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Anna Maria Island

Anna Maria Island is a charming and picturesque destination, offering a perfect blend of old Florida charm and modern amenities. Known for its stunning Gulf Coast beaches, turquoise waters, and soft, white sand, the island is a paradise for beachgoers, sunbathers, and water sports enthusiasts. The community on Anna Maria Island is known for its friendly, laid-back atmosphere, inviting a relaxed lifestyle. Its small-town feel is enhanced by unique local shops, art galleries, and casual to fine dining options, which dot the island, providing a quaint yet vibrant social scene.

View The Market Report
228 GLADIOLUS ST, Anna Maria, FL 34216
Open Sun 12PM-2PM
28

$1,945,000

3 Beds 2 Baths 1,458 SqFt

228 GLADIOLUS ST, Anna Maria, FL 34216

Listed by Amanda Cornett PINEYWOODS REALTY LLC

Stellar MLS
Stellar MLS
418 PINE AVE, Anna Maria, FL 34216
Open Sun 12PM-2PM
73

$3,000,000

4 Beds 3 Baths 2,804 SqFt

418 PINE AVE, Anna Maria, FL 34216

Listed by Stephanie Paxton KW SUNCOAST

Stellar MLS
Stellar MLS
403 N BAY BLVD, Anna Maria, FL 34216
Open Sat 11:30AM-1:30PM
58

$2,473,000

4 Beds 3 Baths 2,112 SqFt

403 N BAY BLVD, Anna Maria, FL 34216

Listed by Ed Taaffe WAGNER REALTY

Stellar MLS
Stellar MLS
306 PALM AVE, Anna Maria, FL 34216
New
63

$1,695,000

3 Beds 3 Baths 1,902 SqFt

306 PALM AVE, Anna Maria, FL 34216

Listed by Kasay Gunter DUNCAN REAL ESTATE, INC.

Stellar MLS
Stellar MLS
417 POINSETTIA RD, Anna Maria, FL 34216
Active
50

$1,499,000

2 Beds 2 Baths 1,540 SqFt

417 POINSETTIA RD, Anna Maria, FL 34216

Listed by Jennifer Orns COMPASS FLORIDA LLC

Stellar MLS
Stellar MLS
416 ALAMANDA RD, Anna Maria, FL 34216
Active
100

$4,095,000

4 Beds 5 Baths 3,102 SqFt

416 ALAMANDA RD, Anna Maria, FL 34216

Listed by Kim Bowersox KELLER WILLIAMS ON THE WATER

Stellar MLS
Stellar MLS
513 N BAY BLVD, Anna Maria, FL 34216
Active
78

$4,495,000

4 Beds 4 Baths 2,602 SqFt

513 N BAY BLVD, Anna Maria, FL 34216

Listed by Jason Sato SATO REAL ESTATE INC.

Stellar MLS
Stellar MLS
112 MAPLE AVE, Anna Maria, FL 34216
Active
91

$4,925,000

5 Beds 5 Baths 2,545 SqFt

112 MAPLE AVE, Anna Maria, FL 34216

Listed by Christy Travis RE/MAX ALLIANCE GROUP

Stellar MLS
Stellar MLS
9407 GULF DR, Anna Maria, FL 34216
Active
68

$6,950,000

9 Beds 9 Baths 4,244 SqFt

9407 GULF DR, Anna Maria, FL 34216

Listed by Gregg Bayer BEACH HOUSE REAL ESTATE LLC

Stellar MLS
Stellar MLS
215 SYCAMORE AVE, Anna Maria, FL 34216
Active
75

$5,895,000

4 Beds 5 Baths 3,250 SqFt

215 SYCAMORE AVE, Anna Maria, FL 34216

Listed by Darcie Duncan DUNCAN REAL ESTATE, INC.

