Location: Anna Maria
Do Not Show Listings
311 POINSETTIA RD, ANNA MARIA, FL 34216
$1,775,000398 Days on yellowkey MLS ID: TB8359176
Bed: 3 Bath: 2.0 Gar: 4 Liv Area Sq Ft: 1296 Built: 1988 Tax: $22,833 (2024)Community: Luana Isles 1St AddSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$22,833
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: Experience the ultimate coastal retreat at 311 Poinsettia Rd in Anna Maria, FL—a home where luxury meets laid-back island living. This beautifully renovated, elevated sanctuary boasts stunning waterfront views, a sparkling pool, and your very own private boat dock with a lift, inviting endless adventures on the water. Enjoy the convenience of RV/boat parking and a generous driveway that sets the stage for memorable gatherings. Just a leisurely stroll to pristine beaches and a quick golf cart ride to lively restaurants and bars, every moment here is infused with warmth, charm, and the promise of a vibrant lifestyle. Welcome home to your dream coastal haven. This property is currently used as a NIGHTLY rental bringing in up to $25,000/month so far this year. Please do not disturb the guests.
Listing is courtesy of: WEICHERT REALTORS EXCLUSIVE PROPERTIES (813-426-2669)
Listing Agent: Thomas Zopf, Ii (727-366-1983)
522 PINE AVE #7D, ANNA MARIA, FL 34216
$555,000285 Days on yellowkey MLS ID: A4657782
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 822 Built: 1973 Tax: $6,625 (2025)Community: BayouSpa: NoCondo
Taxes:$6,625
Tax Year: 2025
Remarks: “Sittin’ on the dock of the Bay…” Welcome to an effortless island retreat designed for relaxed second-home living on Anna Maria Island. This elevated 2-bedroom, 1-bath waterfront condo is being offered turnkey furnished and includes its own deeded boat slip, providing direct access to Tampa Bay and quick passage to open water. Set along a peaceful canal, the home invites you to slow down and unwind. Enjoy morning coffee or evening breezes from your private back patio as manatees glide by and seabirds fill the air. When you are ready to explore, you are perfectly positioned on iconic Pine Avenue, just steps from local shops, dining, and island favorites, with the historic City Pier nearing completion nearby. Inside, the condo offers a clean, comfortable layout with two generously sized bedrooms and a full bath. The space is move-in ready as is, while also offering future flexibility. Many owners in the Bayou Condo Complex have enhanced their units by opening the kitchen to the living area, adding interior laundry, or converting the walk-in closet into an additional bath, creating exciting options to personalize over time. This residence has been lovingly used as a second home and also allows twice-monthly rentals, offering optional income when you are away. The well-maintained Bayou Condo community recently completed new metal roofs in 2025 and features low condo fees, a designated parking space, and ample guest parking. Whether you envision weekend escapes, seasonal stays, or boating adventures right outside your door, this waterfront condo delivers the ultimate lock-and-leave island lifestyle. Schedule your private showing and discover how easy owning a second home on Anna Maria Island can be.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Kathy Harman (941-900-9828)
306 S BAY BLVD, ANNA MARIA, FL 34216
$3,295,00036 Days on yellowkey MLS ID: A4684377
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1752 Built: 1967 Tax: $34,126 (2024)Community: Wells Bay Harbor Sec ASingle Family
Taxes:$34,126
Remarks: Welcome to AMI Swedish Beach House, a beautiful 3-bedroom, 2-bath Bayfront home perfectly positioned on the tranquil shores of Tampa Bay on the renowned Island of Anna Maria. This charming single-story home offers breathtaking water views and the relaxed island lifestyle that makes this area so special. Step outside onto the spacious back patio overlooking some of the most beautiful waters in the world. The perfect spot to enjoy your morning coffee, watch boats glide by, watch the aqua life play or unwind in the evening with the coastal breeze and amazing view of the Sunshine Skyway all lit up. Outdoor living is effortless here with an outdoor shower, gas grill, and dining space for six, ideal for entertaining family and friends. Inside, the home comfortably accommodates guests with two bedrooms featuring king beds—one with sliding door access to the deck and a view to die for as you wake up—and a third bedroom with two full beds. The home is designed for comfort and convenience. With an amazing kitchen with no detail left untouched. A 10 foot island that seats 6+ so everyone can get involved with the chef cooking up the catch of the day. Located just a few blocks from the sugar-white sands and turquoise waters of Tampa Bay, this property offers the best of both worlds—peaceful Bayfront views and easy beach access. You’ll also love being within easy walking distance of Pine Avenue’s shops and restaurants, as well as the free island trolley that travels the entire 7-mile length of Anna Maria Island, making it simple to explore beaches, dining, and local attractions. This home has an unbeatable island location. Discover the charm, beauty, and laid-back luxury of Anna Maria Island living in this exceptional Bayfront getaway.
