Anna Maria Island | Southwest Florida Real Estate

ANNA MARIA ISLAND | Southwest FL Real Estate

Anna Maria Island Homes - Bradenton, FL

Anna Maria is a barrier island on the Gulf of Mexico just west of Bradenton, FL. The island is divided into 3 cities of Anna Maria, Holmes Beach (named after James Holmes, a developer who arrived after World War II and created the 600 acre community) and Bradenton Beach. Longboat Key is on the southern most tip of the island. The island measures just over 7 miles in length and almost 2 miles in width. Key Royale on Holmes Beach is a community made for boaters - most residences have a private dock. It is one of the few island communities with a golf course, too - home to The Key Royale Golf Club which was built on 27 acres. There are many great beaches and fishing piers along with shops, restaurants where you can watch dolphins and manatee swim by and bars with live music. You can also rent boats, jet skis and go parasailing. There are 2 bridges to the island, one on Cortez Road and the other on Manatee Ave., also known as SR 64. Homes on the island include condominiums, villas and townhouses, mobile homes and single family homes ranging in price from the $100,000s to over $22,000,000. Let us help you find your "Piece of Beach Paradise!".

Just Listed | Latest Homes for Sale on Anna Maria Island

145 Crescent Drive, Anna Maria $3,000,000

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 remo...

3 Beds
2 Baths
Lake La Vista Sub SubDv.
34216 Zip Code

111 Peppertree Lane, Anna Maria $5,095,000

This beautiful Anna Maria Island home radiates coastal and salty vibes! Custom designed By Emily Ann Smith, this 4 Bedroom, 4.5 Bathroom, plus bonus loft, home is locate...

4 Beds
4.5 Baths
Gulf View Sub SubDv.
34216 Zip Code

5400 Gulf Drive Unit 14, Holmes Beach image

5400 Gulf Drive Unit 14, Holmes Beach — 5400 Condos $589,500

You must watch the video tour to see how amazingly close to the beach this property is:https://youtu.be/CQy7JVpgxeE. Welcome to your very own beach paradise where you ca...

1 Beds
1 Baths
5400 Condos SubDv.
34217 Zip Code

6006 Gulf Drive Unit 115 - 215, Holmes Beach image

6006 Gulf Drive Unit 115 - 215, Holmes Beach — S $1,250,000

Rarely available (last MLS sale was in 2019) very desirable Gulf front complex centrally located in Holmes Beach! This is the original developer's unit designed with two...

2 Beds
2.5 Baths
Playa Encantada Condominium SubDv.
34217 Zip Code

606 Dundee Lane, Holmes Beach $1,550,000

Looking for that Island get-a-way on a saltwater canal with a boat lift and swimming pool. Look no further, this recently renovated home is on a little slice if heaven. M...

3 Beds
2 Baths
Key Royale SubDv.
34217 Zip Code

6300 Flotilla Drive Unit 103, Holmes Beach image

6300 Flotilla Drive Unit 103, Holmes Beach — 6300 $629,900

This Turn Key, 2-bed and 2-bath, island condo located in Shell Point is a must see! It has been beautifully renovated with NEW FLOORING and SHUTTERS as well as OPEN CONCE...

2 Beds
2 Baths
Shell Point SubDv.
34217 Zip Code

518 Kumquat Drive, Anna Maria $4,200,000

One or more photo(s) has been virtually staged. Exquisite island paradise situated on a deep water canal on Anna Maria’s exclusive north end! Lovingly and meticulously r...

5 Beds
3.5 Baths
Lacios Sub SubDv.
34216 Zip Code

3045 Mariners Cove Drive Unit 113, Cortez image

3045 Mariners Cove Drive Unit 113, Cortez — Mariner's Cove Condo Ii $1,100,000

RARELY AVAILABLE direct, Intercoastal water views from this beautiful, spacious condo located in the private gated community of Mariner’s Cove. Mariner’s Cove is an oasis...

3 Beds
2 Baths
Mariners Cove Condo SubDv.
34215 Zip Code

2914 Gulf Drive, Holmes Beach $1,800,000

Welcome home to this newly renovated 3BD/2BA island home just 1 block to the Gulf of Mexico! Vaulted ceilings, open floor plan and tastefully updated kitchen perfect for ...

3 Beds
2 Baths
Ilexhurst SubDv.
34217 Zip Code

214 Lakeview Drive, Anna Maria $3,350,000

Are you ready to just CHECK OUT… live on a TROPICAL ISLAND and never have to leave? This is the answer! The highly revered NORTHERN tip of ANNA MARIA Island offers the l...