Stellar MLS
Stellar MLS
103 PARK AVE, Anna Maria, FL 34216
Active
61

$5,550,000

5 Beds 5 Baths 4,540 SqFt

103 PARK AVE, Anna Maria, FL 34216

Listed by Dee Munn MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
517 SPRING AVE, Anna Maria, FL 34216
Active
52

$1,600,000

2 Beds 2 Baths 1,200 SqFt

517 SPRING AVE, Anna Maria, FL 34216

Listed by Clay OSteen O'STEEN GROUP INC

Stellar MLS
Stellar MLS
107 PINE AVE, Anna Maria, FL 34216
Active
94

$4,999,999

6 Beds 4 Baths 2,748 SqFt

107 PINE AVE, Anna Maria, FL 34216

Listed by Hannah Hillyard MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
416 MAGNOLIA AVE, Anna Maria, FL 34216
Pending
27

$1,090,000

2 Beds 1 Baths 1,188 SqFt

416 MAGNOLIA AVE, Anna Maria, FL 34216

Listed by Stephen Kring HORIZON REALTY OF ANNA MARIA

Stellar MLS
Stellar MLS
727 JACARANDA RD, Anna Maria, FL 34216
Pending
44

$2,150,000

3 Beds 3 Baths 2,055 SqFt

727 JACARANDA RD, Anna Maria, FL 34216

Listed by Jason Sato SATO REAL ESTATE INC.

Stellar MLS
Stellar MLS
209 WILLOW AVE, Anna Maria, FL 34216
Active
85

$6,795,000

6 Beds 8 Baths 4,154 SqFt

209 WILLOW AVE, Anna Maria, FL 34216

Listed by Jason Sato SATO REAL ESTATE INC.

Stellar MLS
Stellar MLS
889 N SHORE DR, Anna Maria, FL 34216
Active
37

$4,500,000

3 Beds 3 Baths 2,025 SqFt

889 N SHORE DR, Anna Maria, FL 34216

Listed by Jason Sato SATO REAL ESTATE INC.

Stellar MLS
Stellar MLS
165 CRESCENT DR, Anna Maria, FL 34216
Active
45

$1,695,000

3 Beds 2 Baths 1,403 SqFt

165 CRESCENT DR, Anna Maria, FL 34216

Listed by Ryan Sheck ISLAND REAL ESTATE-ANNA MARIA

Stellar MLS
Stellar MLS
406 N SHORE DR, Anna Maria, FL 34216
Active
12

$5,450,000

4 Beds 5 Baths 2,999 SqFt

406 N SHORE DR, Anna Maria, FL 34216

Listed by Jason Sato SATO REAL ESTATE INC.

Stellar MLS
Stellar MLS
319 TARPON ST, Anna Maria, FL 34216
Active
83

$7,195,000

5 Beds 6 Baths 3,484 SqFt

319 TARPON ST, Anna Maria, FL 34216

Listed by Dee Munn MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
107 TUNA ST, Anna Maria, FL 34216
Active
27

$7,750,000

6 Beds 6 Baths 4,345 SqFt

107 TUNA ST, Anna Maria, FL 34216

Listed by John Forberger DOUGLAS ELLIMAN

Stellar MLS
Stellar MLS
811 N SHORE DR, Anna Maria, FL 34216
Active
90

$10,950,000

4 Beds 8 Baths 5,079 SqFt

811 N SHORE DR, Anna Maria, FL 34216

Listed by Jessica Batten SATO REAL ESTATE INC.

Stellar MLS
Stellar MLS
246 GLADIOLUS ST, Anna Maria, FL 34216
Active
52

$1,999,000

3 Beds 3 Baths 1,979 SqFt

246 GLADIOLUS ST, Anna Maria, FL 34216

Listed by Jason Sato SATO REAL ESTATE INC.

Stellar MLS
Stellar MLS
224 CHILSON AVE, Anna Maria, FL 34216
Active
95

$6,344,999

6 Beds 7 Baths 4,525 SqFt

224 CHILSON AVE, Anna Maria, FL 34216

Listed by George DeSear AMI REALTY GROUP

Stellar MLS
Stellar MLS

© 2026 My Florida Regional MLS DBA Stellar MLS. All Rights Reserved. The data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data Last Updated: 05/21/2026 16:01

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