Anna Maria FL Historical Real Estate, Homes for Sale

Looking for that perfect hideaway home featuring one of the best views on the West Coast of Florida? Look no further. This 3 bedroom, 2.5 bathroom + den has the very utmost privacy while still being direct Bayfront with unobstructed views! Upon entering the front gate, you'll be pleasantly surprised by the lush landscaping surrounding while following a bricked pathway to the front door. Entering through the custom arched wood door that are also throughout the home, you are greeted by stunning views of the gorgeous water with Tampa Bay and the Sunshine Skyway directly ahead which include a nightly light show. The open concept and eat-in island are ideal for entertaining guests. There are built in, floor to ceiling bookshelves and a huge living / dining room area. One can enjoy watching inspirational sunrises in the morning from inside or relaxing on the spacious decks. Enjoy the entire upstairs as your master suite with your own private deck. This home is private, stunning views, natural light that overall creates an eclectic and warm vibe. You will fall in love as soon as you walk in. Schedule your private showing today!

706 S Bay Boulevard, Anna Maria

$1,300,000

2 Beds ⋅ 2 Baths ⋅ A4589736 MLS

Welcome to “The Seashell Cottage”, an enchanting vintage gem located in the city of Anna Maria. Step back in time and experience island life like it used to be in this cozy and charming retreat. The sound of the screen door closing behind you will immediately invoke memories from days gone by. Desirable West of Gulf Drive location, a mere 6 houses from the beach. Stroll to the end of the street and put your toes in the sugar sand. Crystal clear water beckons you and you’ll relish the colorful sunsets. This property is currently a vacation rental with projected revenue of over $70,000 for 2023, making it an enticing investment opportunity. The turnkey furnished interior is adorned with woodwork details, multiple built-ins and exudes coastal charm. The exterior features updated hardy siding, Bahama style shutters, and roof was replaced in 2013. The yard is fenced for privacy, and tropical landscaping compliments the outdoor space. The composite deck area is perfect for grilling and dining al fresco. There is a storage shed for your beach items and a refreshing outdoor shower when you return from a day at the beach. Enjoy the convenience of multiple nearby restaurants and shops, and just 4 blocks from Pine Ave. attractions and the city pier. Park your car and explore the island on the free Island Trolley with a nearby stop. This is your opportunity to enjoy the magic of what AMI offers for a fraction of the cost of most island properties.

118 Palmetto Avenue, Anna Maria

$1,749,000

2 Beds ⋅ 2 Baths ⋅ A4588247 MLS

Snuggled beneath a canopy of sea grape trees and enveloped by a myriad of palms and tropical landscaping, sits one of the few remaining and absolutely charming vestiges of Vintage North End Anna Maria Island. This 2 bedroom/2 bath home with accompanying garage sits, sheltered and cozy on 100 feet of road frontage. Mexican Tile flows throughout the Living Area, with soft neutral walls and white planked ceilings. The eat-in kitchen was recently renovated with versatile and timeless white quartz counter tops, stylish white tile and cabinetry and stainless appliances. The open living space provides both a living room and dining room with step down family room. The A/C was replaced in 2022, Impact Windows and Doors were added in 2023 and the ever inviting swimming pool was just resurfaced with pebble tec finish, new coping and pump. Adding to the out of door's charm is the garage space - with bar seating at the roll-up window, game room within, plenty of space for Island toys and an outdoor shower. Easy walking distance to the Rod and Reel Pier, the Gulf Beach at Bean Point and the amenities along Pine Avenue. Owner occupied but had significant rental history a few years back. Offered partially furnished. If you but, pause - this delightful cottage will beckon you into a bygone era.....complete with sensitive updates.