3 Beds
3 Baths
Lake La Vista Sub SubDv.
34216 Zip Code

709 Gladiolus Street, Anna Maria $1,875,000

200 Steps to the beach! Just 4 homes to Bean Point on Anna Maria Island. With its prime location, this versatile property could be used as a vacation home, with the optio...

4 Beds
3 Baths
Shore Acres SubDv.
34216 Zip Code

104 Pelican Drive, Anna Maria $2,599,000

This 3 bedroom, 2 bathroom home is nestled along a canal on the north end of Anna Maria Island. This secluded treasure embodies Florida living at its finest. Spacious 1,...

3 Beds
2 Baths
Luana Isles SubDv.
34216 Zip Code

231 85th Street, Holmes Beach $1,750,000

Welcome to this ideal open design floor plan home in the center of Anna Maria Island, where old Florida charm still exists, relaxation is a way of life, and flip flops ar...

3 Beds
3 Baths
Holmes Beach SubDv.
34217 Zip Code

1801 Gulf Drive N Unit 162, Bradenton Beach image

1801 Gulf Drive N Unit 162, Bradenton Beach — A $675,000

This is a must see ground floor two bedroom two bath unit at the much sought after Runaway Bay. This unit has been completely renovated including both bathrooms and the k...

2 Beds
2 Baths
Runaway Bay SubDv.
34217 Zip Code

759 N Shore Drive, Anna Maria $6,790,000

This new beach house with a total living and entertaining square footage of 10,387 is designed with hints of Frank Lloyd Wright while bringing elements of a true beach ho...

6 Beds
6.5 Baths
Shore Acres SubDv.
34216 Zip Code

12410 Baypointe Terrace, Cortez $2,200,000

Enjoy the ultimate boating and waterfront lifestyle in this nearly 2,900-square-foot residence in the tranquil, gated community of Harbour Landings Estates in Cortez, jus...

4 Beds
3 Baths
Harbour Landing SubDv.
34215 Zip Code

205 Elm Avenue, Anna Maria $3,695,000

Welcome to "Beach Breeze" an awesome beach home that is just a few steps away from the gorgeous powder sand of Anna Maria Islands Gulf water. This coastal cutie features ...

4 Beds
3 Baths
Anna Maria Beach SubDv.
34216 Zip Code

1801 Gulf Drive N Unit 188, Bradenton Beach image

1801 Gulf Drive N Unit 188, Bradenton Beach — B $799,000

Rare opportunity to own this beautiful two-bedroom, two-bathroom, ground floor, BAYFRONT condo at Runaway Bay. Runaway Bay is a premier, award-winning condominium complex...

2 Beds
2 Baths
Runaway Bay SubDv.
34217 Zip Code

629 Dundee Lane, Holmes Beach $3,595,000 ▼

Custom canal front home meticulously designed w/ extremely high end finishes you won't want to miss. This 3,119 Sq. Ft. 4 bedroom, 3 ½ bathroom is spacious and the perfec...

4 Beds
3.5 Baths
Key Royale 9th Add SubDv.
34217 Zip Code

1801 Gulf Drive N Unit 224, Bradenton Beach image

1801 Gulf Drive N Unit 224, Bradenton Beach — 224 $619,900 ▼

Direct pool view 2 BR / 2 BA condo in Runaway Bay. Rarely available! Unmatched and unobstructed view from screened in lanai. This smoke-free and pet-free second-floor con...

2 Beds
2 Baths
Runaway Bay SubDv.
34217 Zip Code

3702 6th Avenue Unit 1, Holmes Beach image

3702 6th Avenue Unit 1, Holmes Beach — Beach View Of Mantte Bldg 1 $690,000

Your Anna Maria Island lifestyle awaits in this 2 bedroom/2 bath coastal island condo overlooking a peaceful park with heated pool and outdoor shower. Just a short stroll...

2 Beds
2 Baths
Beach View Of Manatee Condo SubDv.
34217 Zip Code

1801 Gulf Dr N Unit 287, Bradenton Beach image

1801 Gulf Dr N Unit 287, Bradenton Beach — B $650,000 ▼

A rare opportunity to purchase this beautiful property featuring stunning views of the bay at the much sought after Runaway Bay complex and a short walk to the magnificen...

