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| Address | Bed / Bath | Listing Price |
|---|---|---|
5710 CARISSA STREET
Perfectly placed on a quiet street, this 3BD/2BA elevated island home blends coastal charm with practical comfort, making it equally suited for personal enjoyment or continued success as a vacation rental. The open concept layout invites relaxed living, with a bright kitchen featuring granite counte
Living Area:
1920 Sqft.
|
3
Beds,
2
Baths
|
$1,695,000 |
5005 GULF OF MEXICO DRIVE 4
Designed by award-winning architect, John Cooney, and built by Sarasota’s premier coastal homebuilder, Perrone Construction, this mid-Key classic is simply among Longboat Key’s finest homes.
Steps from the beach and with expansive Gulf and Bay views, this masterpiece offers more than 4300 squar
Living Area:
4630 Sqft.
|
4
Beds,
5
Baths
|
$8,250,000 |
5506 HOLMES BOULEVARD
5506 Holmes Blvd presents a rare development-forward offering in the heart of Anna Maria Island / Holmes Beach.
Ideal for investors interested in a joint-venture build with the current Owner/Architect, or for an end-user seeking a prime coastal residence.
The owners, established architects, have c
Living Area:
2126 Sqft.
|
4
Beds,
3
Baths
|
$1,125,000 |
303 58TH STREET
AMAZING LOCATION • COMPLETELY UPDATED • BRAND NEW POOL • BRAND NEW ROOF • TURN-KEY FURNISHED Casa Bella is a spacious and beautifully updated 4-bedroom, 3-bath home offering more than 2,500 sq ft in the heart of Holmes Beach. Located just steps from shopping and dining and only a 5-MINUTE WA
Living Area:
2524 Sqft.
|
4
Beds,
3
Baths
|
$2,774,999 |
313 58TH STREET B
Welcome to your dream Beach Retreat! This elevated 4-bedroom, 3-bath home offers a perfect blend of comfort and luxury, providing ample space for family gatherings and entertaining friends. Nestled in the heart of Anna Maria Island, this gem is just a stone's throw away from pristine beaches, charmi
Living Area:
1474 Sqft.
|
4
Beds,
3
Baths
|
$1,495,000 |
5390 GULF DRIVE
Just steps from the sugar white sands of the Gulf, this elevated coastal retreat captures the essence of relaxed beachside living with the comfort of thoughtful design. Bright, airy interiors welcome you with an open concept layout where the living area flows seamlessly into a charming kitchen featu
Living Area:
1968 Sqft.
|
2
Beds,
2
Baths
|
$1,500,000 |
308 58TH STREET A
WELCOME to APPLETINI, a charming BEACH HOUSE on ANNA MARIA ISLAND! ~This fun, Key West style pool home has 2 lovely bedrooms & 2 full baths. Enjoy highly desirable & easy ground level living. With its x-large sparkling heated pool, resort style waterfall feature and swim up Tiki umbrella bar, it is
Living Area:
1095 Sqft.
|
2
Beds,
2
Baths
|
$995,000 |
2812 AVENUE B
Welcome to your dream retreat on beautiful Anna Maria Island! This charming coastal cottage is tucked away in the quiet neighborhood of Ilexhurst, perfectly positioned between the Manatee and Cortez bridges for effortless access on and off the Island—and just moments from your favorite beaches, re
Living Area:
1080 Sqft.
|
2
Beds,
2
Baths
|
$824,900 |
526 56TH STREET
Welcome to this 4,995-square-foot architectural masterpiece designed by well-known architect Gene Aubry, featuring five bedrooms, five baths, an office, a second living area and a gym, all on 225 feet of direct bay frontage in Holmes Beach. This bayfront estate in the heart of Anna Maria Island refl
Living Area:
4995 Sqft.
|
5
Beds,
5
Baths
|
$6,950,000 |
5803 IMPERIORE AVENUE
Weekly rental! Exceptional Investment Steps from Holmes Beach. Welcome to Blue Oasis, a fully renovated ground-level retreat just steps from Holmes Beach and the turquoise waters of the Gulf of Mexico. This stunning 2-bedroom, 2-bath home combines modern luxury with island charm. Featuring a versati
Living Area:
1128 Sqft.
|
2
Beds,
2
Baths
|
$1,250,000 |
201 57TH STREET
Welcome to Flip Flop Inn, a wonderful BEACH HOUSE escape tucked away on a quiet street on beautiful Anna Maria Island. This expansive three-level elevated pool home has been thoughtfully updated and offers the perfect blend of comfort, style, and coastal charm. Enter into a spacious foyer with immed
Living Area:
