Location: Anna Maria , 34216
Do Not Show Listings
107 TUNA ST, ANNA MARIA, FL 34216
$7,750,00046 Days on yellowkey MLS ID: A4686563
Bed: 6 Bath: 5.5 Gar: 6 Liv Area Sq Ft: 4345 Built: 2026 Tax: $5,729 (2025)Community: Anna MariaSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,729
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: Under Construction. Blending modern coastal construction with Old Florida charm, 107 Tuna Street offers a level of design, scale, and positioning that is seldom found on Anna Maria. Just 50 feet from sugar-white sand and set on an oversized corner lot along the coveted North End, this residence enjoys a peaceful setting away from the activity of the public beaches, offering a more private, “locals’ luxury” experience just steps from the Gulf’s iconic turquoise waters. The residence’s Key West–inspired architecture sets the tone with deep balconies, porch brackets, generous openings, and a layout that favors natural light and easy indoor-outdoor living. Built with full concrete block construction and engineered to 2026 Florida hurricane standards, the residence offers exceptional durability and peace of mind inherent to premier coastal living. Upper floors are thoughtfully oriented to catch optimal light and frame coastal views, so the home feels bright and connected to its setting throughout the day, even before you step onto the balconies to watch sunsets that stop everything. Inside, vaulted and cathedral ceilings create volume throughout the open-concept living spaces. The main-level primary suite offers both convenience and privacy, complemented by accessible design features including wider doorways, a full bath, and thoughtful flow for long-term livability. A three-stop elevator connects all levels with ease. The kitchen, with its custom wood cabinetry, is designed as both a showpiece and a workspace, anchored by a full Thermador appliance suite, including a 7-burner range, integrated refrigeration, and dishwasher. Adjacent living and dining areas extend effortlessly outdoors, where 3,000+ square feet of covered and open-air living space transforms the home into a true coastal retreat. Here, the outdoor environment is an extension of your everyday living space. A fully integrated alfresco kitchen anchors the space, complemented by three distinct dining areas designed for everything from casual mornings to large-scale entertaining. The expansive 48’ x 25’ free-form pool and spa create a resort-style centerpiece, surrounded by three lounging areas near a private volleyball court. Positioned just a 120-second stroll from one of Anna Maria Island’s most serene stretches of powdery white sand, the home offers immediate access to the Gulf without sacrificing privacy. Just moments from the charm of Pine Avenue with boutique shopping, cafés, and local favorites like Dips and The Donut Experiment, plus local or even waterfront dining at the Sandbar, The Porch, and The Waterfront, all just blocks away, making everyday living feel like a vacation. With projected strong rental income potential, a six-car garage, and a delivery timeline of Summer 2026, 107 Tuna Street represents a compelling opportunity to secure a newly built, design-forward residence in one of Anna Maria Island’s most desirable and tightly held enclaves. Nearby marinas, boating access, and waterfront parks enhance the island lifestyle, while the cultural amenities of downtown Sarasota, St. Armands Circle, and Longboat Key are all within easy reach. SRQ International Airport is approximately 40 minutes away, offering convenient access. This is a setting that balances seclusion and accessibility, where everyday feels like a vacation, and everything you need is effortlessly within reach. Live on Anna Maria Island, ranked by U.S. News & World Report as the #2 Best Family Beach Vacation in the U.S.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: John Forberger (305-905-1842)
216 GLADIOLUS ST, ANNA MARIA, FL 34216
$1,325,00063 Days on yellowkey MLS ID: A4682103
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1218 Built: 1966 Tax: $2,637 (2024)Community: Luana IslesSingle Family
Taxes:$2,637
Tax Year: 2024
Remarks: Currently the lowest priced 3 bedroom home on the north end of Anna Maria Island, this charming bungalow, lovingly held by the same family since the 1970s, presents a rare opportunity to own a cherished island property in one of the most sought after locations on the island. Located in the City of Anna Maria, where short term rentals are permitted with a 1 to 7 day minimum, subject to city registration and compliance, this home blends timeless Old Florida charm with thoughtful modern updates throughout. This single story coastal residence features 3 bedrooms, 2 beautifully renovated bathrooms, and a versatile den or mudroom. Vaulted tongue and groove wood ceilings add warmth and architectural character to the open living space. The kitchen has been completely redesigned with new cabinetry, countertops, and brand new appliances, creating a fresh and inviting heart of the home. New flooring flows throughout, blending classic island charm with a clean, updated coastal style. Situated on a generous 7,500 square foot lot, the property offers rare outdoor space for the north end, complete with mature tropical landscaping, a fenced yard, and ample room to design a custom pool or expanded outdoor living area. A current survey is available to assist with future planning. An outdoor shower, storage shed, and one car garage add everyday convenience, while ample parking, rare for this location, enhances the property’s appeal. A brand new AC system installed in 2025 provides added comfort and peace of mind. From this prime north end setting, enjoy walking or biking to Pine Avenue’s shops and restaurants, Bayfront Park, and the island’s beautiful beaches. Experience island living where golf carts and bicycles replace cars, and every sunset feels close to home. Charming, flexible, and ideally located, this home is well suited as a full time residence, seasonal retreat, or legacy island property. Positioned as the lowest priced 3 bedroom home on the north end of Anna Maria Island, it presents a compelling opportunity in today’s market. Come discover why the north end continues to capture hearts generation after generation.
