Anna Maria, FL Homes for Sale with Pool

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  $3,795,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,077 Sq Ft

  132 Crescent, Anna Maria, FL 34216

  Pre-Construction. To be built. Elegant north end residence to be constructed in 2026. Now is the time to make it your own! Pick all your colors, cabinets, and finishes! This elevated home will be constructed with the newest codes and standards with impact windows. Central location one block from Pine Ave and Trolly stop. Enjoy Bean Point and all the amenities, restaurants, and shops of the North

  Gavin Sebastian ANNA MARIA LIFE REAL ESTATE

  132 Crescent, Anna Maria, FL 34216
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  $1,825,000

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

  612 Fern St, Anna Maria, FL 34216

  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

  Mark Fazzini RE/MAX REALTEC GROUP INC

  612 Fern St, Anna Maria, FL 34216
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  $4,850,000

  • 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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  $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

  Reid Murphy DEVELOPERS REALTY LBK, INC

  9407 Gulf Dr, Anna Maria, FL 34216
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  $3,149,000

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

  705 N Shore Dr, Anna Maria, FL 34217

  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 bedrooms and 3.5 bathrooms,

  Billi Gartman ANNA MARIA LIFE REAL ESTATE

  705 N Shore Dr, Anna Maria, FL 34217
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  $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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  $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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  $5,350,000

  • 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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  $2,875,000

  • 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 ANNA MARIA ISLAND BEACHES RE

  796 Jacaranda Rd, Anna Maria, FL 34216
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  $5,750,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,751 Sq Ft

  329 Tarpon St, Anna Maria, FL 34216

  Experience the charm of Anna Maria Island with this NEWLY COMPLETED CONSTRUCTION. This luxurious home boasts four bedrooms and four and a half baths, offering STUNNING VIEWS. Features include an elevator, a three-car garage, and 3,751 square feet of air-conditioned space, and 7,893 square feet overall. Enjoy premium appliances, elegant wood floors throughout, and an open floor plan that is

  Charles & Gabe Buky COLDWELL BANKER REALTY

  329 Tarpon St, Anna Maria, FL 34216
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  $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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  $2,500,000

  • 5 Beds
  • 4 Baths
  • 2,838 Sq Ft

  733 Holly Rd, Anna Maria, FL 34216

  ***Welcome to Summer Breeze — a rare island gem on Anna Maria Island’s coveted North End.***This elevated 5-bedroom, 4-bath "Old Florida Coastal Retreat" sits on an oversized corner 1⁄4-acre lot surrounded by lush tropical landscaping, just steps from the world-famous Bean Point beaches. Whether you’re seeking a family getaway or a compelling short-term rental opportunity, this home delivers.

  Stacy Cunneen RE/MAX ALLIANCE GROUP

  733 Holly Rd, Anna Maria, FL 34216
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  $3,690,000

  • 5 Beds
  • 4.5 Baths
  • 2,680 Sq Ft

  113 Maple Ave, Anna Maria, FL 34216

  THIS INCREDIBLE CUSTOM BUILT ESTATE IS JUST FIVE HOUSES FROM THE GULF AND NESTLED ON ONE OF THE MOST COVETED STREETS ON ANNA MARIA ISLAND!!! LOCATED WEST OF GULF DRIVE YOU ARE JUST STEPS FROM THE SUGAR-WHITE SANDS AND TURQUOISE WATERS! This beautifully designed coastal home offers over 2,600 square feet of light-filled living space and is currently operating as a successful vacation rental,

  Jay Travis RE/MAX ALLIANCE GROUP

  113 Maple Ave, Anna Maria, FL 34216
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  $4,499,000

  • 4 Beds
  • 4.5 Baths
  • 2,803 Sq Ft

  112 Mangrove Ave, Anna Maria, FL 34216

  Just four houses from the beach, this stunning 4-bedroom, 4.5-bath coastal retreat by Poseidon Adventures Development Group captures the essence of Florida living. Designed for relaxation and effortless entertaining, this custom, high-performance, low-maintenance home offers exceptional comfort for both families and guests.Thoughtfully curated with custom furnishings, high-end fixtures, and

  George DeSear AMI REALTY GROUP

  112 Mangrove Ave, 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

  • 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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  $1,750,000

  • 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

  Cindy Quinn SATO REAL ESTATE INC.

  519 South Dr, Anna Maria, FL 34216
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  $5,500,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 2,220 Sq Ft

  113 Palmetto Ave, Anna Maria, FL 34216

  Under Construction. Welcome to 113 Palmetto Avenue, an architectural showcase by Eason Builders Group. This BRAND NEW 4 bed, 4.5 bath home features BLOCK construction, IMPACT rated glass and is built to the newest of codes for safety and peace of mind. Inside, natural light and coastal tones define every detail—chalk-white shaker cabinetry, laurel-green vanities, polished-nickel fixtures, and

  Jessica Batten SATO REAL ESTATE INC.

