Anna Maria Homes with Gulf/Ocean Frontage

Anna Maria Homes with Gulf/Ocean Frontage

Welcome to Anna Maria, Florida—a charming barrier island that offers a slice of paradise on the Gulf Coast. Known for its pristine beaches, crystal-clear waters, and vibrant sunsets, Anna Maria is the perfect destination for those seeking a serene coastal lifestyle. With its laid-back atmosphere, this quaint island community is characterized by its colorful beach cottages, lush tropical landscaping, and friendly residents who embody the spirit of island living.

One of the most alluring features of Anna Maria is its stunning Gulf and ocean frontage. Imagine waking up to the soothing sounds of the waves lapping against the shore, with the sun rising over the horizon just outside your window. Homes here boast direct access to the beach, allowing residents to indulge in morning strolls along the shore, afternoon swims in the warm Gulf waters, and evenings filled with breathtaking sunsets. Properties with Gulf and ocean frontage are not just homes; they are a lifestyle choice, offering a unique blend of relaxation and adventure.

In Anna Maria, you can find everything from charming beach bungalows to luxurious waterfront estates, each designed to take full advantage of the picturesque surroundings. Whether you are looking for a vacation home, a permanent residence, or an investment property, the real estate options here cater to a variety of tastes and preferences.

Explore the delightful shops, savor fresh seafood at local eateries, and enjoy a myriad of outdoor activities, from kayaking to fishing. Anna Maria is not just a place to live; it’s a community that invites you to embrace the beauty of coastal living. Discover your dream home on Anna Maria Island today and experience the magic of life by the Gulf!

Newest Anna Maria Homes with Gulf/Ocean Frontage

$990,000
2 Beds ⋅ 2 Baths ⋅ San Seair Condo SubDv. ⋅ 33706 Zip Code
Absolute Paradise! This Spacious top quality fully updated Condo in the finest location on St Pete Beach! Turquoise water, sugar sands and epic sunsets can be seen from this corner unit with beautiful ceramic tile floors, a wonderful open kitchen and spa like baths. Relax on the east facing balcony for your daily therapy where you will see the most artistic sunrises possible with amazing bay views from the Don Cesar to Downtown St Petersburg. Wake to stunning beach views! The master suite is comfortably sized and both bedrooms access a north facing balcony with sweeping views from the Gulf to Downtown St Petersburg . A new A/C system in 2026 ensures cool comfort throughout. Light and Bright and Impeccably kept, there will be nothing for you to do except head to the beach. Spend all day beachfront in amazement that the Gulf is in your backyard and cap each evening off on your balcony marveling at yet another stunning sunset!! The Sanseair building is perfectly located and appointed with direct Beach access, a heated beachfront pool, updated lobbies, community room and exercise room with a beach view. You will be impressed by the closet space in this well planned condo and each unit has a storage room as well as community storage for beach chairs and bicycles. The building is well maintained with a new roof in 2021, new electric service in 2026 and the entire building was painted, balconies inspected and upgraded with new railings in 2020 along with numerous other updates. Dining, shopping and more are all within a short distance for your vacation lifestyle. The charm of the historic Don Cesar Hotel and Pass-A-Grille neighborhood as well as the Corey ave Sunday Market will have you falling in love with your new coastal hometown. Also So Convenient to St Petersburg’s downtown dining and arts scene, New bay front pier, major league sports, Downtown Tampa and Tampa Intl. and St Pete Clearwater Airports. St Pete Beach is tops on every list for sun, sand, fun and an amazing lifestyle. You deserve to live on one of the best beaches in the world. Start today!!