Listing is courtesy of: CAPOZELLA REAL ESTATE (941-914-0802)
Listing Agent: Mara Gilmore (941-920-1267)
136 CRESCENT DR, ANNA MARIA, FL 34216
$1,149,999169 Days on yellowkey MLS ID: A4671637
REDUCED by $50,000 (4.2%) on 04/30/2026
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: The Beach Is Calling!!! 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)
811 N SHORE DR, ANNA MARIA, FL 34216
$10,950,00047 Days on yellowkey MLS ID: A4684895
Bed: 4 Bath: 7.0 Gar: 2 Liv Area Sq Ft: 5079 Built: 2021 Tax: $38,715 (2025)Community: Shore Acres First AddSingle Family
Taxes:$38,715
Remarks: Experience one of the most extraordinary waterfront settings on the coveted North End of Anna Maria Island, just moments from the world-renowned shores of Bean Point. Set on over an acre of Gulf-front beachfront land, this rare estate provides exceptional privacy, expansive shoreline, and breathtaking panoramic views of the Gulf of Mexico. In 2019, the property underwent a comprehensive structural and architectural redevelopment that transformed the residence into a modern coastal estate, including major infrastructure upgrades such as updated electrical, plumbing, and HVAC systems, along with new flooring, custom millwork, redesigned bathrooms, cabinetry, lighting, and modern coastal finishes throughout. Originally constructed as an elevated coastal residence, the home was extensively expanded, redesigned, and structurally reimagined to create a three-level retreat designed for elevated island living. The redevelopment included the addition of a private master suite level, construction of a large elevated pool and entertainment deck, and installation of a dramatic three-story architectural water feature, while completely reconfiguring the interior floor plan. Privately gated and approached by a palm-lined drive, the residence welcomes you with a striking 20-foot waterfall entry. Expansive windows capture nearly 270-degree Gulf views, filling the open living spaces with natural light and coastal breezes. The main living areas flow seamlessly to spacious outdoor terraces finished in Brazilian Walnut (IPE) decking—ideal for sunset entertaining overlooking the Gulf. The chef’s kitchen features custom rosewood cabinetry, three ranges, three ovens, a built-in coffee bar, wine refrigeration, and premium Sub-Zero, Wolf, Cove, and Miele appliances. Multiple bedroom suites include ensuite baths and water views, while a dedicated entertainment level features shuffleboard, a poker table, pool table, and lounge space. The top-floor owner’s retreat, accessible by elevator, captures sweeping Gulf views and includes oversized walk-in closets, a private coffee bar, and a spa-style bath with soaking tub and rain shower. Outdoor amenities include a heated ozone saltwater pool with lap feature, elevated entertainment deck, private gym, infrared sauna, and a two-car garage with additional golf cart space. Direct beach access leads to one of the most peaceful stretches of shoreline on Anna Maria Island. Located near the shops and restaurants of Pine Avenue, this property is a rare opportunity to own a fully transformed Gulf-front estate on over an acre of beachfront land on the North End of Anna Maria Island.
