Location: Anna Maria
Do Not Show Listings
111 CEDAR AVE, ANNA MARIA, FL 34216
$3,895,000177 Days on yellowkey MLS ID: A4669701
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2263 Built: 1950 Tax: $35,012 (2024)Community: Anna Maria BeachSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$35,012
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: AMAZING HOME "BLUE CRUSH" ONLY 4 HOUSES TO THE BEACH!!! LOCATIONS LIKE THIS ARE RARELY AVAILABLE WEST OF GULF DRIVE! IT DOES NOT GET BETTER THAN THIS! STEPS TO BEACH AND THE WATERFRONT LIFESTYLE! This exquisite retreat offers the perfect blend of luxury, comfort, and convenience. As you step inside, you'll immediately be drawn to its enticing features. This home has been updated with no expense spared to bring it up to todays standards. Hosting gatherings becomes a delight with the updated and fully equipped kitchen, ensuring seamless meal preparation and service, especially for those poolside occasions with family and friends. The interior of this 3 bedroom, 3 bathroom haven is designed for both comfort and style. The living area, adorned with pocket sliding doors, seamlessly connects to a spacious outdoor deck, creating a harmonious indoor-outdoor living experience. Picture evenings spent watching TV, feeling the gentle breeze, and sipping drinks on the balconies. The kitchen, featuring granite countertops and stainless-steel appliances, is a chef's delight, making cooking a pleasure. An outdoor dining table on the deck provides an ideal setting for enjoying your culinary creations. The sunlit primary bedroom, with a private balcony and a luxurious ensuite bathroom, provides a dreamy retreat. Additional bedrooms include a second bedroom with balcony access and ensuite , a third bedroom with pool deck access, and an additional space could serve as a fourth bedroom, featuring bunk beds. The tropically landscaped backyard is a haven for relaxation. The stunning pool, complete with a sun shelf, invites you to bask in the Florida sun, while the expansive covered patio provides a shaded retreat for family conversations, refreshments, and games. Prime location allows for easy exploration of Pine Avenue's boutiques and culinary delights. Beach access is just a few steps away, offering warm turquoise waters and soft sand. Take a leisurely stroll to Anna Maria Island City Pier or enhance your stay with activities like chartering a fishing trip, a sunset cruise, or paddleboarding through the mangroves. Property is currently a successful rental and has forward bookings in place. Perfect for a second home or investment property. Experience the epitome of island living!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Christy Travis (941-545-5284)
519 LOQUAT DR, ANNA MARIA, FL 34216
$2,995,00061 Days on yellowkey MLS ID: A4683074
1 Days Off yellowkey (back on 4/17/2026)
Bed: 4 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 2606 Built: 1980 Tax: $29,189 (2024)Community: Lacios Sec BSpa: YesSingle Family
Taxes:$29,189
Remarks: Under contract-accepting backup offers. Welcome to 519 Loquat Drive, an exceptional waterfront retreat in the heart of Anna Maria. Positioned on a deep, boatable canal with direct, unobstructed access to Bimini Bay and Tampa Bay, this 4-bedroom, 4-bath residence delivers luxury, location, and a lucrative income opportunity, exceeding $200,000 annually - on pace to surpass $300,000 this year! Completely remodeled in 2025 and offered fully furnished including a sauna, gym, and games, this turnkey home spans over 2,600 square feet and an additional over 1300 plus square feet of non-conforming flex space which features a game room, gym, outdoor kitchen and more. The interior includes luxury vinyl flooring, quartz countertops, hurricane-impact sliders, and an open-concept design built for entertaining. The chef’s kitchen showcases stainless steel appliances, and abundant cabinetry, seamlessly flowing into the living and dining areas with a statement fireplace. This home features four bedrooms, including three with private ensuites. Two full primary ensuites showcase spa-inspired baths, generous closets, and private balcony access. Additional bedrooms offer comfort for family or guests. A dedicated laundry room with custom built-ins, ample storage, and a separate owner’s garage add convenience and functionality. Outdoor living is elevated with a brand-new heated pool and spa, all-new pool equipment, putting green, outdoor kitchen, and outdoor shower. Enjoy immediate boating access, with no bridges - to open water. Trex stairs and balcony decking ensure durability and low maintenance. Upgrades include a new metal roof, brand-new seaball, brand-new dock, new landscaping, one brand-new AC system plus a new mini-split, and a fully renovated interior from top to bottom. Currently operating as a successful Airbnb with strong rental history, this property is equally suited as a high-performing investment or private waterfront residence. Located moments from the sugar-white sands of Bean Point Beach and the shops and dining of Anna Maria, this home offers effortless access to the best of island living!
