Anna Maria Island

A mere seven miles long from tip to tip, Anna Maria Island delights locals and visitors alike with its low-key vibe. This family-oriented beach community is a favorite for its small city charm and beach atmosphere, and it’s no wonder that demand continues to rise for Anna Maria Island beachfront homes. Read More About Anna Maria Island Beachfront and Waterfront Homes for Sale.

Anna Maria Island Real Estate Statistics

Average Price $3.8M
Lowest Price $1.3K
Highest Price $19M
Total Listings 79
Avg. Days On Market 109
Avg. Price/SQFT $1.5K

Property Types (active listings)

Anna Maria

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811 North Shore Drive, ANNA MARIA

$19,000,000

↓ $4,000,000

811 North Shore Drive, ANNA MARIA

4 Beds 8 Baths 4,452 SqFt Residential MLS® # A4559308
826a South Bay Boulevard, ANNA MARIA

$11,495,000

↓ $3,331,000

826a South Bay Boulevard, ANNA MARIA

5 Beds 3 Baths 4,494 SqFt Residential MLS® # A4562901
769 North Shore Drive, ANNA MARIA

$9,999,999

↓ $1,500,001

769 North Shore Drive, ANNA MARIA

4 Beds 4 Baths 3,737 SqFt Residential MLS® # A4555240
803 North Shore Drive, ANNA MARIA

$9,800,000

803 North Shore Drive, ANNA MARIA

4 Beds 5 Baths 4,993 SqFt Residential MLS® # A4568805
224 Chilson Avenue, ANNA MARIA

$7,995,000

224 Chilson Avenue, ANNA MARIA

6 Beds 7 Baths 4,525 SqFt Residential MLS® # A4569034
302 North Shore Drive, ANNA MARIA

$6,777,222

302 North Shore Drive, ANNA MARIA

0 Beds 0 Baths 4,464 SqFt Income MLS® # A4562033
404 North Shore Drive, ANNA MARIA

$6,549,000

404 North Shore Drive, ANNA MARIA

5 Beds 6 Baths 2,964 SqFt Residential MLS® # A4562757
111 Gull Drive, ANNA MARIA

$6,195,000

111 Gull Drive, ANNA MARIA

4 Beds 5 Baths 2,905 SqFt Residential MLS® # A4558015
110 Spring Avenue, ANNA MARIA

$6,100,095

110 Spring Avenue, ANNA MARIA

5 Beds 5 Baths 2,925 SqFt Residential MLS® # T3439172
727 North Shore Drive, ANNA MARIA

$5,995,000

↓ $455,000

727 North Shore Drive, ANNA MARIA

3 Beds 2 Baths 1,564 SqFt Residential MLS® # A4559354
50 North Shore Drive, ANNA MARIA

$5,995,000

50 North Shore Drive, ANNA MARIA

4 Beds 5 Baths 3,055 SqFt Residential MLS® # A4563018
839 North Shore Drive Lot 24 Or 25, ANNA MARIA

$5,985,000

↑ $1,490,000

839 North Shore Drive Lot 24 Or 25, ANNA MARIA

0 Beds 0 Baths 0 SqFt Land MLS® # A4560067
307 Magnolia Avenue, ANNA MARIA

$5,895,000

307 Magnolia Avenue, ANNA MARIA

7 Beds 7 Baths 3,145 SqFt Residential MLS® # A4551213
515 Villa Rosa Way, ANNA MARIA

$5,500,000

515 Villa Rosa Way, ANNA MARIA

4 Beds 5 Baths 3,007 SqFt Residential MLS® # A4570832
705 Gladiolus Street, ANNA MARIA

$5,495,000

705 Gladiolus Street, ANNA MARIA

6 Beds 6 Baths 4,042 SqFt Residential MLS® # A4529273
112 Mangrove Avenue, ANNA MARIA

$5,495,000

↓ $200,000

112 Mangrove Avenue, ANNA MARIA

4 Beds 5 Baths 2,803 SqFt Residential MLS® # A4559508
106 Beach Ave, ANNA MARIA

$4,995,000

↓ $355,000

106 Beach Ave, ANNA MARIA

5 Beds 4 Baths 3,452 SqFt Residential MLS® # A4541244
304 North Shore Drive, ANNA MARIA

$4,650,000

↓ $125,000

304 North Shore Drive, ANNA MARIA

4 Beds 5 Baths 3,400 SqFt Residential MLS® # A4553887
421 Pine Avenue, ANNA MARIA

$4,650,000

↓ $345,000

421 Pine Avenue, ANNA MARIA

6 Beds 7 Baths 3,545 SqFt Residential MLS® # A4559375
406 North Shore Drive A & B, ANNA MARIA

$4,595,000

406 North Shore Drive A & B, ANNA MARIA

4 Beds 4 Baths 2,056 SqFt Residential MLS® # A4565372
132 Crescent, ANNA MARIA

$4,495,000

↓ $455,000

132 Crescent, ANNA MARIA

5 Beds 6 Baths 3,072 SqFt Residential MLS® # A4556692

Anna Maria Island Beachfront and Waterfront Homes for Sale

Unlike some other popular Florida destinations, you won’t find miles of high-rise condos, restaurant chains or hotel chains on the island, but you will find incredible white sand beaches and a unique collection of beautiful beachfront homes and condos to choose from. You’ll also find some great opportunities to get out on the water, with boating, fishing and, of course, the beach popular pastimes for those living on and visiting Anna Maria Island