2703 Sqft.
|
3
Beds,
3
Baths
|
$1,765,000 |
2908 AVENUE B
Under Construction. Under Construction by Award-Winning Builder
Stunning 4 bedroom, 3.5 bath modern coastal contemporary home by Modus Builders — recipient of the 2025 Home of the Year honors earlier this year — located at 2908 Avenue B on Holmes Beach, with an estimated completion of May 2
Living Area:
2701 Sqft.
|
4
Beds,
4
Baths
|
$3,150,000 |
305 55TH STREET
Welcome to "Black Pearl"! Discover refined island living in this exceptional 2024 custom-built residence, ideally situated just 1.5 blocks from the pristine Gulf beaches. Designed with sophistication and comfort in mind, this 4-bedroom, 4-bath elevated home offers a seamless blend of modern elegance
Living Area:
3010 Sqft.
|
4
Beds,
4
Baths
|
$4,395,000 |
4006 5TH AVENUE
NEW METAL ROOF COMING SOON! Check out "La Isla Bonita"on Holmes Beach! A successful vacation rental property just 5 minutes (400 steps) to the gorgeous Anna Maria Island beaches! This concrete block construction has a total of 3515 total sq.ft. This contemporary QUALITY BUILT home in 2006 with an EL
Living Area:
3088 Sqft.
|
4
Beds,
4
Baths
|
$1,600,000 |
2406 AVENUE C
Don’t miss this rare chance to own this newer construction home on beautiful Anna Maria Island. This 7 bedroom 7 1/2 bath house is being sold fully furnished making it a breeze to move in or start renting right away. Inside you will find wonderful designer touches in every room including a gorgeou
Living Area:
2821 Sqft.
|
7
Beds,
8
Baths
|
$4,000,000 |
2415 AVENUE B
Don’t miss this rare chance to own this newer construction home on beautiful Anna Maria Island. This 6 bedroom, 5 full bath, 2 1/2 bath house is being sold fully furnished making it a breeze to move in or start renting right away. Inside you will find wonderful designer touches in every room inclu
Living Area:
3400 Sqft.
|
6
Beds,
7
Baths
|
$4,500,000 |
2714 AVENUE C
LOCATION LOCATION LOCATION!!! Don't miss out on this great opportunity to start fresh and rebuild to make this home your own! Located on a quiet street and in a monthly rental zone so you don't have busy vacation rentals around you. Right down the street from the trolley stop, making it very conveni
Living Area:
1041 Sqft.
|
3
Beds,
2
Baths
|
$550,000 |
2213 AVENUE C
Don’t miss this rare chance to own this newer construction home on beautiful Anna Maria Island. Whether you're a sun seeker, water enthusiast, or nature lover, the location of this captivating home offers a luxurious escape with seven bedrooms and seven and a half baths, and just moments away from
Living Area:
3265 Sqft.
|
7
Beds,
8
Baths
|
$3,450,000 |
2813 AVENUE E
One or more photo(s) has been virtually staged. Don’t miss this rare opportunity to own an exceptional property featuring TWO charming coastal cottages just steps from the pristine Gulf beaches of Anna Maria Island! Perfectly situated right across the street from the Gulf, this property offers unb
Living Area:
1558 Sqft.
|
5
Beds,
3
Baths
|
$1,440,000 |
4003 5TH AVENUE
Your Lucky Day~ buyer Financing Fell through & Back on the Market!! Mediterranean-inspired coastal luxury meets the laid-back charm of island living in this fully furnished, elevated Anna Maria Island Villa, just one block from the Gulf and a short stroll to Skinny’s and Manatee Beach. With no HOA
Living Area:
2200 Sqft.
|
3
Beds,
3
Baths
|
$1,550,000 |
2305 AVENUE C
Welcome to Floridaze! A newly constructed 6-bedroom and 5.5-bathroom luxury home. Located less than a 1-minute walk to the gorgeous beaches of Anna Maria Island. You will feel like the crystal-clear blue waters of the Gulf of Mexico are in your very own backyard! Located between the Gulf of Mexico a
Living Area:
3082 Sqft.
|
7
Beds,
6
Baths
|
$3,100,000 |
2913 GULF DRIVE
Step onto the spacious screened front porch, now featuring Timber Tech by Azek Porch Collection decking, framed by original Pecky Cypress siding, and enjoy the timeless charm of this lovingly restored 1940s 2 bed / 2 bath craftsman beach cottage just steps from the Gulf. This home blends Old Florida
Living Area:
1048 Sqft.
|
2
Beds,
2
Baths
|
$1,174,900 |
201 N HARBOR DRIVE
Discover an unparalleled living experience in this architecturally stunning island residence, meticulously renovated in 2022 by Richard Haas of Haas Modern Architecture & Design with bespoke floating stairs seamlessly blending cutting-edge design with luxurious amenities, all set against the backdro
Living Area:
