Anna Maria, FL Homes for Sale with Pool

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  /57

  $7,500,000

  • 4 Beds
  • 6 Baths
  • 3,778 Sq Ft

  513 Villa Rosa Way, Anna Maria, FL 34216

  Rarely does a home of this architectural distinction and waterfront presence become available on Anna Maria Island. Tucked within the private residential enclave of Villa Rosa, this custom-built coastal estate offers a level of craftsmanship, privacy, and lifestyle reserved for the island’s most exceptional properties. Inspired by timeless European architecture, the residence is defined by

  Kimberly Dunn, LLC COLDWELL BANKER REALTY

  513 Villa Rosa Way, Anna Maria, FL 34216
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  /69

  $2,290,000

  • 4 Beds
  • 3.5 Baths
  • 2,203 Sq Ft

  115 Los Cedros Dr, Anna Maria, FL 34216

  Located on the highly sought-after North End of Anna Maria Island, 115 Los Cedros—known as Oceans Blue—offers an exceptional location just steps from the Gulf beaches and the shops and dining of Pine Avenue. Set on a 10,000 square foot lot, this single-story Anna Maria Island beach house combines luxury, comfort, and peace of mind. The residence currently offers four bedrooms, with the

  Elizabeth Blandford SALTY MERMAID REAL ESTATE LLC

  115 Los Cedros Dr, Anna Maria, FL 34216
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  /58

  $3,250,000

  • 5 Beds
  • 3.5 Baths
  • 1,983 Sq Ft

  117 Willow Ave, Anna Maria, FL 34216

  Exceptional island retreat located on beautiful Anna Maria Island, just one block from the beach and a short stroll to the charming shops and restaurants along Pine Avenue. This custom-built 2,000 sq. ft. home offers the perfect blend of coastal luxury and investment potential. Designed with an open-concept floor plan, the residence features 5 bedrooms, 3 1/2 baths, providing ample space for

  Karen McCall BEACH HOUSE REAL ESTATE LLC

  117 Willow Ave, Anna Maria, FL 34216
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  /28

  $1,995,000

  • 3 Beds
  • 2 Baths
  • 1,458 Sq Ft

  228 Gladiolus St, Anna Maria, FL 34216

  Anna Maria Island Income-Producing Beach Retreat | 3BR/2BA | Oversized Pool + SpaExceptional opportunity to own an elevated 3-bedroom, 2-bath home on Anna Maria Island, just a short walk to the beach. Whether you’re looking for a personal island getaway, full-time residence, or a successful vacation rental investment, this property offers the perfect combination of lifestyle and income

  Amanda Cornett PINEYWOODS REALTY LLC

  228 Gladiolus St, Anna Maria, FL 34216
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  /54

  $2,199,000

  • 4 Beds
  • 2 Baths
  • 1,472 Sq Ft

  108 Pelican Dr, Anna Maria, FL 34216

  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

  Jessica Batten SATO REAL ESTATE INC.

  108 Pelican Dr, Anna Maria, FL 34216
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  /97

  $9,850,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 3.5 Baths
  • 4,728 Sq Ft

  801 N Shore Dr, Anna Maria, FL 34216

  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

  Becky Sirigotis COMPASS FLORIDA LLC

  801 N Shore Dr, Anna Maria, FL 34216
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  /63

  $2,945,000

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

  704 Gladiolus St, Anna Maria, FL 34216

  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

  Erin Leathem ISLAND REAL ESTATE-ANNA MARIA

  704 Gladiolus St, Anna Maria, FL 34216
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  /68

  $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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  /34

  $2,999,000

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

  505 S Bay Blvd, Anna Maria, FL 34217

  Let the island breeze guide you home to 505 S Bay Boulevard, a waterfront haven where the world slows down and coastal living feels like poetry. Tucked along the tranquil north end of Anna Maria Island, this elevated five-bedroom, five-bath home invites you to experience a lifestyle wrapped in beauty, comfort, and pure island magic. Step inside and discover more than 3,200 square feet of

  Brenda Wade KELLER WILLIAMS SOUTH TAMPA

  505 S Bay Blvd, Anna Maria, FL 34217
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  /62

  $2,950,000

  • 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. Price reduced — dramatic value on Anna Maria Island! This rare north-end bayfront home offers nearly 3,000 sq ft under air with 4 bedrooms, 3 baths, a private pool and panoramic Tampa Bay views including the Sunshine Skyway Bridge. Step through the white picket fence into updated, open-concept living with high ceilings, light wood-look laminate

  Elizabeth Blandford SALTY MERMAID REAL ESTATE LLC

  893 N Shore Dr, Anna Maria, FL 34216
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  /51

  $1,995,000

  • 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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  /58

  $1,900,000

  • 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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  /45

  $1,695,000

  • 3 Beds
  • 2 Baths
  • 1,403 Sq Ft

  165 Crescent Dr, Anna Maria, FL 34216

  Charming coastal retreat located at 165 Crescent Dr in the heart of Anna Maria! This beautifully maintained 3-bedroom, 2-bath home offers the perfect blend of comfort and island living. Featuring a private pool and spa, this property is ideal for relaxing or entertaining guests. The outdoor space is a true highlight, complete with a built-in grill and outdoor shower—perfect after a day at the