610 N Bay Boulevard, Anna Maria

$1,995,000

2 Beds ⋅ 3 Baths ⋅ A4588798 MLS

Stunning 2 bedroom, 3 bath waterfront home located at the north end of Anna Maria Island on a quiet street. Completely remodeled and updated with top of the line amenities & professional, interior design. This home has great natural lighting, a spacious screened lanai that offers extended living & entertaining space, hurricane impact rated windows, doors & garage door, and a 50 -year rated roof installed in 2015.Waterproof COREtec Plus luxury flooring throughout. Hop on your boat for a day of fishing, or enjoy watching manatees right from the dock. This gorgeous home offers tasteful, turn-key furnishings. Just a short walk to the beach & Gulf of Mexico.

265 Gladiolus Street, Anna Maria

$2,800,000

4 Beds ⋅ 3 Baths ⋅ A4588229 MLS

Step into the enchanting world of Naut 2 Shabby Cottage & Bungalow homes, a unique offering that combines the charm of two distinct residences in one prime location. The main home features 3 bedrooms and 2 full baths, while the separate guest house boasts 1 bedroom and 1 bath. This versatile property invites you to make it your own, whether using one house for yourself and the other for rental, guests, or even a business on the island. Zoned ROR (Retail/Residential), this property is a rare find right in Downtown Anna Maria, mere feet from both the Bay, Anna Maria City Pier, and the Gulf of Mexico. Positioned on one of the most popular streets in Anna Maria, this location puts you in the heart of all the island's vibrant happenings. Walk out to the famous city pier, art walks, museums, restaurants, and shops. Sit on your front porch and soak in the lively entertainment that surrounds you. This home is the epitome of island living, offering proximity to the beach for bike rides and bay adventures with kayaks. The property features two charming cottage homes, each with its own unique character, complemented by a private saltwater pool and spa. The short-term rental zone makes renting a breeze, and this property is already a popular choice in the rental program. As you step into the family compound, you'll be greeted by a newer heated saltwater pool and spa with a water fountain and custom lights. The landscape and turf, along with a 6-foot privacy fence, create a serene oasis. The property is thoughtfully zoned ROR, allowing for a blend of residential, office, and retail uses. Sold turnkey-furnished, this property is ready for you to move in and enjoy, with future rentals already in place. Recent upgrades include a new pool pump in 2023, a new mini-split in the living room of the bungalow, a washer and dryer in 2021, and a 2019 electric riser. The front of the home boasts a 2019 roof, stone on the driveway, and outdoor pool furniture and umbrellas. The saltwater pool and hot tub are equipped with an app for convenient control from your phone. Other improvements include artificial turf, landscaping, and irrigation, a 6-foot privacy fence with gates, custom paint on the back porch, updated fixtures, two televisions, two dehumidifiers, artwork and painting on the back of the house and signs. Hurricane impact windows and doors were installed in 2017, and the main house received a new AC unit in 2014, with a water heater replacement in 2017. The property was termite-tented in 2018 with a transferable warranty, and in 2011, two other mini-splits were added to the small bungalow home. This is your opportunity to acquire your dream Florida homes, providing ample space for everyone and creating an inviting haven for entertainment. Come and experience the magic of Naut 2 Shabby Cottage & Bungalow homes – your perfect retreat in paradise.

