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

117 7th Street N Unit 35, Bradenton Beach image

117 7th Street N Unit 35, Bradenton Beach — Unit 35 $429,000

Looking for a fun BEACH TOWN with everything close by and walking distance to the beautiful white sands and amazing blue waters of the Gulf of Mexico? Feel the wonderful...

1 Beds
1 Baths
Bay View Terrace SubDv.
34217 Zip Code

301 N Bay Boulevard, Anna Maria $1,795,000

Cleared Lot with Amazing Bay Views. Plans Completed. Conveyable City Permit In-Hand. Ready for you to build!!! Price includes vacant lot, completed plans, and transferrab...

Anna Maria Beach Second Add SubDv.
34216 Zip Code

501 Gulf Drive N Unit 108, Bradenton Beach image

501 Gulf Drive N Unit 108, Bradenton Beach — Na $549,000

Bridgeport - a popular Gulf to Bay Community in Bradenton Beach. This two bedroom/two bath unit provides open living space, ceramic tile throughout, quartz countertops, ...

2 Beds
2 Baths
Bridgeport Condominium SubDv.
34217 Zip Code

903 N Shore Drive Unit A, Anna Maria image

903 N Shore Drive Unit A, Anna Maria $7,900,000

The Ultimate Beach Front Paradise on Anna Maria Island where the stunning panoramic views of the bay will captivate you while you enjoy your own private beach! The renta...

4 Beds
4.5 Baths
Shore Acres SubDv.
34216 Zip Code

4307 Gulf Dr Unit 206, Holmes Beach image

4307 Gulf Dr Unit 206, Holmes Beach — East $599,000

Have you have ever dreamed of a beach escape? Well here it is! This is the one you've been waiting for. Rarely available Cayman Cay turnkey furnished second floor 2 bedro...

2 Beds
2 Baths
Cayman Cay Villas Condominium SubDv.
34217 Zip Code

522 Pine Avenue Unit 2D, Anna Maria image

522 Pine Avenue Unit 2D, Anna Maria — 2d $659,000

This updated 2 bedroom, 1.5 bathroom waterfront condo is on the second floor and is located in the Bayou, Anna Maria City's only condo complex. Tucked back off of bustlin...

2 Beds
1.5 Baths
Bayou SubDv.
34216 Zip Code

810 S Bay Boulevard Unit A, Anna Maria image

810 S Bay Boulevard Unit A, Anna Maria $7,495,000

Welcome to “Skyway View”. First, the name says it all. Looking out from the rear of the home you have a fabulous view of the Sunshine Skyway Bridge, Tampa Bay, and the Gu...

4 Beds
4.5 Baths
Bayview Beach SubDv.
34216 Zip Code

3017 Avenue E, Holmes Beach $3,985,000

Welcome to luxury coastal living on Anna Maria Island! This gorgeous island retreat is only one short block away from pristine powder sand and stunning turquoise water be...

4 Beds
4.5 Baths
Ilexhurst SubDv.
34217 Zip Code

5325 Marina Drive Unit 423, Holmes Beach image

5325 Marina Drive Unit 423, Holmes Beach — Island Building $699,000

Waterline Villas & Marina, Marriott's Autograph Collection is a sophisticated and stylish boutique hotel with 37 fully TURN-KEY furnished condos with a premier waterfront...

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

113 Cedar Avenue, Anna Maria $1,900,000

Charming ground level cottage built in 1930, located west of Gulf Drive in the city of Anna Maria. This cottage features two bedrooms, one and one half bath, living room...

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

1801 Gulf Drive N Unit 279, Bradenton Beach image

1801 Gulf Drive N Unit 279, Bradenton Beach — A $450,000 ▼

Dreamy Island Life Awaits! This beautiful unit is the perfect destination for an unforgettable beach getaway. Situated right across the street from beach access, you'll b...

1 Beds
1 Baths
Runaway Bay SubDv.
34217 Zip Code

706 S Bay Boulevard, Anna Maria $4,950,000

Looking for that perfect hideaway artist retreat featuring one of the best views on the West Coast of Florida? Look no further. This 3 bedroom, 2.5 bathroom + den has t...