  113 Palmetto Ave, Anna Maria, FL 34216
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  $3,495,500 Open Mon 10:30AM - 12PM

  • 5 Beds
  • 4 Baths
  • 2,763 Sq Ft

  120 White Ave, Holmes Beach, FL 34217

  Nestled on Anna Maria Island’s most famous street, this beautifully renovated coastal retreat boasts five spacious bedrooms and four luxurious bathrooms, offering the perfect blend of comfort and style. Designed for seamless indoor-outdoor living, it features multiple porches where you can bask in the island breeze. Expansive sliding doors open to a generous deck, creating a natural flow between

  Charles & Gabe Buky COLDWELL BANKER REALTY

  120 White Ave, Holmes Beach, FL 34217
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  $3,575,000

  • 4 Beds
  • 4 Baths
  • 3,053 Sq Ft

  213 Oak Ave, Anna Maria, FL 34216

  Experience Florida coastal living at its finest in this exceptional custom-built home featured inSouthern Living Magazine. Uniquely located, this house is a short walk to white sand beachesand a short cruise to the Bay and Gulf. This classic Key West styled beauty was renovated andenlarged four years ago.The lush front yard features a circular paver driveway, a gorgeous Royal

  James Patterson SMITH & ASSOCIATES REAL ESTATE

  213 Oak Ave, Anna Maria, FL 34216
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  $2,995,000

  • 4 Beds
  • 4 Baths
  • 2,507 Sq Ft

  101 Sunset Ln, Anna Maria, FL 34216

  Built in 2002 by respected Whitehead Construction, this elevated coastal residence is ideally positioned just a short walk from the Gulf of Mexico, offering a relaxed island lifestyle paired with thoughtful updates and versatile living spaces. Set on a lush, quarter-acre lot in the desirable Sunset Cove area of Anna Maria Island, the home is surrounded by mature tropical landscaping that creates

  Roger Pettingell COLDWELL BANKER REALTY

  101 Sunset Ln, Anna Maria, FL 34216
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  $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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  $4,186,000

  • 5 Beds
  • 6 Baths
  • 3,640 Sq Ft

  727 Key Royale Dr, Holmes Beach, FL 34217

  Exquisite Waterfront Luxury Home with Breathtaking Gulf Views nestled in the picturesque shores of Key Royale in Holmes Beach on Anna Maria Island. Welcome to an unparalleled coastal retreat in the exclusive North Point Harbor Community. This custom-built, 3,640 sq. ft. luxury waterfront estate boasts 5 full bedrooms plus a bonus room, 4 full bathrooms, and 2 half bathrooms downstairs, offering

  Razin McFarland ENGEL & VOLKERS TAMPA DOWNTOWN

  727 Key Royale Dr, Holmes Beach, FL 34217
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  $1,295,000 Open Sat 11AM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,252 Sq Ft

  208 84th St, Holmes Beach, FL 34217

  Stunning Fully Renovated Island Retreat-Turnkey Paradise Awaits! This beautifully updated 2-bedroom, 2-bath home has been thoughtfully transformed with high-end finishes throughout, offering a seamless blend of style, comfort, and functionality. Step inside to an inviting open floor plan that creates an effortless flow between the living, dining, and kitchen areas — ideal for everyday living or

  Charity Cowden RE/MAX ALLIANCE GROUP

  208 84th St, Holmes Beach, FL 34217
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  $3,675,000

  • 4 Beds
  • 3.5 Baths
  • 4,330 Sq Ft

  718 Key Royale Dr, Holmes Beach, FL 34217

  Elevated living, literally and figuratively. Over 6000 sq/ft of spacious indoor/outdoor accommodation, island breezes, top-notch finishes, nestled into a quiet neighborhood. It’s the best of everything on Anna Maria Island. The home, custom built by one of the island's most prominent builders, is loaded with options you’ll love. Travertine and high-end hardwood flooring in living areas and

  Jason Skowronski COMPASS FLORIDA LLC

  718 Key Royale Dr, Holmes Beach, FL 34217
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  $1,110,000

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

  210 84th St, Holmes Beach, FL 34217

  One or more photo(s) has been virtually staged. Pool Home on Anna Maria IslandJust steps from the Gulf of Mexico, this 2-bedroom, 2-bath coastal cottage offers 1,200 sq ft of living space on a 9,000 sq ft lot. Enjoy your private pool surrounded by island breezes, or stroll to Holmes Beach, boutique shops, and dining. Whether you’re seeking a full-time residence, vacation getaway, or

  Chisa Stephenson REAL BROKER, LLC.

  210 84th St, Holmes Beach, FL 34217
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  $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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  $16,750,000

  • 5 Beds
  • 6.5 Baths
  • 8,563 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 & Gabe Buky COLDWELL BANKER REALTY

  104 Sunset Ln, Holmes Beach, FL 34217

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