509 Pine Avenue Unit A, Anna Maria

$2,999,999

3 Beds ⋅ 2 Baths ⋅ A4587368 MLS

EXTRAORDINARY waterfront views, you have to see to believe!! Nestled on a quiet cul-da-sac, on Anna Maria Island’s coveted North End, this custom-built turnkey furnished, 3 bedroom, 2 bath home has a 118’ curved waterfront seawall offering panoramic views of one of the widest open water canals on the island. Property sits on a 9,147 square foot lot, giving you plenty of space, privacy and tranquility. A grand entry opens to an expansive living area with vaulted ceilings, skylights and tiled flooring throughout. The open concept kitchen is adjacent to the dining area providing seamless flow between the kitchen and living room, making it ideal for entertaining. The master suite is a private oasis, offering a walk- in closet, and en-suite. The two additional bedrooms are equally spacious and well-appointed, providing comfort and convenience for family members and guests along with phenomenal storage that can be used as an Owner’s Lock-up. The true highlight of this home is the outdoor living space. Full-length glass sliders at the back of the home lead to a screened lanai where you can experience true coastal living - feel the tropical breezes, listen to ocean waves and spot manatees from this favorite indoor/outdoor space. Step out to the massive pool deck with private spa and newly remodeled pool. The back yard is beautifully landscaped with gorgeous mature trees adding to the privacy and serenity of the property. Take in sunsets or fish from the private dock, which also includes a10,000lb. boat lift. Just a short distance from the Islands pristine beaches, charming shops, and renowned restaurants. This home is a perfect island investment with impressive rental income and as a private retreat for making memories with your family. This gorgeous home and property are a dream come true for those seeking the ultimate coastal living experience!

113 Gull Drive, Anna Maria

$1,150,000

2 Beds ⋅ 1 Baths ⋅ A4582331 MLS

Under contract-accepting backup offers. LOCATION, LOCATION, LOCATION... Originally built in 1905, this beach bungalow is in one of the most prime locations on the North End of Anna Maria Island. In the city of Anna Maria a block off the strip of restaurants and shoppes of Pine Ave, walking distance to the city pier, or the Gulf side beach to see nightly sunsets. Perfect for a primary residence or a NIGHTLY vacation rental, you cannot beat this location!!! With Solar panels, room for a POOL & bungalow charm, you don't want to miss this opportunity to own a piece of Anna Maria's history (originally built by & owned by George Bean!) Call to view it today before it's gone!

428 Spring Avenue, Anna Maria

$3,200,000

4 Beds ⋅ 3 Baths ⋅ A4582507 MLS

WELCOME TO BEACH BREEZE, YOUR GATEWAY TO PARADISE ON ENCHANTING ANNA MARIA ISLAND!!! IDEAL LOCATION ON THE NORTH END OF THE ISLAND JUST STEPS AWAY FROM THE BEACH. SUCCESSFUL VACATION RENTAL WITH FORWARD BOOKINGS IN PLACE!! You are just a stone's throw away from the pristine white sands of Anna Maria Island Beach and the charming island boutiques and restaurants that adorn Pine Ave. This ground-level retreat features four inviting bedrooms, including a private suite, and three well-appointed bathrooms. Step into the bright and welcoming living room and unwind in style. The kitchen boasts modern updates, including quartz countertops and stainless-steel appliances, while the convenient island with seating for three is perfect for quick snacks and leisurely breakfasts. Gather around the picnic-style dining table that seats six or opt for alfresco dining on the deck, where a patio table offers a picturesque setting for meals. The master bedroom is a tropical haven for relaxation, direct access to the pool deck, and an ensuite bathroom featuring dual vanities and a luxurious walk-in shower. The second and third bedroom are both ample size. The second bathroom features a convenient shower/tub combination, perfect for refreshing after a sun-soaked day on the beach. The fourth bedroom and ensuite bathroom offer privacy separate from the pool deck. Your days at Beach Breeze will be filled with fun and relaxation. Make a splash in the updated private heated pool, surrounded by lush tropical landscaping, and unwind in the soothing spa after your island explorations. The outdoor patio sets the stage for delightful backyard BBQs, with an outdoor dining table where you can savor delicious meals. LOCATION DOES NOT GET ANY BETTER THEN THIS! PERFECT HOME FOR INVESTMENT, PERSONAL USE OR TEAR DOWN AND BUILD YOUR DREAM HOME!