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Jessica Batten (941-962-3380)
213 OAK AVE, ANNA MARIA, FL 34216
$3,400,000116 Days on yellowkey MLS ID: TB8462487
4 Days Off yellowkey (back on 4/28/2026)
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3053 Built: 1985 Tax: $12,721 (2024)Community: Laguna Maria RevSpa: YesSingle Family
Taxes:$12,721
Remarks: Under contract-accepting backup offers. Experience Florida coastal living at its finest in this exceptional custom-built home featured in Southern Living Magazine. Uniquely located, this house is a short walk to white sand beaches and a short cruise to the Bay and Gulf. This classic Key West styled beauty was renovated and enlarged four years ago. The lush front yard features a circular paver driveway, a gorgeous Royal Poinciana tree, an assortment of local palms and a majestic Canary Island Date Palm. The front walkway is cut from limestone slabs, replicating ocean coral. Featuring 4 bedrooms and 4 bathrooms this thoughtfully designed residence offers an open floor plan filled with abundant natural light creating a bright and welcoming atmosphere throughout with quality craftsmanship and timeless coastal style. Two screened porches and a backyard deck invite indoor-outdoor living. Inside the open floor plan features a bright spacious great room highlighted by a two-story vaulted cathedral ceiling. A stylish granite-mantled fireplace with mermaid statues beautifies this unique space. The adjoining dining room and kitchen offer granite countertops, stainless steel appliances and customized cabinets. The main suite’s spacious bedroom has well-appointed custom-built nightstands, bookshelves, and a glass and mirrored-shelved head board. There is a walk-in closet and French doors leading to the back deck with canal views. The ensuite tiled bathroom has a spa-like feel with an electric toilet, separate dual sinks, granite countertops and a combined walk-in shower and steam room. Another main floor suite has a tiled bathroom, a sit-down, walk-in Jacuzzi-styled tub, an electric toilet and granite counter top. The upstairs bedroom extends the length on the second floor with a tiled bathroom, a bathtub and shower. The backyard is a tropical oasis complete with a Tiki Hut, a midnight- blue-bottomed resort- style pool trimmed with natural stone, a waterfall, a bronze dolphin fountain, a hot tub, an enclosed hot-water outdoor shower, and old growth Coconut, King, Sable, Bismark, Foxtail, and Christmas palm and giant bird-of-paradise trees. Situated on the canal is a forty-seven foot wooden dock and boat lift, allowing direct water access via Bimini Bay and Anna Maria Sound to open waters and endless water adventures. A spacious multi-car garage provides plenty of room for stowing bikes, golf carts, and beach gear. Just a short stroll to the sugar-white sand beaches, this picturesque property is perfectly located to enjoy the beach, the bays and Gulf waters.
Listing is courtesy of: SMITH & ASSOCIATES REAL ESTATE (727-342-3800)
Listing Agent: James Patterson (941-730-9296)
418 PINE AVE, ANNA MARIA, FL 34216
$3,000,00015 Days on yellowkey MLS ID: A4690403
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2804 Built: 2007 Tax: $26,566 (2025)Community: Anna Maria Beach Third AddSpa: NoSingle Family
Taxes:$26,566
Remarks: Positioned along the most sought-after stretch of Pine Avenue—known for its vibrant coastal charm, boutique shopping, dining, and steady pedestrian traffic, 418 Pine Avenue offers a truly rare opportunity to own a waterfront property with coveted ROR zoning. Properties like this are few and far between, especially those that combine direct water access with the ability to create both a luxury lifestyle and a dynamic income-producing asset in the heart of one of the island’s most iconic corridors. This elevated, solid concrete home features 4 bedrooms and 3 bathrooms, each bedroom offering spacious walk-in closets complete with custom closet systems. The open-concept floor plan is designed to maximize natural light and water views, seamlessly blending indoor and outdoor living. Step out onto the expansive main-level balcony or enjoy one of three additional balconies—two overlooking the water and two facing the lively energy of Pine Avenue. The ROR zoning creates exceptional flexibility for income potential. Envision renting the upper-level residence while activating the lower level as a waterfront-facing business such as a boutique retail shop, professional office, art gallery, wellness studio, café, or even a unique waterfront business concept like a paddleboard/kayak outfitter, dockside café, or marine-focused experience. The combination of visibility from Pine Avenue and direct water frontage is incredibly rare and valuable. Boating enthusiasts will appreciate having only one fixed bridge to open water, along with a private dock where marine life is frequently seen right in your backyard. The outdoor space is equally impressive, featuring a pool and ample room for entertaining, dining, and enjoying the Florida lifestyle year-round. Additional highlights include impact windows and doors throughout, plantation shutters, newer HVAC system, metal roof, and fresh interior paint. Whether you’re searching for a primary residence, a luxurious second home, or a high-performing investment with unmatched zoning advantages, this property delivers on every level. Being sold complete with professional design services to help you elevate and personalize the space.
