Anna Maria, FL Homes for Sale with Pool

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  $3,895,000

  • 3 Beds
  • 3 Baths
  • 2,263 Sq Ft

  111 Cedar Ave, Anna Maria, FL 34216

  AMAZING HOME "BLUE CRUSH" ONLY 4 HOUSES TO THE BEACH!!! LOCATIONS LIKE THIS ARE RARELY AVAILABLE WEST OF GULF DRIVE! IT DOES NOT GET BETTER THAN THIS! STEPS TO BEACH AND THE WATERFRONT LIFESTYLE! This exquisite retreat offers the perfect blend of luxury, comfort, and convenience. As you step inside, you'll immediately be drawn to its enticing features. This home has been updated with no expense

  Jay Travis RE/MAX ALLIANCE GROUP

  111 Cedar Ave, Anna Maria, FL 34216
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  $5,495,000

  New Construction Open Sun 11AM - 2PM

  • 5 Beds
  • 5.5 Baths
  • 3,260 Sq Ft

  411 Palm Ave, Anna Maria, FL 34216

  Introducing The Palm—an iconic waterfront estate where exceptional architecture, resort-inspired living, and the unmistakable charm of Anna Maria Island come together to create a remarkable home. More than a home, The Palm captures the very best of Anna Maria Island living. Thoughtfully custom built by Eason Builder Group, this newly completed waterfront residence features five bedrooms, five

  Jay Travis RE/MAX ALLIANCE GROUP

  411 Palm Ave, Anna Maria, FL 34216
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  $2,945,000

  $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,415 Sq Ft

  704 Gladiolus St, Anna Maria, FL 34216

  Relish the quiet neighborhood of this North End beauty! Just a hop, skip and a jump to Beach and Bay from this 4 bed/3 bath pool home with private elevator. This ideally appointed home has an open floor plan with TWO living rooms, a large third floor porch with peeks of the water, dual zone air conditioning, and a fabulous, spacious kitchen with Bosch appliances, custom lighting throughout, and

  Erin Leathem ISLAND REAL ESTATE-ANNA MARIA

  704 Gladiolus St, Anna Maria, FL 34216
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  $6,950,000

  • 9 Beds
  • 8.5 Baths
  • 4,244 Sq Ft

  9407 Gulf Dr, Anna Maria, FL 34216

  Located on picturesque Anna Maria Island, this exceptional 9-bedroom, 8.5-bathroom coastal retreat offers 4,244 sq ft of heated living space with luxurious amenities throughout. The open-concept interior features an oversized kitchen with a spacious quartz island, upgraded appliances, and a wet bar for entertaining. Enjoy the multiple balconies or the rooftop deck, showcasing Gulf of Mexico views

  Greg Bayer BEACH HOUSE REAL ESTATE LLC

  9407 Gulf Dr, Anna Maria, FL 34216
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  $2,750,000

  $445K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 3,202 Sq Ft

  505 S Bay Blvd, Anna Maria, FL 34217

  Grandfathered to accommodate up to 12 guests—a rare and increasingly valuable advantage on Anna Maria Island—505 S Bay Boulevard offers an exceptional opportunity for investors seeking one of the island's highest-performing vacation rental properties. Unlike many homes subject to today's stricter occupancy regulations, this property retains its coveted higher occupancy allowance, creating

  Brenda Wade KELLER WILLIAMS SOUTH TAMPA

  505 S Bay Blvd, Anna Maria, FL 34217
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  $2,950,000

  $1M PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,933 Sq Ft

  893 N Shore Dr, Anna Maria, FL 34216

  One or more photo(s) has been virtually staged. If you're looking for exceptional value on Anna Maria Island, this is it! Combining a prime north-end bayfront location, private pool, recent major upgrades, and breathtaking Tampa Bay views, this property represents one of the best waterfront opportunities currently available.Best-priced full bayfront pool home on the desirable north end of

