Browse All Anna Maria FL 5 Bedroom Properties for Sale

Welcome to your dream beach home on Anna Maria Island, where luxury meets laid-back island living. This beautifully renovated and reimagined 5-bedroom, 4.5-bathroom retreat is just steps from the pristine sandy shores, offering the perfect blend of elegance and coastal charm. As you step into the inviting foyer on the ground floor, you have the option to take the staircase or the newly installed elevator to the main living space on the third floor. Here, you'll be greeted by a bright, open area featuring a spacious and breezy balcony with stunning Gulf views. The light-filled interior boasts a seamless flow, perfect for enjoying the relaxed beach lifestyle. The heart of the home is the gourmet kitchen, boasting high-end KitchenAid appliances, designer cabinets, and sleek quartz countertops. Whether you're preparing a casual meal or entertaining guests, this kitchen is sure to impress. The spacious dining area and family room on this level create an ideal setting for gatherings and relaxation. The second floor houses the luxurious master suite, offering a private balcony and a spa-like en-suite bathroom. A guest suite and laundry room are also located on this floor, providing comfort and privacy for all. The ground floor features three additional bedrooms, one with a private en-suite, providing ample space for family and guests. This level also includes access to the fenced backyard oasis, complete with a large spa, tiki bar, and outdoor kitchen. This is your personal paradise for hosting barbecues, relaxing with a drink, or soaking up the sun in total privacy. This home is fully furnished with tasteful, high-quality furnishings that complement its beachy yet sophisticated style. Recent upgrades include a new metal roof, impact windows and doors, new plumbing, and the modern elevator, ensuring convenience and peace of mind. Located in the heart of Anna Maria Island, this property is perfectly positioned for enjoying all the island has to offer. You're just steps from the iconic Sandbar Restaurant and one block from historic Pine Avenue, with its charming shops, eateries, and local attractions. Currently used as a successful short-term rental with local management, this home is a fantastic investment opportunity or a dream residence for those seeking the ultimate beach lifestyle. Discover the perfect blend of luxury and relaxed coastal living in this exceptional Anna Maria Island home. Schedule your private tour today and experience the magic of island life!

110 Spring Avenue, Anna Maria

$5,895,000

5 Beds ⋅ 4.5 Baths ⋅ A4616606 MLS

Welcome to this amazing fully furnished 5 bedroom , 4.5-bathroom home located on one of the premier streets of Anna Maria Island! LOCATED WEST OF GULF DRIVE, 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 tropical landscaping. Step inside and experience the open and spacious main living area, featuring a great room floor plan that seamlessly connects to an incredible deck through sliding glass doors. This expansive outdoor space offers ample room for outdoor dining and a comfortable sitting area, allowing you to fully embrace the island lifestyle. The kitchen is a chef's dream, boasting high-end appliances, a designer backsplash, a large center island with a breakfast bar, and stylish pendant lights. Retreat to the luxurious master suite at the end of a day filled with beach adventures. It features a sitting area and an incredible bathroom with dual sinks, a garden tub, and a walk-in shower. An additional guest bedroom on the same floor offers the convenience of an ensuite bathroom. Upstairs you will find three bedrooms and two bathrooms as well as a wetbar/coffee area. Step outside to the expansive area featuring an outdoor kitchen, dining area and turf area perfect for entertaining and hanging out. The roof top balcony offers breathtaking views of the Gulf, creating a serene setting for relaxation. The amount of outdoor living space in this home is truly one of a kind.The backyard of this home is your own private tropical oasis, complete with a heated pool and spa. Here, you can indulge in luxury living on Anna Maria Island and enjoy the tranquil surroundings. The finishes and attention to detail throughout the home are unmatched, ensuring an exceptional living experience. Whether you're in search of your forever home or a lucrative investment property, this is the one for you. With its prime location just a short distance to Pine Ave, where you'll find a variety of restaurants, shops, and the City Pier, this home offers the perfect blend of convenience and tranquility. Don't miss out on the opportunity to own this incredible property. Schedule a showing today and secure your chance to own a piece of Anna Maria Island's luxury living.

