Location: Anna Maria
Do Not Show Listings
727 JACARANDA RD, ANNA MARIA, FL 34216
$2,150,00038 Days on yellowkey MLS ID: A4688612
2 Days Off yellowkey (back on 5/8/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2055 Built: 1980 Tax: $27,869 (2025)Community: Shore AcresSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$27,869
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
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 is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Jason Sato (941-778-7200)
270 GLADIOLUS ST, ANNA MARIA, FL 34216
$1,770,00088 Days on yellowkey MLS ID: A4682093
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1326 Built: 1967 Tax: $20,985 (2025)Community: Luana IslesSpa: YesSingle Family
Taxes:$20,985
Remarks: Located just blocks from the beach, White Palms is a 3-bedroom, 2-bathroom island home situated on a large corner lot with a spacious backyard, offering excellent outdoor living close to the Gulf. The corner location provides added openness, while mature palms and established landscaping create a private coastal setting. The home features a bright, open layout designed for comfortable island living, with well-sized bedrooms and recently updated finishes throughout. The main living areas connect seamlessly to the outdoor spaces, making it ideal for both everyday living and entertaining. The backyard centers around a private pool, creating a true outdoor retreat with ample space for lounging and gathering. Whether used as a primary residence, second home, or seasonal escape, the layout offers flexibility and function. Located in Anna Maria's nightly vacation rental area, White Palms is an established rental property with documented income, offering immediate investment potential alongside its lifestyle appeal. Just a short walk to the sand, this property combines beach proximity, outdoor space, and proven rental performance in one well-located island home.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Dee Munn (407-346-4422)
212 OAK AVE, ANNA MARIA, FL 34216
$3,950,000292 Days on yellowkey MLS ID: A4659522
Bed: 5 Bath: 5.0 Liv Area Sq Ft: 3844 Built: 1979 Tax: $34,591 (2024)Community: Bimini Bay EstatesSpa: YesSingle Family
Taxes:$34,591
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: STUNNING RENOVATED 5 BEDROOM POOL HOME ON A DEEP WATER CANAL ONLY STEPS FROM THE BEACH!!! Nestled on the highly coveted north end of Anna Maria Island, this beautifully renovated and turnkey furnished 5-bedroom, 5-bathroom home spans 3,844 sq. ft. of luxurious living space. Perfectly situated on a deep-water canal with direct Gulf of Mexico access, this home is a dream for boating enthusiasts while also being just moments from the island’s pristine beaches. Upon entering, you’ll be greeted by a flood of natural light, creating a bright and airy atmosphere that welcomes you into this thoughtfully designed home. The living room offers ample seating and flows seamlessly into the adjacent dining room, where elegance meets functionality. With light flooring and coastal tones throughout, the home exudes a relaxed yet sophisticated vibe. The dining room opens easily to the kitchen and outdoor pool area, making it an ideal space for entertaining. The gourmet kitchen is a chef's delight, featuring quartz countertops, custom cabinetry, stainless steel appliances, and a cozy breakfast bar. From the living room, large sliding glass doors provide effortless access to the pool, creating a perfect blend of indoor and outdoor living. The first floor hosts three spacious bedrooms, each with excellent closet space, and three beautifully updated bathrooms, all exuding modern elegance. The expansive game room and laundry area combine fun and practicality, equipped with two washers and dryers, a second refrigerator, ample cabinetry, and a ping-pong table. Whether you’re hosting family or friends, this well-designed layout provides comfort for all. Upstairs you will find an additional two bedrooms and two bathrooms with an outdoor deck overlooking the canal. Renovated in 2023 and 2025, this home boasts an array of high-end upgrades including new appliances, new flooring, remodeled bathrooms, new lighting and fans, an outdoor kitchen, a new electric fireplace, freshly painted interiors and exteriors, new patio sliders, new putting green, a new front entrance door, and updated back doors. Step outside into the breathtaking backyard, and you'll instantly be transported to your own private tropical retreat. The heated salt water pool and spa invite relaxation, while the outdoor kitchen, covered cabana with a dining area, tiki hut, and hammock offer multiple options for entertaining or unwinding. The putting green and dock complete this outdoor haven, where you can fish, relax, or simply enjoy the island lifestyle. Deep water canal with no bridges to the Bay, ICW and Gulf of Mexico. This home is an exceptional investment opportunity, benefiting from a transferable BERT HARRIS ACT RIGHT, ALLOWING SHORT-TERM RENTALS FOR UP TO 12 GUEST--a rare and valuable advantage. With a proven rental history, this property appeals equally to investors and those seeking a tranquil personal retreat. Every detail has been meticulously curated to create the perfect island home. Ideally located, this home is just a short stroll to the Anna Maria City Pier and the charming shops and restaurants along Pine Avenue. Whether you're looking for the ultimate vacation getaway or an income-generating property, this is truly a slice of paradise on Anna Maria Island.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Christy Travis (941-545-5284)