  Elizabeth Blandford SALTY MERMAID REAL ESTATE LLC

  893 N Shore Dr, Anna Maria, FL 34216
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  $1,995,000

  $130K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,968 Sq Ft

  307 Spring Ave, Anna Maria, FL 34216

  ~~~~~ PRICE DROP ~~~~~ Come take a look at this amazing Anna Maria home ready for you and your family to come live in paradise. Villa Maria is ready for you! An amazing 3 bedroom, 2 bathroom and a half bath just 2.5 blocks away from some of the most coveted beaches in the country. This popular vacation rental is perfectly nestled in the city of Anna Maria. Walking distance, a bike ride or short

  Billi Gartman ANNA MARIA LIFE REAL ESTATE

  307 Spring Ave, Anna Maria, FL 34216
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  $1,900,000

  $300K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  155 Crescent Dr, Anna Maria, FL 34217

  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

  Andrea Miller DUNCAN REAL ESTATE, INC.

  155 Crescent Dr, Anna Maria, FL 34217
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  $4,490,000

  $360K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,055 Sq Ft

  50 N Shore Dr, Anna Maria, FL 34216

  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

  Jay Travis RE/MAX ALLIANCE GROUP

  50 N Shore Dr, Anna Maria, FL 34216
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  $5,000,000

  • 4 Beds
  • 4.5 Baths
  • 3,385 Sq Ft

  519 Villa Rosa Way, Anna Maria, FL 34216

  This stunning property, situated on the premier private street of Anna Maria, was designed for the perfect blend of island indoor living and outdoor entertaining. Completed in 2017, this 3385sq ft open-plan luxury home has over 2000 SQ FT OF EXTERIOR PORCHES (6 porches). The ROOFTOP LOOKOUT DECK has expansive views extending from Tampa Bay to the Gulf of Mexico beaches. The outdoor movie deck,

  Ed Taaffe WAGNER REALTY

  519 Villa Rosa Way, Anna Maria, FL 34216
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  $2,495,000

  • 4 Beds
  • 3 Baths
  • 1,640 Sq Ft

  110 Palm Ave, Anna Maria, FL 34217

  Discover the ultimate island retreat just three homes from the sugar-white sands and turquoise waters of the Gulf of Mexico. Situated on an oversized 8,250-square-foot lot, this beautifully appointed 4-bedroom, 3-bath home offers nearly 1,700 square feet of coastal living and features a desirable open floor plan designed for gathering and entertaining. The thoughtfully designed layout includes

  Billi Gartman ANNA MARIA LIFE REAL ESTATE

  110 Palm Ave, Anna Maria, FL 34217
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  $7,500,000

  New Construction

  • 6 Beds
  • 6.5 Baths
  • 2,984 Sq Ft

  107 Maple Ave, Anna Maria, FL 34216

  This turn-key custom built six bedroom six and a half bathroom luxury home on Anna Maria Island is an exceptional beach investment property offering the perfect balance of passive rental income and personal coastal living. Located on one of the most private and prestigious streets on Anna Maria Island just steps from beach access the home offers Gulf of Mexico views and a proven short term rental

  Marisol Horner THE KAPLAN GROUP RE LLC

  107 Maple Ave, Anna Maria, FL 34216
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  $4,925,000

  • 5 Beds
  • 4.5 Baths
  • 2,545 Sq Ft

  112 Maple Ave, Anna Maria, FL 34216

  STUNNING HOME WEST OF GULF DRIVE! WELCOME TO THIS AMAZING FULLY FURNISHED 5 BEDROOM, 4.5 BATHROOM HOME LOCATED ON ONE OF THE PREMIER STREETS OF ANNA MARIA ISLAND!! With only 5 houses to the beach, this new construction gem is an absolute treasure. From the moment you set foot on the property, you'll be captivated by the thoughtfully designed custom features, including a paver driveway and lush

  Jay Travis RE/MAX ALLIANCE GROUP

  112 Maple Ave, Anna Maria, FL 34216
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  $5,150,000

  $200K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 2,870 Sq Ft

  915 N Shore Dr, Anna Maria, FL 34216

  DIRECT BEACHFRONT - This residence generated nearly $500,000 in income for 2025! Positioned on the pristine shores of the north end of Anna Maria Island, this extraordinary direct beachfront estate offers a rare opportunity to own a luxury coastal retreat while building lasting generational wealth through an exceptional income-producing opportunity. Offered turnkey furnished, this stunning