3 Beds
2.5 Baths
Wells Bay Harbor SubDv.
34216 Zip Code

105 4th Street S Unit 2, Bradenton Beach image

105 4th Street S Unit 2, Bradenton Beach $5,750,000

This gorgeous 8-bedroom 6+ bath DUPLEX in Bradenton Beach is finally for sale! Perfectly located only steps from the Gulf of Mexico and features unrivaled ocean views. Th...

8 Beds
Casa Playa At Bradenton Beach SubDv.
34217 Zip Code

8310 Marina Drive, Holmes Beach $1,325,000

Located in the coastal beach haven of Holmes Beach on Anna Maria Island, this marvelous property makes for the ideal home for those seeking a laid-back beachy retreat, a ...

2 Beds
2 Baths
Holmes Beach SubDv.
34217 Zip Code

620 North Point Drive, Holmes Beach image

620 North Point Drive, Holmes Beach $2,795,000

Be inspired by this Key Royale coastal Florida waterfront renovation on Anna Maria Island. The home naturally flows from inside out, capturing water views from most every...

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

5400 Gulf Drive Unit 6, Holmes Beach image

5400 Gulf Drive Unit 6, Holmes Beach — Building 2, Unit 6 $479,900

Experience Anna Maria Island at it's best! Are you ready for the slower pace of "Island Life" with tons of vintage Florida charm? 5400 Gulf Drive is a beach front 55+ com...

1 Beds
1 Baths
5400 Condos SubDv.
34217 Zip Code

105 4th Street S Unit WEST, Bradenton Beach image

105 4th Street S Unit WEST, Bradenton Beach $2,875,000

This gorgeous 4 bedroom 3.5 Bath home / half duplex in Bradenton Beach is finally for sale! Perfectly located only steps from the Gulf of Mexico and features unrivaled oc...

4 Beds
3.5 Baths
Cortez Beach SubDv.
34217 Zip Code

105 4th Street S Unit EAST, Bradenton Beach image

105 4th Street S Unit EAST, Bradenton Beach $2,875,000

This gorgeous 4 bedroom 3.5 Bath home / half duplex in Bradenton Beach is finally for sale! Perfectly located only steps from the Gulf of Mexico and features unrivaled oc...

4 Beds
3.5 Baths
Cortez Beach SubDv.
34217 Zip Code

2915 Avenue C, Holmes Beach $895,000

This 2BD/2BA elevated getaway is located in a quiet area and is nestled up to a mangrove preserve in the heart of Holmes Beach. Just a short stroll to the beach and easy ...

2 Beds
2 Baths
Ilexhurst SubDv.
34217 Zip Code

228 Gladiolus Street, Anna Maria $2,495,000

location, location, location! This sublime, newly renovated and turnkey 3BED/2BATH is perfectly located on the north side of the island! This amazing home is elevated...

3 Beds
2 Baths
Luana Isles SubDv.
34216 Zip Code

3801 E Bay Drive Unit 107, Holmes Beach image

3801 E Bay Drive Unit 107, Holmes Beach — 3801 $625,000

Waterfront views and a fantastic island location. Convenient to both the north and south ends of the island and easy off the island into town. Perfect 2 bedroom/ 2 bath c...

2 Beds
2 Baths
Sunbow Bay Ph Iv SubDv.
34217 Zip Code

700 N Shore Drive, Anna Maria $2,495,000

Tarpon Pointe is the perfect spot in a great location on the north end of Anna Maria. You enter this freshly updated turnkey furnished 2 bedroom, 2 bath home from a larg...

2 Beds
2 Baths
Wells Terrace SubDv.
34216 Zip Code

1801 Gulf Drive N Unit 233, Bradenton Beach image

1801 Gulf Drive N Unit 233, Bradenton Beach $539,000

Immaculate property and priced to sell. The owners have taken immense pride in maintaining this beautiful unit over their long ownership, and this is a must see in Runawa...

2 Beds
2 Baths
Runaway Bay SubDv.
34217 Zip Code

316 Iris Street, Anna Maria $2,495,000

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...

3 Beds
3 Baths
Luana Isles SubDv.
34216 Zip Code

306 58th Street Unit A, Holmes Beach image

306 58th Street Unit A, Holmes Beach $1,390,000

LOCATION, LOCATION, LOCATION! Investment opportunity on the amazingly popular Anna Maria Island! This income producing duplex is within walking distance to the beach, sho...