513 N BAY BLVD, ANNA MARIA, FL 34216
$4,495,0008 Days on yellowkey MLS ID: A4691979
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2602 Built: 2026 Tax: $9,574 (2025)Community: Shore AcresSpa: YesSingle Family
Taxes:$9,574
Remarks: Welcome to The Beachwood! Discover coastal elegance in this brand-new constructed home with elevator on the coveted North End of Anna Maria Island. This exceptional 4-bedroom, 4-bathroom home offers the ultimate island lifestyle with contemporary elegance and breathtaking views. Boasting a private heated saltwater pool & spa surrounded by tropical palms, multiple spacious balconies, and a ooftop deck with spectacular views of the Gulf, this home is designed for effortless entertaining and unforgettable sunsets. Inside you will find a spacious open living area with a chef’s kitchen including high end Thermador appliances, bar with a wine and beverage fridge, and cozy fireplace to relax. Tastefully furnished and decorated with calming colors and natural materials, this open design also allows for plenty of natural light and inviting views of the mature tropical landscape. Enjoy the beauty of the custom wood features in the home like the live edge teak mantel, and the upstairs coffee and beverage bar cut out of Brazilian hardwood. You can read and study in the privacy of the office with built-in bookshelves or relax outside the office on the balcony. Either side of the home features custom IPE wood and metal gated fences for luxuriousness and ultimate privacy. There’s a large two-car garage with plenty of storage space. The home is secured with impact and hurricane sliders and windows. Perfectly situated between the beautiful beaches of Bean Point and Pine Avenue, you’re just steps away from serene bayfront beaches, restaurants, boutique shopping, and waterfront recreation. Whether you’re relaxing in the spa after a day at the beach or hosting friends on the rooftop with panoramic vistas of Tampa Bay and the Skyway Bridge, every detail invites you to unwind in paradise. Schedule your private showing today!
306 S BAY BLVD, ANNA MARIA, FL 34216
$3,295,00064 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)
115 LOS CEDROS DR, ANNA MARIA, FL 34216
$2,290,000145 Days on yellowkey MLS ID: A4675725
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2203 Built: 1957 Tax: $25,977 (2025)Community: Island CedarsSpa: YesSingle Family
Taxes:$25,977
Remarks: Located on the highly sought-after North End of Anna Maria Island, 115 Los Cedros—known as Oceans Blue—offers an exceptional location just steps from the Gulf beaches and the shops and dining of Pine Avenue. Set on a 10,000 square foot lot, this single-story Anna Maria Island beach house combines luxury, comfort, and peace of mind. The residence currently offers four bedrooms, with the flexibility for a possible fifth bedroom, along with 3.5 baths, including two ensuite bedrooms and an additional half bathroom that is ideal for guests. An additional 706 square feet of added living space creates a spacious and functional layout well suited for a primary residence, vacation home, or investment property. The light-filled interior showcases vaulted ceilings, terrazzo floors, and an open-concept design that flows seamlessly to the outdoor living areas. The updated kitchen features new shaker-style cabinetry, quartz countertops, custom tile backsplash, and stainless steel appliances, ideal for entertaining after a day at the beach. Expansive sliding doors open to a private outdoor oasis with a resort-style saltwater pool, swim-up sun shelf, and heated spa, surrounded by lush tropical landscaping and professional lighting. Enjoy peaceful mornings and sunset evenings from your private deck overlooking Lake Marsha, offering a rare waterfront setting for kayaking, fishing, or relaxing. This meticulously upgraded Anna Maria Island beach house includes a new metal roof, hurricane impact-rated windows, sliders, and exterior door, and fully renovated bathrooms with custom tile, glass shower enclosures, and Kohler fixtures. The home is fully flood-protected with a hammerhead flood barrier system on all sliders, exterior door and windows, providing added security and confidence for coastal living. Whether used as a primary residence, vacation home, or investment property, Oceans Blue at 115 Los Cedros offers a rare combination of location, 10,000 square foot lot size, flexible bedroom configuration, added square footage, luxury upgrades, and comprehensive flood protection—just moments from the beach and the vibrant energy of Pine Avenue on Anna Maria Island. ** Property information received from third-party sources is considered reliable but is not guaranteed. All information should be independently verified by buyers and buyer's agent.