  Hannah Hillyard MICHAEL SAUNDERS & COMPANY

  915 N Shore Dr, Anna Maria, FL 34216
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  $2,785,000

  $140K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,412 Sq Ft

  796 Jacaranda Rd, Anna Maria, FL 34216

  BEAUTIFUL COASTAL HOME ONLY STEPS AWAY FROM THE PRISTINE BEACHES ON BEAN POINT. THIS 4 BEDROOM 2.5 BATH HAS QUALITY FINISHES THROUGHOUT INCLUDING SOLID GRANITE SURFACES, SOLID WOOD CABINETS, HARDWOOD FLOORS, VOLUME CEILINGS, NEW S/S APPLIANCES, ELEVATOR, AND COMES TURNKEY FURNISHED WITH A COASTAL DECOR. OUTSIDE IT HAS A METAL ROOF, IMPACT WINDOWS AND DOORS, HARDI SIDING, AND TROPICAL LANDSCAPING.

  Greg Bayer BEACH HOUSE REAL ESTATE LLC

  796 Jacaranda Rd, Anna Maria, FL 34216
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  $1,595,000

  • 3 Beds
  • 3 Baths
  • 2,019 Sq Ft

  317 N Bay Blvd, Anna Maria, FL 34216

  FINANCING FELL THROUGH BACK ON THE MARKET!!! Welcome to your dream getaway, an adorable bungalow located on the north end of Anna Maria Island, directly across from the beach and a lovely park. This charming 3-bedroom, 3-bathroom home is perfect for a full-time residence, an income-generating rental, or a part-time retreat—all in an unbeatable location. Step inside to discover a welcoming living

  Martha Jones DUNCAN REAL ESTATE, INC.

  317 N Bay Blvd, Anna Maria, FL 34216
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  $6,100,000

  New Construction $395K PRICE DROP

  • 6 Beds
  • 6.5 Baths
  • 4,525 Sq Ft

  224 Chilson Ave, Anna Maria, FL 34216

  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

  George DeSear AMI REALTY GROUP

  224 Chilson Ave, Anna Maria, FL 34216
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  $2,499,900

  • 4 Beds
  • 4 Baths
  • 2,826 Sq Ft

  517 Kumquat Dr, Anna Maria, FL 34216

  This 4 bed/4 bath waterfront pool home is on a quiet cul de sac, in the city of Anna Maria, with views of Bimini Bay! Roomy and inviting, with no bridges to the Bay, this boater’s paradise also allows short term rentals! The spacious floor plan invites you to relax. Whether you are preparing meals in your open kitchen with freshly painted cabinetry, stainless steel appliances and oversized

  Erin Leathem ISLAND REAL ESTATE-ANNA MARIA

  517 Kumquat Dr, Anna Maria, FL 34216
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  $1,750,000

  • 2 Beds
  • 2 Baths
  • 1,109 Sq Ft

  709 Fern St, Anna Maria, FL 34216

  Welcome to "Birdsong"! Discover the perfect blend of island charm and modern comfort in this beautifully updated 2-bedroom, 2-bath home located in one of Anna Maria Island’s most desirable neighborhoods. Just a 3-minute walk to the pristine Gulf beaches, this property offers the ideal setting for full-time living, a second home, or a high-performing investment. Step inside to an inviting

  Sean Sabbia RE/MAX ALLIANCE GROUP

  709 Fern St, Anna Maria, FL 34216
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  $1,949,500

  $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,843 Sq Ft

  312 Hardin Ave, Anna Maria, FL 34216

  WELCOME to Bimini Bay – Your Oasis Awaits! Step into your dream getaway at Bimini Bay, where this stunning home offers everything you need for the perfect beach house in paradise. Ideal for both vacationers and renters alike, this four-bedroom, three-bathroom retreat is nestled in the charming heart of Anna Maria. As you enter Bimini Bay, you'll be greeted by high ceilings and an expansive living

  Billi Gartman ANNA MARIA LIFE REAL ESTATE

  312 Hardin Ave, Anna Maria, FL 34216
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  $10,950,000

  • 5 Beds
  • 8 Baths
  • 5,079 Sq Ft

  811 N Shore Dr, Anna Maria, FL 34216

  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

  Jessica Batten SATO REAL ESTATE INC.

  811 N Shore Dr, Anna Maria, FL 34216
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  $3,250,000

  $250K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,020 Sq Ft

  242 Gladiolus St, Anna Maria, FL 34217

