Location: 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)
612 FERN ST, ANNA MARIA, FL 34216
$1,795,000116 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
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2025
Middle School: Martha B. King Middle
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)
216 GLADIOLUS ST, ANNA MARIA, FL 34216
$1,325,00041 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
Remarks: Lovingly held by the same family since the 1970s, this north end Anna Maria Island bungalow 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 1–7 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/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 all new appliances, creating a fresh and inviting heart of the home. New flooring flows throughout, blending classic island charm with updated coastal style. Situated on a generous 7,500 square foot lot, the property offers rare outdoor space for the north end, 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, complemented by ample parking rarely found in this location. 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. Currently among the most competitively priced 3-bedroom homes available in the City of Anna Maria. 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)
915 N SHORE DR, ANNA MARIA, FL 34216
$5,350,000117 Days on yellowkey MLS ID: A4674863
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2870 Built: 2017 Tax: $70,059 (2025)Community: Shore AcresSpa: YesSingle Family
Taxes:$70,059
Remarks: Direct Beachfront Luxury with Exceptional Rental Income on Anna Maria Island. Discover the ultimate in coastal elegance with this direct beachfront home on the shores of Anna Maria Island. A rare beachfront home sold turnkey furnished that seamlessly blends refined luxury with a proven record of outstanding short-term rental performance. Recently enhanced with numerous upgrades including new sliding doors on the upper level—this home showcases high end finishes and expansive walls of glass that capture sweeping views of Tampa Bay and the iconic Sunshine Skyway Bridge. The spacious living and dining areas open through floor-to-ceiling sliders to a generous bayfront balcony, creating an effortless indoor–outdoor flow for entertaining or peaceful relaxation. The gourmet kitchen is a chef’s delight, featuring shaker cabinetry, a large island with seating, quartz countertops, and new premium stainless-steel appliances including a gas range. Each of the four bedrooms is a private retreat, complete with an en-suite bath and its own balcony framed by tropical scenery. Additional recent upgrades include new ground-level outdoor furnishings, refreshed tropical landscaping with exterior lighting, and newly painted interior and exterior spaces. The covered poolside lounge and dining area on the ground level are the perfect setting for waterfront living—just steps from the sand. As evening falls, enjoy the mesmerizing glow of the Skyway Bridge from your own serene getaway. Set on the pristine beachfront of Anna Maria Island, this home features timeless architecture, a spectacular coastal setting, and an unparalleled opportunity for both personal enjoyment and exceptional rental revenue. This 4-bedroom, 4-bath residence produced nearly $500,000 for 2025, $456,000 booked for 2024, and $464,000 in 2023. Future 2026 reservations in place Comprehensive rental history and future booking details for 2025 and 2026 are available upon request. A rare chance to own a true beachfront sanctuary.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Hannah Hillyard (941-744-7358)
111 PALMETTO AVE, ANNA MARIA, FL 34216
$5,125,00053 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.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Christy Travis (941-545-5284)
519 SOUTH DR, ANNA MARIA, FL 34216
$1,598,000116 Days on yellowkey MLS ID: A4675370
REDUCED by $97,000 (5.7%) on 04/01/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2131 Built: 1972 Tax: $26,805 (2024)Community: Wells Bay Harbor Sec ASpa: YesSingle Family
Taxes:$26,805
Remarks: “Anna Maria Oasis” is a Bimini Bay Coastal Classic, perfectly positioned on the coveted north end in the City of Anna Maria. With deep-water access directly from your backyard, no bridges to the bay or the Gulf of Mexico, and a 50’ dock with pilings already in place for lift installation, this property is truly a boater’s and fisherman’s paradise. Originally built in 1972, the home was completely transformed in a top-to-bottom remodel in 2025, blending modern luxury with timeless island charm. No detail was overlooked. Highlights include imported Filipino shell stone flooring throughout, all-new drywall, insulation, plumbing, electrical, paint, fixtures, kitchen, and fresh landscaping. The living space was thoughtfully expanded with energy-efficient mini-split systems, increasing the under-air square footage from 1,582 sq ft to approximately 2,131 sq ft, offering enhanced comfort and flexibility. Additional upgrades include a new pool (2019), new AC unit 2025 and new roof (2020). Designed for effortless indoor-outdoor living, this home is ideal for entertaining, launching a sunset cruise, or unwinding while taking in tranquil water views. This one-of-a-kind island property delivers the ultimate coastal lifestyle. Don’t miss this rare opportunity to own waterfront luxury in the heart of Anna Maria—where elegant design meets laid-back island living. Currently an active vacation rental please see remarks for link to the site.
