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

106 5th Street S, Bradenton Beach $4,395,000

Under Construction. Welcome to your dream coastal oasis! This brand-new, turnkey furnished construction home in Bradenton Beach offers a perfect blend of luxury, comfort,...

8 Beds
7.5 Baths
Ilexhurst SubDv.
34217 Zip Code

1801 Gulf Drive N Unit 248, Bradenton Beach image

1801 Gulf Drive N Unit 248, Bradenton Beach — Bldg D $590,000

This turnkey condo unit in Runaway Bay is designed to unlock your real estate dreams, whether you're looking for a personal haven or an investment property. Situated in t...

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 — D $530,000

This second floor two bathroom/two bedroom unit is being sold as turnkey furnished. This unit is located in a tranquil setting featuring a private lanai that overlooks a ...

2 Beds
2 Baths
Runaway Bay SubDv.
34217 Zip Code

1325 Gulf Drive N Unit 125, Bradenton Beach image

1325 Gulf Drive N Unit 125, Bradenton Beach — 125 $675,000

Rarely available ground level 2 bed 1 bath condo at the award winning Tortuga Inn Beach Resort. This unit comes turnkey furnished with a solid rental history and future r...

2 Beds
1 Baths
Tortuga Condo SubDv.
34217 Zip Code

212 Pine Avenue Unit R, Anna Maria image

212 Pine Avenue Unit R, Anna Maria — 212r $1,350,000

212 Pine Avenue is a charming, coastal residence nestled in the picturesque heart of Anna Maria, Florida. This inviting home captures the essence of island living with it...

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

104 29th Street Unit 1, Holmes Beach image

104 29th Street Unit 1, Holmes Beach — 1 $1,200,000 ▼

Relax on your Deck that looks out to the view of the Gulf -beach. Located on a very quiet street across the street from the beach. This newly remodeled sophisticated and ...

3 Beds
2 Baths
Holmes Beach SubDv.
34217 Zip Code

1801 Gulf Drive N Unit 187, Bradenton Beach image

1801 Gulf Drive N Unit 187, Bradenton Beach — B $675,000

THE ONLY GROUND FLOOR UNIT AVAILABLE CURRENTLY AT RUNAWAY BAY. This rarely available ground floor beautiful two-bedroom, two-bathroom, bayfront condo at Runaway Bay. En...

2 Beds
2 Baths
Runaway Bay SubDv.
34217 Zip Code

3311 Gulf Drive Unit 3, Holmes Beach image

3311 Gulf Drive Unit 3, Holmes Beach — Tropical Sunset $979,000

Located right across the street from the world famous Anna Maria Island beaches, this two bedroom condo is newly remodeled and updated is less than 100 steps away from th...

2 Beds
2 Baths
Tropical Sunset SubDv.
34217 Zip Code

804 N Shore Drive, Anna Maria $6,875,000

A MASTERPIECE OF DESIGN AND CONSTRUCTION!!! Discover the epitome of luxury living in this captivating gem nestled within the sought-after North Shore of Anna Maria Island...

7 Beds
3 Baths
Shore Acres SubDv.
34216 Zip Code

2910 Gulf Drive Unit A & B, Holmes Beach image

2910 Gulf Drive Unit A & B, Holmes Beach $995,000

This duplex offers an amazing opportunity to own your own multi-unit home and/or rental for under a million dollars on the highly sought-after, beautiful island of Anna M...

4 Beds
Ilexhurst SubDv.
34217 Zip Code

5400 Gulf Drive Unit 32, Holmes Beach image

5400 Gulf Drive Unit 32, Holmes Beach — 8 $975,000

One or more photo(s) has been virtually staged. Indulge in the epitome of coastal luxury living with this impeccably newly renovated 2-bedroom, 2-bathroom condominium, pe...

2 Beds
2 Baths
5400 Condos SubDv.
34217 Zip Code

413 63rd Street, Holmes Beach $675,000

Anna Maria Island is recognized as having some of the greatest beach towns in America. Its sugar-like sandy beaches, embraced by the crystal clear, turquoise-blue waters...