Listing is courtesy of: ANNA MARIA LIFE REAL ESTATE (941-567-6253)
Listing Agent: Billi Gartman (941-545-8877)
303 S BAY BLVD, ANNA MARIA, FL 34216
$4,795,00036 Days on yellowkey MLS ID: A4684390
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2657 Built: 2015 Tax: $62,179 (2024)Community: Wells Bay Harbor Sec ASpa: YesSingle Family
Taxes:$62,179
Remarks: ~~~ MUST SEE FLY THROUGH VIDEO ATTACHED ~~~ Experience elevated island living in Anna Maria's Best; this custom three-level, five-bedroom, three-and-a-half-bath AND 5 DECKS! This island home offers stunning views and exceptional indoor-outdoor living. Designed for both comfort and entertaining, the main living level features a spacious open-concept layout with a large living area, dining space for ten, and a gourmet kitchen highlighted by an impressive 10-foot island—perfect for gathering with family and friends. A large laundry room and convenient half bath are also located on this level. Professionally designed with color, comfort and perfection in mind. Just off the living room step outside to enjoy an expansive balcony a with full views of Tampa Bay and it's sparkling water. If you need your own balcony, there are more! Enjoy the cozy balcony overlooking the private pool, hot tub, and putting green, creating the ultimate outdoor retreat. The primary suite is located on the second floor, offering privacy along with a spacious en-suite bath. Wake up to the amazing view and step straight out to the balcony for breakfast and coffee. There are two additional bedrooms to provide ample accommodations for family and guests. Take a ride in the elevator, that starts in the garage and goes all the way to the top, up to the third level features two additional bedrooms, a full bath, and an inviting media room complete with an 80" TV, beverage cooler, and bar, making it the perfect space for relaxing or entertaining. Open up the large sliders while you watch the game and the let the ocean breeze create the vibe. With yet another large covered balcony for over flow or just chilling with a cocktail as you take in one of the MANY stunning sunsets of the year. If the pool is your scene, Anna Maria's Best has a large pool, hot tub and tons of seating so you can catch some rays, read a book in the shade or take on the team in on the putt putt green. When you return from the beach, you can rinse off in the fully enclosed outdoor shower. At the top, a rooftop deck delivers breathtaking 360-degree views of the island and spectacular vistas of Tampa Bay, providing an unforgettable place to watch sunrises, sunsets, and everything in between. Additional highlights include a 4+ car garage and a prime island location just minutes from shops, restaurants, piers, and a quick golf cart ride to the beautiful beaches of the Gulf of Mexico. This exceptional home offers the perfect blend of luxury, views, and island convenience. Come live your Anna Maria Life in Anna Maria's Best NOW!