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Laura Rode (941-724-9957)
865 N SHORE DR, ANNA MARIA, FL 34216
$2,999,00075 Days on yellowkey MLS ID: TB8472180
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1754 Built: 1950 Tax: $12,367 (2024)Community: Shore Acres ResubdividedSingle Family
Taxes:$12,367
Elementary School: None
High School: None
Middle School: None
Remarks: Brand new metal roof! Fully updated, beach front stunner! Situated on the highly coveted north end of Anna Maria Island, this location is unbeatable—just steps from the stunning sunsets and sugary sands of Bean Point, and a short walk to shopping and dining hotspots on Pine Ave. Whether you’re looking for a permanent residence, vacation getaway, or short term rental, this home is move-in ready, can come furnished, and is ready to welcome you to beautiful Anna Maria Island. The open floorplan offers panoramic views of Tampa Bay from the kitchen, dining and living rooms ideal for watching wildlife, sailboats, and the twinkling lights of the Skyway Bridge. The kitchen is newly renovated with brand new appliances, cabinetry and counter tops. Additional updates include roof (2026), AC (2025), water heater (2025), new interior paint (2025), updated lighting and hardware, newly reinforced seawall. The sandy backyard with a new patio, is the perfect beach hangout spot to grill, relax, and even cast a line and fish from your own backyard. Designed for beach living, this island home includes ample storage for all your gear, including a large laundry room, multiple storage closets, and a detached 1-car garage—perfect for your beach essentials, island golf cart, and bikes. This beachfront gem offers everything you need to embrace the ultimate Anna Maria Island lifestyle.
Listing is courtesy of: PEOPLE'S CHOICE REALTY SVC LLC (813-933-0677)
Listing Agent: Lauren Haseman (813-240-4407)
517 SPRING AVE, ANNA MARIA, FL 34216
$1,800,0009 Days on yellowkey MLS ID: A4689815
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1985 Tax: $20,257 (2025)Community: Anna Maria BeachSingle Family
Taxes:$20,257
Tax Year: 2025
Remarks: Welcome to the highly sought after North end of Anna Maria Island. 2 Bed / 2 Bath Island Home featuring: Open Floor Plan, Spacious Kitchen, Front & Back Balconies & Large Fenced Back Yard. Just steps away from the Morning Sunrise or Evening Sunsets, Take your Pick. A short walk to the Anna Maria City Beach & the bustling offering of shops & dining venues on Pine Avenue. Use your creativity to convert the large open 1st floor workshop into your personal 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, Convenience, & investment potential. This one is definitely worth a visit. Call today to schedule your private showing.
Listing is courtesy of: O'STEEN GROUP INC (941-527-4227)
Listing Agent: Clay Osteen (941-704-7038)
101 SUNSET LN, ANNA MARIA, FL 34216
$2,995,00083 Days on yellowkey MLS ID: A4679879
0 Days Off yellowkey (back on 3/25/2026)
Bed: 4 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 2507 Built: 2002Monthly Fee: $63 Tax: $29,226 (2024)Community: Sunset CoveSpa: NoSingle Family
Taxes:$29,226
Remarks: Under contract-accepting backup offers. 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
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
518 SPRING AVE, ANNA MARIA, FL 34216
$4,050,00046 Days on yellowkey MLS ID: A4685202
REDUCED by $150,000 (3.6%) on 04/16/2026
Bed: 6 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 3165 Built: 2024 Tax: $43,837 (2025)Community: Anna Maria BeachSpa: YesSingle Family
Taxes:$43,837
Remarks: Dreaming of Island Living? This custom-built coastal home perfectly captures the essence of luxury island living on beautiful Anna Maria Island. This exceptional six-bedrooms, six-and-a-half-baths residence spans over 3,100 square feet and was thoughtfully designed with no expense spared or detail overlooked. The open concept living & dining space includes a chef inspired kitchen which boasts solid wood cabinetry, quartz countertops, and upgraded appliances. Each serene bedroom is its own private retreat, complete with ensuite baths, custom tilework, and spa-like features. Made for entertaining with expansive spaces to enjoy RELAXING inside OR out. Your private resort style backyard is a true sanctuary with a sparkling oversized heated pool and spa surrounded by lush landscaping and durable low maintenance turf with putt-putt golf. A covered lanai and multiple balconies provide inviting spaces for relaxing, dining, and family fun. Whether you’re soaking up the sun poolside or enjoying the sunrise from the Bay AND sunset views from the Gulf from the rooftop deck, the outdoor living experience is unmatched. This coastal beauty will come completely Designer Turn-Key Furnished with upscale coastal finishes throughout. CURRENTLY A RENTAL PROPERTY WITH FORWARD BOOKINGS IN PLACE!!! This home is perfect for a full-time residence, vacation home or investment property and is ideally located on the North End of Anna Maria Island. Stroll one street over to beloved Pine Avenue and browse through the numerous shops and restaurants. The Bay and famous "almost rebuilt" Anna Maria City Pier are at the end of the street. AND the island's world-renowned Gulf beaches are a few blocks away. Hop on your bikes or golf cart to experience Anna Maria's full charm. Your ISLAND DREAM HOME AWAITS!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-778-7777)