3820 Gulf Boulevard Unit 608, St Pete Beach
$3,250,000
5 Beds ⋅ 3 Baths ⋅ Coney Island SubDv. ⋅ 33706 Zip Code
Own one of Treasure Island's rarest beachfront compounds. Featuring The Pink Flamingo and The Blue Dolphin—two fully renovated Gulf-front homes generating nearly $300,000 in annual gross rental income—this turnkey legacy property offers the perfect blend of luxury living, proven cash flow, and irreplaceable direct beach frontage. Celebrated for their distinctive 1950s retro coastal theme, The Pink Flamingo and The Blue Dolphin have become iconic beachfront destinations, where vintage Old Florida charm meets modern comfort. Every detail has been thoughtfully designed to capture the nostalgia of a bygone era while providing today's guests with the quality and amenities they expect. The result is a truly memorable experience that has earned nothing but 5-star reviews and a loyal base of repeat visitors who return year after year. Behind the timeless aesthetic lies a property that has been meticulously updated for peace of mind and long-term value. Both homes feature impact-rated windows and doors, combining enhanced storm protection with energy efficiency, quiet interiors, and abundant natural light—all while preserving their unique character and curb appeal. With an established rental business, proven financial performance, and nearly $300,000 in annual gross revenue, you'll step into immediate cash flow while enjoying the flexibility to use the property however you choose. Live in one home and rent the other, continue operating both as premier vacation rentals, or create the ultimate multi-generational beachfront retreat for family and friends. The Pink Flamingo offers spacious accommodations, vibrant retro-inspired décor, and breathtaking Gulf views that make every stay unforgettable. Just steps away, The Blue Dolphin complements the experience with its own distinctive personality and inviting atmosphere, creating the perfect pairing for larger groups, extended families, or dual rental opportunities. Together, they form a one-of-a-kind beachfront compound that simply cannot be replicated. Step outside and the Gulf of Mexico becomes your backyard. Spend your mornings with coffee overlooking the water, your afternoons with your toes in the sugar-white sand, and your evenings watching spectacular sunsets from your private beachfront oasis. It's the quintessential Florida lifestyle that guests rave about and one that few properties can truly offer. For investors, the value extends well beyond the real estate itself. You're acquiring an established hospitality business with a proven operating history, exceptional guest satisfaction, and a recognizable identity that sets it apart in a competitive market. The combination of all 5-star ratings, repeat clientele, and turnkey operations provides a solid foundation for continued success from day one. Perfectly situated in the heart of Treasure Island, you're just minutes from waterfront dining, shopping, boating, entertainment, and John's Pass while still enjoying the privacy and tranquility of direct beachfront living. Properties offering two separate Gulf-front homes, a proven six-figure income stream, distinctive branding, modern upgrades, and an irreplaceable location are extraordinarily rare. The Pink Flamingo and The Blue Dolphin are more than vacation rentals—they are beloved destinations that blend nostalgia, luxury, and investment potential into one unforgettable opportunity. Note - There is also a second lot included that is in front of the lot with the houses.

12609 Sunshine Lane, Treasure Island
$779,000
3 Beds ⋅ 2 Baths ⋅ Sand Key Condo-South Beach 2 SubDv. ⋅ 33767 Zip Code
A perfect blend of abundant living space and ideal beachfront location in the heart of Sand Key! Set along one of the most pristine beaches that Florida has to offer, this rarely available 3BR residence comes updated and move-in ready. No need to compromise living space as this property offers an open concept layout that spans 1624 square feet with plenty of room for family and friends. The upgrades begin the moment you enter with angled walls that open the space, gorgeous 18-inch ceramic tile flooring, floor to ceiling sliding doors that access a 25ft. balcony with captivating views of the Gulf and Intracoastal, 5-inch base boards, and crown molding. All doors and windows are protected by electric hurricane shutters. The chef's kitchen is perfectly configured for entertaining and features custom wood cabinets, stainless steel appliances, and granite countertops with great counter space. The bedrooms are all spacious with generous storage and the owner's retreat features dual closets and updated en suite bath with solid wood cabinets and upscale tile work. The second bedroom is conveniently located right across from the updated second bath. A large 3rd bedroom is split and includes dual closets as well. This property also comes with a premium under building parking space and storage unit for your beach toys! South Beach II is an idyllic gated community that features lush tropical landscaping and a private, tranquil setting. Enjoy breathtaking sunsets from the tiki huts and swim in the heated resort-style pool that overlooks the Gulf. Other amenities include a fitness room, clubroom for social gatherings, and onsite manager. Close to everything including fabulous shops, restaurants, entertainment, and the Jolley Trolley! Call now to schedule your tour. Virtual tours are also available.