Listing is courtesy of: KW SUNCOAST (941-792-2000)
Listing Agent: Stephanie Paxton (941-932-5509)
120 MAPLE AVE, ANNA MARIA, FL 34216
$1,545,00091 Days on yellowkey MLS ID: A4680151
REDUCED by $30,000 (1.9%) on 04/28/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1506 Built: 1973 Tax: $16,951 (2024)Community: Gulf View Sub Of Anna Maria KeySingle Family
Taxes:$16,951
Elementary School: None
High School: None
Middle School: None
Remarks: Prime Beachside Retreat – Steps to the Sand on Anna Maria Island! Discover coastal living at its finest in this beautifully remodeled and updated 3-bedroom, 2-bathroom single-family home, perfectly positioned west of Gulf Drive in the heart of Anna Maria. Just a short stroll (literally steps away) from the pristine, sugar sandy beaches of the Gulf of Mexico, this residence offers effortless access to turquoise waters, breathtaking sunsets, and the relaxed island vibe that makes Anna Maria a sought-after paradise. The home boasts modern upgrades throughout, including fresh finishes, an open and inviting floor plan, and thoughtful touches that blend comfort with contemporary style. The spacious layout is ideal for families, weekend getaways, or as a high-demand vacation rental investment. One of the standout features? Ample room to add your dream pool—imagine lazy days by your private oasis, just moments from the beach! West of Gulf Drive means no busy roads to cross for beach access, putting you in the most desirable pocket of the island. Enjoy peaceful mornings with the sound of waves, evening walks along the shore, and the charm of nearby Pine Avenue’s shops, restaurants, and cafes—all while owning a piece of true Anna Maria magic. Whether you’re seeking a primary residence, second home, or lucrative rental property, this beachside gem delivers the ultimate in Florida coastal sophistication and easy island living. Don’t miss your chance to own steps from the Gulf—schedule your private showing today!
Listing Agent: James Wilson (727-331-4353)
903 N SHORE DR #B, ANNA MARIA, FL 34216
$5,595,00077 Days on yellowkey MLS ID: A4682764
2 Days Off yellowkey (back on 4/28/2026)
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2915 Built: 2020 Tax: $55,181 (2024)Community: Shore AcresSpa: YesSingle Family
Taxes:$55,181
Remarks: Welcome to this stunning show stopping property on the North End of Anna Maria Island very well known as Beachfront Bliss. Enjoying panoramic views of the bay will captivate you while also having your own private beach! This 4 bedroom, 4.5 bathroom home is one of the highest producing rental properties on the north end of the island. The rental income on this property is outstanding with 2026 having $455,251 on the books thus far! The location doesn't get any better as it’s located directly on the bay, steps from Bean Point and a short stroll to the heart of Anna Maria, Pine Ave where all the boutiques and restaurants are. Unwind in the open living space, where an abundance of natural light and breathtaking views creates a tranquil atmosphere. Enjoy viewing dolphins and manatees from the plush furniture without even leaving the home! The primary bedroom has a private balcony to capture the picturesque sunrises and breathtaking views of the illuminated Sunshine Skyway Bridge colors at Night. While the additional three bedrooms has its own ensuite bathroom and walk-in closet, ensuring a comfortable and private retreat. Kids (and adults!) LOVE the game room featuring classic video games to family board games and puzzles, the game room is the perfect spot for lively entertainment. Golden Tee Golf and a variety of classic games provide hours of enjoyment for the whole family. Step outside into an expansive outdoor space designed for leisure and recreation. Lounge on the sandy beach, take a dip in the heated pool or oversized hot tub, or play a round on the putting green. The outdoor living area features a wet bar and a large Weber Genesis gas grill, perfect for alfresco dining. Enjoy the tropical oasis with outdoor Sonos speakers, an aquarium selfie wall, and various beach gear and toys. Large 2 car garage and an elevator for convenience. Being its first time on the market, this opportunity to own this unique piece of property won’t last long!