Listing Agent: Sabrina Ullmann (203-300-8181)
270 GLADIOLUS ST, ANNA MARIA, FL 34216
$1,770,00068 Days on yellowkey MLS ID: A4682093
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1326 Built: 1967 Tax: $20,985 (2025)Community: Luana IslesSpa: YesSingle Family
Taxes:$20,985
Remarks: Located just blocks from the beach, White Palms is a 3-bedroom, 2-bathroom island home situated on a large corner lot with a spacious backyard, offering excellent outdoor living close to the Gulf. The corner location provides added openness, while mature palms and established landscaping create a private coastal setting. The home features a bright, open layout designed for comfortable island living, with well-sized bedrooms and recently updated finishes throughout. The main living areas connect seamlessly to the outdoor spaces, making it ideal for both everyday living and entertaining. The backyard centers around a private pool, creating a true outdoor retreat with ample space for lounging and gathering. Whether used as a primary residence, second home, or seasonal escape, the layout offers flexibility and function. Located in Anna Maria's nightly vacation rental area, White Palms is an established rental property with documented income, offering immediate investment potential alongside its lifestyle appeal. Just a short walk to the sand, this property combines beach proximity, outdoor space, and proven rental performance in one well-located island home.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Dee Munn (407-346-4422)
313 HAMMOCK CIR, ANNA MARIA, FL 34216
$3,995,00063 Days on yellowkey MLS ID: A4682229
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3755 Built: 2017 Tax: $42,872 (2025)Community: Coconut BayouSpa: YesSingle Family
Taxes:$42,872
Remarks: This waterfront coastal retreat embodies refined island luxury, offered completely turnkey and thoughtfully designed for both elevated living and exceptional entertaining. Positioned on a quiet cul-de-sac the home makes an immediate impression with its stately architecture, paver driveway, lush tropical landscaping, and landscape lighting that beautifully illuminates the property at dusk. Inside, travertine flooring flows throughout, complemented by crown molding in every room and tray ceilings that add architectural depth and sophistication across all three levels. The top floor serves as the heart of the home, where an expansive living and dining area is framed by large sliders that capture vibrant sunset skies and lead to two generous balconies, seamlessly blending indoor and outdoor living. The chef’s kitchen is a showpiece, appointed with premium Monogram appliances, a professional gas range with pot filler, custom cabinetry, striking backsplash detail, and abundant counter space designed for effortless entertaining. The living room offers an abundance of natural light that frames a beautiful fireplace adding an elevated ambiance. Designer lighting, custom stair railings, and carefully curated finishes create a cohesive coastal elegance that feels both polished and welcoming. The mid-level hosts 4 spacious bedrooms enhanced with shiplap accent walls in select rooms, adding warmth and texture, along with a comfortable family room that opens to an oversized balcony overlooking the tranquil bayou. A private elevator provides convenient access to every floor, while modern enhancements including a security system, Sonos sound system inside and out, solar panels, and a tankless hot water heater deliver efficiency and peace of mind. Outdoors, the property transforms into a true waterfront oasis featuring a sparkling heated pool and spa, fire features, expansive paver deck, screened-in patio lounge area, and multiple covered spaces ideal for year round enjoyment. The private dock is equipped with electric and water, offering boating access and completing the ultimate Florida lifestyle experience. The pass-through two car garage, paired with separate storage rooms is designed to accommodate lifestyle amenities and the home’s location within a short-term rental zone presents outstanding investment potential. From sunrise coffee on the balcony to sunset reflections dancing across the bayou, every detail of this exceptional residence has been thoughtfully designed to capture the very best of coastal living.