1430 Gulf Boulevard Unit 406, Clearwater Beach
$669,000
2 Beds ⋅ 2 Baths ⋅ Redington Towers Bldg 2 Condo SubDv. ⋅ 33708 Zip Code
Direct, unobstructed Gulf views from the 8th floor of Redington Towers Building 2. This corner 2-bedroom, 2-bath residence offers 1,330 SF with water views from nearly every room. Offered FURNISHED — arrive with a suitcase and start living the beach life the same day — and owners are willing to sell unfurnished as well. The open great room and dining area flow from a roomy kitchen with granite counters, wood cabinetry, and closet pantry, straight out to the private balcony, where sunset over the Gulf is the nightly show. Both oversized bedrooms are bright, with the primary enjoying Gulf views right from bed. Impact windows throughout, plus hurricane shutters on the main living areas, and the A/C (new 2020) has documented maintenance with a clean 2025 service report. The answer to today's #1 condo question: this building's milestone inspection and Structural Integrity Reserve Study are COMPLETE and the sellers' share is fully paid. A clean, inspected building for the new owner. Redington Towers is a gated, 24-hour guard-attended Gulf-front community: heated waterfront pool, clubhouse, fitness center, billiard room, library, BBQ area, covered parking with EV charging, and private storage (parking + storage convey). Set on the white sand of Redington Shores, one of Pinellas County's most desirable beach stretches, minutes to dining and shopping, 25 minutes to St. Pete–Clearwater International and about 40 to Tampa International. Full-time residence, beach retreat, or income property (leasing permitted, 90-day minimum each association). No-pet community. Easy appointment showings. Come watch a sunset from the balcony.

17920 Gulf Boulevard Unit 803, Redington Shores
$575,000
2 Beds ⋅ 2 Baths ⋅ Landmark Towers 1 SubDv. ⋅ 33767 Zip Code
LANDMARK TOWERS is a gated community on SAND KEY. This two bedroom, two bath condo is offered fully furnished and ready to occupy or lease. Direct and unobstructed view of the beach and Gulf. LANDMARK TOWERS I offers tennis and pickleball courts, heated pool and spa, shuffleboard and locked bicycle and kayak storage on ground floor. Assigned under building parking space and plenty of guest parking. Convenient storage locker located in laundry room across the hall. This is a gated community with guards 24/7. Easy access to public transportation and airports. SHOPPES ON SAND KEY across the street for shopping and restaurants.

1230 Gulf Boulevard Unit 403, Clearwater Beach
$659,000
2 Beds ⋅ 2 Baths ⋅ Landmark Towers 2 SubDv. ⋅ 33767 Zip Code
LANDMARK II is a gated community on beautiful SAND KEY. This two bedroom, two bath unit offers direct and unobstructed views of beach and Gulf. Sold "as is". The unit has electric storm shutters on west side and sliding doors have been replaced. Assigned under building parking space and plenty of guest parking available. The property offers heated pools, spa, tennis/pickleball, shuffle board, 24/7 guards and onsite management. The flexibility to add personal touches to this unit allows you to customize the space according to your preferences. There is a 2nd floor sundeck with gas grill, gazebo and seating. Walking distance to THE SHOPPES ON SAND KEY for restaurants and shopping. Convenient to airports and public transportation. Room sizes are approximate.

1250 Gulf Boulevard Unit 706, Clearwater Beach
$650,000
2 Beds ⋅ 3 Baths ⋅ South Paula Point Condo SubDv. ⋅ 34698 Zip Code
Exceptional corner waterfront residence offering refined coastal living and sweeping water views in the heart of the coveted Dunedin Causeway. Positioned on the second floor, this light-filled condo welcomes you with an elegant open-concept main level designed to showcase the surrounding scenery and create an effortless flow for entertaining. The beautifully appointed kitchen is anchored by an expansive quartzite island with seating, complemented by matching countertops, upgraded appliances, thoughtfully designed cabinetry, and a pantry that blends everyday function with sophisticated style. The spacious living and dining area opens through sliding doors to a private balcony with a retractable awning, creating an inviting outdoor retreat for morning coffee, coastal breezes, and unforgettable sunset views. A corner fireplace adds warmth and architectural interest while discreetly concealing additional closet storage. Upstairs, two private suites offer comfort and separation, each featuring an en-suite bath and three closets. The waterside primary suite is a true retreat, complete with a step-out balcony showcasing spectacular south-facing views of St. Joseph Sound and the Intracoastal Waterway. Hurricane-rated windows and doors with shutters provide added confidence and peace of mind. Enjoy a resort-inspired waterfront lifestyle with community amenities including a pool, clubhouse, lush landscaped grounds, and beautifully maintained common areas. Ideally located just minutes from Honeymoon Island and Caladesi Island State Park, with easy access to Downtown Dunedin, the Pinellas Trail, waterfront parks, boutique dining, shopping, breweries, galleries, beaches, Clearwater, and area airports. A rare opportunity to enjoy elevated, low-maintenance waterfront living in one of Dunedin’s most desirable coastal destinations.