Listing Agent: Jason Sato (941-778-7200)
110 OAK AVE #A, ANNA MARIA, FL 34216
$849,000108 Days on yellowkey MLS ID: A4678588
REDUCED by $25,000 (2.9%) on 04/28/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 640 Built: 1947Monthly Fee: $1 Tax: $11,258 (2025)Community: Anna Maria Beach CottagesCondo
Taxes:$11,258
Remarks: Old Florida Charm – Income-Producing Property! Looking for a true Old Florida beach cottage experience with exceptional rental income? This elevated cottage on Anna Maria’s sought-after North End is just steps from the Gulf—no car needed! This fully managed, hands-off rental allows nightly stays, with all future bookings conveying for seamless income. This turnkey-furnished home blends coastal charm with modern updates, featuring a newer kitchen with Quartz counters, custom cabinetry, and new appliances, flooring and a spacious private deck. The primary suite offers a walk-in closet and updated ensuite bath, while the second bath includes double sinks and a jacuzzi tub. Located in a boutique resort with a private pool, picnic areas, and complimentary bikes, beach gear, and water toys, guests return year after year. Walk to Pine Ave’s shops or hop on the free trolley to explore the island. With pet-friendly ownership and a 6-month owner occupancy option, this turnkey investment is perfect for personal getaways and immediate passive income. Don’t miss this rare opportunity—schedule your showing today! Please note- the HOA Adjusts based on monthly income.
522 PINE AVE #7D, ANNA MARIA, FL 34216
$555,000306 Days on yellowkey MLS ID: A4657782
1 Days Off yellowkey (back on 4/28/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 822 Built: 1973 Tax: $6,625 (2025)Community: BayouSpa: NoCondo
Taxes:$6,625
Remarks: Under contract-accepting backup offers. “Sittin’ on the dock of the Bay…” Welcome to an effortless island retreat designed for relaxed second-home living on Anna Maria Island. This elevated 2-bedroom, 1-bath waterfront condo is being offered turnkey furnished and includes its own deeded boat slip, providing direct access to Tampa Bay and quick passage to open water. Set along a peaceful canal, the home invites you to slow down and unwind. Enjoy morning coffee or evening breezes from your private back patio as manatees glide by and seabirds fill the air. When you are ready to explore, you are perfectly positioned on iconic Pine Avenue, just steps from local shops, dining, and island favorites, with the historic City Pier nearing completion nearby. Inside, the condo offers a clean, comfortable layout with two generously sized bedrooms and a full bath. The space is move-in ready as is, while also offering future flexibility. Many owners in the Bayou Condo Complex have enhanced their units by opening the kitchen to the living area, adding interior laundry, or converting the walk-in closet into an additional bath, creating exciting options to personalize over time. This residence has been lovingly used as a second home and also allows twice-monthly rentals, offering optional income when you are away. The well-maintained Bayou Condo community recently completed new metal roofs in 2025 and features low condo fees, a designated parking space, and ample guest parking. Whether you envision weekend escapes, seasonal stays, or boating adventures right outside your door, this waterfront condo delivers the ultimate lock-and-leave island lifestyle. Schedule your private showing and discover how easy owning a second home on Anna Maria Island can be.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Kathy Harman (941-900-9828)
865 N SHORE DR, ANNA MARIA, FL 34216
$2,999,00088 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
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)
107 PINE AVE, ANNA MARIA, FL 34216
$4,999,99925 Days on yellowkey MLS ID: A4688961
Bed: 6 Bath: 0.0 Liv Area Sq Ft: 2748 Built: 1968 Tax: $21,717 (2025)Community: Anna Maria BeachApartment
Taxes:$21,717
Remarks: For Investors looking to purchase property on the desirable north end of the Anna Maria Island, this unique and rare 4-unit apartment building is an exceptional investment opportunity. Welcome to Gulf Queen Apartments just 50 feet from the sugary sandy beaches of Anna Maria Island. Situated on nearly 7,400 sq ft lot, the property also presents future redevelopment potential—offering investors the flexibility to build new in this prime coastal location. This turnkey furnished, ground level 4-plex has two apartments with two bedrooms and one bathroom; and two apartments with one bedroom and one bath. Gulf Queen Apartments offers immediate income potential in one of Florida’s most sought-after beach markets. The units showcase polished terrazzo flooring, open-concept living and kitchen areas, and tasteful coastal décor. Recent upgrades include renovated kitchens with granite countertops, updated bathrooms, and new furnishings throughout—creating an inviting, guest-ready environment. The 2-bedroom units comfortably accommodate up to four guests, making the property ideal for group bookings such as family vacations, reunions, or wedding parties. Anna Maria is known as a desirable wedding destination. The entire building can be rented out to accommodate wedding guests or other family gathering venues, or each unit can be rented individually. The property also has two golf cart charging stations to accommodate guests who want to tour the island in their rented golf cart. The property is located next door to the Sand Bar Restaurant which hosts many wedding guests from around the world each year. The property is also located on famous Pine Avenue, a street that runs from Tampa Bay to the Gulf of Mexico. The property's 107 Pine Avenue address is walkable to numerous shops and restaurants that stretch from the Bay to the Gulf. The location is unmatched—just steps to the beach, as well as the vibrant shops and dining along Pine Avenue, and convenient access to the free island trolley. Guests can easily stroll or bike to Bean Point, or enjoy nearby favorites like The Waterfront Restaurant and The Sandbar Restaurant. Whether you’re seeking a vacation rental portfolio or a redevelopment opportunity in a premier beach destination, Gulf Queen Apartments delivers value, location, and income potential. Vacation Rental bookings available upon request. Call for a private viewing of this unique property today.