  Named "A Wave From It All" by the sellers, this exceptional coastal property offers high-end finishes and a layout designed for seamless indoor/outdoor living. The outdoor pool area serves as a private tropical oasis, perfect for relaxation. The main residence features three bedrooms, each with a king bed and ensuite bathroom. The kitchen is equipped with a Sub-Zero refrigerator, a Wolf range and

  Stephanie Bell FRAN MAXON REAL ESTATE

  242 Gladiolus St, Anna Maria, FL 34217
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  $2,795,000

  • 4 Beds
  • 4 Baths
  • 1,800 Sq Ft

  112 Cedar Ave, Anna Maria, FL 34216

  Completely remodeled 4-bedroom, 4-bathroom coastal retreat blending the charm of an original beach home with modern luxury. The upstairs features two spacious king-sized suites, each with beautifully appointed en-suite bathrooms. The rear primary suite opens to an expansive private deck with a comfortable seating area, while the front suite offers its own deck—perfect for morning coffee or

  Charles Buky COLDWELL BANKER REALTY

  112 Cedar Ave, Anna Maria, FL 34216
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  $5,295,000

  $200K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,287 Sq Ft

  118 Mangrove Ave, Anna Maria, FL 34216

  Welcome to 118 Mangrove Ave, a slice of tropical paradise in the heart of Anna Maria. This 4-bedroom, 4.5-bath residence offers an exceptional blend of luxury, comfort, and coastal convenience. Turnkey furnished and thoughtfully appointed, it is designed to meet every need and desire.Vaulted ceilings and abundant natural light create an open, airy ambiance throughout the spacious floor plan.

  George DeSear AMI REALTY GROUP

  118 Mangrove Ave, Anna Maria, FL 34216
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  $1,000,000

  $200K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  210 84th St, Holmes Beach, FL 34217

  Island living awaits at 210 84th Street, Holmes Beach, FL 34217. This 2-bedroom, 2-bathroom pool home offers the perfect opportunity to own a piece of Anna Maria Island, one of Florida's most desirable Gulf Coast destinations.Designed for enjoying the Florida lifestyle, the property features a private pool, comfortable indoor living spaces, and outdoor areas ideal for relaxing after a day at

  Chisa Stephenson REAL BROKER, LLC

  210 84th St, Holmes Beach, FL 34217
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  $2,950,000

  $500K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,214 Sq Ft

  605 N Point Dr, Holmes Beach, FL 34217

  Nestled at one of the highest elevations on Anna Maria Island, this exceptional coastal retreat is located in the highly sought-after North Point Harbour community of Holmes Beach. Built in 2012 with hurricane-rated windows and doors, the home offers both refined elegance and peace of mind, perfectly blending luxury with the relaxed sophistication of island living.A cheerful front porch

  Becky Sirigotis COMPASS FLORIDA LLC

  605 N Point Dr, Holmes Beach, FL 34217
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  $2,295,000

  $55K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 2,039 Sq Ft

  131 White Ave, Holmes Beach, FL 34217

  Fabulous opportunity to own a charming, elevated home with a total of 5 bedrooms, 4.5 bathrooms, private heated pool, west of Gulf Drive and only steps to the beach. The split layout of the home and the charming updates make this the perfect island retreat or investment property. The main living area consists of 3 bedrooms, 2.5 baths, updated kitchen with solid surface counters and

  Kimberly Roehl ISLAND DESTINATIONS

  131 White Ave, Holmes Beach, FL 34217
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  $16,750,000

  • 5 Beds
  • 6.5 Baths
  • 8,962 Sq Ft

  104 Sunset Ln, Holmes Beach, FL 34217

  Imagine owning a beach retreat on an island beloved by travelers from around the world yet still cherished for its warm, small-town charm. Newsweek recently named Anna Maria Island the #1 Most Popular Beach Town in America, and nestled along its pristine shoreline is Sunset Dream, an extraordinary 8,563 sq ft under-air contemporary beachfront estate designed to celebrate panoramic Gulf views at

  Charles Buky COLDWELL BANKER REALTY

  104 Sunset Ln, Holmes Beach, FL 34217

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