112 Maple Avenue, Anna Maria

$4,250,000

5 Beds ⋅ 4.5 Baths ⋅ A4614196 MLS

Welcome to your island oasis! This stunning modern waterfront home redefines relaxation. Step through the double front doors and behold the tropical backyard. Ascend to the main living level via custom handrail-adorned stairs or the convenient elevator. The open-concept space features 8” white oak wood floors, wood-beamed ceilings, and designer Reginald Andrews lighting. The gourmet kitchen boasts waterfall Cambria Stone Quartz countertops and top-of-the-line stainless appliances. Pocket sliding doors lead to the terrace with pool and water views, seamlessly blending indoor and outdoor living. The master suite, complete with a private terrace, Porcelanosa tile finishes, Moen Align fixtures, and Caesarstone quartz countertops, offers a true retreat. Three additional en-suite bedrooms, a den, and an expansive bonus room with custom built-in bunk beds are meticulously finished. Enjoy island and water views from the terraces on all levels. Outside, the Trex deck surrounds the resort-style pool and spa, just steps away from an outdoor shower and pool bath. The private dock provides water access to the Gulf of Mexico, perfect for boating, kayaking, and water toys. Additional highlights include a rooftop deck with 360-degree views, all within walking distance of restaurants, boutiques, and the white sandy beaches of Anna Maria and Pine Ave.

108 Tern Drive, Anna Maria

$6,500,000

5 Beds ⋅ 5.5 Baths ⋅ A4612343 MLS

This recently constructed home on Anna Maria Island overlooking a stunning canal is just one block from the pristine Gulf of Mexico beaches and a short walk to the restaurants and boutiques on Pine Ave. This luxurious 5-bedroom, 5.5 bath retreat offers a spectacular backyard with a private pool and swim up bar, in-ground spa, a covered shellcrete patio with seating, a ping pong table, and a BBQ grill. The coastal home features two garages and a private drive accommodating four vehicles. The main living floor has an open layout with bright natural lighting, a plush living area with sofas and a TV. The kitchen is equipped with upgraded stainless steel Bosch appliances and quartz countertops. There are many dining areas including the cozy kitchen nook, kitchen island, formal dining room, or on the balcony overlooking the canal. The 5 beautifully designed bedrooms feature elegant decor, chic furnishings, bedside lighting, and ensuite bathrooms. The second floor houses 3 bedrooms with king beds and full baths, a half bathroom for guest use, and a walk-in laundry room with a washer and dryer. The third floor includes a seating area with a table and chairs, a TV area, a wet bar, and two primary suites accessible by elevator or stairs. These suites feature king beds, private terraces, walk-in closets, and ensuite bathrooms with large glass-walled showers. Additionally, the rooftop deck provides an ideal spot for relaxation and taking in the views. This home offers a blend of luxury, comfort, and convenience, making it an exceptional choice for your Anna Maria Island life!!

404 North Shore Dr, Anna Maria

$12,650,000

5 Beds ⋅ 5.5 Baths ⋅ A4608114 MLS

JUST COMPLETED! BRAND NEW CONSTRUCTION!!! Gulf Front Luxury Living is at its Absolute Best in this Exquisite Estate in the Heart of Anna Maria! It will be love at first sight when you enter this stunning FULLY FURNISHED 5 Bedroom, 5.5 Bathroom Gulf Front Estate. This home has it all including endless views of The Gulf of Mexico. With over 4,936 square feet under air, this home features Control 4 smart home automation, expansive living spaces with custom, designer finishes, in-ceiling speakers, custom built-ins and motorized Lutron blinds throughout. Take the master staircase or commercial-grade elevator to the open-concept, main living area which features an oversized, luxurious living room with views of the crystal blue waters of the Gulf as you look out through the floor-to-ceiling, pocket sliding doors containing the highest quality windows. The main living level also features a gorgeous Gulf front dining room, detailed gourmet chef's kitchen featuring Sub Zero and Wolf appliances, separate walk-in pantry, conversation full bar sitting area with a walk-in and a custom outdoor kitchen on the lanai. Then, continue up the grand staircase to your private hideaway master suite which includes an oversized bedroom, sitting and lounge area, balcony, walk-in designer closet, large designer bath area with spectacular finishes and, of course, more amazing Gulf views! This floor also features two additional guest suites. On the ground level, the expansive Gulf-front swimming pool and enormous surrounding deck offers significant, additional entertaining space. Professional landscaping placed with privacy in mind, a 4-car garage and a paved driveway with plenty of room for both owner and guest vehicles. All of this and you are a short stroll from the shops and restaurants of Pine Avenue. Call me today to make your dream of owning an exquisite, luxurious Gulf-front Estate a reality!