3928 Sqft.
|
5
Beds,
4
Baths
|
$4,950,000 |
2713 AVENUE C
CUSTOM QUALITY HOME REMODEL: Welcome to Turquoise Beach Bungalow—your perfect slice of island life. Completely reimagined inside and out in 2024–2025, this vibrant coastal retreat combines classic island charm with modern comfort and craftsmanship. Every detail has been thoughtfully considered,
Living Area:
1477 Sqft.
|
3
Beds,
2
Baths
|
$1,199,000 |
2915 AVENUE C
PRIME LOCATION | BRAND NEW RENOVATIONS | ELEVATED-LUXURY-LIVING | ELEVATOR | FENCED SALTWATER POOL | MOVE-IN READY |
Located on a peaceful street and embraced by the natural beauty of a mangrove preserve, this elevated coastal residence delivers privacy, modern luxury, and a coveted Holmes Beach li
Living Area:
1040 Sqft.
|
2
Beds,
2
Baths
|
$1,189,000 |
220 36TH STREET
Great New Price on this Ultimate Gulfside Retreat on Holmes Beach, Anna Maria Island!
NO WATER INTRUSION IN MAIN LIVING AREAS FROM RECENT HURRICANES and NO HOA! Just 200 feet from the sugar-sand shores and turquoise waters of the Gulf of Mexico, this updated, coastal-inspired three-level beach ho
Living Area:
2016 Sqft.
|
3
Beds,
4
Baths
|
$1,900,000 |
405 28TH STREET
This newly renovated waterfront home on Anna Maria Island features nearly 80 feet of prime canal frontage, providing breathtaking views from almost every room of the property. A private boat dock and lift make this residence a paradise for boating enthusiasts, while also being only steps away from t
Living Area:
3748 Sqft.
|
6
Beds,
4
Baths
|
$3,230,000 |
207 PEACOCK LANE
This completely updated Anna Maria Island 3 bedroom 2.5 Bathroom pool home is situated on a cul-de-sac, and features hurricane-rated windows, metal roof, concrete block construction and garage. Property is in a Weekly rental zone with a successful rental history, making this BEAUTIFUL BEACH HOME a p
Living Area:
1713 Sqft.
|
3
Beds,
3
Baths
|
$1,750,000 |
4105 4TH AVENUE
STEPS FROM THE GULF – LUXURY SIX-BEDROOM COASTAL RETREAT IN HOLMES BEACH | Discover Summer’s Retreat, an architectural masterpiece where luxury meets the legendary white sands of Anna Maria Island. This remarkable six-bedroom, six-and-a-half-bath coastal estate represents one of the island’s m
Living Area:
2453 Sqft.
|
6
Beds,
7
Baths
|
$2,690,000 |
307 57TH STREET
Coastal elegance meets modern living in this beautifully updated Holmes Beach retreat located on the peaceful stretch of 57th Street—one of the narrowest parts of Anna Maria Island. This prime location offers the least crowded beach access on the island, just steps from the shoreline.
The home
Living Area:
1490 Sqft.
|
3
Beds,
3
Baths
|
$1,349,000 |
2813 GULF DRIVE
Pre-Construction. To be built. Build your dream home just steps from the beach. Take in panoramic sunsets from your private rooftop. Enjoy the peace of mind that comes with high-quality, hurricane-resilient construction. Modern, energy-efficient design ensures comfort, security, and long-term value.
Living Area:
2180 Sqft.
|
3
Beds,
2
Baths
|
$2,500,000 |
2410 AVENUE B
BRAND NEW CUSTOM CONSTRUCTION ON ANNA MARIA ISLAND HAS IT ALL. IT IS LOCATED 2 BLOCKS TO THE BEACH AND A BLOCK TO THE BAY. THIS NEW HOME HAS 7 BEDROOMS, 5 BATHS AND LARGE OPEN CONCEPT LIVING AND DINING AREA WITH WOOD LOOK CERAMIC TILE THROUGHOUT. KITCHEN AND BATHS FEATURE CUSTOM TILE DESIGN AND QUAR
Living Area:
2852 Sqft.
|
7
Beds,
7
Baths
|
$2,870,000 |
3720 GULF DRIVE
Exceptional Gulf-Front Opportunity in the Heart of Holmes Beach! Discover the perfect blend of island charm and coastal luxury with this rare gulf-front parcel on Anna Maria Island. Ideally located just steps from the sugar-white sands, and surrounded by the vibrant energy of Holmes Beach’s shops,
Living Area:
2437 Sqft.
|
4
Beds,
2
Baths
|
$3,100,000 |
145 50TH ST
Welcome to Mango Tango! This stunning 4-bedroom, 3.5-bath coastal retreat is perfectly positioned less than three blocks from the sugar-white sands and turquoise waters of the Gulf of Mexico. Currently operating as a high-performing vacation rental, this property offers the ultimate combination of i
Living Area:
