Location: Bimini Bay Estates, Anna Maria
Do Not Show Listings
224 CHILSON AVE, ANNA MARIA, FL 34216
$6,344,99927 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$17,567
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
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)
50 N SHORE DR, ANNA MARIA, FL 34216
$4,850,00090 Days on yellowkey MLS ID: A4677955
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3055 Built: 2020 Tax: $44,429 (2025)Community: Bimini Bay EstatesSpa: YesSingle Family
Taxes:$44,429
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: An exceptional opportunity to experience true island living where waterfront boating and beach access come together—just minutes apart—on Anna Maria Island. This beautifully designed 4-bedroom, 4.5-bath turnkey furnished coastal residence offers a rare blend of luxury, comfort, and lifestyle, ideally situated on a tranquil canal while remaining only moments from the island’s world-famous white-sand beaches. Homes offering private boating access this close to the beach are increasingly difficult to find on Anna Maria Island. From this property, enjoy the freedom of launching your boat from your own backyard, paddleboarding at sunrise, or cruising to open water—then return home and head to the beach cart in minutes. It is this seamless balance of water, sand, and island convenience that truly sets this home apart. Built in 2020 and thoughtfully designed for modern coastal living, the home features a bright, open floor plan filled with natural light and enhanced by coastal-inspired finishes and refined details throughout. The gourmet kitchen serves as the heart of the home, equipped with top-of-the-line stainless steel appliances, quartz countertops, a wine refrigerator, and generous prep and storage space—perfect for entertaining after a day on the water or hosting family and friends. Each of the four bedrooms includes a private en-suite bath, offering comfort and privacy for owners and guests alike. An elevator provides easy access to all levels, adding convenience for everyday living. Outdoor living is where this home truly shines. The private backyard retreat features a heated pool and spa with sun exposure, an expansive pool deck, lush tropical landscaping, and multiple outdoor living and dining areas designed for relaxing, entertaining, and enjoying the island breeze. Whether you’re gathering for sunset cocktails, enjoying a quiet evening under the stars, or unwinding after a beach day, this space feels like a personal resort. For boating enthusiasts, the property offers a private 16’ dock and an oversized boat slip measuring approximately 12’ x 35’, providing direct access to Tampa Bay and the Gulf. This setup is ideal for daily cruising, fishing excursions, paddleboarding, or simply enjoying the peaceful waterfront setting. Situated on an unusually large lot for Anna Maria Island with over 12,000 sq ft , the home also provides ample parking, a spacious driveway, garage, and dedicated golf cart storage—features that add meaningful convenience for both owners and guests in this sought-after location. Located in the heart of Anna Maria Island, this property places you just minutes from pristine beaches, Pine Avenue’s charming boutiques and dining, Bean Point’s legendary sunsets, local art galleries, and the island’s laid-back, walkable, golf-cart-friendly lifestyle. Known for its relaxed pace, vibrant community, and old-Florida charm, Anna Maria Island continues to be one of Florida’s most beloved coastal destinations. Whether you are searching for a full-time residence, a luxury second home, or a proven income-producing vacation rental with forward bookings already in place, this exceptional property offers unmatched versatility and long-term value. Combining waterfront access, beach proximity, turnkey luxury, and an unbeatable island location, this home represents a rare chance to own one of Anna Maria Island’s most desirable lifestyle properties.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Christy Travis (941-545-5284)
209 WILLOW AVE, ANNA MARIA, FL 34216
$6,795,00011 Days on yellowkey MLS ID: A4688392
Bed: 6 Bath: 7.0 Gar: 3 Liv Area Sq Ft: 4154 Built: 2021 Tax: $69,298 (2025)Community: Bimini Bay EstatesSingle Family
Taxes:$69,298
Remarks: Discover coastal luxury at 209 Willow in the heart of Anna Maria Island on a very sought out quiet street. This stunning canal-front home offers the perfect blend of relaxed island living and high-end amenities, just 10 houses from the pristine sugar-sand beaches of the Gulf while situated on a canal, you get the best of both worlds! Step inside to this 6 bedroom, 6 bathroom, 2 half bath, thoughtfully designed home. This home has never been a rental, it is very well taken care of. The interior has just about every feature you can think of, natural light, soaring ceiling, impact slider doors/windows, wet bar, very large wine cooler, whole house generator for peace of mind, a water filtration system/softener, and a pressure booster. Each bedroom is spacious and has its own private en-suite bathroom ensuring your family and guests have their own privacy. Current owners are using the 6th bedroom as an office, or you can turn it into a bedroom. Kids will love the fun built-in bunk bed room, while still plenty of space to play too. If desired, an upstairs closet has washer/dryer hookups if you wanted an additional set on upper level. Relax on the rooftop deck with breathtaking views or unwind on the lower deck complete with comfortable loungers. The highlight is the resort-style backyard: a heated pool and spa with a beautiful Shellcrete bar accented by shimmering sea glass. Includes a refrigerator and grill. A screened-in covered downstairs area provides shaded comfort, while boaters will appreciate the private dock and lift right on the canal—perfect for quick access to the Intracoastal and Gulf waters. The epoxy-finished 3-car garage adds durability and style to your storage space. Big outdoor shower so you can rinse off after the sandy beach. Located on a quiet canal yet incredibly convenient, this home sits in one of Anna Maria’s most desirable spots. Enjoy easy access to world-class beaches, charming island dining, and everything the Florida Gulf Coast has to offer. Whether you’re seeking a primary residence, a vacation retreat, or an exceptional investment property, 209 Willow Avenue delivers island elegance with every modern comfort.