2 Beds
2 Baths
Seaside Gardens SubDv.
34217 Zip Code

411 63rd Street, Holmes Beach $650,000

One or more photo(s) has been virtually staged. Anna Maria Island with its sugar-like sandy beaches, embraced by the crystal clear, turquoise-blue waters of the Gulf of M...

2 Beds
2 Baths
Seaside Gardens SubDv.
34217 Zip Code

208 Palmetto Avenue, Anna Maria $1,800,000

Awesome location just one short block to the beach with direct beach access and conveniently located to shops, restaurants, trolley stop and community center. This cute ...

2 Beds
2 Baths
Anna Maria Beach SubDv.
34216 Zip Code

4004 128th Street W Unit 902, Cortez image

4004 128th Street W Unit 902, Cortez — 4004 $1,125,000

Perfect for the boater! This 3 bedroom, 3 bath condo in Cortez, Florida is a waterfront paradise that combines the privacy of a single-family home with the amenities of ...

3 Beds
3 Baths
Smugglers Landing SubDv.
34215 Zip Code

307 North Bay Boulevard, Anna Maria image

307 North Bay Boulevard, Anna Maria $2,200,000

One or more photo(s) has been virtually staged. Discover coastal living at its finest with this charming elevated three-bedroom, three-full bath home located on Anna Mari...

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

243 Willow Avenue, Anna Maria $3,475,000

Welcome to paradise on Anna Maria Island! Nestled on the picturesque Willow Avenue, this 3-bedroom, 4-bathroom canal front home is a waterfront oasis that captures the es...

3 Beds
4 Baths
Bimini Bay Estates SubDv.
34216 Zip Code

2914 Gulf Drive, Holmes Beach $1,750,000

Welcome to your dream beach retreat in the heart of Holmes Beach! This fully renovated 3 bedroom, 2 bath beach house offers a harmonious blend of modern luxury and coasta...

3 Beds
2 Baths
Ilexhurst SubDv.
34217 Zip Code

915 N Shore Drive, Anna Maria $6,450,000

DIRECT BEACHFRONT! Relish a captivating island lifestyle in this beautiful waterfront home on north Anna Maria Island. This well-appointed home offers a maximum return on...

4 Beds
4 Baths
Shore Acres SubDv.
34216 Zip Code

428 Spring Avenue, Anna Maria $1,150,000

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...

2 Beds
1 Baths
Anna Maria Beach SubDv.
34216 Zip Code

101 7th Street S Unit A, Bradenton Beach image

101 7th Street S Unit A, Bradenton Beach $6,485,000

Under Construction. UNDER CONSTRUCTION..GULF VIEWS from every floor!! This spectacular custom built Eason Builder’s Group home will be just steps from the pearly white be...

5 Beds
5.5 Baths
Cortez Beach SubDv.
34217 Zip Code

3920 Mariners Way Unit 321C, Cortez image

3920 Mariners Way Unit 321C, Cortez — Mariners Cove 321c $1,250,000

Luxury Coastal Living at Its Finest! Step into your very own piece of paradise with this stunning 2nd-floor corner unit overlooking the serene Inter-coastal waters and ...

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

117 Maple Avenue, Anna Maria $3,350,000

Nestled just a short stroll from the sugary white sands of Palmetto Beach, Coral Kai offers the quintessential coastal living experience. This almost brand new, Ross Cust...

3 Beds
3.5 Baths
Gulf View Sub SubDv.
34216 Zip Code

205 Elm Avenue, Anna Maria $3,200,000

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. SUCCESS...

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

2500 Gulf Drive N, Bradenton Beach image

2500 Gulf Drive N, Bradenton Beach $6,385,000

Welcome to Oceanfront Paradise, a NEWLY RENOVATED beachfront home with breathtaking ocean views and direct beach access! This five-bedroom, five-bathroom, and two-half-ba...

5 Beds
5.5 Baths
Ilexhurst SubDv.
34217 Zip Code

107 Palm Avenue, Anna Maria $3,400,000

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 th...