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Darcie Duncan (941-779-0304)
821 S BAY BLVD, ANNA MARIA, FL 34216
$7,995,00077 Days on yellowkey MLS ID: A4679859
0 Days Off yellowkey (back on 4/15/2026)
Bed: 5 Bath: 5.5 Gar: 5 Liv Area Sq Ft: 4964 Built: 2025 Tax: $14,490 (2025)Community: South Bay BlvdSpa: YesSingle Family
Taxes:$14,490
Remarks: Under contract-accepting backup offers. A rare expression of modern island luxury, this newly constructed Polynesian-inspired estate is ideally positioned on South Bay Boulevard in Anna Maria, offering privacy, architectural distinction, and sweeping bay views. Thoughtfully designed around a private, lush interior courtyard, the home centers on a resort-style pool and spa that seamlessly connect to covered outdoor living areas, creating a true indoor-outdoor lifestyle. The residence offers 5 bedrooms, 6 bathrooms, and expansive living spaces defined by clean architectural lines, warm wood accents, and walls of glass that frame tranquil water and tropical landscape views. The open main living level is ideal for entertaining at scale, anchored by a chef’s kitchen featuring custom cabinetry, a full walk-in pantry, and an oversized island, complemented by generous dining and gathering spaces that open directly to the pool courtyard. The primary suite is a private retreat, offering a custom-designed walk-in closet with a dedicated laundry area and a spa-inspired bath with a soaking tub positioned before picture windows overlooking the bay. A dramatic indoor-outdoor shower further enhances the immersive waterfront experience. Outdoor living is elevated with multiple covered terraces, a tranquil spa beneath a living green ceiling, and an expansive rooftop deck showcasing panoramic water views—perfect for sunset enjoyment and evening entertaining. Additional highlights include an elevator servicing all levels, premium finishes throughout, and thoughtfully designed spaces that balance luxury with everyday livability. Located just moments from Anna Maria’s renowned beaches, dining, and shopping, this exceptional residence presents a rare opportunity to own a newly built architectural masterpiece on the bay.
Listing Agent: Charles Buky (941-228-6086)
807 S BAY BLVD, ANNA MARIA, FL 34216
$2,300,00069 Days on yellowkey MLS ID: A4680500
2 Days Off yellowkey (back on 4/15/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1969 Built: 1981 Tax: $11,465 (2025)Community: Bay HarborSingle Family
Taxes:$11,465
Remarks: Under contract-accepting backup offers. Experience the perfect blend of modern luxury and coastal functionality in this impeccably maintained canal-front retreat. Located on the prestigious North End of Anna Maria Island, this property offers the best of both worlds: a serene, full-time sanctuary or a high-performing investment (7 nights or less). Originally transformed by a total remodel and significant additions in 2016, this elevated 3-bedroom, 2-bathroom residence offers a sophisticated island lifestyle on an expansive, oversized lot of over 10,000 square feet. The home is thoughtfully designed for both comfort and accessibility, featuring a private elevator that services the residence with ease. The interior transitions seamlessly from open-concept living areas to a unique ground-level bonus room. This versatile space is fully climate-controlled with its own bathroom, making it an ideal candidate for a private guest suite, a secluded home office, or a premier media/game room. Outside, the property is a true maritime sanctuary. Boaters will appreciate the 10,000 lb boat lift and the peace of mind provided by a newer seawall - all installed in 2012. The outdoor possibilities are as vast as the lot itself; with ample room to install a custom pool and outdoor kitchen, you can create the ultimate backyard oasis. Whether you are enjoying the breeze from the elevated decks or embarking on a sunset cruise from your backyard, 807 S Bay Blvd represents a rare opportunity to own a waterfront home built for the modern Floridian lifestyle - a true boater’s sanctuary!
Listing Agent: Lindsey Strickland (941-737-3491)
109 TERN DR, ANNA MARIA, FL 34216
$1,499,00041 Days on yellowkey MLS ID: A4685406
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1223 Built: 1968 Tax: $17,706 (2025)Community: Luana IslesSingle Family
Taxes:$17,706
Remarks: Delightful waterfront home on the famed North end of Anna Maria Island. This 2 bedroom 2 bathroom home offers incredible opportunities for adventure. Whether it is the sand of the Gulf beaches you seek or if enjoying the water from a boat, kayak, or paddle board is your thing the choice is yours. Another incredible benefit of this location is the proximity to Pine Ave, full of fun shopping and eateries. Generously sized lot is positioned on a cul-de-sac providing privacy due to no through traffic. Concrete block paired with a metal roof creates a formidable structure. As you enter the home you will be welcomed by a sense of coziness. The kitchen features solid wood cabinetry and exquisite Taj Mahal quartzite countertops. Entertaining is aided by the in-ceiling home speaker system. Enjoy year around serene water views from the 300 square foot screened-in lanai equipped with four ceiling fans. Single car garage for all your storage needs or get creative for a possible third bedroom. The large lot leaves ample room for a pool to the front of the house. Schedule a showing today and discover if this piece of paradise if right for you.