Listing is courtesy of: SALTY MERMAID REAL ESTATE LLC (941-224-3304)
Listing Agent: Liz Blandford (941-224-3304)
103 SUNSET LN, ANNA MARIA, FL 34216
$2,395,000185 Days on yellowkey MLS ID: A4669996
REDUCED by $300,000 (11.1%) on 05/01/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2800 Built: 1998Monthly Fee: $50 Tax: $11,476 (2024)Community: Sunset CoveSingle Family
Taxes:$11,476
Remarks: A premier setting defines this offering. Tucked at the end of a quiet cul-de-sac in Sunset Cove—a rare enclave that prohibits weekly rentals—this elevated beach residence presents an exceptional retreat for tranquil island living. Become part of a true neighborhood community, whether in full-time residence or seasonal escape, with breathtaking Gulf vistas just a stone’s throw from the sugar-white sands of Anna Maria Island and dedicated beach access moments away. Designed by acclaimed architect H. Patterson Fletcher, this distinctive home embodies Frank Lloyd Wright–inspired principles, celebrating harmony with nature, fluid open spaces, and an abundance of natural light. Custom-built and solidly constructed, it occupies an expansive walled lot mere steps from the shoreline—offering the rare canvas to envision a private pool and bespoke outdoor sanctuary. Spanning three thoughtfully appointed levels, the 3-bedroom, 2.5-bath residence with bonus room welcomes guests through a gracious foyer, with an oversized garage below providing exceptional storage. Within, vaulted ceilings and an expansive wall of sliding glass doors bathe the living room in soft, filtered light while framing serene views of swaying palms and shimmering Gulf waters. Off the living area sliders open to a generous elevated screened lanai—an inviting setting for languid afternoons, twilight gatherings, and al fresco dining. The open-concept kitchen and living area flow together effortlessly, anchored by new appliances, a polished granite island, custom solid-wood cabinetry, and a double sized skylight that draws the sky inside. The primary suite offers a private balcony beyond its own wall of sliders, complemented by a spacious en suite bath and dual walk-in closets. The upper level is a study in versatility—an adaptable retreat featuring two distinct sleeping areas and a full bath, accommodating visiting family and friends with comfort and privacy. When not hosting, the space transforms effortlessly into a den, library, home office, or creative studio. Wraparound windows and a rooftop deck reveal sweeping water and treetop panoramas—an ideal vantage for sunrise coffee, golden-hour cocktails, and starlit evenings. While poised for cosmetic refinement, this residence's architectural provenance, enduring construction, generous grounds, and incomparable location make it an extraordinary canvas for a true luxury beach retreat.