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Cindy Quinn, Pa (941-780-8000)
270 GLADIOLUS ST, ANNA MARIA, FL 34216
$1,770,00059 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 Agent: Dee Munn (407-346-4422)
116 HAMMOCK RD, ANNA MARIA, FL 34216
$2,395,000118 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)
403 N BAY BLVD, ANNA MARIA, FL 34216
$2,549,90058 Days on yellowkey MLS ID: A4682522
REDUCED by $100,100 (3.8%) on 04/01/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2112 Built: 1991 Tax: $29,831 (2024)Community: Anna Maria Beach Second AddSpa: NoSingle Family
Taxes:$29,831
Remarks: THIS PROPERTY IS AVAILABLE TO SHOW YOUR BUYERS MONDAY 4/13/26 & TUESDAY 4/14/26 - LARGE $100K PRICE REDUCTION - NOW PRICED TO SELL - AVAILABLE TO SHOW FRIDAY 4/10/26 AFTER 10AM. PLEASE CALL REALTOR TO SCHEDULE. Welcome to island living at its finest on the world-renown north end of Anna Maria Island. This exceptional property offers stunning sunrise views over the bay and an unbeatable location just steps from Bayfront Park, where you can enjoy a sandy beach and tranquil waters. Prefer more privacy? Relax and unwind in your own fenced-in tropical backyard featuring a private pool and lush landscaping. This turnkey, beautifully maintained 4-bedroom, 3-bathroom home features an open-concept floor plan designed for comfortable coastal living and entertaining. Spacious wrap-around porches provide the perfect setting to enjoy refreshing island breezes and picturesque water views. The home boasts a large kitchen and dining area ideal for hosting family and friends. The primary suite offers a luxurious ensuite bath complete with double vanities, a stylish soaking tub, and a separate walk-in shower. Two of the four bedrooms open directly onto the expansive second-floor porch, showcasing breathtaking bay views. Ideally located near boutique shopping, ice cream shops, charming gift stores, and premier dining, this home is also just minutes from the historic Anna Maria City Pier. The Gulf beaches are easily accessible by golf cart or bicycle, making every day feel like a vacation. Whether you are seeking a personal island retreat or a strong income-producing investment, this property offers excellent rental potential with daily rentals permitted. Pack your bags and start living the island lifestyle — "No Worries, Bay Happy".