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Justin Powell (941-718-0294)
311 POINSETTIA RD, ANNA MARIA, FL 34216
$1,775,000406 Days on yellowkey MLS ID: TB8359176
Bed: 3 Bath: 2.0 Gar: 4 Liv Area Sq Ft: 1296 Built: 1988 Tax: $22,833 (2024)Community: Luana Isles 1St AddSingle Family
Taxes:$22,833
Remarks: Experience the ultimate coastal retreat at 311 Poinsettia Rd in Anna Maria, FL—a home where luxury meets laid-back island living. This beautifully renovated, elevated sanctuary boasts stunning waterfront views, a sparkling pool, and your very own private boat dock with a lift, inviting endless adventures on the water. Enjoy the convenience of RV/boat parking and a generous driveway that sets the stage for memorable gatherings. Just a leisurely stroll to pristine beaches and a quick golf cart ride to lively restaurants and bars, every moment here is infused with warmth, charm, and the promise of a vibrant lifestyle. Welcome home to your dream coastal haven. This property is currently used as a NIGHTLY rental bringing in up to $25,000/month so far this year. Please do not disturb the guests.
Listing is courtesy of: WEICHERT REALTORS EXCLUSIVE PROPERTIES (813-426-2669)
Listing Agent: Thomas Zopf, Ii (727-366-1983)
12106 GULF DR, ANNA MARIA, FL 34216
$6,495,00082 Days on yellowkey MLS ID: A4679008
REDUCED by $500,000 (7.1%) on 04/14/2026
Bed: 4 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3469 Built: 2005 Tax: $63,179 (2024)Community: Anna Maria Beach First AddSpa: NoSingle Family
Taxes:$63,179
Remarks: Unobstructed Gulf views define this true Gulf-front home on one of the most desirable stretches of Anna Maria Island. With nothing between the property and the shoreline, the balcony captures nearly three-quarters of a mile of uninterrupted beach frontage—an exceptionally rare vantage point created by the natural contour of the island to the north. Very few homes on AMI offer a view corridor this wide or this direct. Built in 2005 by Whitehead Construction, a respected builder in Manatee County, the home is well constructed and offers a layout well-suited for an immediate move-in or a next chapter renovation. The 4-bedroom, 5.5-bath design includes two Gulf-facing decks: one off the main living area and a private third-floor terrace exclusive to the primary suite. The location is one of the island’s best. Positioned at Coconut and Gulf, the home benefits from quieter traffic patterns while still offering walkable access to Pine Avenue’s coffee shops, restaurants, and boutiques. Sunset views are a nightly event, and beach access is just steps from the door. Additional features include a private pool, space for a covered outdoor kitchen, and a two-car garage with room for a golf cart and beach gear. At the time of construction, finishes were in the top tier for the island, and the home is now ready for a thoughtful update to match its premier location. Opportunities like 12106 Gulf are limited on Anna Maria Island. True Gulf-front ownership, a wide and unobstructed view corridor, and a location that delivers both privacy and walkability make this property stand out. Savvy buyers seeking the best views on the island will recognize the significance of this address.
Listing is courtesy of: REEL COASTAL PROPERTIES, LLC (941-265-3247)
Listing Agent: William Worth (214-707-6296)
801 N SHORE DR, ANNA MARIA, FL 34216
$10,850,000101 Days on yellowkey MLS ID: A4676858
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4728 Built: 2005 Tax: $64,344 (2024)Community: Shore Acres First AddSpa: NoSingle Family
Taxes:$64,344
Remarks: 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. Thoughtfully curated and offered turnkey furnished, this extraordinary home is appointed with bespoke furnishings and window treatments by Italian artisans, complemented by world-renowned works of art that elevate every space. 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.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Becky Sirigotis (941-201-8000)
224 CHILSON AVE, ANNA MARIA, FL 34216
$6,344,99936 Days on yellowkey MLS ID: A4686584
Bed: 6 Bath: 6.5 Gar: 4 Liv Area Sq Ft: 4525 Built: 2024 Tax: $17,567 (2024)Community: Bimini Bay EstatesSpa: YesSingle Family
Taxes:$17,567