4 Beds
Holmes Beach SubDv.
34217 Zip Code

4337 Marina View Way, Cortez $1,880,000 ▼

Under Construction. PreConstruction. To Be Built. Welcome to Hunter's Point. This 3 bedroom, 2.5 bathroom home is the 2nd largest lot in Hunters Point and destined to ...

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

505 Spring Avenue, Anna Maria $2,150,000

Whispering Whale Retreat is a lovely elevated home with 4 bedrooms and 2 bathrooms. Located on the prestigious Northern end of Anna Maria Island this versatile home incor...

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

515 70th Street, Holmes Beach $1,299,000

Come see this quaint and charming one level 2 bedroom, 2 bathroom home on a quiet canal street in Holmes Beach! There is great natural light throughout the entire home an...

2 Beds
2 Baths
Bay Palms SubDv.
34217 Zip Code

616 Fern Street, Anna Maria $1,600,000

LOCATION, LOCATION, LOCATION! Nestled in highly coveted north Anna Maria Island, this unique property will have you just 300 steps from the Gulf of Mexico and high and dr...

3 Beds
2 Baths
Shore Acres SubDv.
34216 Zip Code

1801 Gulf Drive N Unit 216, Bradenton Beach image

1801 Gulf Drive N Unit 216, Bradenton Beach — F $624,000

"Endless Memories" is successful 2B/2B vacation rental in POPULAR RUNAWAY BAY! This one offers is ALL: WEEKLY RENTALS, ON SITE management* 100ft to the gorgeous sandy AMI...

2 Beds
2 Baths
Runaway Bay SubDv.
34217 Zip Code

600 Manatee Ave Unit 202, Holmes Beach image

600 Manatee Ave Unit 202, Holmes Beach — 1 $569,000

EXPANSIVE views of the Anna Maria Sound & Intracoastal Waterway greet you as you enter. Over 18' of glass sliders overlooking the water all the way to the twinkling light...

1 Beds
1 Baths
Westbay Cove SubDv.
34217 Zip Code

5400 Gulf Drive Unit 14, Holmes Beach image

5400 Gulf Drive Unit 14, Holmes Beach — 4 $579,500

Welcome to your very own beach paradise where you can view the sunsets while sipping a glass of wine. Be sure to watch a video tour of this property:https://youtu.be/CQy7...

1 Beds
1 Baths
5400 Condos SubDv.
34217 Zip Code

3948 Mariners Way Unit 222, Cortez image

3948 Mariners Way Unit 222, Cortez — 3948 $999,000

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

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

5623 Gulf Drive, Holmes Beach $1,499,999

Auction Property. EVERTONE is WELCOME to BID. Financed and cash buyers OK…..This property is For Sale by AUCTION. Auction sale held at the home on Sat. June 17 at 11am. P...

3 Beds
2 Baths
Cobb Sub SubDv.
34217 Zip Code

515 Bayview Drive, Holmes Beach $3,995,000

ANNA MARIA ISLAND CHARM WITH SPECTACULAR WATER VIEWS! This stunning vintage Florida home is on the intracoastal waterway and is perfectly situated to make it your full-t...

4 Beds
3 Baths
Sunrise Park SubDv.
34217 Zip Code

222 17th Street N Unit 222, Bradenton Beach image

222 17th Street N Unit 222, Bradenton Beach — 222 $942,500 ▼

BEACH TO BAY COMPLEX HAS THE BEST OF BOTH WORLDS. THIS CONDO IS A SHORT WALK TO THE WHITE SANDY BEACHES, AND THE INTERCOASTAL WATERWAY. IT HAS 3 BEDS AND 2 FULL BATHS, ...

2 Beds
2 Baths
Bradenton Beach Club SubDv.
34217 Zip Code

6401 Holmes Boulevard Unit B, Holmes Beach image

6401 Holmes Boulevard Unit B, Holmes Beach $999,000 ▼

THIS PERFECT ISLAND GETAWAY AWAITS YOU! JUST A TWO MINUTE WALK TO THE BEACH AND A GOLF CART RIDE TO SHOPS AND RESTAURANTS, THIS CENTRALLY LOCATED 2BD/2BA HALF DUPLEX RESI...