2040 Sqft.
|
4
Beds,
4
Baths
|
$2,195,000 |
2908 GULF DRIVE
Anna Maria Island invites you to purchase your own piece of paradise right here! The property search stops with this beautifully renovated 3 bedroom, 2 bath luxury home. Walk into a lush private backyard with a new heated saltwater pool and spa perfect for entertaining! Unbeatable location between t
Living Area:
1350 Sqft.
|
3
Beds,
2
Baths
|
$1,499,000 |
3702 5TH AVENUE
Coastal Elegance Meets Modern Luxury Just Minutes from the Gulf. Discover the ultimate island living with this newer custom-built luxury beach home, just moments from the pristine shores of the Gulf. Designed for both style and functionality, this home features 4 spacious bedrooms, 4.5 bathrooms, pl
Living Area:
2784 Sqft.
|
4
Beds,
5
Baths
|
$3,395,000 |
300 N 22ND STREET
LIVE THE ISLAND LIFESTYLE IN THIS CHARMING 1940'S - COTTAGE , THIS 3-BEDROOM,1 BATH HOME ELEVATED ABOVE A 2 CAR GARAGE IS JUST STEPS AWAY FROM THE BEACH AND THE BAY, IDEALLY LOCATED IN THE HEART OF BRADENTON BEACH. WHETHER YOU AR LOOKING FOR A PERSONAL RETREAT OR A VACATION RENTAL,THIS PROPERTY ALLO
Living Area:
1030 Sqft.
|
3
Beds,
1
Bath
|
$900,000 |
2918 AVENUE E
One or more photo(s) has been virtually staged. This incredible home is built like a fortress. This architect designed concrete tri-level residence was constructed with artistry and represents a masterpiece of strength framed by a concrete girdle wrapped around solid pilings. Wake up to the scent of
Living Area:
2262 Sqft.
|
3
Beds,
2
Baths
|
$1,800,000 |
5608 HOLMES BOULEVARD
GREAT VACATION rental history with many repeat guests!!!! This charming home at the beach could be all yours. Nestled in the heart of Holmes Beach, where you can take a short stroll down Holmes Boulevard to city center where you will find adorable shops and restaurants where you can sit, sip, and d
Living Area:
1195 Sqft.
|
3
Beds,
2
Baths
|
$1,100,000 |
130 50TH STREET
Luxury Beach Retreat Just 2 Minutes from the Gulf! Welcome to Beach Breeze, a coastal oasis designed for pure relaxation and unforgettable memories. This beautifully appointed 6-bed, 4.5-bath home blends high-end luxury with the easy comfort of beachside living—perfect as a personal getaway or a s
Living Area:
2947 Sqft.
|
6
Beds,
5
Baths
|
$2,849,000 |
2408 AVENUE B
Come visit before it is too late, the seller is motivated. You should be able to close before Christmas and enjoy your island cottage home for this year's holidays and forever after...... Welcome to “Bungalow Breeze”. What you see is a fully permitted and totally renovated reincarnation of an ?
Living Area:
896 Sqft.
|
2
Beds,
2
Baths
|
$998,900 |
2300 AVENUE B
BRAND NEW ROOF AND HURRICANE IMPACT WINDOWS ALL THROUGHOUT!!
Imagine waking up to stunning views of the turquoise Gulf of America, with the soft white sand of Anna Maria Beach just 95 steps away. This extraordinary duplex offers a rare opportunity to own a piece of coastal paradise, with each side
Living Area:
2832 Sqft.
|
4
Beds,
5
Baths
|
$2,624,000 |
2203 AVENUE B
Welcome to Beach-Bliss! Only 2 blocks away from Gulf of Mexico Beaches! The perfect oasis nestled on the serene shores of Bradenton Beach,
this 5-bed, 4.5-bath home with a Rental Income that has undergone a full transformation, inside and out, offering the ultimate coastal living experience. Step o
Living Area:
2796 Sqft.
|
5
Beds,
5
Baths
|
$2,999,000 |
2516 AVENUE A
This exquisite waterfront home is perfectly situated just 3 blocks away from the island's seven miles of sandy beaches!! This luxury property features 8 spacious bedrooms, 8.5 bathrooms, and nautical-themed decor throughout. The home offers a private oversized heated pool and spa, a rooftop deck wit
Living Area:
4270 Sqft.
|
8
Beds,
9
Baths
|
$6,500,000 |
2210 AVENUE C A & B
Under Construction. GULF VIEWS FROM THE LARGE OPEN DECK. Under construction.. Each floor features 2 BEDROOMS/2 BATHS EACH plus a den or office. RESIDENCE IS APPX 1400 SF ON SINGLE FLOOR AND HAVE A LARGE OPEN DECK 10X28 (280SF) which is accessed from the MBR AND great room. The home was designed wit
Living Area:
2800 Sqft.
|
4
Beds,
4
Baths
|
$1,950,000 |