Remarks: Step into unparalleled luxury with this fully furnished, 6-bedroom, 7-bathroom deep-water canal-front estate, perfectly situated just two blocks from the pristine sands of Anna Maria Island. This isn’t just a home, it’s a statement, and a legacy investment all in one extraordinary package. Crafted with full concrete block construction, this residence is engineered for strength, security, and longevity, featuring hurricane impact-rated windows and doors and a Cat 5-rated roof. Every detail has been designed to provide absolute peace of mind, whether you’re seeking a lavish year-round retreat or a premium income-generating property. Inside, the home is a masterclass in modern coastal elegance. Soaring ceilings, expansive walls of glass, and curated designer lighting flood the interiors with natural light, creating an atmosphere of serene sophistication. The gourmet chef’s kitchen is a showpiece, boasting custom cabinetry, dramatic quartz countertops, a sculptural concrete range hood, a full Sub-Zero appliance suite, and a hidden walk-in Butler’s pantry, blending beauty with function flawlessly. Every space has been thoughtfully curated from the open-concept living and dining areas to multiple covered balconies and loggias that embody effortless indoor-outdoor living. The primary suite is a sanctuary, complete with a spa-inspired bathroom, walk-in closet, and private balcony overlooking the sparkling water. The rooftop deck is an entertainer’s dream and a private retreat all in one. Designed for gatherings under the stars or quiet moments of reflection, this oversized outdoor space offers panoramic views of the canal, the island, and golden Gulf sunsets, with multiple seating and lounge areas for ultimate comfort and luxury. Step outside to your private tropical oasis. The backyard features a resort-style pool and spa, lush palms, and generous lounging areas, all framing a deep-water canal with direct, bridge-free access to the Gulf of Mexico, making it perfect for boating enthusiasts. Offered fully turnkey furnished, professionally designed with luxury pieces throughout, this home allows immediate enjoyment or a high-end rental income stream. With demand for premium Anna Maria Island vacation homes at an all-time high, this property offers both an unmatched lifestyle and an exceptional investment opportunity. Words and photos only hint at the experience. To truly appreciate the craftsmanship, scale, and sheer beauty, a private tour is essential. Don’t miss your chance to claim this crown jewel of Anna Maria Island. Schedule your exclusive showing today.
Listing is courtesy of: AMI REALTY GROUP (941-794-0204)
Listing Agent: George Desear (941-725-7163)
612 FERN ST, ANNA MARIA, FL 34216
$1,795,000125 Days on yellowkey MLS ID: TB8456599
2 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1472 Built: 1991 Tax: $25,404 (2025)Community: Shore Acres Fourth AddSpa: NoSingle Family
Taxes:$25,404
Remarks: Under contract-accepting backup offers. Great Income Opportunity! Short-Term Rental approved on Airbnb, VRBO, etc! Over $174,000 in Yearly Rental Income with upside! Wake up every day in true island paradise at Anna Maria Chateau! Ideally positioned at the northern tip of the exclusive Anna Maria Island, just moments from the iconic Bean Point and minutes from some of the world’s most celebrated beaches, this pristine coastal retreat offers the ultimate blend of luxury, comfort, and location. From the moment you step inside, you’re welcomed by soaring ceilings and a bright, open great room floor plan designed for effortless entertaining and relaxed island living. Exceptional custom craftsmanship shines throughout, showcasing hand-scraped hickory wood floors, beautiful tongue-and-groove ceilings and walls, and thoughtful architectural details at every turn. The heart of the home is the chef-inspired kitchen, perfectly situated off the family room and equipped with stainless steel appliances, a French-style refrigerator, classic white shaker cabinetry, granite countertops, and a spacious island with breakfast bar seating ideal for gathering with family and friends. The spacious primary suite serves as a private retreat, featuring an en-suite bath with dual sinks and granite countertops. Two additional well-appointed bedrooms share a full bath, providing comfortable accommodations for guests and plenty of space for everyone to unwind. Multiple common areas throughout the home invite relaxation and connection. Step outside and experience resort-style living. Sip your morning coffee on the oversized upstairs deck, take a refreshing dip in the heated saltwater pool, or enjoy friendly competition in the expansive recreation room. The elevated first floor offers ample storage for all your water toys, bikes, and beach gear. This exceptional property offers incredible versatility perfect as a full-time residence, a private island getaway, or a highly desirable income-producing rental in one of Florida’s most sought-after destinations. Bonus: This elevated home experienced NO interior damage during the 2024 storms, providing added peace of mind. Recent updates include: brand-new water heater (2025) and new pool pump (2024). Love the island’s golf-cart-friendly lifestyle? There’s plenty of space for golf cart parking and more. Cruise by golf cart, bike, or take a leisurely walk to nearby restaurants, boutiques, and local favorites, all just blocks from your doorstep. This is your opportunity to own a true slice of paradise on one of Florida’s most beloved islands—Anna Maria Island.