205 Elm Avenue, Anna Maria

$3,400,000

2 Beds ⋅ 2 Baths ⋅ A4582222 MLS

WELCOME TO MERMAID'S PURSE, YOUR IDYLLIC GETAWAY NESTLED IN THE HEART OF THE NORTH END OF ANNA MARIA ISLAND! SECOND HOUSE FROM THE BEACH!!! Just a short walk away from the renowned Pine Avenue boutiques and dining establishments, this home promises the ultimate retreat. This charming SUCCESSFUL RENTAL boasts two well-appointed bedrooms and two modern bathrooms. The highlight of this tropical haven is undoubtedly the private pool, inviting you to take a refreshing dip or bask in the warm Florida sun. The spacious living area serves as a central gathering point for friends and family, where you can plot out your Anna Maria Island adventures or simply unwind. The fully equipped kitchen leaves no culinary desire unfulfilled, with ample counter space making meal preparation a breeze. Share quick snacks at the kitchen island or savor a cup of morning coffee on the balcony overlooking the lush surroundings. For those looking to dine in style, there's a dedicated dining area. Additionally, a cozy seating area on the covered patio sets the scene for delightful BBQ cookouts. Retreat to the primary bedroom, a haven where you can rest and be serenaded by the gentle sway of Florida palm trees. After a day filled with sun-soaked beach adventures and island escapades, pamper yourself in the first bathroom's luxurious walk-in shower. The second bedroom boast an ensuite bathroom with a contemporary walk-in shower. PROPERTIES LIKE THIS DON'T COME ON THE MARKET OFTEN. USE AS A PRIMARY HOME, VACATION RENTAL OR TEAR DOWN AND BUILD YOUR DREAM HOME STEPS TO THE BEACH!!!

107 Palm Avenue, Anna Maria

$1,485,000

U8211360 MLS

Auction Property. Excellent opportunity to own this Tropical Paradise just a short stroll to the pristine beaches on the north end of ANNA MARIA ISLAND! This Duplex is on an over-sized corner lot and features a bright and spacious 2BR 1BA unit with terrazzo flooring, open kitchen with corian counters and dining area, enclosed Florida room which could easily be used as a 3rd BR providing additional rental income, plus attached private 1 car garage with laundry. The second unit is a charming 1BR 1BA, corian counters in the kitchen with a bar top and eating space and terrazzo flooring throughout. The enormous backyard has a patio where you can relax, barbeque, catch some rays and indulge in the island lifestyle! This Duplex provides the potential to live in one unit and rent out the other, rent both units or explore the possibility with the City's Building Dept. per current FEMA guidelines for a condo or SFR conversion or tear down and build an elevated SFR on this huge 8,438 sq. ft. lot and design your own perfect piece of heaven! Each unit has its own electric meter and the water meter is shared. The Island of Anna Maria has NO RENTAL RESTRICTIONS and this amazing property is just 2 blocks to the quaint boutiques and local cuisine on Historic Pine Ave. Take in the sights and explore the entire island by bike, golf cart or hop on the FREE trolley and visit the beautiful sugar sand beaches, Rod & Reel Pier, Bayfront Park, art gallery, museum, community center or plan a fishing charter and soak up all the beauty of this magical island! Just 9 miles to Longboat Key and a 40 minute drive to the Sarasota/Bradenton airport and I-75. Don’t miss this fantastic chance to add this gem to your investment portfolio and embrace a laid back atmosphere and experience the Island Lifestyle! (AUCTION DATE: 10/22 - 10/25).

216 Magnolia Avenue Unit A, Anna Maria

$1,292,000

2 Beds ⋅ 2 Baths ⋅ A4576715 MLS

Welcome to "Sea'Esta" a ground level sweet and cozy beach house on gorgeous Anna Maria Island! You will feel right at home in this totally updated property, this beach house has just been refreshed with new paint & furniture and offers a fantastic location. You are just a few flip flop steps away from the Rod and Reel pier, access to the Gulf Beach at Bean Point and all of the shops and restaurants of Pine Avenue. You are also only a very short walk away from one of our Island Trolley Stops that will take you all around the Island so you can explore with ease. Sea'Esta comes turnkey furnished and offers 2 bedrooms plus a den and 2 baths. This property has been decorated and designed with relaxation and comfort in mind. Sea'Esta offers ceramic plank tiled floors, vaulted ceilings, newer metal roof, newer A/C, hurricane shutters, the list goes on and on. This property is currently an active vacation rental. There is no room for a pool, non-conforming lot. *Property information received from third-party sources is considered reliable but is not guaranteed. All information should be independently verified by buyers and buyer's agent.

