Island.

240 Gladiolus Street, Anna Maria
517 Spring Avenue, Anna Maria
$1,500,000
2 Beds ⋅ 2 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code
One or more photo(s) has been virtually staged. MAJOR PRICE REDUCTION $100,000...Allowing You Endless Possibilities for Improvements. Welcome to the highly sought after North end of Anna Maria Island. Just steps away from the Morning Sunrise or Evening Sunsets, Take your Pick. This 2 Bed / 2 Bath Island Home Features an Open Floor Plan, Spacious Kitchen, Front & Back Balconies, Large Fenced Back Yard and Ample Parking Both Under House and Extended Driveway. Use your creativity to convert the large open 1st floor workshop into your Personal Space, Home Office, or Outdoor Entertaining Venue. The large backyard can easily accommodate a Pool, Putting Green, Bocci Ball Court, or whatever suites your fancy. Excellent vacation rental income opportunity as well. A perfect combination of Island comfort. A short walk to the Anna Maria City Beach and the bustling offering of shops & dining venues on Pine Avenue. Not to mention the soon to be completed, (October 2026), Anna Maria Island City Pier. "PIERADISE" will feature an Open-Air Neighborhood Bar & Grill, Bait & Tackle Shop and Open Dock Fishing. Island Living at its Best with Great Rental Income Potential Option. This one is definitely worth a visit. Call today to schedule your private showing.

517 Spring Avenue, Anna Maria
513 Villa Rosa Way, Anna Maria
$7,295,000
4 Beds ⋅ 6 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code
Homes of this architectural caliber are rarely offered for sale - and even more rarely as a fully curated estate. Every furnishing, antique, original artwork, lighting fixture, textile, and accessory has been thoughtfully selected specifically for this residence, including the linens and towels. Bespoke furnishings, fine antiques, original art, and an extraordinary collection of antique Persian rugs create a truly turnkey estate where architecture and interiors exist in perfect harmony. Nestled within the private enclave of Villa Rosa, this custom-built coastal property offers exceptional craftsmanship, privacy, and a lifestyle reserved for Anna Maria Island's finest properties. Inspired by timeless European architecture, the home showcases reclaimed wood beams, marble flooring, handcrafted millwork, and designer finishes throughout. At the heart of the home, the chef's kitchen features a statement Lacanche range, Sub-Zero refrigeration, custom cabinetry, and a large island designed for gathering and entertaining. Outdoor living is equally impressive, with a fully equipped Lynx kitchen, built-in pizza oven, covered lounge with a wood-burning fireplace, and multiple terraces for relaxation and entertaining. The rooftop observation terrace offers panoramic island views and breathtaking Gulf sunsets, while lush tropical landscaping surrounds a private heated and cooled pool, creating a secluded coastal retreat. Situated on a protected deep-water canal with direct, bridge-free access to Tampa Bay and the Gulf of Mexico, the property includes a private dock and 10,000-pound boat lift, making waterfront living effortless. Villa Rosa is among Anna Maria Island's most coveted residential communities, where rental restrictions help preserve a quiet neighborhood atmosphere. Just moments away are world-famous beaches, waterfront dining, boutique shopping along Pine Avenue, and the laid-back coastal lifestyle that defines the island. More than a waterfront home, this is a fully realized estate - an extraordinary blend of design, craftsmanship, and a curated collection offered as one exceptional property.

513 Villa Rosa Way, Anna Maria
872 North Shore Drive, Anna Maria
$1,650,000
4 Beds ⋅ 2 Baths ⋅ Shore Acres SubDv. ⋅ 34216 Zip Code
BEAUTIFUL WATER VIEWS. This four-bedroom, two-bath stilt home with a two-car garage offers magnificent, expansive views of Tampa Bay from every level. Designed to capture the beauty of its surroundings, the home features impact-rated windows and sliding glass doors throughout, complemented by stylish plantation shutters. Tile floors flow throughout both living levels and bedrooms. The first level boasts a spacious living and dining room combination alongside an open kitchen complete with granite countertops, stainless steel appliances, wood cabinetry, and an island cooktop—perfect for entertaining. This level also includes a guest bedroom and a full bathroom with a walk-in shower. On the second level, the primary suite offers a large walk-in closet and an en suite bath with a walk-in shower. Two additional bedrooms are located down the hall, along with a convenient inside laundry closet housing the washer and dryer. Both guest bedrooms enjoy stunning blue water views of Tampa Bay. The true money shot awaits on the third-level rooftop deck, where panoramic views stretch all the way around Anna Maria —the perfect setting for sunrise coffee or sunset gatherings. The spacious backyard provides ample room for a pool, and with some updating, this property could truly shine and reach its full potential.