809 N Shore Drive, Anna Maria

$2,875,000

5 Beds ⋅ 4 Baths ⋅ A4603232 MLS

New look, new price! This 5 Bedroom Anna Maria Island home just completed a COASTAL REFRESH. Come home to your Happy place at 508 Spring Avenue, nestled on stunning Anna Maria Island. Located within one of the most prestigious areas on the island, it is just steps away from Pine Avenue, with its adorable shops, wonderful restaurants, and the famous Anna Maria Pier. A short bike ride will get you to Bean Point. This house represents one of the best values on the island. A rental giant, grossing well over $200k in rental income, including time left for owner usage. 2024 has $166K booked (reflecting over 50 nights of owner use) and $51K already booked for 2025! One of the few properties in Anna Maria, which is Bert Harris approved, allowing up to 14 guests. The home's recent renovations give it the quintessential coastal life vibe. Set up with two separate gathering areas for family and friends, there are living rooms and private balconies on both the main floor and the upper floor. New furniture has been added to both living rooms. New flooring throughout along with new kitchen countertops! The backyard has a beautiful family pool, surrounded by coconut trees, that includes a shallow area for small children to walk in and play in as well as a built-in bar/table area for the adults. Adjacent to the pool is a recreation space with a flat panel tv, and foosball and ping pong tables. This 5 bedroom, 4 bath home is turnkey rental furnished and ready for your enjoyment! Don't miss out on this newly renovated beach house! The primary bedroom is a coastal paradise with a fantastic ensuite bathroom with a double vanity, a walk-in shower, and a soaking tub, and this room has access to the second-floor balcony. On each living floor is a King bedroom and a Bunk bedroom. The first-floor King bedroom has an ensuite bathroom with a walk-in shower, and on each floor is a hall bathroom with a shower and tub combination. Additionally, there is a Queen sleeper sofa and a Twin sleeper sofa. Room Details -Primary Bedroom, 2nd floor: King bed, balcony access, and ensuite bathroom with soaking tub and walk-in shower -Second Bedroom, 1st floor: King bed and ensuite bathroom with walk-in shower -Third Bedroom, 2nd floor: King Bed -Fourth Bedroom, 2nd floor: Twin Bunk bed and Twin bed -Fifth Bedroom, 1st floor: Twin Bunk bed and Twin bed -Living Area: One Queen and One Twin Sleeper Sofa The backyard is beautifully landscaped with coconut palms and native species. The heated lagoon pool has a built-in dining table, and there are plenty of Adirondack chairs and a BBQ grill on the pool deck. Adjacent to the pool area is a recreation room with a Flat Panel LED TV, Foosball Table, Ping Pong Table, and a comfortable large sitting area. This home is equipped with wireless Internet, a XBOX gaming system, and assorted beach items. Highlights • Private Pool • 10-minute walk to the beach • Ping Pong Table and Foosball table • Short walk to AMI City Pier, Pine Ave, and Bayfront Park

508 Spring Avenue, Anna Maria

$2,750,000

5 Beds ⋅ 3 Baths ⋅ A4602242 MLS

Under contract-accepting backup offers. This exquisite turnkey furnished residence offers a ready-made vacation retreat in the heart of Anna Maria Island. Situated just a block away from the vibrant Pine Avenue, this coastal-inspired property encompasses a main house boasting 3 bedrooms and 2 baths, complemented by a charming guest cottage featuring 2 bedrooms and 1 bath. Built in 2015, the home epitomizes modern comfort and style, with tasteful decor throughout. Step inside to discover a spacious gourmet kitchen seamlessly flowing into the inviting living areas, perfect for hosting gatherings and creating lasting memories. Beyond the interiors, the outdoor living space beckons, featuring a private heated pool with cocktail table and sun shelf all situated between the main house and guest cottage, providing an idyllic setting for relaxation and entertainment amidst the island's tropical ambiance. The unique layout of the home is perfect for a multitude of uses, offering separate spaces for privacy and togetherness. Enjoy the convenience of a 1-car garage, providing ample storage space for a vehicle and beach essentials. Conveniently located within walking distance to both Gulf and Bay beaches, as well as a myriad of dining and shopping options along Pine Avenue, Jersey Girl offers unparalleled access to Anna Maria's coveted amenities. Short-term rentals are allowed, adding to the versatility and investment potential of this remarkable property. With a Bert Harris Exemption, this property is approved to sleep 12 people per Anna Maria City code, presenting an exceptional investment opportunity. Whether you're seeking a primary residence, a second home, or a lucrative vacation rental, Jersey Girl offers versatile possibilities. Make Jersey Girl your own slice of coastal paradise.