120 MAPLE AVE, ANNA MARIA, FL 34216
$1,575,00070 Days on yellowkey MLS ID: A4680151
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1506 Built: 1973 Tax: $16,951 (2024)Community: Gulf View Sub Of Anna Maria KeySingle Family
Taxes:$16,951
Elementary School: None
High School: None
Middle School: None
Remarks: Prime Beachside Retreat – Steps to the Sand on Anna Maria Island! Discover coastal living at its finest in this beautifully remodeled and updated 3-bedroom, 2-bathroom single-family home, perfectly positioned west of Gulf Drive in the heart of Anna Maria. Just a short stroll (literally steps away) from the pristine, sugar sandy beaches of the Gulf of Mexico, this residence offers effortless access to turquoise waters, breathtaking sunsets, and the relaxed island vibe that makes Anna Maria a sought-after paradise. The home boasts modern upgrades throughout, including fresh finishes, an open and inviting floor plan, and thoughtful touches that blend comfort with contemporary style. The spacious layout is ideal for families, weekend getaways, or as a high-demand vacation rental investment. One of the standout features? Ample room to add your dream pool—imagine lazy days by your private oasis, just moments from the beach! West of Gulf Drive means no busy roads to cross for beach access, putting you in the most desirable pocket of the island. Enjoy peaceful mornings with the sound of waves, evening walks along the shore, and the charm of nearby Pine Avenue’s shops, restaurants, and cafes—all while owning a piece of true Anna Maria magic. Whether you’re seeking a primary residence, second home, or lucrative rental property, this beachside gem delivers the ultimate in Florida coastal sophistication and easy island living. Don’t miss your chance to own steps from the Gulf—schedule your private showing today!
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: James Wilson (727-331-4353)
57 N SHORE DR, ANNA MARIA, FL 34216
$1,890,000110 Days on yellowkey MLS ID: A4676196
1 Days Off yellowkey (back on 4/7/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1240 Built: 1980 Tax: $21,447 (2024)Community: The ArroyoSpa: YesSingle Family
Taxes:$21,447
Remarks: Under contract-accepting backup offers. 57 North Shore Drive: The Art of Island Living Discover the perfect balance of classic Anna Maria charm and contemporary coastal elegance. Tucked away at the corner of North Shore Drive and Palmetto Avenue, this serene retreat sits just two short blocks from the Gulf’s velvet sands. Here, the best of the island is at your doorstep—from the quiet beauty of the shore to the morning coffee spots and hidden gems along Pine Avenue. Thoughtfully Reimagined Freshly renovated with a keen eye for detail, this home is a turnkey sanctuary designed for modern peace of mind. Every inch has been updated to marry style with resilience, featuring: A Bright, Airy Kitchen: The heart of the home, featuring brand-new finishes and high-end stainless steel appliances. Seamless Upgrades: New hurricane-impact windows and a Garrison Aluminum flood protection system ensure your piece of paradise is as secure as it is beautiful. Modern Essentials: From the new HVAC and LED lighting to the redesigned bathrooms, every system has been refreshed for effortless living. Your Private Tropical Escape The outdoor space is a true island oasis, set on an oversized, lushly landscaped lot. Spend your afternoons lounging by the custom saltwater lap pool or unwinding in the spa, all framed by swaying palms and tropical greenery. The screened lanai serves as a shaded sanctuary, perfect for hosting casual sunset dinners or simply listening to the breeze after a day in the surf. Sun-Soaked & Effortless Inside, the single-level layout flows with natural light, capturing that coveted "barefoot luxury" feel. The Living Quarters: Three comfortable bedrooms and three bathrooms are complemented by fresh, coastal-inspired décor. The Bonus Space: An air-conditioned garage provides a versatile extra layer of living, complete with a full bath and laundry area. Ready for You: Sold with its new, meticulously chosen furnishings, the home invites you to move right in and start living the island dream from day one. A Premier Opportunity Whether you envision a permanent change of pace, a family getaway, or a sophisticated investment, 57 N Shore Drive delivers. Currently a successful vacation rental, this property offers the rare chance to own a piece of Anna Maria’s most sought-after lifestyle—where every day feels like a Saturday. * Note: Property Information received from third-party sources is considered reliable but not guaranteed. All information should be independently verified by buyers and buyers agent.