2 Beds
2 Baths
Runaway Bay SubDv.
34217 Zip Code

105 36th Street, Holmes Beach $5,995,000

TWO PROPERTIES sitting directly on the Gulf of Mexico Beaches in Holmes Beach!! Both properties just had a refresh, including paint exterior and interior and new decorati...

5 Beds
4 Baths
Holmes Beach SubDv.
34217 Zip Code

723 Key Royale Drive, Holmes Beach image

723 Key Royale Drive, Holmes Beach $3,979,000

Key Royale direct bayfront - This 2-story Anna Maria Island single-family home is at the end of Key Royale Drive which is a part of the North Point Harbour Association an...

3 Beds
3.5 Baths
North Point Harbour SubDv.
34217 Zip Code

9605 Gulf Drive, Anna Maria $5,875,000

Under Construction. This UNIQUE AND EXTRAORDINARY custom home will have all the amenities that you can ever dream of in a beach house. This Stunning home will feature 5 B...

5 Beds
5.5 Baths
Arroyo The SubDv.
34216 Zip Code

2601 Gulf Drive N Unit 507, Bradenton Beach image

2601 Gulf Drive N Unit 507, Bradenton Beach $295,000

Sandpiper 55+ Resort Co-Op is on beautiful Anna Maria Island on Floridas Gulf Coast. This cozy gem is a one bedroom one bath coastal furnished unit that comes turn key an...

1 Beds
1 Baths
Sandpiper Resort Coop SubDv.
34217 Zip Code

102 68th Street Unit 102, Holmes Beach image

102 68th Street Unit 102, Holmes Beach — 102 68th St $825,000 ▼

Direct Gulf front condo available on beautiful Anna Maria Island. The islands best beach is just a few steps away from this turnkey furnished unit! Enjoy full time, as a ...

1 Beds
1.5 Baths
Seaside Beach House SubDv.
34217 Zip Code

303 74th Street Unit A, Holmes Beach image

303 74th Street Unit A, Holmes Beach $1,390,000

This is a beautifully appointed single story half duplex located just a stroll away from the sandy beaches and the Gulf of Mexico. Shops, bars and restaurants are also cl...

3 Beds
2 Baths
Bay Palms SubDv.
34217 Zip Code

604 North Point Dr, Holmes Beach $1,698,000

Enjoy this 3 bedroom, 2 bath canal front home in prestigious North Point Harbour on Key Royale in Holmes Beach, Florida. This Anna Maria Island home is within walking dis...

3 Beds
2 Baths
North Point Harbour SubDv.
34217 Zip Code

202 70th Street Unit A, Holmes Beach image

202 70th Street Unit A, Holmes Beach $4,885,888

Under Construction. Under Construction....Stunning new build just a block from the pearly sands of the Gulf! This unique, contemporary home will be showstopper...complete...

4 Beds
4.5 Baths
West Wind Shores SubDv.
34217 Zip Code

514 71st Street, Holmes Beach $1,850,000

The Anna Maria Island beach and boating lifestyle awaits you! Almost everything in this immaculate 2B+DEN/2B waterfront home has recently been updated! New PVC plumbing (...

3 Beds
2 Baths
Bay Palms Unit 9 SubDv.
34217 Zip Code

1801 Gulf Drive N Unit 133, Bradenton Beach image

1801 Gulf Drive N Unit 133, Bradenton Beach — E $675,000

This is a must see ground floor two bedroom and two bath unit at the much sought after Runaway Bay. This unit faces east/west and is bright and airy with a view of the l...

2 Beds
2 Baths
Runaway Bay SubDv.
34217 Zip Code

634 Key Royale Drive, Holmes Beach image

634 Key Royale Drive, Holmes Beach $4,500,000

One of the Islands FIRST CERTIFIED ENEGY EFFICENT HOMES!!! Built by SHORELINE BUILDERS this beautiful home meets ENERGY STAR guidelines for energy efficiency! ENERGY STAR...

4 Beds
3.5 Baths
Key Royale SubDv.
34217 Zip Code

4520 121st Street W, Cortez $624,900 ▼

Reside in the oldest surviving coastal fishing village in Florida, in the historic community of Cortez, located by the Gulf of Mexico and buffered by the barrier islands,...

4 Beds
3 Baths
Cortez Add To Cortez SubDv.
34215 Zip Code

100 6th Street S Unit 1, Bradenton Beach image

100 6th Street S Unit 1, Bradenton Beach $6,875,000

Under Construction. Contemporary design meets waterfront luxury in this Brand-New Construction home built in the heart of Bradenton Beach on Anna Maria Island. Exquisite ...