433 S Paula Drive Unit 32, Dunedin
$229,000
2 Beds ⋅ 2 Baths ⋅ Sand Pebble Pointe Condo 03 SubDv. ⋅ 34668 Zip Code
Virtually Staged. Experience the ultimate coastal lifestyle in this stunning condo featuring breathtaking open Gulf views from your private sanctuary. Welcome to 1112 Bay Blvd in the desirable community of Sand Pebble Pointe, offering a well-maintained 1,025 sq. ft. layout designed for comfortable living. This charming property features an updated kitchen, elegant plantation shutters, and an effortless, ground maintenance-free lifestyle. Enjoy convenience and peace of mind in a fantastic location that is ready for you to move right in. You’ll enjoy access to luxury amenities including a 24/7 manned gate guard, resort-style pools, a gym, tennis courts, a private beach, a putting green, a dedicated boat yard with slips available, a private storage unit and parking spot. You are perfectly positioned just minutes from local favorites like Whiskey Joe’s, Hooters, and Whiskey River for waterfront dining. Plus, the charm of historic downtown New Port Richey is only a short drive or boat cruise away, offering endless shopping and entertainment options.

4620 Bay Boulevard Unit 1112, Port Richey
$1,200,000
2 Beds ⋅ 2 Baths ⋅ Dans Island On Sand Key Condo SubDv. ⋅ 33767 Zip Code
Virtually Staged. Welcome to Dan's Island on Sand Key! Experience breathtaking panoramic Gulf views from every room in this exceptional end-unit residence featuring wraparound balconies and an abundance of natural light. This spacious split-bedroom floor plan offers maximum privacy and effortless coastal living. The expansive primary suite easily accommodates a king-size bed and boasts stunning Gulf views. The luxurious en-suite bath features custom mahogany double vanities, dual sinks, a relaxing soaking tub, an oversized walk-in shower, and premium fixtures throughout. Designed for both everyday living and entertaining, the spacious living room showcases a beautifully rebuilt fireplace and flows seamlessly into the gourmet kitchen. The kitchen is appointed with solid wood cabinetry, quartz countertops, a stone backsplash, and a charming breakfast nook where you can enjoy spectacular water views with your morning coffee. The generously sized guest suite also enjoys Gulf views and includes a large walk-in California Closet. The beautifully updated guest bath features custom cabinetry and an elegant double stone walk-in shower with frameless glass doors. Additional conveniences include an interior laundry room with utility sink and abundant storage. Dan's Island offers an outstanding resort-style lifestyle with premium amenities, including: Heated Gulf-front swimming pool, Spa, Fitness center, Racquetball court, Billiards room, Party and social room. Ideally located on the pristine beaches of Sand Key, this is luxury Gulf-front living at its finest, offering spectacular sunsets, expansive water views, and the perfect blend of comfort, elegance, and resort-style amenities.