Listing is courtesy of: SALTY MERMAID REAL ESTATE LLC (941-224-3304)
Listing Agent: Liz Blandford (941-224-3304)
108 PELICAN DR, ANNA MARIA, FL 34216
$2,295,00053 Days on yellowkey MLS ID: A4680808
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1472 Built: 1994 Tax: $10,106 (2024)Community: Luana IslesSingle Family
Taxes:$10,106
Remarks: Located on the north end of Anna Maria, this elevated canal-front home is a true boater’s paradise with direct water access and a private dock. This 4-bedroom property underwent an extensive interior remodel, showcasing modern upgrades and coastal living at its finest. The open-concept layout is filled with natural light and offers comfortable living spaces ideal for both everyday living and vacation enjoyment. Step outside to an expansive back deck overlooking the peaceful canal — the perfect setting for relaxing or entertaining. Outdoors, a new pool and refreshed entertaining area further enhance the Florida lifestyle. Ideally situated near beaches, dining, and shopping, this home captures the very best of Anna Maria Island waterfront living and is perfectly suited as a full-time residence or a short-term rental investment.
Listing Agent: Jessica Batten (941-962-3380)
866 N SHORE DR, ANNA MARIA, FL 34216
$1,949,00059 Days on yellowkey MLS ID: A4680714
REDUCED by $50,000 (2.5%) on 03/31/2026
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 1904 Built: 1951 Tax: $16,227 (2024)Community: Shore Acres ResubdividedSpa: YesSingle Family
Taxes:$16,227
Remarks: Don't miss your chance to own a fully remodeled home in the City of Anna Maria. Extensively remodeled 4-bedroom, 4-bath home on North Shore Drive in the City of Anna Maria, featuring significant structural and finish upgrades throughout. This light-filled residence offers an open-concept layout with raised ceilings, refined coastal finishes, and expanded living space. Two bedrooms feature private en-suite bathrooms, with an additional two full guest bath conveniently accessible from the bedrooms and main living areas. Renovations include enclosed patio and garage areas to create an additional en-suite bedroom, expanded kitchen, dedicated laundry room, and approximately 294 square feet of added living space. Major improvements include new electrical and plumbing services; new drywall with DensGlass moisture-resistant panel; a new HVAC system with supplemental mini-split units; spray foam roof insulation; hurricane-impact windows and sliders; and new flooring throughout. The kitchen features all-new cabinetry, countertops, a large center island with breakfast bar, and Samsung appliances including: refrigerator, ice maker, wine cooler, microwave, dishwasher, and chilling drawers. Bathrooms have been fully updated with new tile and high-end plumbing fixtures. Outdoor upgrades include a private heated pool with new heater and pump, expanded paver decking, new fencing, updated landscaping, refreshed exterior stucco, and full interior and exterior paint. Ideally located just steps from the beach and close to Pine Avenue shops and dining, this is a move-in-ready island home offering modern upgrades, thoughtful design, and an unbeatable location—schedule your private showing and experience Anna Maria Island living at its best.
107 ELM AVE, ANNA MARIA, FL 34216
$5,145,000643 Days on yellowkey MLS ID: A4615677
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2432 Built: 2012 Tax: $56,527 (2023)Community: Anna Maria Beach Sub First AddSpa: NoSingle Family
Taxes:$56,527
Tax Year: 2023
Remarks: Beachfront Oasis is elegant European design luxury home that has been professionally decorated and has spectacular beach views from every room. Floor to ceiling glass allows full views of the beach and aqua tropical gulf waters. The clean lines of the homes upscale design allow you to just sit back, relax and enjoy the stunning open beach view on any of the four beachfront decks. Indulge in the home’s high-end finishes from the moment you walk in the door including a private elevator to all floors. Once you’re on the main level you’re welcomed by breathtaking views, the high-end kitchen and open concept living and dining areas that are perfect for entertaining. The high-end kitchen offers stainless steel appliances, induction stove top and built-in oven. The kitchen island provides the perfect spot for entertaining as you prepare a gourmet meal or simple treats. On the top level there are two separate master suites, both with king beds, their own private baths and private beach front balconies. On the main level, off the living room, is another bedroom with a queen bed and another private balcony. The outdoor area features a private pool and beach area with outdoor lounge chairs plus a table and chairs to enjoy poolside refreshments. Beachfront Oasis is ideally located on the quiet north-end of Anna Maria Island. It is one block from the charming Pine Ave shops, restaurants and attractions. On the bayside of Pine Ave is the Anna Maria City Pier and Waterfront Restaurant.