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Jason Sato (941-778-7200)
9403 GULF DR, ANNA MARIA, FL 34216
$8,000,000432 Days on yellowkey MLS ID: A4633389
Bed: 9 Bath: 8.5 Gar: 2 Liv Area Sq Ft: 3983 Built: 2020 Tax: $49,941 (2024)Community: 7044700; Bimini Bay Estates; Lot 61; Pb 8/75Single Family
Taxes:$49,941
Remarks: 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- GREAT RENTAL OPPORTUNITY. 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.
Listing is courtesy of: ANNA MARIA ISLAND BEACHES RE (941-567-5234)
Listing Agent: Gregg Bayer (941-799-9096)
319 TARPON ST, ANNA MARIA, FL 34216
$7,195,00021 Days on yellowkey MLS ID: A4684329
Bed: 5 Bath: 5.5 Liv Area Sq Ft: 3484 Built: 2026 Tax: $14,648 (2025)Community: Bimini Bay EstatesSingle Family
Taxes:$14,648
Remarks: New construction waterfront estate offering over 7,000 square feet of stunning indoor-outdoor living, delivered fully turnkey furnished. Positioned on a quiet dead-end street, this 5-bedroom, 5.5-bath residence captures sweeping long canal views from every level along a 75’ wide waterway. Designed for modern coastal living with elevated finishes, open-concept spaces, and seamless indoor-outdoor flow. A chef’s kitchen anchors the main living area, while well-appointed bedrooms provide comfort and flexibility. Built to current coastal standards with elevated construction, reinforced systems, and a full-service elevator. Outdoor living features a resort-style pool, multiple entertaining areas, and a dramatic third-floor balcony with panoramic water views. A premier island listing that combines luxury, privacy, and exceptional waterfront living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Dee Munn (407-346-4422)
242 OAK AVE, ANNA MARIA, FL 34216
$7,499,000173 Days on yellowkey MLS ID: A4668575
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3722 Built: 2020Community: Bimini Bay EstatesSingle Family
Taxes:
Tax Year:
Remarks: There is a quieter side of Anna Maria Island that not everyone experiences. At 242 Oak Avenue, life unfolds in a way that feels entirely your own. Tucked away from the crowds, this rare waterfront retreat is designed for stillness, privacy, and uninterrupted views across Bimini Bay. With no neighboring rooftops competing for your attention, the setting is defined by open water, coastal breezes, and the natural rhythm of island life. Positioned on a remarkable triangular parcel with over 500 feet of water frontage, this gated, elevated residence offers water views from every room. The open-concept design creates a seamless connection between indoor and outdoor living, anchored by a dramatic great room with vaulted ceilings and expansive glass doors that disappear into the walls, opening to an oversized covered lanai. The chef’s kitchen is thoughtfully designed with custom imported cabinetry and distinctive finishes, flowing effortlessly into both formal dining and outdoor entertaining spaces. Just beyond, the lanai becomes a true extension of the home, complete with a full outdoor kitchen, Teppanyaki dining, fire table, lounge areas, and a whirlpool spa, all set against panoramic bay views. The main residence features two luxurious primary suites with private ensuites, while a separate guest house, connected by a covered bridge, offers two additional bedrooms, a full bath, and kitchenette, creating an ideal private retreat for family and guests. Outdoor living continues at every level. A resort-style pool with fire and water features is surrounded by lush tropical landscaping, leading to a private waterfront fire pit along your own sandy shoreline. For boating enthusiasts, the property is equally exceptional, featuring a 60-foot dock, 12,000 lb. boat lift, and direct access to Tampa Bay and the Gulf of Mexico. Now offered with a significant $500,000 price adjustment, this is a rare opportunity to secure one of the island’s most distinctive waterfront estates. This pricing opportunity is available for a limited time through April 15, 2026.
Listing Agent: Kathy Harman (941-900-9828)
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