2 Beds
2 Baths
Anna Maria Beach SubDv.
34216 Zip Code

522 Pine Avenue Unit 8A, Anna Maria image

522 Pine Avenue Unit 8A, Anna Maria — 8 $699,000

LOCATION…LOCATION…LOCATION! One of the most sought-after condo communities on beautiful Anna Maria Island! Located on historic Pine Ave, this one of a kind 2-bedroom, 2-b...

2 Beds
2 Baths
Bayou Vista SubDv.
34216 Zip Code

3015 Avenue E W, Holmes Beach $5,275,000

JUST COMPLETED!!! Your own piece of paradise!! Stunning 4-bedroom, 4.5-bathroom luxury beach home with an ELEVATOR just one block from the pearly white beaches and crysta...

4 Beds
4.5 Baths
Ilexhurst SubDv.
34217 Zip Code

4104 128th Street W Unit 703, Cortez image

4104 128th Street W Unit 703, Cortez — 4104 $774,999 ▲

Beautifully renovated 2BR/2BA waterfront condo, including 40FT. boatslip, has been updated from top to bottom! Updated bathroom fixtures, interior doors, plantation shutt...

2 Beds
2 Baths
Smugglers Landing SubDv.
34215 Zip Code

2203 Avenue B, Bradenton Beach $3,850,000

Welcome to Beach-Bliss! The perfect oasis nestled on the serene shores of Bradenton Beach, this remarkable 5-bedroom, 4.5-bathroom home has undergone a comprehensive tran...

5 Beds
4.5 Baths
Ilexhurst SubDv.
34217 Zip Code

6006 Gulf Drive Unit 211, Holmes Beach image

6006 Gulf Drive Unit 211, Holmes Beach — 6006 S $985,000

Enjoy island living in this maintenance free GULF FRONT condo complex – the highly sought-after Playa Encantada community! This gorgeous 2BD/2BA condo with awesome VIEWS...

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

94 N Shore Drive, Anna Maria $3,250,000

Welcome to AMI Oasis! This home is the ultimate getaway with private pool, gorgeous outdoor living space, and your own putting green! Main floor features a beautiful up...

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

2209 Avenue C, Bradenton Beach $3,990,000

Welcome to Casa Del Mar - Your Ultimate Gulfside Getaway! Experience the epitome of luxury and relaxation at Casa Del Mar, a magnificent three-level vacation home WITH EL...

5 Beds
5.5 Baths
Ilexhurst SubDv.
34217 Zip Code

506 69th Street, Holmes Beach $1,699,995

Discover the epitome of coastal living in this exquisite 2-bedroom, 2-bathroom home, nestled just a few blocks away from the pristine shores of Anna Maria Island. Step in...

2 Beds
2 Baths
Bay Palms SubDv.
34217 Zip Code

801 North Shore Drive, Anna Maria $12,000,000

This one-of-a-kind, direct Gulf Front, Turnkey oasis is located on the northern tip of Anna Maria Island, recognized as one of the greatest beach towns in America. Its su...

4 Beds
3.5 Baths
Shore Acres SubDv.
34216 Zip Code

3701 E Bay Drive Unit 8B, Holmes Beach image

3701 E Bay Drive Unit 8B, Holmes Beach — 3701 $725,000

Looking for a beautiful waterfront property that combines convenience, luxury, and stunning views? Look no further than this magnificent 2/3 home with extra air condition...

2 Beds
3 Baths
Sunbow Bay SubDv.
34217 Zip Code

2406 Avenue C, Bradenton Beach $4,200,000

Don’t miss this rare chance to own this brand new construction home on beautiful Anna Maria Island. This 7 bedroom 7 1/2 bath house is being sold fully furnished making i...

7 Beds
7.5 Baths
Ilexhurst SubDv.
34217 Zip Code

3806 6th Avenue, Holmes Beach — N/A $1,150,000

Don't miss this opportunity to own your own slice of paradise on Anna Maria Island in the highly sought after subdivision of Villages of Holmes Beach. This stunning home ...