6 Beds
6.5 Baths
Cortez Beach SubDv.
34217 Zip Code

608 S Bay Boulevard, Anna Maria $5,995,000

Brand New Custom Bayfront house in the North End of Anna Maria built on an oversized 60’ wide lot with panoramic breathtaking open-water bay-views of the Skyway Bridge. A...

4 Beds
4.5 Baths
Anna Maria Beach SubDv.
34216 Zip Code

3805 E Bay Drive Unit 207, Holmes Beach image

3805 E Bay Drive Unit 207, Holmes Beach — E $699,000

Location says it all! This beautiful direct bayfront condo is the perfect place to have your morning coffee and watch the dolphins and pelicans fish as the sun rises ove...

2 Beds
2 Baths
Sunbow Bay SubDv.
34217 Zip Code

1441 Gulf Drive N Unit 1441, Bradenton Beach image

1441 Gulf Drive N Unit 1441, Bradenton Beach — Bermuda Bay Club $1,450,000

100 YARDS TO THE BEACH, Anna Maria Island BAYFRONT townhome - phenomenal, panoramic bay VIEWS of Anna Maria Sound and partial Gulf of Mexico VIEWS! Bermuda Bay Club is a ...

3 Beds
2.5 Baths
Bermuda Bay Club SubDv.
34217 Zip Code

771 Jacaranda Road, Anna Maria $2,495,000

Step in to Limelight. This beautifully appointed, furnished 3BD/2BA residence is located on the north end of Anna Maria with a direct beach access steps away. Let the nat...

3 Beds
2 Baths
Shore Acres Second Add SubDv.
34216 Zip Code

200 S Harbor Drive, Holmes Beach $2,750,000

Welcome to Paradise at Harbor Side, a wonderful 5 Bedroom, 3.5 Bathroom waterfront property located in a prime location in Holmes Beach. Step outside your front door and...

5 Beds
3.5 Baths
Holmes Beach SubDv.
34217 Zip Code

116 45th Street, Holmes Beach $2,875,000

COASTAL BEAUTY IS WEST OF GULF AND A BLOCK TO THE BEACH. THIS CUSTOM HOME HAS SOLID WOOD CABINETS, SOLID GRANITE SURFACES, TILE FLOORS, S/S APPLIANCES AND COMES TURNKEY ...

5 Beds
4.5 Baths
Holmes Beach SubDv.
34217 Zip Code

145 50th Street, Holmes Beach $2,195,000

Welcome to Mango Tango! This Anna Maria Island beach home is 4 bedrooms and 3.5 bathrooms and is so close to the Gulf of Mexico beaches! This is currently a vacation rent...

4 Beds
3.5 Baths
Holmes Beach SubDv.
34217 Zip Code

270 Gladiolus Street, Anna Maria $1,895,000

This lovely Island cottage with 2 bedrooms, 2 baths + office is calling your name. Huge corner lot on preferred north end of Anna Maria and walkable to many area attrac...

2 Beds
2 Baths
Luana Isles SubDv.
34216 Zip Code

752 N Shore Drive, Anna Maria $3,850,000

GREAT COASTAL HOME ON N SHORE DRIVE IS RIGHT ACROSS THE STREET FROM THE BEACH. THIS CUSTOM HOME WAS BUILT WITH HIGH END FINISHES INSIDE AND OUT. INSIDE IS SOLID WOOD CA...

5 Beds
4.5 Baths
Anna Maria Beach SubDv.
34216 Zip Code

210 Periwinkle Plaza, Anna Maria $2,650,000 ▼

Nice price adjustment! Enjoy living the relaxed Anna Maria lifestyle on your canal front home that is one and a half blocks to the Gulf of Mexico. 90ft water frontage ho...

3 Beds
2 Baths
Laguna Maria SubDv.
34216 Zip Code

504 70th Street, Holmes Beach $1,395,000

Looking for a island retreat this centrally located Holmes Beach 2 bedroom 2 bath home has been tastefully updated. New vinyl flooring throughout, updated kitchen, update...

2 Beds
2 Baths
Bay Palms SubDv.
34217 Zip Code

1801 Gulf Drive N Unit 114, Bradenton Beach image

1801 Gulf Drive N Unit 114, Bradenton Beach — H $675,000 ▲

Rarely available ground floor beautifully updated unit in the resort community of Runaway Bay. This updated 2 bedroom 2 bathroom condo has it all and comes fully furnish...