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Mark Fazzini (727-485-9981)
111 PALMETTO AVE, ANNA MARIA, FL 34216
$5,125,00062 Days on yellowkey MLS ID: A4682245
REDUCED by $125,000 (2.4%) on 04/07/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 2677 Built: 2025 Tax: $16,293 (2025)Community: Anna Maria BeachSpa: YesSingle Family
Taxes:$16,293
Remarks: Experience elevated island living in this exceptional brand-new custom four bedroom four and a half bath coastal retreat by Eason Builders Group Construction, ideally positioned west of Gulf Drive on Anna Maria Island just moments from the sugar-white sands and turquoise waters of the Gulf. Thoughtfully designed to capture both refined personal enjoyment and outstanding vacation rental performance, this architecturally striking residence blends sophisticated design, superior craftsmanship, and effortless indoor-outdoor living in one of the island’s most coveted locations. From the moment you enter, soaring ceilings with rich wood detail and expansive walls of impact-rated glass create a dramatic yet relaxed coastal ambiance filled with natural light. The open-concept floor plan is ideal for entertaining, seamlessly connecting the main living areas while maintaining an intimate, luxurious feel. The chef’s kitchen serves as the heart of the home, featuring an oversized quartz island with ample seating, custom cabinetry, premium appliances, designer lighting, and abundant storage. The kitchen flows effortlessly into the spacious great room, highlighted by a sleek modern fireplace and dramatic sliding glass doors that open to covered terraces, creating the ultimate setting for indoor-outdoor gatherings. The private elevator offers convenience & accessibility. Step outside to your private resort-style backyard oasis where a stunning heated pool with elevated spa takes center stage. Generous covered lounge areas, outdoor dining space, and lush tropical landscaping provide both privacy and year-round enjoyment, offering owners & guests a true boutique resort experience. Whether hosting sunset cocktails or enjoying a quiet afternoon poolside, this outdoor environment is designed for relaxation and entertainment. Each beautifully appointed bedroom offers a tranquil retreat, while spa-inspired bathrooms elevate daily living with freestanding soaking tubs, glass-enclosed showers, dual vanities, & upscale designer finishes. A thoughtfully designed custom bunk room enhances flexibility & maximizes short-term rental occupancy, making the home especially appealing for larger groups & multi-generational stays. Crowning the residence is an expansive rooftop deck delivering sweeping Gulf views. This spectacular vantage point creates an unforgettable setting for sunset gatherings, morning coffee, or evening stargazing—one of the most desirable features for both homeowners & vacation guests alike. Beyond the property itself, embrace the quintessential island lifestyle. Leave the car behind & explore by golf cart or bicycle, cruising to the charming boutiques, art galleries, & acclaimed restaurants along Pine Avenue. Enjoy morning beach walks, afternoons on the water, and evenings filled with breathtaking Gulf sunsets just steps from your door. Built with impact windows and doors, high-end designer finishes, and meticulous attention to detail throughout, this residence offers both peace of mind and enduring quality. With projected annual rental revenue of approximately $400,000, the home presents a compelling investment opportunity while delivering an unparalleled luxury lifestyle. Combining prime west-of-Gulf Drive positioning, exceptional craftsmanship, resort-style amenities, and strong income potential, this remarkable property represents the very best of Anna Maria Island living.
116 HAMMOCK RD, ANNA MARIA, FL 34216
$2,395,000127 Days on yellowkey MLS ID: A4675510
0 Days Off yellowkey (back on 4/12/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2366 Built: 1969 Tax: $16,464 (2025)Community: Island CedarsSpa: NoSingle Family
Taxes:$16,464
Remarks: Under contract-accepting backup offers. Discover Mia Bella — a rare canal-front estate on Anna Maria Island’s coveted North End. Set on an oversized 11,000+ square-foot lot with more than 94 feet of boatable canal frontage, this exceptional property offers direct boating access to the Intracoastal Waterway, Tampa Bay, and the Gulf of Mexico, along with a private dock. Located on a quiet residential street just steps from the sandy beaches and two blocks from Pine Avenue’s shops and dining, Mia Bella delivers the ultimate island lifestyle where location truly matters. Completely restored and thoughtfully updated, this distinctive property blends Old Florida charm with modern coastal design. The estate includes a spacious single-level main house and an attached glass-wrapped villa, both positioned to capture tranquil canal and pool views framed by mangroves and passing boats. The main residence offers three bedrooms and three full bathrooms, including two ensuite suites, along with an oversized two-car garage — a rare and highly sought-after feature for an island home with plenty of space for a golf cart. Restored terrazzo floors create a light, breezy coastal feel throughout. The brand-new kitchen features classic white shaker-style cabinetry, quartz countertops, and stainless steel appliances and opens to the main living areas designed for easy indoor–outdoor flow. Hurricane-impact doors, windows, and sliders are installed throughout the main house, which is fully flood-protected with Hammerhead flood barriers and also features a new metal roof for added durability. All bathrooms have been fully updated with fiberglass showers, quartz vanity tops, and Kohler fixtures. The attached villa is a true showpiece, surrounded on three sides by floor-to-ceiling glass and highlighted by a dramatic lofted ceiling. The ground level includes a sleeping area, kitchenette, two-story living space, and a full bath, while a spiral staircase leads to a charming second-floor loft bedroom (access is outside via the 2nd floor deck) — a fun and flexible retreat for guests. Mature tropical landscaping and professional lighting provide privacy and ambiance throughout the property, creating a serene island setting. Mia Bella offers additional protection with Hammerhead flood barriers at the front entry, both garage doors, and the back sliding door. Recent improvements include impact-rated openings, new kitchen cabinets, bathroom vanities, a boat dock, redesigned decks, a resurfaced pool, new pool equipment, and a new metal roof. The list goes on and on. Offered fully furnished and operating as a successful vacation rental with strong income history and future bookings in place, Mia Bella is ideal as a luxurious second home or a high-performing investment. Oversized lot, premier North End location, boatable canal frontage with dock access, rare oversized garage, and thoughtfully designed storm and flood protection for the main house make this a truly special Anna Maria Island property. *Property information deemed reliable but not guaranteed. Buyer and Buyers agent to verify.