Listing is courtesy of: WAGNER REALTY (941-383-5577)
Listing Agent: Ed Taaffe (636-346-6165)
801 N SHORE DR, ANNA MARIA, FL 34216
$10,850,00092 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)
136 CRESCENT DR, ANNA MARIA, FL 34216
$1,199,999147 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
$2,945,000324 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)
785 JACARANDA RD, ANNA MARIA, FL 34216
$1,999,900394 Days on yellowkey MLS ID: A4644607
2 Days Off yellowkey (back on 2/25/2026)
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1500 Built: 1980 Tax: $23,744 (2024)Community: Shore Acres 1St AddSpa: YesSingle Family
Taxes:$23,744
Remarks: Under contract-accepting backup offers. OHHHH THE UPDATES!! BRAND NEW KITCHEN and flooring...and updates galore! There is so to enjoy about this great investment home! This is the perfect beach haven, just a hop, skip & a jump to the Gulf beach! Just steps to Bean Point, this elevated 3 bed/2.5 bath pool home is a great income property! Updated with beautiful coastal style, this home is designed for relaxing. Start the day sipping coffee on your screened porch or enjoy the space around your open dining table! Stretch out in the family room where the coastal comfort welcomes you with shiplap walls, large updated windows, new lighting, fresh paint and furnishings. Upstairs you will find your large bedroom with its private porch, walk in closet, updated en suite and peeks of the Gulf! Both guest rooms also enjoy an updated (2024) bathroom and the gorgeous coastal décor! Whether you're lounging at the poolside bar, relishing the breeze on the screened porches, relishing the comfort of your cozy bed, or using your back gate to pop over to the sugar sand beach, you will love the island life from every spot of this updated home! From all the UPDATED appliances, the metal roof, the luxury vinyl plank flooring, the NEW doors & door frames, the NEW paint (inside & out), the NEW lighting and the NEW fans, to all the UPDATED décor - this beach house is picture perfect! And outside you will relish the added landscaping and palm trees, lighted stair way, privacy wall, covered bar and your heated pool and spa! Enjoy a cocktail and the game while floating in the pool, and easy access to your beach toy storage space! Inside and out this island home welcomes relaxation and enjoyment! AND you will REALLY enjoy the short term rental income! It’s time for your island life to begin…
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
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.
12106 GULF DR, ANNA MARIA, FL 34216
$6,995,00073 Days on yellowkey MLS ID: A4679008
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: Sterling Worth (214-707-6296)
419 ALAMANDA RD, ANNA MARIA, FL 34216
$3,150,00025 Days on yellowkey MLS ID: A4686802
1 Days Off yellowkey (back on 4/8/2026)
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2185 Built: 2022 Tax: $31,509 (2025)Community: Shore Acres Fourth AddSpa: YesSingle Family
Taxes:$31,509
Remarks: Under contract-accepting backup offers. Welcome to Paradise Blu, a newly built island retreat on Anna Maria Island’s highly coveted north end, just moments from the shoreline and designed for both exceptional living and strong rental performance. Featured in Travel & Leisure Magazine as a recommended vacation rental, this property offers a rare opportunity to own a home with proven appeal on a national level. This thoughtfully designed 4-bedroom residence features ensuite baths in every bedroom plus an additional half bath, offering comfort and privacy for owners and guests alike. Soaring ceilings and an open, light-filled layout create a refined yet relaxed coastal atmosphere, ideal for effortless island living. Step outside to your private tropical oasis, where a resort-style pool and spa are surrounded by lush landscaping, creating the perfect setting for entertaining or unwinding after a day on the water. Amazing panoramic views of the bay and the gulf from the roof top deck. Enjoy coffee for sunrise or your favorite cocktail at sunset. Ideally located just a one-minute walk to Tampa Bay and only two blocks from the world-renowned Bean Point, the home captures the essence of Anna Maria Island’s most sought-after lifestyle. Whether you are seeking a refined second home, a full-time residence, or a high-performing vacation rental, Paradise Blu delivers a rare combination of location, design, and investment potential on the north end of Anna Maria Island. Schedule your private showing and experience firsthand what makes Paradise Blu one of the most compelling opportunities on Anna Maria Island today.