Listing is courtesy of: ANNA MARIA ISLAND BEACHES RE (941-567-5234)
Listing Agent: Gregg Bayer (941-799-9096)
527 MAGNOLIA AVE, ANNA MARIA, FL 34216
$2,095,000414 Days on yellowkey MLS ID: A4640924
REDUCED by $100,000 (4.6%) on 04/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1924 Built: 1994 Tax: $23,200 (2024)Community: Lardas Unit ThreeSingle Family
Taxes:$23,200
Remarks: Tucked away along a tranquil canal in the heart of Anna Maria, this exceptional 3-bedroom, 2-bathroom waterfront retreat offers the perfect blend of coastal elegance and island convenience. Being sold turnkey with a strong rental history and bookings in place, this property is an ideal investment opportunity or full-time residence. Designed for effortless indoor-outdoor living, the spacious 1,900+ square foot interior features an open-concept layout, a fully equipped kitchen, and inviting living spaces filled with natural light. The primary suite provides a private escape with an ensuite bath, while the additional bedrooms offer plenty of space for family and guests. Step outside to your personal oasis, where a heated pool overlooks the tranquil canal, and a private dock provides easy access to Tampa Bay and the Gulf—perfect for boaters and water enthusiasts alike. A two-car garage offers ample storage for beach gear and golf carts, while the property’s zoning allows for rentals of any duration, maximizing its income potential. Just moments from white sandy beaches, Pine Avenue’s charming boutiques, and renowned dining, this is a wonderful opportunity to own a perfect little slice of island life!
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Darcie Duncan (941-779-0304)
313 MAGNOLIA AVE, ANNA MARIA, FL 34216
$1,575,000397 Days on yellowkey MLS ID: A4643248
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1424 Built: 1985 Tax: $19,130 (2024)Community: Bimini Bay Colony ClubSpa: NoSingle Family
Taxes:$19,130
Remarks: Welcome to your dream getaway on Anna Maria Island! THIS HOME HAS A BRAND NEW ROOF! Nestled in a prime location midway between the enchanting Tampa Bay and the pristine Gulf of Mexico waters, this meticulously maintained home offers the perfect blend of convenience and relaxation. Unbeatable location that allows you to stroll effortlessly to Anna Maria's hotspots, from Ginny's to the iconic Sandbar, Two Scoops, the charming Donut Shop, and a plethora of other shops and restaurants. The local trolley system, easily accessible, lets you explore the entire seven-mile-long island with ease. This thoughtfully designed home boasts three bedrooms for guests, two well-appointed bathrooms, and a spacious open living, dining, and kitchen area with a cathedral ceiling. The kitchen is a chef's delight, featuring updated cabinets and granite countertops and a center island with breakfast bar. An indoor laundry room adds valuable convenience, a highly desirable feature for both guest and owners. After a day of sun-soaked adventures, return to your private tropical oasis and indulge in a refreshing dip in the generously sized heated pool and spa. The sprawling backyard provides the ideal setting for relaxation and unwinding. Offered turnkey furnished, this home is not only a delightful retreat but also a savvy investment opportunity. With a proven track record of income generation and repeat bookings in place, it's a seamless transition into the vibrant vacation rental market. The location offers exceptional accessibility, with easy drives to Tampa, Sarasota and multiple airports, making travel convenient for both weekend visitors and longer stays. Nearby shopping, dining and entertainment options further enhance the appeal. Pack your bathing suits and immerse yourself in the laid-back luxury of Anna Maria Island – your slice of paradise awaits!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Christy Travis (941-545-5284)
727 JACARANDA RD, ANNA MARIA, FL 34216
$2,150,00010 Days on yellowkey MLS ID: A4688612
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2055 Built: 1980 Tax: $27,869 (2025)Community: Shore AcresSingle Family
Taxes:$27,869
Remarks: Incredible, spacious home with a private heated pool - close to the beach!! This 3 bedroom, 2.5 bathroom elevated home is located in a desirable area of Anna Maria Island, you're only a one-and-a-half-block walk from Bean Point Beach to the north and a short distance to Pine Avenue's shops and restaurants to the south. Colorful, fun lighting and art throughout gives it that beachy feel. Enjoy so many great features like high wooden ceilings, large windows, natural light, and a wrap-around screened balcony. The balcony overlooks the private heated pool and outdoor dining area below. Inside, use the kitchen's stainless steel appliances and granite countertops to whip up a delicious meal. Schedule a showing today!