3 Beds
2 Baths
Village At Holmes Beach SubDv.
34217 Zip Code

12622 Safe Harbour Drive, Cortez $2,000,000

Experience resort-style living in the gated coastal community of Harbour Landings. This pristine residence is a true gem and offers the ultimate Florida lifestyle. As you...

4 Beds
3.5 Baths
Harbour Landing SubDv.
34215 Zip Code

205 Peacock Lane Unit B, Holmes Beach image

205 Peacock Lane Unit B, Holmes Beach $1,395,000

Located in the heart of Holmes Beach, this charming Key West style 3 bed, 2 bath property is only a short walk to the white sands of the Gulf of Mexico. Lush, tropical la...

3 Beds
2 Baths
Holmes Beach SubDv.
34217 Zip Code

501 Gulf Drive N Unit 209, Bradenton Beach image

501 Gulf Drive N Unit 209, Bradenton Beach — Bridgeport $549,000

On Bradenton Beach, centrally located Bridgeport has direct access across the street to one of the best Beaches in the World and is owned by the Condo Association which p...

2 Beds
2 Baths
Bridgeport Condominium SubDv.
34217 Zip Code

216 Magnolia Avenue Unit A, Anna Maria image

216 Magnolia Avenue Unit A, Anna Maria $1,525,000

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...

Anna Maria Beach SubDv.
34216 Zip Code

516 Kumquat Drive, Anna Maria $5,425,000

Welcome to Open Palms a Luxury Waterfront Home located on one of the few canals in the City of Anna Maria with open water access with no bridges. Although zoned for weekl...

4 Beds
3 Baths
Lacios Sub SubDv.
34216 Zip Code

4200 Gulf Drive Unit 201, Holmes Beach image

4200 Gulf Drive Unit 201, Holmes Beach — Gulfsands $995,000

Paradise found! Check out this 2-bedroom / 2-bathroom DRIECT BEACH FRONT condo! Featuring a large heated pool, elevator, private beach access, lush tropical landscaping, ...

2 Beds
2 Baths
Gulfsands Condominium SubDv.
34217 Zip Code

5325 Marina Drive Unit 133, Holmes Beach image

5325 Marina Drive Unit 133, Holmes Beach — Lodge $675,000

Waterline Villas and Marina is the Tropical Oasis you have been looking. This one of a kind boutique style 37 unit condo building that is part of the Marriott's Autograph...

2 Beds
2 Baths
Waterline Villas & Marina SubDv.
34217 Zip Code

5325 Marina Drive Unit 131, Holmes Beach image

5325 Marina Drive Unit 131, Holmes Beach — Lodge $675,000

This is your chance to own your Island retreat right on Anna Maria Island... Waterline Villas and Marina is a 37 unit condo building that is part of the Marriott's Autogr...

2 Beds
2 Baths
Waterline Villas & Marina SubDv.
34217 Zip Code

3601 E Bay Drive Unit 203, Holmes Beach image

3601 E Bay Drive Unit 203, Holmes Beach — N/A $635,000 ▼

The saying about real estate being all about “location, location, location” is certainly true with this condo, which is located four-tenths of a mile from the Anna Maria ...

2 Beds
2 Baths
Sandy Pointe Condo SubDv.
34217 Zip Code

2815 Avenue C, Holmes Beach $1,425,000 ▼

Welcome to your dream island retreat on the highly sought-after Anna Maria Island! This turn-key furnished, stunning 3-bedroom, 2-bathroom single family home offers the e...

3 Beds
2 Baths
Ilexhurst SubDv.
34217 Zip Code

315 Hammock Circle, Anna Maria $3,100,000

This modern contemporary “Hammock House” is located in the most sought-after area of Anna Maria Island, the North end. This Anna Maria home on a large .2 acre lot offers...

3 Beds
3.5 Baths
Island Cedars SubDv.
34216 Zip Code

534 67th Street, Holmes Beach $7,750,000 ▼

Brand New!!! Custom Coastal Elegant Home, ready to call your own. No waiting to build, no waiting to remodel. Your new home was custom built with all luxuries you wanted ...

6 Beds
6.5 Baths
Bay Palms 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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John Gregory

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