872 North Shore Drive, Anna Maria
801 N Shore Drive, Anna Maria
$8,250,000
4 Beds ⋅ 4 Baths ⋅ Shore Acres SubDv. ⋅ 34216 Zip Code
Rising gracefully on the sugar-white sands of Bean Point, The Golden Dolphin is a timeless Gulf-front residence that blends enduring craftsmanship with inspired artistry. The main living level unfolds into a grand living and dining area, where a full wall of sliders frame endless Gulf views and spectacular sunsets. The expansive balcony is an entertainer’s dream, featuring a fully equipped Lynx outdoor kitchen and a beautifully carved fireplace—an inviting setting for al fresco dining or evenings by the fire. Inside, the chef’s kitchen is outfitted with Sub-Zero, Viking, and Miele appliances, seamlessly combining performance and elegance. A refined library retreat, complete with a fireplace and exquisitely carved bookcases, offers a quiet haven for reading or reflection. The third floor is devoted to luxurious private living. The palatial primary ensuite is a serene sanctuary with spa-like amenities and opens to its own Gulf-facing balcony. Here, a soaking tub, rain shower, and an additional fireplace create an indulgent, resort-style experience. Also on this level are a gracious guest suite, a whimsical children’s ensuite bedroom, and a conveniently located laundry room. The first floor welcomes you with a dramatic foyer featuring soaring ceilings and an elevator. Just beyond lies the imaginative Captain’s Quarters, a fantastical space designed to replicate the galley of a pirate’s lair—both playful and unforgettable. An expansive office follows, showcasing granite countertops and intricately carved walls with integrated drawers and shelving, offering both beauty and function. Outdoors, the home transforms into a private oasis. The grotto-style pool provides shaded comfort and is adorned with multiple water features, while a surrounding fireplace and dining area create an intimate setting for gathering. Beyond the pool, a sun-drenched private patio invites leisurely afternoons of relaxation and sunbathing. Built to stand the test of time, The Golden Dolphin is constructed with concrete and rebar throughout and engineered with advanced drainage systems designed to reroute floodwaters. This exceptional residence has sustained no damage from past hurricanes, offering peace of mind alongside its unparalleled beauty. A rare offering on Anna Maria Island, The Golden Dolphin is a masterful expression of luxury, resilience, and coastal elegance—where art, architecture, and the Gulf converge in perfect harmony.

801 N Shore Drive, Anna Maria
837 N Shore Drive, Anna Maria
$3,890,000
Wells Sub SubDv. ⋅ 34216 Zip Code
Presenting LOT 25 a rare opportunity to secure a beautiful buildable bayfront lot on the north end of Anna Maria Island, offering sweeping unobstructed water views, Skyway bridge views and an unparalleled coastal lifestyle. Located just moments from the pristine shores of Bean Point, this property provides coveted beach access to one of the island’s most peaceful stretches of sand. This exceptional lot is ready for your dream home, and the seller is offering a custom build-to-convey option, allowing you to enjoy a seamless design-and-build experience. Create a luxury coastal retreat tailored to your style—whether modern, elevated coastal, or classic island architecture. Perfectly positioned near the beach, shops, dining, and the island’s natural beauty, this property is ideal for a full-time residence, vacation home, or high-end investment with the property zoned for nightly rentals. You do also have the option to purchase both lots 24 and 25.

