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$999,000
2 Beds ⋅ 2 Baths ⋅ A4684724 MLS
You must see this charming 1940s Craftsman cottage tucked into the historic heart of Anna Maria Island! This beautifully renovated two-bedroom, two-bath homestead blends timeless Old Florida character with effortless coastal charm. The home’s distinctive pecky pine exterior pay homage to its heritage while creating a warm, inviting island aesthetic that reflects the relaxed spirit of Anna Maria’s historic beach community. Inside, the home opens into a light-filled open floor plan designed for easy coastal living and effortless entertaining. The living, dining, and kitchen areas flow seamlessly together, creating a welcoming gathering space filled with natural light and breezy island ambiance. Whether enjoying a quiet morning coffee or hosting friends after a day at Anna Maria’s beautiful beaches, the layout makes the home feel both spacious and intimate. A convenient indoor laundry room is thoughtfully tucked away, adding modern practicality to this historic retreat. The home features a well-designed split floor plan, offering privacy and comfort for residents and guests alike. The primary bedroom suite includes a private ensuite bath, creating a peaceful retreat at the end of the day. On the opposite side of the home, the second bedroom features charming built-in bunks, perfect for family or visiting guests, with easy access to the second full bath. Step outside to discover a beautifully landscaped private pool enclosure, surrounded by lush tropical greenery that creates a tranquil island oasis. It’s the perfect spot to relax, unwind, and soak in the peaceful rhythm of Anna Maria’s laid-back island lifestyle. All of this is located just two blocks from Anna Maria’s world-famous sugar-sand beaches, and only moments from the island’s beloved restaurants, charming boutiques, and local shops. Spend your days biking to breakfast cafés, strolling to dinner with sunset views, or exploring the unique coastal storefronts that make Anna Maria so special. This lovingly restored cottage offers a rare opportunity to own a piece of historic island charm paired with modern comfort in one of Florida’s most treasured beach communities.

2913 Gulf Drive, Holmes Beach
$1,450,000
2 Beds ⋅ 2 Baths ⋅ A4679231 MLS
BUILD YOUR BAYFRONT DREAM HOME... Gorgeous views of the bay & Intracoastal Waterway from this property on a quiet, serene street. Home was remediated after the hurricanes of 2024 and is now a blank slate for a new owner to create their forever home on the water. This 2/2 home has good bones, vaulted ceilings and a nice floor plan to reinvent OR raze current structure to build a magnificent bayfront home on Anna Maria Island. Ideally situated right on the bay and just a short stroll to the beach with easy access... Waterfront parcel, PI#74413.0010/9 will convey with this sale.

2316 Canasta Drive, Bradenton Beach
$1,100,000
2 Beds ⋅ 2 Baths ⋅ A4678032 MLS
Welcome to "Captains Quarters" this luxury duplex is recently renovated and centrally located on Anna Maria Island with over $140k in projected rental revenue for 2026. This property underwent a full renovation in 2023 with full permits for new windows, electric, ac, and plumbing. This island retreat features a brand new heated saltwater pool and spa nestled among the palm trees with a secluded beach alley access. Each side features it's own kitchen, living and dining area. The gourmet kitchen in both units features quartz countertops, new shaker cabinets and stainless steel appliances. This home is being sold turn-key furnished. Property is currently being used as a vacation rental. Call today for your private showing!

3016 Gulf Drive, Holmes Beach
$1,125,000
2 Beds ⋅ 2 Baths ⋅ A4678029 MLS
Welcome to "Pineapple Paradise" this luxury duplex is recently renovated and centrally located on Anna Maria Island with over $140k in rental revenue projected for 2026. This property underwent a full renovation in 2023 with full permits for new windows, electric, ac, and plumbing. This island retreat features a brand new heated saltwater pool and spa nestled among the palm trees with a secluded beach alley access. Each side features it's own kitchen, living and dining area. The gourmet kitchen in both units features quartz countertops, new shaker cabinets and stainless steel appliances. This home is being sold turn-key furnished. Property is currently being used as a vacation rental. Call today for your private showing!

3014 Gulf Drive, Holmes Beach
$675,000
2 Beds ⋅ 2 Baths ⋅ A4655549 MLS ⋅ Avenue B By The Bay BLDG.
Virtually Staged. Perfectly positioned between the Gulf of Mexico and Sarasota Bay, this elevated coastal home offers the best of island living just steps from the water in both directions. Whether it’s morning walks along the bay or sunset evenings on the beach, this location delivers the Florida lifestyle buyers are searching for. Inside, the home features a bright, open layout with updated flooring throughout and a fully renovated kitchen complete with shaker-style cabinetry, granite countertops, stainless steel appliances, and a modern tile backsplash. The open living and dining space flows seamlessly to a private upper-level deck—ideal for relaxing, entertaining, or enjoying the coastal breeze. The primary bedroom also offers direct access to the deck, creating a true indoor-outdoor living experience. Both bathrooms have been tastefully updated with modern finishes, including a walk-in shower and upgraded vanities. The elevated design provides covered parking and additional storage space below, offering both convenience and functionality. Recent updates and well-maintained systems, including the roof, add to the overall value and peace of mind. Located in the heart of Bradenton Beach, this property places you just moments from the white sand beaches of Anna Maria Island, local dining, shops, and nearby parks with tennis courts and bayfront views. Whether you’re searching for a primary residence, vacation getaway, or investment opportunity, this home offers flexibility and an unbeatable coastal location.

2513 Avenue B Unit B, Bradenton Beach
$874,000
3 Beds ⋅ 1 Baths ⋅ A4650913 MLS
***PRICE DROP & BRAND NEW EFFICIENT HVAC INSTALLED!!** LIVE THE ISLAND LIFESTYLE IN THIS CHARMING 1940'S - COTTAGE , THIS 3-BEDROOM,1 BATH HOME ELEVATED ABOVE A 2 CAR GARAGE IS JUST STEPS AWAY FROM THE BEACH AND THE BAY, IDEALLY LOCATED IN THE HEART OF BRADENTON BEACH. WHETHER YOU AR LOOKING FOR A PERSONAL RETREAT OR A VACATION RENTAL,THIS PROPERTY ALLOWS SHORT TERM RENTALS GIVING YOU FLEXIBILITY AND A FINANCIAL OPPORTUNITY . ENJOY THE CONVENIENCE OF BEING CLOSE TO SHOPS, RESTAURANTS,AND A FREE TROLLEY SERVICE, PLUS TAKE IN THE BREATHTAKING SUNSETS RIGHT FROM YOUR DOOR STEP. WITH A SPACIOUS CORNER LOT THERE IS ROOM TO INSTALL A POOL OR CREATE YOUR DREAM OUT DOOR PATIO - DON'T MISS OUT ! MAKE THIS ISLAND GEM YOURS.

300 N 22nd Street, Bradenton Beach