2 Beds
2 Baths
Runaway Bay SubDv.
34217 Zip Code

1801 Gulf Drive N Unit 250, Bradenton Beach image

1801 Gulf Drive N Unit 250, Bradenton Beach — 1801 $675,000

Looking for the perfect income producing Vacation home well this one is for you. Turnkey Furnished!! This second floor unit overlooks the canal and lush landscaping that...

2 Beds
2 Baths
Runaway Bay SubDv.
34217 Zip Code

310 Clark Drive, Holmes Beach $2,295,000

Welcome to this beautifully appointed 4BD/3.5 bath home in a central island location. The main living area offers lots of natural light, crown moldings, open living/dinin...

4 Beds
3.5 Baths
Clark & Palm SubDv.
34217 Zip Code

6509 Gulf Drive, Holmes Beach $3,850,000

The magic of Anna Maria Island is embraced throughout this newly built home while affording maximum return on investment with short-term, weekly rental opportunities to p...

4 Beds
4.5 Baths
West Wind Shores SubDv.
34217 Zip Code

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Testimonials

Lisa Salvato - 5 stars! John is fabulous! He listened to what we wanted and emailed us only properties that applied. We live in New York and were interested in purchasing a Florida property. Having never met him prior to our visit to view the key properties of interest, from his e-mails, we didn't know what to expect . We feel like we hit the jackpot, John was professional, courteous and went out of his way to show us condos in a spread-out area. We have now closed on that purchase. Thank-you John for being a great negotiator and knowledgeable in your field. Your follow-through beyond the closing is appreciated and impressive. Thank-you Leslie for your work in the background to follow-up with all of the condo documents. We have sold and purchased homes before and John is at the top! February 2018

Robert Theofel — Above and beyond! Every aspect of the home buying process from initial search to closing went without a hitch due to Leslie and John’s expertise. When searching for a home, we received recommendations that were within our search criteria and the team was always available to show the homes that we selected. The recommendations we received during the negotiating, buying and closing process were excellent and we were able to close within a month of the initial viewing of the property. I would highly recommend them to anyone looking to buy a home!

Curt Johnson — My wife and I needed to sell our house, however there was much to do to get it ready. John and Leslie let us know how to fix-up the house to get the best possible response at the showings. We got it done and sold our house within 2 days of listing it with them. I think one of the best things I walked away with from the experience is how I felt trusting them with my home knowing that they had my best interest at hand. I would recommend John and Leslie to anyone who wants to be successful in selling or buying a home.

Jennifer Pearson — Leslie and John went above and beyond to help us sell our home! We had relocated 1900 miles away as we were trying to sell our house. They were in constant contact with us regarding the house and showings. They helped us find maintenance people when needed and even completed some things themselves. We would highly recommend them and should we return to the area, we will definitely use them to purchase a home!

Valerie Bologna — 5 stars! John helped my husband and I find a condo in Sarasota while we are living in another state. If there was something that we were interested in, he would go out right away and take pictures of the place and e-mail them to us. He never made us feel like we were wasting his time even though our purchase was not a million dollar listing! In a few years we will be calling on John again to find us a permanent place to live instead of seasonally. My husband and I appreciate all that he and his wife Leslie have done for us to make this purchase go as smooth as possible and we feel like we have gained new friends as well!

Victoria Harlow — 5 stars! Leslie went above and beyond with advice on staging, open houses, and cleaning and caring for my property while I was absent. Her teammate and husband John make a stellar team. I was so happy to get a great offer so close to my asking price. Awesome work! Thank-you for being vigilant and for the awesome care you took with selling my house. Your are the best that I've encountered after selling three houses over the years!

Edy Campos — 5 stars! - Can't get any better than John! He helped me all the way until the end, gives great advice, works fast, follows up and doesn't waste time. If you are serious about finding a place to call "home", I really recommend John Gregory!

Nancy Gallagher — If you're looking for a new home in Florida, John is a tireless agent to have on your side! If he doesn't know the answer to a question (which is rare) he will find it and in a timely manner! I highly recommend his services.

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Anna Maria Island Real Estate Search

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ANNA MARIA ISLAND | Southwest FL Real Estate

Anna Maria Island Homes - Bradenton, FL

Just Listed | Latest Homes for Sale on Anna Maria Island

Address Search

Community Info & Listings

Sarasota County (click on each line)

Manatee County (click on each line)

Helpful Links (click on each line)

Testimonials

Connect With Us