Listing is courtesy of: SALTY MERMAID REAL ESTATE LLC (941-224-3304)
Listing Agent: Liz Blandford (941-224-3304)
136 CRESCENT DR, ANNA MARIA, FL 34216
$1,199,999156 Days on yellowkey MLS ID: A4671637
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1068 Built: 1970 Tax: $16,574 (2025)Community: Lake La Vista RepSingle Family
Taxes:$16,574
Remarks: Best priced Anna Maria City move in ready single family home with room for a pool. Anna Maria Island charming remodeled coastal cottage. Newer metal roof, ALL impact windows and sliders in place for added peace of mind. NEW A/C, Washer/Dryer, Refrigerator, Dishwasher, Bedroom Carpets and Interior Doors. 2024 Now is the time for new owners to make 136 Crescent Dr their own island oasis. Whether you are looking or a primary residence, second home or investment property this home is an ideal opportunity. Located in the quiet and serene City of Anna Maria on the north end where short term rentals are welcome. Just north of quaint shops and restaurants of renowned Pine Avenue and Anna Maria City Pier. Bayfront beach park, Rod and Reel Pier and tranquil Bean Point are all nearby. Gulf beaches with their soft white sand, turquoise waters and dazzling sunsets await your presence. Careful consideration was given to the interior remodel a few years ago. Bright wide plank ceramic tile flooring throughout the living area. Kitchen offers plantation shutters, quartz countertops, recessed lighting, soft close cabinetry, stainless steel appliances, breakfast bar and cozy dining nook surrounded by stylish built in storage. Spacious comfortable living area opens to private screened lanai surrounded by lush tropical plantings. Lovely primary suite offers king size bedding, sliders to screened lanai and private bath with walk in shower and granite countertops. Secondary bedroom adorned with built in nightstands, recessed TV console and pocket door to hall bath for another en suite. Both bedrooms offer closets with built ins, plush carpeting, plantation shutters and ceiling fans. Relax on the private rear patio and you’ll be surrounded by a plethora of tropical plantings of Bougainvillea, Crotons, Birds of Paradise, Ixora and Schefflera to name a few. Fresh new plantings blooming this Spring. Carport offers kayak/bike storage, utility closet and outdoor shower. Room for a pool if you desire. Voluntary HOA available to enjoy the day dock and kayak launch. Come an explore the whole island experience with free trolley to shops/dining of Holmes Beach and eclectic mix of stores along Bridge Street and Bradenton Beach.
Listing is courtesy of: ISLAND REAL ESTATE-ANNA MARIA (941-778-6066)
Listing Agent: Liz Codola (941-812-3455)
704 GLADIOLUS ST, ANNA MARIA, FL 34216
$2,945,000333 Days on yellowkey MLS ID: A4653068
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2415 Built: 2014 Tax: $34,331 (2024)Community: Shore Acres Third AddSpa: NoSingle Family
Taxes:$34,331
Remarks: PRICE CHANGE! You are just a short walk to Beach and Bay from this quality constructed 4 bed/3 bath pool home with private elevator. This ideally appointed home has TWO living rooms, large third floor porch with peeks of the water, dual zone air conditioning, open floor plan with spacious kitchen, Bosch appliances, custom lighting throughout, and covered pool deck in your private yard with mature landscaping. The quiet street in the coveted North End of Anna Maria allows short term rentals and enjoys easy access to some of your island favorites, including Pine Avenue. Storage abounds with two car garage space, ample cabinetry and custom closets. You will love the abundant features of this beautiful home, including high ceilings, plantation shutters, and 18 inch tile and plank wood flooring. Come enjoy the peace and serenity of this perfect island paradise!
Listing Agent: Erin Leathem (941-448-5616)
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