Listing Agent: Kathy Harman (941-900-9828)
413 POINSETTIA RD, ANNA MARIA, FL 34216
$1,595,00089 Days on yellowkey MLS ID: A4677921
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1677 Built: 1972 Tax: $18,534 (2024)Community: Luana IslesSingle Family
Taxes:$18,534
Remarks: Back on the Market with a substantial price Adjustment!!!! Take another look at 413 Poinsettia Rd. Once you walk through the door you will be welcomed by the new fresh bright clean interior finishes. The wall of patio doors at the rear of the home let the sunshine into the vaulted family room and open kitchen. This Is a concrete block home, with a metal roof and impact windows throughout. Its bones were not damaged during 2024’s storms. Unfortunately, water did get into the home. However, the owners did it right. Once they were able to start, their builder immediately cleaned and remediated the damaged interior. He obtained the required permits to make the home better than before. The sellers did not stop by doing just the bare minimums. While the walls of the homes were open, they replaced the electrical panel bringing it up to today’s codes. They also replaced the old cast iron sewer pipes under the home with new PVC and installed new tile throughout the living area. The rear sliding doors were replaced with new up-to-date impact resistant panels. Once all this work was completed, the interior was renewed. All new kitchen and bathroom vanities were installed with new quartz countertops. All the appliances are new. The home was re-furnished and is now ready to move in and enjoy. All you need to do is add your own personal touches and transform this home into your own private oasis or a killer vacation rental. This home has a large, screened lanai on the rear that could be converted into a third bedroom with an ensuite bath. The room would have its own access to a secluded brick patio on the side of the house. There also appears to be room for a cozy cocktail pool at the front of the home. The property has 74 feet of deeded canal front with a 30-foot dock constructed with concrete, wood and Trex decking. This is the perfect spot to launch your kayak and maybe sail with the manatees who visit out back. (Check out the photos) The dock gives access to your boat lift, nestled in the mangroves that provide privacy from the water. Should you want to play in the sand, the Gulf Beach is about 500 steps away and the Bay Beach is about 200 steps from your door. Today’s home buyers need to be aware there are many homes on the island that were remediated after the storms with no building permits. City’s Code Enforcement is identifying them one by one. The homeowners will be required to apply for a “permit after the fact”. Do not get caught buying an unpermitted home. This could cause you problems in the future. This does not affect this home. Call to see this beautiful gem on the north end of Anna Maria. It will not last long. Note: also available for sale is the owners 2009 Scout 201 bay boat with a 150HP Yamaha outboard.
Listing Agent: John Damato, Ii (941-737-3354)
155 CRESCENT DR, ANNA MARIA, FL 34216
$2,200,00034 Days on yellowkey MLS ID: A4684535
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1512 Built: 1963 Tax: $24,963 (2024)Community: Lake La Vista RepSingle Family
Taxes:$24,963
Remarks: Your private island retreat awaits in this exquisitely renovated coastal cottage, situated on an oversized lot North of Pine Avenue in the city of Anna Maria. This solid concrete block, ground level residence offers 3 bedrooms and 2 bathrooms with a bright, open layout design that embodies refined island living. Inside, elegant ceramic tile flooring, hurricane impact windows, and expansive living spaces create an inviting yet sophisticated atmosphere. The spacious living room flows seamlessly into the great room, offering the perfect setting for both relaxed coastal living and stylish entertaining. The designer chef’s kitchen features beautifully refinished cabinetry, a classic subway tile backsplash, stainless steel appliances, and a chic breakfast bar for casual dining. The serene primary suite offers a private en-suite bath, while two additional guest bedrooms provide comfortable accommodations for family and visitors. An oversized two car garage adds both convenience and storage. Step outside to your secluded backyard sanctuary, where lush tropical landscaping surrounds a sparkling pool and private cabana. Artificial turf and thoughtfully placed LED landscape lighting create an ambiance perfect for evening gatherings or peaceful island nights. This exceptional property is part of a voluntary HOA providing access to six community boat docks with direct entry to the sparkling waters of Tampa Bay and the Gulf of Mexico. Just a short stroll away, you’ll find the pristine white sands of Bean Point, the boutiques and dining along Pine Avenue, the City Pier, the local farmer’s market, and the convenient island trolley. Experience the very best of Anna Maria Island living and schedule your showing today to claim your slice of paradise.
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Andrea Miller (860-541-1050)
107 TUNA ST, ANNA MARIA, FL 34216
$7,750,00024 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
Taxes:$5,729
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)
311 POINSETTIA RD, ANNA MARIA, FL 34216
$1,775,000397 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)
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