Once home to native tribes, Spanish explorers first passed the island en route to the mainland in the mid 1500s. The island was first settled, however, closer to the beginning of the 20th century. While a couple of different stories are told, some say the island was named to honor the Virgin Mary and her mother.

The name carried on as wealthy developers moved in, forming the Anna Maria Beach Company. Developers constructed homes and sidewalks, mapped out streets and installed the island’s water system. Once a place only reachable by boat, a bridge in the early 1920s finally linked up the island with the mainland, leading more people to visit and discover the possibilities of life on the island.

Fast-forward a century from its beginning and Anna Maria Island is now one of Florida’s most popular and desirable locations, especially when it comes to Florida beachfront homes for sale. Many of the island’s residential properties are single-family homes, but condos are certainly in demand. This leads many buyers to search out one of the exceptional Anna Maria Island beachfront condos for sale, as well. Of course, there are also many investment properties that account for the thousands of seasonal vacation rentals at home on the island.

Options in terms of Anna Maria Island beachfront condos for sale include a cozy mid-century design just steps from the beach, or a convenient condo with the added bonus of community swimming pools, tennis courts and a fishing pier with kayak storage. Buyers are sure to delight in the available beachfront condos of Anna Maria Island.

With dramatic views overlooking the sand and water, enjoy the ease of a condo lifestyle right on the island. This affords the enjoyment of living in an amenity-rich environment, coupled with the luxury of residing in one of the available beachfront condos of Anna Maria Island.

Beachfront and waterfront homes are part of the appeal of an island lifestyle as well, and Anna Maria Island certainly does not disappoint in this category. Some of the most impressive beachfront homes Anna Maria Island are easily priced well into the multi-million range. The price, however, affords the advantage of living directly on the sand and just steps from the water, complimented by such luxurious extras as swimming pools, tennis courts and full views of the Gulf from the unique Anna Maria Island beachfront homes for sale.

With direct Gulf frontage, these Anna Maria waterfront homes for sale easily surpass the expectations of Florida buyers, with your choice of a newer construction home with more modern inclusions or a charming beach bungalow that’s been lovingly updated over the years. When it comes to Anna Maria Island beachfront homes for sale, you cannot go wrong with one of the many available options.

When searching for a property on the island, note that Anna Maria Island is actually made up of three distinct areas. Anna Maria sits on the northern side, Holmes Beach takes up the middle section of the island and Bradenton Beach is found on the southern edge. Altogether the three areas account for around 8,500 residents and the option to choose from a unique collection of beachfront homes Anna Maria Island.

While many people are interested in Anna Maria waterfront homes for sale for personal use and investment opportunities, in recent years local officials have heavily targeted tourism. Millions of investment dollars are now being used to draw in visitors to the island.

That’s led developers to change over some of the old mid-century homes to multi-family rentals. It’s now possible to find a range of unique lodging on Anna Maria Island, from a traditional bed and breakfast to a resort or vacation rental.

Opportunities for outdoor recreation blend with an island lifestyle to create even more opportunity for visitors and locals. While there are some nearby golf courses on the mainland, Key Royale Club is the island’s only golf course and country club. Found in Holmes Beach, this nine-hole walking course also includes a clubhouse with room for dining.

If fishing is more your speed, you’ll find full and half-day charters leaving from Holmes Beach. The opportunity of the island also presents room for boating and area wildlife and marine-life spotting.

During select months of the year sea turtles nest on the island. It’s also a bird sanctuary, with cranes and pelicans, plus sandpipers, hawks, osprey and even nesting bald eagles. Out in the water you’re likely to spot Bottlenose dolphins, trout, mackerel and snapper.

While shopping and dining opportunities may not be as diverse as they are on the mainland, Anna Maria Island certainly has some unique options. They include a charming old cottage turned restaurant called Sign of the Mermaid, plus the appropriately named Sandbar Restaurant, where you can dine or enjoy a cocktail right out on the sand.

The island is home to around 20 restaurants and a collection of shops, some of which cater to locals and some cater to tourists. If you want to explore, it’s easy to jump on the free trolley running along Gulf Drive.

A big draw of the barrier island, however, exists with the unique Florida beachfront homes for sale. When it comes to the enjoyment of an authentic Southwest Florida lifestyle, come home to the unique possibilities of real estate on Anna Maria Island.