1600 Gulf Boulevard Unit 414, Clearwater
$2,300,000
3 Beds ⋅ 3 Baths ⋅ Ultimar Three Condo SubDv. ⋅ 33767 Zip Code
Step into the inviting entryway with hardwood floors, designer wallpaper & shell mirror. Exceptional Clearwater Beach completely remodeled condo features fantastic waterfront views of the Gulf, direct access to a vast Sand Key white sand beach and ideal vantage points for scenic sunrises to sunsets. The spacious open floor plan is accented by wall-to-wall, floor-to-ceiling windows and sliding glass doors that provide unobstructed views from nearly every room. Spanning 2,563 square feet, this updated three-bedroom, three-bathroom home feels even more expansive due to 10-foot-high ceilings throughout that optimize the abundant natural light and natural beauty defining this location. Two covered balconies create ideal areas for Al fresco dining, entertaining guests or relaxing while relishing the east to west elevated views from this eleventh floor residence. Designed for convenience and comfort, the layout includes a formal living room and family room, dining area that easily accommodates seating for friends & family, a fully outfitted gourmet kitchen with custom cabinetry, stainless steel appliances, quartz counters, countertop dining, and adjoining walk-in pantry, a separate laundry room plus butler’s pantry. Split bedroom plan provides privacy for owners as well as guests. The primary bedroom ensuite includes direct access to the Gulfside balcony, a walk-in closet and luxurious bath with marble shower, marble tub surround, custom cabinetry dual sink vanity with marble top. Designer lighting throughout & designer furnishing included. Sun shades at windows & sliders with remote in the living room & primary bedroom. The Ultimar is a world class condo complex on Sand Key of famous Clearwater Beach. Miles of pure white sand. Lush tropical landscaped grounds are expertly maintained. 24 hr guard gated. True Resort Style complex has 3 geothermal heated pools w/spas, 3 tennis courts, pickle ball, basketball court, putting green, croquet lawn, grill area, firepit area, shuffleboard, corn hole, gym, steam & sauna, billiards rm, media rm, social rm with catering kitchen and baby grand piano. Walk to great restaurants & shops or catch the Beach Trolley right out in front of the building. A short drive to Tampa & the airport plus all of the sports venues of our championship teams. START LIVING THE FLORIDA BEACH LIFESTYLE TODAY!! Buyer to verify room dimensions. Sold furnished & turnkey. PRIVATE GARAGE #101 in parking garage. Call for your private tour!

1560 Gulf Boulevard Unit 1101, Clearwater Beach
$149,000
2 Beds ⋅ 2 Baths ⋅ Imperial Cove 12 SubDv. ⋅ 33764 Zip Code
Welcome to the highly desirable Imperial Cove 55+ waterfront community in the heart of Clearwater! This spacious 2-bedroom, 2-bathroom condominium offers a bright, open layout with generously sized living spaces designed for both comfort and easy entertaining. The expansive living and dining areas flow seamlessly, creating an inviting atmosphere, while the large bedrooms provide plenty of room to relax and unwind. Enjoy peaceful lake views from your home and embrace the maintenance-free Florida lifestyle. Indulge in an impressive array of amenities, including a waterfront clubhouse, heated swimming pool, shuffleboard courts, fitness facilities, walking paths, fishing piers, and a full calendar of social activities, making it easy to stay active and connected. The community is known for its beautifully maintained grounds and scenic waterfront setting. Conveniently located just minutes from Clearwater's world-famous beaches, shopping, dining, medical facilities, and airports, this condominium is the perfect place to enjoy everything Florida living. Don't miss this opportunity to own a beautiful home in one of Clearwater's most sought-after waterfront communities!

19029 Us Highway 19 N Unit 21F, Clearwater
$660,000
1 Beds ⋅ 1 Baths ⋅ Jacaranda Beach Villas Condo SubDv. ⋅ 33706 Zip Code
DIRECT GULF FRONT, Top 7th floor, fully furnished, 535 sq.ft, 1 bedroom Suite with incredible Gulf views from balcony and room. This Condo-Hotel suite has two queen beds in a separate bedroom and a sofa bed that pulls out into a double bed in the other room, along with refrigerator, microwave, stove top, and sitting and eating area. This suite offers an exceptional price value. Excellent total turn-key rental income from the first class management rental program is already in place. Stay up to 28 days a year. Existing rental management agreement with the Tradewinds resort transfers to buyer. The Tradewinds offers over 1000' of Sandy Gulf-Front Beach on over 40 acres that will have you will feel as though you are in a Tropical Paradise. Ten pools, 13 food and beverage outlets, water slides, water activities, fitness facilities, and pickle ball and tennis courts are just a few of the very many amenities. The Tradewinds has a long established track record with hosting many weddings and conventions. What an opportunity. Perfect for a 1031 exchange. This resort offers it all !

5500 Gulf Boulevard Unit 7221, St Pete Beach
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