Listing Agent: Jason Sato (941-778-7200)
209 WILLOW AVE, ANNA MARIA, FL 34216
$6,795,00012 Days on yellowkey MLS ID: A4688392
Bed: 6 Bath: 7.0 Gar: 3 Liv Area Sq Ft: 4154 Built: 2021 Tax: $69,298 (2025)Community: Bimini Bay EstatesSingle Family
Taxes:$69,298
Remarks: Discover coastal luxury at 209 Willow in the heart of Anna Maria Island on a very sought out quiet street. This stunning canal-front home offers the perfect blend of relaxed island living and high-end amenities, just 10 houses from the pristine sugar-sand beaches of the Gulf while situated on a canal, you get the best of both worlds! Step inside to this 6 bedroom, 6 bathroom, 2 half bath, thoughtfully designed home. This home has never been a rental, it is very well taken care of. The interior has just about every feature you can think of, natural light, soaring ceiling, impact slider doors/windows, wet bar, very large wine cooler, whole house generator for peace of mind, a water filtration system/softener, and a pressure booster. Each bedroom is spacious and has its own private en-suite bathroom ensuring your family and guests have their own privacy. Current owners are using the 6th bedroom as an office, or you can turn it into a bedroom. Kids will love the fun built-in bunk bed room, while still plenty of space to play too. If desired, an upstairs closet has washer/dryer hookups if you wanted an additional set on upper level. Relax on the rooftop deck with breathtaking views or unwind on the lower deck complete with comfortable loungers. The highlight is the resort-style backyard: a heated pool and spa with a beautiful Shellcrete bar accented by shimmering sea glass. Includes a refrigerator and grill. A screened-in covered downstairs area provides shaded comfort, while boaters will appreciate the private dock and lift right on the canal—perfect for quick access to the Intracoastal and Gulf waters. The epoxy-finished 3-car garage adds durability and style to your storage space. Big outdoor shower so you can rinse off after the sandy beach. Located on a quiet canal yet incredibly convenient, this home sits in one of Anna Maria’s most desirable spots. Enjoy easy access to world-class beaches, charming island dining, and everything the Florida Gulf Coast has to offer. Whether you’re seeking a primary residence, a vacation retreat, or an exceptional investment property, 209 Willow Avenue delivers island elegance with every modern comfort.
411 ALAMANDA RD, ANNA MARIA, FL 34216
$1,900,000287 Days on yellowkey MLS ID: A4656727
4 Days Off yellowkey (back on 2/25/2026)
Bed: 8 Bath: 0.0 Liv Area Sq Ft: 2880 Built: 1972 Tax: $23,445 (2024)Community: Shore Acres Fourth AddApartment
Taxes:$23,445
Remarks: Under contract-accepting backup offers. Incredible opportunity on the North end of Anna Maria Island. Located in the heart of the city of Anna Maria. Short walks to the Gulf or Bay beaches and all of the lovely attractions on Pine Avenue. Currently on the massive, lots 3&4, 11,500 square foot lot sits two duplex units. A total of FOUR short term 2 bed 1 bath units in Anna Maria!!! Units are ready for your vision, just waiting to become instagram famous. Units like this are few and far between on the North end. 3 of 4 units are equipped with washer/dryer hookups. If having the most famous duplex in Anna Maria is not your thing, then there is potential to build two single family homes on lots 3&4 or an enormous single family home. The gentlemen who acquired this property more than a half century ago had a dream for his family, now it's your turn.