890 N Shore Drive, Anna Maria

$1,995,000

3 Beds ⋅ 3 Baths ⋅ A4571629 MLS

Don't miss out on this great opportunity to remodel or rebuild and make this home your own! This 3 bedroom, 3 bathroom home plus an office is located on a wide canal and a quiet street on the north end of Anna Maria Island. The home also has an additional Florida room, large garage, laundry room and composite dock. New paint and new carpet. Room for a pool, survey attached. Vacant and easy to show, use ShowingTime button!

316 Iris Street, Anna Maria

$2,500,000

3 Beds ⋅ 3 Baths ⋅ A4569083 MLS

This 3 bedroom 3 bath canal front home is located on the desirable Oak Ave. in the city of Anna Maria with a direct shot to the Gulf beach! Very spacious and open with a large dining room overlooking the water. There are tile floors throughout, newer windows, and new a/c unit. Boat lovers will love the private boat basin to park your boat. Very private setting with six mango trees!

232 Oak Avenue, Anna Maria

$9,945,000

5 Beds ⋅ 3 Baths ⋅ A4562901 MLS

Beach to Bay! Enjoy sunrise to sunsets from the only estate size lot from Tampa Bay to Bimini Bay. This stunning one-level, 5 bedroom home boasts 4,500 square feet on almost an acre of a subdividable lot. This one-of-a-kind property has everything you could ask for: panoramic views of Tampa Bay, heated pool, private beach and 4 private boat slips adjacent to Galati's Marina. It is perfect for lounging on the beach or an adventure on the water. Walk or hop on your golf cart to the best restaurants on Anna Maria or shops on Pine Ave. Completely remodeled November 2019. This property checks all the boxes!!

826A S Bay Boulevard, Anna Maria

$1,995,000

4 Beds ⋅ 2 Baths ⋅ A4556347 MLS

Under contract-accepting backup offers. ****PRICE REDUCTION**** Welcome to “A Time Out”, a unique historic home situated on the north end of Anna Maria Island just steps from Bean Point. The original 2-bedroom home was built in 1948 by the friends and family of Clarence Foley, a paralyzed Navy war veteran. Since then, locally recognized Gagne Construction has substantially renovated it. Gagne expanded it into the magnificent 4-bedroom, 2-bath coastal cottage you see here. From the front you are greeted by mature Sea Grape trees nestled in lush tropical vegetation. From the front porch rockers, you have peeks of Tampa Bay directly across the street. For the anglers, swimmers and sun lovers in your family, there are many walkable city access points to the waters of Tampa Bay and the Gulf of Mexico. Pine Avenue shopping is a leisurely walk away. Upon entering the home, the first thing that catches your eye is the view through the living room into the tropical oasis and pool beyond. The living room and dining room will be roomy and comfortable for you and your family. The kitchen was tastefully finished in muted colors, solid surface countertops and stainless-steel appliances. Two queen-sized bedrooms and a full bath with a large glass shower are located on the first floor. During the last renovation, a FEMA-approved second story was added. This upstairs addition offers two more bedrooms, a full bath with a tub, and a second lounging area with a TV to let the younger guests watch TV or play video games. There is also a small deck overlooking North Shore Drive with peeks of Tampa Bay. One upstairs bedroom features two built-in bunks with dedicated closets and a full-sized desk with a monitor. This is a perfect place to work or study remotely should you need it. The other bedroom has a queen-sized bed and its own closet/dressing room connecting to the bathroom. The home is sold turn-key furnished. The sellers have provided a list of items to be removed before closing. have saved the best for last. Let us go out to the backyard. When you step onto the covered deck off the kitchen, you are surrounded by a secluded tropical oasis. In front of you is a freeform pool with a natural stone decking surrounding it. To your right, the pool deck continues under the second story addition providing a covered area for the grill. This area also acts as the driveway to access the golf cart garage under the addition. This garage has an extra set of double doors opening to the pool. You can easily transform it into a trendy tiki bar. Behind the garage is a large private outdoor hot/cold shower and changing area. Under the stairs to the second story addition is a large, locked owners storage area. Finally, there is a 30 Amp level 2 car charger on the side of the home This property has it all. It can be an island forever home, a second home or a phenomenal vacation rental. The owners stay here from mid-November to mid-April, but it still generates over $50K/yr. in only off-season rentals. Make sure you open the video link and explore the home in 3D. The sellers are very motivated to sell. BRING AN OFFER!!!!