2 Beds
2 Baths
Holmes Beach SubDv.
34217 Zip Code

803 N Shore Drive, Anna Maria $9,800,000

This Direct Waterfront Turnkey Furnished home boasts over 4993 sq. ft. in living space with 4 bedrooms 4 baths and unobstructed views of the Gulf of Mexico located in the...

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

2908 Avenue B, Holmes Beach $775,000

RARE LOT FIND IN HOLMES BEACH! Spectacular New Build opportunity! 50FT WIDE x 105FT DEEP LOT (5,249 SQFT/.1205 ACRES). Vacant Lot At the end of a Private cul-da-sac that ...

Ilexhurst SubDv.
34217 Zip Code

1437 Gulf Drive N Unit 26, Bradenton Beach image

1437 Gulf Drive N Unit 26, Bradenton Beach — Berm Bay, Bldg 1 $1,049,000

Thiis a beautifully remodeled unit, with all updated appliances, new AC, new countertops, new flooring. Kitchen has been updated with new appliances. Both bathrooms have...

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

224 Chilson Avenue, Anna Maria $7,995,000

Under Construction. Stunning new CANAL front build just two blocks to the pearly white beaches of Anna Maria. This contemporary home will be showstopper...complete with 6...

6 Beds
6.5 Baths
Bimini Bay Estates SubDv.
34216 Zip Code

629 Key Royale Drive, Holmes Beach image

629 Key Royale Drive, Holmes Beach $4,769,000

Don’t miss this opportunity to live directly on the open water with stunning views of Tampa Bay/Anna Maria Sound. Located in Key Royale with immediate access to Tampa Ba...

Key Royale SubDv.
34217 Zip Code

4231 Marina View Way, Cortez $1,699,500

Pre-Construction. To be built. Welcome to Hunter's point, our 3 bedroom, 2.5 bathroom home is a perfect fit for you! This waterfront home is an intelligently powered home...

3 Beds
2.5 Baths
Hunters Point SubDv.
34215 Zip Code

232 Oak Avenue, Anna Maria $2,650,000 ▼

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 ...

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

3803 E Bay Drive Unit 6, Holmes Beach image

3803 E Bay Drive Unit 6, Holmes Beach — 3803 $599,900

This 3 bedroom 3 bath condo is centrally located in the interior of the Sunbow Bay community. Spacious open floor plan from the kitchen throughout the great room looking ...

3 Beds
3 Baths
Sunbow Bay SubDv.
34217 Zip Code

4909 Gulf Drive Unit 2A, Holmes Beach image

4909 Gulf Drive Unit 2A, Holmes Beach $785,000

Welcome to your DREAM BEACH getaway! This TURNKEY FURNISHED 2 bed 2 bath raised half-duplex is everything you've been searching for. Located in sought-after Anna Maria Is...

2 Beds
2 Baths
34217 Zip Code

643 Key Royale Drive, Holmes Beach image

643 Key Royale Drive, Holmes Beach $6,100,000

Spectacular custom home with huge Tampa Bay views on Anna Maria Island. This massive waterfront retreat boasts over 5,000 square feet under air and features luxury amenit...

4 Beds
4 Baths
Key Royale SubDv.
34217 Zip Code

106 11th Street S Unit A, Bradenton Beach image

106 11th Street S Unit A, Bradenton Beach $1,567,111

"short stories"... Perfect opportunity to build a 4-5 bedroom vacation home. Just a 100 feet to bradenton beach. walking distance to restaurants in downtown bradenton bea...

2 Beds
2 Baths
Cortez Beach SubDv.
34217 Zip Code

208 75th Street, Holmes Beach $1,999,000

This 3 bedroom, 2.5 bathroom home is very well maintained and steps away from the Gulf of Mexico Beaches!! This unique home feels like you are in a hidden jungle with th...

3 Beds
2.5 Baths
Bay Palms SubDv.
34217 Zip Code

840 N Shore Drive, Anna Maria $2,549,000 ▼

New Hardie siding, new metal roof, and DEP pool permit in hand. Here is a rare opportunity to own a duplex on the North end of Anna Maria that is just steps away from the...

6 Beds
4 Baths
Wells Sub SubDv.
34216 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