  Ryan Sheck ISLAND REAL ESTATE-ANNA MARIA

  165 Crescent Dr, Anna Maria, FL 34216
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  /89

  $4,650,000 Open House 5/24

  • 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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  /79

  $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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  /63

  $2,855,000

  • 4 Beds
  • 3.5 Baths
  • 2,421 Sq Ft

  705 N Shore Dr, Anna Maria, FL 34217

  ~~~~ PRICE IMPROVEMENT ~~~~. Stunning Family Vacation Home in Anna Maria, FL! Yellowbird, 705 North Shore Dr., Anna Maria. Nestled on the beautiful North End of Anna Maria Island, Yellowbird is a luxurious family vacation home that embodies old Florida charm and offers an ideal location just a quick stroll from the stunning white sandy beaches of the Gulf. This spacious retreat features 4

  Billi Gartman ANNA MARIA LIFE REAL ESTATE

  705 N Shore Dr, Anna Maria, FL 34217
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  /46

  $1,575,000

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft

  313 Magnolia Ave, Anna Maria, FL 34217

  Welcome to your dream getaway on Anna Maria Island! THIS HOME HAS A BRAND NEW ROOF! Nestled in a prime location midway between the enchanting Tampa Bay and the pristine Gulf of Mexico waters, this meticulously maintained home offers the perfect blend of convenience and relaxation. Unbeatable location that allows you to stroll effortlessly to Anna Maria's hotspots, from Ginny's to the iconic

  Jay Travis RE/MAX ALLIANCE GROUP

  313 Magnolia Ave, Anna Maria, FL 34217
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  /68

  $7,500,000 New Construction

  • 6 Beds
  • 6.5 Baths
  • 6,500 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 ARC REALTY GROUP

  107 Maple Ave, Anna Maria, FL 34216
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  /58

  $2,549,900

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft

  403 N Bay Blvd, Anna Maria, FL 34216

  $100,000 PRICE REDUCTION – Now Priced to Sell | Luxury Island Home on North End of Anna Maria Island | Bay Views | Pool | TurnkeyWelcome to exceptional island living on the highly sought-after north end of Anna Maria Island, where homes like this rarely become available.This beautifully maintained turnkey 4-bedroom, 3-bathroom coastal residence offers stunning sunrise views over the bay, an

  Ed Taaffe WAGNER REALTY

  403 N Bay Blvd, Anna Maria, FL 34216
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  /91

  $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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  /85

  $5,250,000

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

  915 N Shore Dr, Anna Maria, FL 34216

  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

  Hannah Hillyard MICHAEL SAUNDERS & COMPANY

  915 N Shore Dr, Anna Maria, FL 34216
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  /61

  $2,785,000

  • 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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  /35

  $2,200,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  401 N Shore Dr, Anna Maria, FL 34216

  Stunning Fully Remodeled 3-Bedroom Home with Pool & Spa – Prime North End Location. Welcome to your dream coastal retreat! This beautifully remodeled 3-bedroom, 2-bath home was completely transformed in the spring of 2025 and professionally decorated with designer furnishings. Since the renovation, the home has never been occupied—offering a truly brand-new interior experience. Every detail was

  Dave Marcinko NDC REALTY, LLC

  401 N Shore Dr, Anna Maria, FL 34216
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  /95

  $6,344,999 New Construction

  • 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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  /35

  $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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  /48

  $1,949,500

  • 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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  /45

  $1,598,000

  • 3 Beds
  • 2 Baths
  • 2,131 Sq Ft

  519 South Dr, Anna Maria, FL 34216

  “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

  Jessica Batten SATO REAL ESTATE INC.

  519 South Dr, Anna Maria, FL 34216
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  /90

  $10,950,000

  • 4 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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  /97

  $5,495,000

  • 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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  /50

  $1,649,000

  • 2 Beds
  • 2 Baths
  • 1,540 Sq Ft

  417 Poinsettia Rd, Anna Maria, FL 34216

  Some homes are simply felt before they are fully understood. The moment you arrive at 417 Poinsettia Road, something shifts — the salt air, the sound of water moving gently at the canal's edge, the way the light falls across the pool in the late afternoon. This home is designed for the honest and unhurried experience of Anna Maria Island that we call "Island Time". Tucked on the north end of the

  Jennifer Orns COMPASS FLORIDA LLC

  417 Poinsettia Rd, Anna Maria, FL 34216
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  /92

  $3,250,000 Open Fri 1PM - 4PM

  • 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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  /53

  $2,295,000

  • 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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  /65

  $2,950,000

  • 4 Beds
  • 3.5 Baths
  • 2,040 Sq Ft

  117 81st St, Holmes Beach, FL 34217

  Welcome to 117 81st Street in Holmes Beach, a custom-designed coastal retreat steps to the beach that has been completely renovated inside and out, offering the perfect blend of modern luxury and effortless island living. This beautifully updated 4-bedroom, 3.5-bath home is being sold turnkey furnished, making it move-in ready or immediately available as a high-performing rental investment. The

  Matthew Huffman COLDWELL BANKER REALTY

  117 81st St, Holmes Beach, FL 34217

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