868 N Shore Drive, Anna Maria

$2,195,000

3 Beds ⋅ 2 Baths ⋅ A4553339 MLS

Anna Maria ISLAND LIFE at its very finest! The owner has SPARED NO EXPENSE in remodeling this cozy island home by using every inch of the property to its fullest- no remodeling needed here. NEW HURRICANE IMPACT windows and sliding doors, recently replaced METAL ROOF, PIPES, and AIR CONDITIONERS are just a few of the big-ticket items. LESS THAN A QUARTER MILE from Pine Avenue where you will find dining, shopping, and beach cafes, a quarter mile to the AMI CITY PIER, and a half mile to the soft sand BEACHES on Anna Maria Island. Enter through the gates of the FULLY ENCLOSED, oversized lot and follow the coral stepping stones through the TURF FOREVER LAWN yard is felt backed and has been laid over crushed granite. There are three Brazilian Ipe decks that afford plenty of space to entertain. You will love sipping morning coffee in the shady front yard full of EXOTIC LANDSCAPING which provides privacy from the quiet street. The front door enters the open concept kitchen/dining area where DuChateau hardwood floors stretch throughout the kitchen, living, and two spare bedrooms. A custom chandelier hangs over the dining table- only two in the world exist! Sub-Zero, Wolf, and Cove LUXURY APPLIANCES ensure you have the highest quality for storing and cooking your daily meals. The sleek concrete countertops and sink have been handcrafted using premium material and boast refined Rohl Faucets at the kitchen and master bath sinks, including a beverage faucet. A bone-char WHOLE HOUSE FILTER has been installed for all water entering the home and additionally, a Pure Water REVERSE OSMOSIS SYSTEM has been installed to ensure the purest drinking water. Continue through the home into the owners suite paying special attention to the impressive stone flooring, historic 500 YEAR OLD STONES from Jerusalem. The walls of the master bedroom have been generously coated with AMERICAN CLAY which regulates humidity and temperature in the home while also releasing negative ions to help filter pollen and dust- to give you the most calming, peaceful rest each and every night. Not only is the home under central AC, but the owner has also installed FOUR MINI SPLIT AC units with UV LIGHT FILTERS to allow each room to be cooled to the occupants preferred temperature. Continue following the coral stepping stones to the lavish back yard or step out from the living room or the newly remodeled POOL BATH onto the MARBLE POOL DECK that surrounds the HEATED, SALT WATER POOL which sits privately in the tropically landscaped oasis among bamboo, orchids, papaya, banana and more. These gorgeous island plants are in beds of Beach Pebble that will never mold or mildew. Enjoy evening meals under the pergola on yet another expansive Brazilian Ipe deck large enough to host friends and family. Don’t miss this RARE OPPORTUNITY to own your own private piece of unparalleled luxury island life. Schedule a showing today!

145 Crescent Drive, Anna Maria

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Anna Maria Historical Real Estate