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Darcie Duncan (941-779-0304)
313 HAMMOCK CIR, ANNA MARIA, FL 34216
$3,995,00083 Days on yellowkey MLS ID: A4682229
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3755 Built: 2017 Tax: $42,872 (2025)Community: Coconut BayouSpa: YesSingle Family
Taxes:$42,872
Remarks: This waterfront coastal retreat embodies refined island luxury, offered completely turnkey and thoughtfully designed for both elevated living and exceptional entertaining. Positioned on a quiet cul-de-sac the home makes an immediate impression with its stately architecture, paver driveway, lush tropical landscaping, and landscape lighting that beautifully illuminates the property at dusk. Inside, travertine flooring flows throughout, complemented by crown molding in every room and tray ceilings that add architectural depth and sophistication across all three levels. The top floor serves as the heart of the home, where an expansive living and dining area is framed by large sliders that capture vibrant sunset skies and lead to two generous balconies, seamlessly blending indoor and outdoor living. The chef’s kitchen is a showpiece, appointed with premium Monogram appliances, a professional gas range with pot filler, custom cabinetry, striking backsplash detail, and abundant counter space designed for effortless entertaining. The living room offers an abundance of natural light that frames a beautiful fireplace adding an elevated ambiance. Designer lighting, custom stair railings, and carefully curated finishes create a cohesive coastal elegance that feels both polished and welcoming. The mid-level hosts 4 spacious bedrooms enhanced with shiplap accent walls in select rooms, adding warmth and texture, along with a comfortable family room that opens to an oversized balcony overlooking the tranquil bayou. A private elevator provides convenient access to every floor, while modern enhancements including a security system, Sonos sound system inside and out, solar panels, and a tankless hot water heater deliver efficiency and peace of mind. Outdoors, the property transforms into a true waterfront oasis featuring a sparkling heated pool and spa, fire features, expansive paver deck, screened-in patio lounge area, and multiple covered spaces ideal for year round enjoyment. The private dock is equipped with electric and water, offering boating access and completing the ultimate Florida lifestyle experience. The pass-through two car garage, paired with separate storage rooms is designed to accommodate lifestyle amenities and the home’s location within a short-term rental zone presents outstanding investment potential. From sunrise coffee on the balcony to sunset reflections dancing across the bayou, every detail of this exceptional residence has been thoughtfully designed to capture the very best of coastal living.
411 ALAMANDA RD, ANNA MARIA, FL 34216
$1,900,000315 Days on yellowkey MLS ID: A4656727
1 Days Off yellowkey (back on 5/5/2026)
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)
215 SYCAMORE AVE, ANNA MARIA, FL 34216
$5,895,00022 Days on yellowkey MLS ID: A4689780
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3250 Built: 2026 Tax: $14,220 (2025)Community: Anna Maria BeachSpa: YesSingle Family
Taxes:$14,220
Remarks: Welcome to a rare offering on the coveted north end of Anna Maria Island — a brand-new coastal sanctuary where architectural sophistication meets the timeless charm of Old Florida. Ideally positioned just steps from the sugar-white sands of the Gulf and moments from the boutique shops, galleries, and countless dining options of historic Pine Avenue and the surrounding area, this exceptional 4-bedroom, 4.5-bath residence captures the essence of elevated island living — and sits within one of the island’s most desirable short-term rental zones. Designed with a refined, light-filled aesthetic, the home welcomes you with wide-plank hardwood flooring and a seamless flow between spaces that feel at once elegant and effortless. At the heart of the main level, a designer kitchen serves as the showpiece — outfitted with custom cabinetry, a generous island with seating, premium appliances, a dedicated wet bar, and a fully appointed butler’s pantry that makes entertaining feel second nature. Multiple gathering areas, including a secondary upstairs family room, offer a thoughtful balance of togetherness and retreat. The primary suite is a private sanctuary of understated luxury, anchored by a spa-inspired bath with a sculptural soaking tub, oversized walk-in shower, and bespoke designer finishes. Three of the four bedrooms enjoy their own private ensuites, and every bedroom features a walk-in closet — a refined blend of privacy and comfort for family and guests alike. Step outside to a fully screened ground-level living area that functions as a true extension of the home, complete grilling area and lounge designed for year-round enjoyment. Beyond, a private tropical oasis unfolds around a sparkling pool with integrated spa and a gas firepit framed by lush landscaping and a vinyl privacy fence that creates a secluded, resort-caliber setting for gathering or quiet escape. Every detail has been considered for ease and longevity, including Lutron lighting controls, three-zone climate systems, a metal roof, outdoor shower, and a three-car garage. Offered fully furnished, the property is delivered as a true move in ready opportunity. Beyond the walls of the home lies the magic of the north end — the most coveted and character-rich stretch of Anna Maria Island, known for its pristine beaches, the legendary white sands of Bean Point where the Gulf meets Tampa Bay and the walkable, tree-lined corridor of Pine Avenue with its celebrated restaurants, cottage shops, and cafés. Days begin with sunrise strolls along the shore and end with sunset dinners just minutes from your front door. With short-term rentals permitted, unmatched walkability to both the beach and Pine Avenue, and a rare combination of design, location, and lifestyle, this residence represents one of the most compelling offerings on Anna Maria Island — a legacy property with exceptional income potential in Florida’s most storied coastal village.