837 N Shore Drive, Anna Maria
839 N Shore Drive, Anna Maria
$3,890,000
Wells Sub SubDv. ⋅ 34216 Zip Code
Presenting LOT 24 a rare opportunity to secure a beautiful buildable bayfront lot on the north end of Anna Maria Island, offering sweeping unobstructed water views, Skyway bridge views and an unparalleled coastal lifestyle. Located just moments from the pristine shores of Bean Point, this property provides coveted beach access to one of the island’s most peaceful stretches of sand. This exceptional lot is ready for your dream home, and the seller is offering a custom build-to-convey option, allowing you to enjoy a seamless design-and-build experience. Create a luxury coastal retreat tailored to your style—whether modern, elevated coastal, or classic island architecture. Perfectly positioned near the beach, shops, dining, and the island’s natural beauty, this property is ideal for a full-time residence, vacation home, or high-end investment with the property zoned for nightly rentals. You do also have the option to purchase both lots 24 and 25.

839 N Shore Drive, Anna Maria
873 N Shore Drive, Anna Maria
$2,550,000
Shore Acres SubDv. ⋅ 34216 Zip Code
Prime waterfront lot located in Anna Maria. This rare vacant parcel offers direct water frontage. Property is cleared and ready for construction, providing the perfect site for a custom coastal residence. Situated on a quiet street within close proximity to beaches, shopping, dining, and island amenities. Enjoy wide water views and direct view of the Sunshine Skyway Bridge. Don’t miss this exceptional opportunity to build your dream home on the water in Anna Maria.

873 N Shore Drive, Anna Maria
229 Willow Avenue, Anna Maria
$6,375,000
5 Beds ⋅ 5 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code
Here is your chance to own a 5 bed/4.5 bath custom waterfront residence on one of the most coveted streets in the City of Anna Maria. Enjoy the rare luxury of having direct boat access in your backyard while just a short walk to the pristine shores of the Gulf. This home offers the best of both waterfront lifestyles. Thoughtfully designed with a modern coastal aesthetic, the home features high-end appliances, custom trim details throughout, and smart home integration for effortless convenience. Each bedroom offers a private en-suite bath. A custom built-in bunk room maximizes space (sleeping up to 5) with craftsmanship that speaks to intentional design, adding versatility for guests or family. Privately tucked away on the third floor, you have the expansive primary suite that offers a serene and secluded retreat, featuring a large walk-in shower and soaking tub. Open the sliding glass doors and you are greeted with a generous private balcony that invites quiet moments of relaxation. Anchored by an oversized island, the kitchen is a chef and entertainer’s dream, featuring a gas range by Wolf, a Sub-Zero refrigerator, and a 24-bottle wine fridge. The main living level balcony is outfitted with built-in outdoor cabinetry and a premium ceramic grill, creating a fully functional alfresco cooking space just steps from the kitchen. The kitchen is the centerpiece of this well-designed floor plan that allows for the living and dining spaces to come together effortlessly. Built-in storage in the living room offers seamless organization without disrupting the clean aesthetic, while a dedicated coffee bar adds a touch of everyday luxury and convenience. Another major convenience is the elevator that gives you access to all levels of the home. These subtle yet meaningful touches are found throughout the home, reflecting a level of care and quality rarely seen. On the ground level you have a beautifully constructed cabana space that blurs the line between indoors and out, overlooking a meticulously turfed lawn and an expansive pebble finish pool that shimmers like cut glass. On rainy days, the pool cabana offers a theater like movie experience equipped with a large tv that includes a Sonos surround system and plenty of space for indoor gaming. Lime rock landscape adds geological gravitas, while an outdoor shower and a tucked-away kayak rack offer an unexpected delight. For the nautical connoisseur, the composite dock with an elevator lift provides open-water access with ease. The garage offers ample space for 2 cars, a golf cart, and all your beach toys. This meticulously maintained home has never been a vacation rental, but this could be a wonderful investment property that allows for short-term stays. Come schedule your private showing today!