Listing Agent: Hannah Hillyard (941-744-7358)
404 NORTH SHORE DR, ANNA MARIA, FL 34216
$5,487,000701 Days on yellowkey MLS ID: A4612343
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3159 Built: 2023 Tax: $5,846 (2023)Community: 7074800; 302 Coconut Avenue; Lot 1; Pb 0070/0185Spa: YesSingle Family
Taxes:$5,846
Tax Year: 2023
Remarks: 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!!
Listing is courtesy of: BEACH HOUSE REAL ESTATE LLC (941-216-3793)
Listing Agent: Gregg Bayer (941-799-9096)
103 PARK AVE, ANNA MARIA, FL 34216
$5,650,00022 Days on yellowkey MLS ID: A4689581
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4540 Built: 2012 Tax: $78,291 (2025)Community: Banyan Tree Estates IiiSpa: YesSingle Family
Taxes:$78,291
Remarks: LUXURY COASTAL LIVING AT IT’S FINEST! This one-of-a-kind residence, designed by Emily Anne Smith, stands on one of the most sought-after streets in Anna Maria, just one home from the Gulf and a short walk to the charm of Pine Avenue. The location offers an exceptional combination of beach proximity, walkability, and privacy. Thoughtfully designed for both entertaining and multi-generational living, the home offers over 4,500 square feet of curated living space with distinct gathering areas throughout. The main living room opens to a front verandah and features a fireplace, with an additional fireplace located in the primary suite. The kitchen, designed for both function and presentation, featuring marble countertops and backsplash, custom cabinetry, a butler’s pantry, and dual sinks is well-suited for both everyday use and larger gatherings. Emily Anne Smith is known for her mindful and timeless coastal design, and this home reflects that level of craftsmanship throughout. The property includes a main residence and a separate cottage, providing flexibility and privacy with a total of 5 bedrooms and 4.5 bathrooms. Additional features include multiple verandahs, two dedicated study spaces, and a well-designed outdoor living area with a pool, shower, and lounge space. The private guest quarters with separate entrance offers an ideal setup for extended family, guests, or private accommodation. This is a rare opportunity to own a thoughtfully designed home in a premier Anna Maria location, with Gulf views and exceptional sunset exposure.
Listing Agent: Dee Munn (407-346-4422)
270 GLADIOLUS ST, ANNA MARIA, FL 34216
$1,770,00081 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.
108 PELICAN DR, ANNA MARIA, FL 34216
$2,199,00074 Days on yellowkey MLS ID: A4680808
REDUCED by $96,000 (4.2%) on 04/25/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1472 Built: 1994 Tax: $10,106 (2024)Community: Luana IslesSingle Family
Taxes:$10,106
Remarks: Located on the north end of Anna Maria, this elevated canal-front home is a true boater’s paradise with direct water access and a private dock. This 4-bedroom property underwent an extensive interior remodel, showcasing modern upgrades and coastal living at its finest. The open-concept layout is filled with natural light and offers comfortable living spaces ideal for both everyday living and vacation enjoyment. Step outside to an expansive back deck overlooking the peaceful canal — the perfect setting for relaxing or entertaining. Outdoors, a new pool and refreshed entertaining area further enhance the Florida lifestyle. Ideally situated near beaches, dining, and shopping, this home captures the very best of Anna Maria Island waterfront living and is perfectly suited as a full-time residence or a short-term rental investment.