Listing Agent: Justin Powell (941-718-0294)
889 N SHORE DR, ANNA MARIA, FL 34216
$4,500,00012 Days on yellowkey MLS ID: A4688600
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2025 Built: 1998 Tax: $39,176 (2025)Community: Shore AcresSingle Family
Taxes:$39,176
Remarks: This Bayfront home is calling your name! Perfectly positioned directly on the bay, this 3-bedroom, 2.5-bathroom residence offers breathtaking water views from almost every window, inviting the serene beauty of Tampa Bay inside. Step into an open, light-filled layout designed for relaxation and entertaining. The spacious interiors flow effortlessly, with generous living areas that frame panoramic bay vistas. Multiple balconies provide the ideal spots to savor morning coffee, sunrise, or the gentle bay breeze while watching dolphins play and boats glide by. Long, private driveway and attached garage offering ample parking for family and guests. Whether you’re hosting a weekend getaway or enjoying everyday island life, there’s plenty of room for boats, cars, and more. Just minutes from Anna Maria’s world-famous white-sand beaches, Pine Avenue’s charming shops and restaurants, this home combines privacy and convenience in one of the island’s most desirable north-end locations. Experience true Florida waterfront living—where every day feels like a vacation. Don’t miss this rare opportunity to own a slice of paradise on Anna Maria Island!
406 N SHORE DR, ANNA MARIA, FL 34216
$5,450,00014 Days on yellowkey MLS ID: A4688020
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 2999 Built: 2026 Tax: $7,499 (2025)Community: 406 North Shore DriveSingle Family
Taxes:$7,499
Remarks: Under Construction. Luxury residence coming soon in the heart of Anna Maria! This 4 bedroom, 4.5 bathroom + den home is just a short stroll to the sparkling Gulf waters and situated on a lagoon. The main floor has high ceilings and natural light with an open concept living area. With multiple spacious balconies and a rooftop deck, you have many choices to relax, dine and enjoy the outdoors. The views from the rooftop deck are stunning! The kitchen, a chef’s dream with high-end appliances. Additional features include custom cabinetry, quartz counters, elevator that goes to all levels, impact windows and doors and so much more. 3 car garage for plenty of parking space and beach toys. The backyard oasis has living and dining areas, heated pool and spa, perfect for entertaining. It's perfect for year-round living, an island getaway or vacation rental as 1-7 day rentals are permitted. Located on the North End of Anna Maria Island, you are just a short walk to all the boutiques and dining on and off Pine Avenue.
165 CRESCENT DR, ANNA MARIA, FL 34216
$1,695,00013 Days on yellowkey MLS ID: A4688325
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1403 Built: 1961 Tax: $20,366 (2025)Community: Lake La VistaSingle Family
Taxes:$20,366
Remarks: Charming coastal retreat located at 165 Crescent Dr in the heart of Anna Maria! This beautifully maintained 3-bedroom, 2-bath home offers the perfect blend of comfort and island living. Featuring a private pool and spa, this property is ideal for relaxing or entertaining guests. The outdoor space is a true highlight, complete with a built-in grill and outdoor shower—perfect after a day at the beach. Currently operating as a successful vacation rental, this home presents an excellent investment opportunity or a personal getaway. Inside, the home offers a bright and inviting layout with plenty of natural light and a functional floor plan. Whether you're looking for a turnkey rental property or your own slice of paradise, this home delivers. Just a short distance to the beach, local shops, and dining, this property captures the essence of Anna Maria Island living. Don’t miss this opportunity to own a piece of paradise!
Listing is courtesy of: ISLAND REAL ESTATE-ANNA MARIA (941-778-6066)
Listing Agent: Ryan Sheck (863-581-4005)
110 OAK AVE #A, ANNA MARIA, FL 34216
$874,00087 Days on yellowkey MLS ID: A4678588
REDUCED by $25,000 (2.8%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 640 Built: 1947Monthly Fee: $1 Tax: $11,258 (2025)Community: Anna Maria Beach CottagesCondo
Taxes:$11,258
Remarks: Old Florida Charm – Income-Producing Property! Looking for a true Old Florida beach cottage experience with exceptional rental income? This elevated cottage on Anna Maria’s sought-after North End is just steps from the Gulf—no car needed! This fully managed, hands-off rental allows nightly stays, with all future bookings conveying for seamless income. This turnkey-furnished home blends coastal charm with modern updates, featuring a newer kitchen with Quartz counters, custom cabinetry, and new appliances, flooring and a spacious private deck. The primary suite offers a walk-in closet and updated ensuite bath, while the second bath includes double sinks and a jacuzzi tub. Located in a boutique resort with a private pool, picnic areas, and complimentary bikes, beach gear, and water toys, guests return year after year. Walk to Pine Ave’s shops or hop on the free trolley to explore the island. With pet-friendly ownership and a 6-month owner occupancy option, this turnkey investment is perfect for personal getaways and immediate passive income. Don’t miss this rare opportunity—schedule your showing today! Please note- the HOA Adjusts based on monthly income.