229 Willow Avenue, Anna Maria
120 Hammock Road, Anna Maria
$1,895,000
3 Beds ⋅ 3 Baths ⋅ Island Cedars SubDv. ⋅ 34216 Zip Code
Virtually Staged. Some photos have been virtually staged. Waterfront living, situated in a peaceful, natural, ”Old Florida” setting , surrounded by tropical seagrapes, palm trees and mangroves this ground-level, canal-lined 3 bedroom, 3 bath property is located in an ideal spot on the north end of Anna Maria island in the city of Anna Maria. Two blocks to the shops and food on Pine Avenue, three blocks to the Anna Maria trolley stop, four blocks to the white sand of Coconut Avenue beach on the Gulf of Mexico, five blocks to the Anna Maria city pier and a seven minute idle boat ride from your dock in back to Tampa Bay. Very walkable/bikeable as there are ten restaurants within eight blocks. A sunny, open concept interior with windows that bring the outside in. New appliances, new AC, new water heater, new flooring, new kitchen cabinets with a beverage cooler and quartz counter tops. Freshly painted and wallpapered with big bedrooms and a comfortably large master bedroom with His and Her bathrooms. Three bathrooms total, two with showers and one with a bathtub. Canal side sunroom with a cozy, elevated fireplace for those cool days and a detached two car garage that has more living space potential. On the mangrove-lined canal is an 8’x24’ dock with room for your boat and plenty of room to entertain. Look for the manatees gliding by and watch for the flying wild-eyed mullet. Maybe a dolphin will pop up! House is also on a dead-end street for added protection and does not attract beach day-trip parkers. Plenty of room for a pool or two. Come take a look at the perfect spot to enjoy Anna Maria.

120 Hammock Road, Anna Maria
9403 Gulf Dr, Anna Maria
$8,000,000
9 Beds ⋅ 9 Baths ⋅ Bimini Bay Estates SubDv. ⋅ 34216 Zip Code
This stunning 9-bedroom, 8.5-bathroom beachfront property offers 3,983 sq ft of heated interior space and comes FULLY FURNISHED with luxurious details throughout. The home boasts an open-concept layout with vibrant living areas, a well-appointed chef’s kitchen, and multiple decks for enjoying ocean views. This home completed in 2020, has a custom private pool with a lazy river-inspired style, a putting green, and a rooftop deck offering 360 water views. Each of the 7 king-sized bedrooms features chic designs, ensuite baths, with many including private balconies. The primary suite includes a large tub, step-in shower, and a private ocean-view balcony. Additional amenities include a convenient elevator, laundry room, and a bar area with a wine fridge. The property’s modern coastal elegance blends perfectly with functional design, creating a space ideal for everyday living or hosting guests- Located on Anna Maria Island, this home offers beach access and endless opportunities to enjoy the sun and sand. Experience the ultimate blend of luxury and comfort in this meticulously designed coastal haven. PROJECTED RENTAL INCOME OF 450K.

9403 Gulf Dr, Anna Maria
404 North Shore Dr, Anna Maria
$5,487,000
5 Beds ⋅ 6 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code
This recently constructed home on Anna Maria Island overlooking a stunning canal is just one block from the pristine Gulf of Mexico beaches and a short walk to the restaurants and boutiques on Pine Ave. This luxurious 5-bedroom, 5.5 bath retreat offers a spectacular backyard with a private pool and swim up bar, in-ground spa, a covered shellcrete patio with seating, a ping pong table, and a BBQ grill. The coastal home features two garages and a private drive accommodating four vehicles. The main living floor has an open layout with bright natural lighting, a plush living area with sofas and a TV. The kitchen is equipped with upgraded stainless steel Bosch appliances and quartz countertops. There are many dining areas including the cozy kitchen nook, kitchen island, formal dining room, or on the balcony overlooking the canal. The 5 beautifully designed bedrooms feature elegant decor, chic furnishings, bedside lighting, and ensuite bathrooms. The second floor houses 3 bedrooms with king beds and full baths, a half bathroom for guest use, and a walk-in laundry room with a washer and dryer. The third floor includes a seating area with a table and chairs, a TV area, a wet bar, and two primary suites accessible by elevator or stairs. These suites feature king beds, private terraces, walk-in closets, and ensuite bathrooms with large glass-walled showers. Additionally, the rooftop deck provides an ideal spot for relaxation and taking in the views. This home offers a blend of luxury, comfort, and convenience, making it an exceptional choice for your Anna Maria Island life!!

404 North Shore Dr, Anna Maria

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