403 N BAY BLVD, ANNA MARIA, FL 34216
$2,549,90087 Days on yellowkey MLS ID: A4682522
REDUCED by $100,100 (3.8%) on 04/01/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2112 Built: 1991 Tax: $29,831 (2024)Community: Anna Maria Beach Second AddSpa: NoSingle Family
Taxes:$29,831
Remarks: $100,000 PRICE REDUCTION – Now Priced to Sell | Luxury Island Home on North End of Anna Maria Island | Bay Views | Pool | TurnkeyWelcome to exceptional island living on the highly sought-after north end of Anna Maria Island, where homes like this rarely become available.This beautifully maintained turnkey 4-bedroom, 3-bathroom coastal residence offers stunning sunrise views over the bay, an unbeatable location just steps from Bayfront Park, and easy access to a sandy beach and calm waterfront waters.With a $100,000 price reduction, this property is now positioned as one of the best opportunities for a luxury beach home, vacation rental investment, or full-time island residence on Anna Maria Island. Enjoy your own fenced-in tropical backyard retreat, featuring: Private swimming pool with in-pool umbrellas, Lush, mature landscaping, Outdoor lounging and entertaining areas, Seamless indoor-outdoor island living.This Anna Maria Island luxury home features a bright, open-concept floor plan designed for entertaining and relaxed coastal living: Spacious living and dining areas, Large chef-style kitchen ideal for gatherings, and Wrap-around porches on multiple levels for bay breezes and water views, including nightly views of the lite-up Skyway Bridge. Two upstairs bedrooms open directly to the expansive second-floor porch, offering panoramic bay views and unforgettable sunrise beach views over the Gulf of Mexico. The oversized primary suite includes a spa-inspired ensuite bathroom with: Dual vanities, Large private soaking tub, Walk-in shower, and Luxury finishes throughout This Premier Island Location provides access to Walk, Bike, or Golf Cart Everywhere. Perfectly positioned near: Boutique shops, cafes, and ice cream parlors, waterfront dining and local restaurants, and the historic charm of the north-end of the island. Just minutes from the iconic Anna Maria City Pier, and easily accessible to Gulf beaches by golf cart or bicycle, this location defines true Florida island lifestyle living. This property is also a high-performing opportunity for investors:, Daily rentals permitted, Strong short-term rental demand on Anna Maria Island, and Ideal for luxury vacation rental income or second home use. Whether you are searching for a luxury waterfront home on Anna Maria Island, a high-income vacation rental property, or a private coastal retreat, this home delivers unmatched location, lifestyle, and value. Pack your bags and start living the Island Dream - Don't Worry - Bay Happy!
Listing is courtesy of: WAGNER REALTY (941-383-5577)
Listing Agent: Ed Taaffe (636-346-6165)
110 SPRING AVE, ANNA MARIA, FL 34216
$3,000,000155 Days on yellowkey MLS ID: A4673879
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2925 Built: 1996 Tax: $36,243 (2025)Community: Anna Maria BeachSpa: YesSingle Family
Taxes:$36,243
Remarks: Welcome to one of Anna Maria Island's most distinctive addresses — a 5-bedroom, 4.5-bath luxury coastal residence steps from the Gulf that offers something exceptional even by island standards: C1 neighborhood commercial zoning that permits a ground-floor business with two floors of refined residential living above. The flexibility here is remarkable, and the Gulf-front setting is simply unmatched. Completely reimagined in 2022 and positioned one property from the Gulf, the home reflects the very best of modern coastal design. Wide-plank flooring, custom cabinetry, designer lighting, and an expansive open-concept layout create an effortless backdrop for both everyday living and elevated entertaining. The chef's kitchen — anchored by stone countertops, premium appliances, and a generous island — flows seamlessly into the living and dining spaces. A private elevator connects all three levels with quiet elegance, enhancing accessibility and the overall sense of arrival. Each bedroom suite is a serene coastal sanctuary. The primary retreat elevates the experience further with a spa-inspired bath and private terrace access, while multiple balconies, covered lounge areas, and a swim-spa extend the living spaces outdoors. Impact windows and doors, elevated construction, and modern mechanicals deliver lasting durability and meaningful insurance advantages. Already a proven Airbnb performer and delivered fully furnished and turn-key, this property generates strong rental income when not in personal use. For the discerning buyer seeking a luxury Gulf-front home, a high-performing investment, a multigenerational retreat, or a live-work opportunity unlike anything else on the island — this C1-zoned address delivers it all, just steps from the Gulf and the iconic Sand Bar Restaurant.