423 Spring Avenue, Anna Maria

$4,500,000

5 Beds ⋅ 5 Baths ⋅ T3509233 MLS

Discover your own piece of PARADISE on Anna Maria Island's North end with this stunning Custom Elevated-Built WATERFRONT home. Perfectly situated for easy access to Anna Maria Pier, pristine beaches, waterfront dining, and Pine Avenue's shopping delights, this home offers unparalleled convenience and BREATHTAKING VIEWS! Indulge in culinary delights in the gourmet kitchen featuring two expansive islands, amazing quartz countertops, and top-of-the-line appliances. With five spacious bedrooms, including 4 with private bathrooms, multiple living areas, and a bonus loft, this home offers ample space for RELAXATION and entertaining. Dive into LUXURY with a heated saltwater pool and enjoy boating adventures with the boat dock and lift on the canal. Eco-friendly features such as a rainwater cistern system and energy-efficient elements ensure sustainable living. Additional perks include an elevator servicing all floors, and dual garages with storage. With over $100k in vacation rental income and potential to exceed $200k annually, this turn-key ready home offers both a LUXURIOUS LIFESTYLE and investment opportunity. All furnishings are included, making it truly turnkey. This home, with a grandfathered clause allowing accommodation for up to 12 people instead of the current 8 person max capacity, presents an ideal VACATION GETAWAY with substantial rental income potential. Escape to WATERFRONT LIVING at its finest – schedule your private viewing today!

505 S Bay Boulevard, Anna Maria

$8,800,000

5 Beds ⋅ 5.5 Baths ⋅ A4582858 MLS

Pre-Construction. To be built. ELEGANT 5 BEDROOM, 5.5 BATH, 5 CAR GARAGE ESTATE HOME ON ANNA MARIA ISLAND!!! THIS IS TRULY ONE OF A KIND HOME WITH AN ELEVATOR, .29 ACRE LOT AND DESIGNER FINISHES THROUGHOUT!!! NO EXPENSE SPARED IN THE DESIGN AND BUILD OF THIS PROPERTY. This luxurious masterpiece boasts unparalleled features and meticulous attention to detail. Situated on an oversized lot, this property offers serenity and tranquility amidst lush tropical landscaping. Located just a stone's throw away from both the beach and the bay, your coastal oasis awaits. Upon entering, you'll be greeted by an expansive floor plan designed for comfort and style. The massive kitchen is a chef's delight, featuring Fisher and Paykel appliances, a generously sized island with a breakfast bar, and designer pendant lights that illuminate the high-end wood cabinets and quartz countertops. The butler's pantry is a delightful addition, enhancing your culinary experience. Each of the five bedrooms is an ensuite retreat, complete with walk-in closets, ensuring privacy and convenience for everyone. The master bedroom is exceptionally spacious, featuring two individual massive walk-in closets. The master bathroom is a spa-like haven, offering a relaxing tub and an oversized walk-in shower adorned with designer tile and high-end finishes. Entertainment and leisure opportunities abound on this property. A 5-car garage provides ample space for your vehicles and storage needs. The large laundry room adds practicality to your daily routines. The highlight of the outdoors is the inviting pool and spa, surrounded by lush landscaping, creating a serene and private retreat right at your doorstep. This home is a masterpiece of luxury and sophistication, thoughtfully designed for the most discerning buyer. Don't miss the opportunity to make this paradise your own.

305 Tarpon Street, Anna Maria

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Equal Housing Opportunity. All information contained herein deemed reliable but not guaranteed. Buyers should personally verify all information. All content Copyright 1998-2024 Great Smoky Mountains Association of Realtors. All rights reserved. Last updated .

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