866 N SHORE DR, ANNA MARIA, FL 34216
$1,949,00080 Days on yellowkey MLS ID: A4680714
REDUCED by $50,000 (2.5%) on 03/31/2026
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 1904 Built: 1951 Tax: $16,227 (2024)Community: Shore Acres ResubdividedSpa: YesSingle Family
Taxes:$16,227
Remarks: Don't miss your chance to own a fully remodeled home in the City of Anna Maria. Extensively remodeled 4-bedroom, 4-bath home on North Shore Drive in the City of Anna Maria, featuring significant structural and finish upgrades throughout. This light-filled residence offers an open-concept layout with raised ceilings, refined coastal finishes, and expanded living space. Two bedrooms feature private en-suite bathrooms, with an additional two full guest bath conveniently accessible from the bedrooms and main living areas. Renovations include enclosed patio and garage areas to create an additional en-suite bedroom, expanded kitchen, dedicated laundry room, and approximately 294 square feet of added living space. Major improvements include new electrical and plumbing services; new drywall with DensGlass moisture-resistant panel; a new HVAC system with supplemental mini-split units; spray foam roof insulation; hurricane-impact windows and sliders; and new flooring throughout. The kitchen features all-new cabinetry, countertops, a large center island with breakfast bar, and Samsung appliances including: refrigerator, ice maker, wine cooler, microwave, dishwasher, and chilling drawers. Bathrooms have been fully updated with new tile and high-end plumbing fixtures. Outdoor upgrades include a private heated pool with new heater and pump, expanded paver decking, new fencing, updated landscaping, refreshed exterior stucco, and full interior and exterior paint. Ideally located just steps from the beach and close to Pine Avenue shops and dining, this is a move-in-ready island home offering modern upgrades, thoughtful design, and an unbeatable location—schedule your private showing and experience Anna Maria Island living at its best.
212 SPRING AVE, ANNA MARIA, FL 34216
$3,660,000371 Days on yellowkey MLS ID: A4650724
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 2704 Built: 2019 Tax: $33,175 (2023)Community: Anna Maria BeachSpa: YesSingle Family
Taxes:$33,175
Remarks: CUSTOM BUILT HOME IS CENTRALLY LOCATED IN Anna Maria 2 BLOCKS TO THE BEACH AND ONLY A BLOCK AWAY FROM ALL THE SHOPS AND RESTAURANTS ON PINE AVE. THIS HOME WAS BUILT WITH ALL THE HOME WAS BUILT WITH ALL HIGH END FINISHES INCLUDING WOOD GRAIN TILE FLOORS, SOLID WOOD CABINETS, QUARTZ COUNTERTOPS, CUSTOM TRIM PACKAGE, VAULTED CEILINGS, AND COMES TURNKEY FURNISHED WITH A COASTAL DECOR. OUTSIDE THERE IS A LARGE HEATED POOL AND SPA WITH SUN SHELF, SURROUNDED BY TROPICAL LANDSAPING ARTIFICIAL TURF AND EVEN A PUTTING GREEN. THIS WILL MAKE THE PERFECT SECOND HOME ON Anna Maria Island WITH GREAT RENTAL POTENTIAL.
9403 GULF DR, ANNA MARIA, FL 34216
$8,000,000454 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 8/75Spa: YesSingle 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.
246 GLADIOLUS ST, ANNA MARIA, FL 34216
$1,999,00048 Days on yellowkey MLS ID: A4686725
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1979 Built: 2014 Tax: $31,986 (2025)Community: Luana IslesSpa: NoSingle Family
Taxes:$31,986
Remarks: Kick off your shoes and come enjoy this Island home with a truly Anna Maria feel. This is a relaxing and spacious mini-estate comprising a 2 bedroom, 2 bath main house and a 1 bedroom/1 bath guest cottage. Decorated in tranquil coastal chic of pastels and with gorgeous polished pine floors. The kitchen is perfect for entertaining and cooking fabulous meals in your granite and stainless gourmet chef’s kitchen. Entertain guests in your spacious open living area that flows onto an expansive sitting deck, nestled in the tree tops where you can totally relax and put your feet up. Downstairs is a comfortable dining area for grilling, ping pong or corn hole! Sun bathe on the loungers or take a dip in the heated pool surrounded by lush landscaping providing so much privacy. A delightful separate cottage affords privacy while reflecting all the attractive design features of the main house, and you also have two separate laundry rooms for everyone’s convenience. Set up your private showing today!
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