222 WILLOW AVE, ANNA MARIA, FL 34216
$4,800,000350 Days on yellowkey MLS ID: A4649861
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3265 Built: 2018 Tax: $50,928 (2024)Community: MarquisSingle Family
Taxes:$50,928
Remarks: Welcome to SeaLuxe, where luxury meets the beach! Located on one of the most desirable streets on Anna Maria Island. SeaLuxe is a home thats perfectly positioned to put you just a short walk away from a world-renowned beach or to Pine Ave where you can find locally owned shops and restaurants. This coastal retreat features 3,265 sqft of indoor living space, 4-bedrooms all with ensuite bathrooms, and 2 powder baths. Once inside, you are welcomed by an open concept living space bathed in natural light, featuring high ceilings and a seamless flow between spaces. The gourmet kitchen is a chef’s dream with form and function, equipped with premium stainless-steel appliances, walk in pantry, quartz countertops, solid wood cabinetry, and a large island with seating. The spacious primary bedroom offers a serene retreat with a luxurious ensuite bath featuring a soaking tub, walk-in shower, and a generous walk-in closet. Take the elevator to the top floor where you will find an inviting movie room equipped with a wet bar and beverage fridge, a powder bath, and one of the four bedrooms. On the ground level of this luxurious property, you have an area that is designed for ultimate relaxation and entertainment, featuring a stylish entertainment room with a pool table for indoor fun. Step outside to a resort-style outdoor space complete with a gorgeous pool, spa, and sun shelf, all surrounded by lush landscaping and a beautifully turfed area. An expansive covered patio offers the perfect setting for al fresco dining and grilling, making it easy to unwind or entertain in true island style. SeaLuxe perfectly blends sophisticated coastal design with exceptional comfort, offering not just a luxurious escape but a highly successful, turnkey vacation rental investment with future reservations in place. Schedule your private showing today and see why so many guests fall in love with this home!
Listing Agent: Joey Hutchinson (941-518-5585)
9403 GULF DR, ANNA MARIA, FL 34216
$8,000,000433 Days on yellowkey MLS ID: A4633389
Bed: 9 Bath: 8.5 Gar: 2 Liv Area Sq Ft: 3983 Built: 2020 Tax: $49,941 (2024)Community: 7044700; Bimini Bay Estates; Lot 61; Pb 8/75Single Family
Taxes:$49,941
Remarks: This stunning 9-bedroom, 8.5-bathroom beachfront property offers 3,983 sq ft of heated interior space and comes FULLY FURNISHED with luxurious details throughout. The home boasts an open-concept layout with vibrant living areas, a well-appointed chef’s kitchen, and multiple decks for enjoying ocean views. This home completed in 2020, has a custom private pool with a lazy river-inspired style, a putting green, and a rooftop deck offering 360 water views. Each of the 7 king-sized bedrooms features chic designs, ensuite baths, with many including private balconies. The primary suite includes a large tub, step-in shower, and a private ocean-view balcony. Additional amenities include a convenient elevator, laundry room, and a bar area with a wine fridge. The property’s modern coastal elegance blends perfectly with functional design, creating a space ideal for everyday living or hosting guests- GREAT RENTAL OPPORTUNITY. Located on Anna Maria Island, this home offers beach access and endless opportunities to enjoy the sun and sand. Experience the ultimate blend of luxury and comfort in this meticulously designed coastal haven.
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