Listing is courtesy of: KW COASTAL LIVING II (941-556-0500)
Listing Agent: Rebecca Adams (815-540-1560)
915 N SHORE DR, ANNA MARIA, FL 34216
$5,250,000146 Days on yellowkey MLS ID: A4674863
REDUCED by $100,000 (1.9%) on 05/04/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2870 Built: 2017 Tax: $70,059 (2025)Community: Shore AcresSpa: YesSingle Family
Taxes:$70,059
Remarks: Direct Beachfront Luxury with Exceptional Rental Income on Anna Maria Island. Discover the ultimate in coastal elegance with this direct beachfront home on the shores of Anna Maria Island. A rare beachfront home sold turnkey furnished that seamlessly blends refined luxury with a proven record of outstanding short-term rental performance. Recently enhanced with numerous upgrades including new sliding doors on the upper level—this home showcases high end finishes and expansive walls of glass that capture sweeping views of Tampa Bay and the iconic Sunshine Skyway Bridge. The spacious living and dining areas open through floor-to-ceiling sliders to a generous bayfront balcony, creating an effortless indoor–outdoor flow for entertaining or peaceful relaxation. The gourmet kitchen is a chef’s delight, featuring shaker cabinetry, a large island with seating, quartz countertops, and new premium stainless-steel appliances including a gas range. Each of the four bedrooms is a private retreat, complete with an en-suite bath and its own balcony framed by tropical scenery. Additional recent upgrades include new ground-level outdoor furnishings, refreshed tropical landscaping with exterior lighting, and newly painted interior and exterior spaces. The covered poolside lounge and dining area on the ground level are the perfect setting for waterfront living—just steps from the sand. As evening falls, enjoy the mesmerizing glow of the Skyway Bridge from your own serene getaway. Set on the pristine beachfront of Anna Maria Island, this home features timeless architecture, a spectacular coastal setting, and an unparalleled opportunity for both personal enjoyment and exceptional rental revenue. This 4-bedroom, 4-bath residence produced nearly $500,000 for 2025, $456,000 booked for 2024, and $464,000 in 2023. Future 2026 reservations in place Comprehensive rental history and future booking details for 2025 and 2026 are available upon request. A rare chance to own a true beachfront sanctuary.
Listing Agent: Hannah Hillyard (941-744-7358)
112 MAPLE AVE, ANNA MARIA, FL 34216
$4,925,0009 Days on yellowkey MLS ID: A4692033
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2545 Built: 2024 Tax: $49,263 (2025)Community: Gulf View Sub Of Anna Maria KeySpa: YesSingle Family
Taxes:$49,263
Remarks: STUNNING HOME WEST OF GULF DRIVE! WELCOME TO THIS AMAZING FULLY FURNISHED 5 BEDROOM, 4.5 BATHROOM HOME LOCATED ON ONE OF THE PREMIER STREETS OF ANNA MARIA ISLAND!! With only 5 houses to the beach, this new construction gem is an absolute treasure. From the moment you set foot on the property, you'll be captivated by the thoughtfully designed custom features, including a paver driveway and lush tropical landscaping. Step inside and experience the open and spacious main living area, featuring a great room floor plan that seamlessly connects to an incredible deck through sliding glass doors. This expansive outdoor space offers ample room for outdoor dining and a comfortable sitting area, allowing you to fully embrace the island lifestyle. The kitchen is a chef's dream, boasting high-end appliances, a designer backsplash, a large center island with a breakfast bar, and stylish pendant lights. Retreat to the luxurious master suite at the end of a day filled with beach adventures. It features a sitting area and an incredible bathroom with dual sinks, a garden tub, and a walk-in shower. An additional guest bedroom on the same floor offers the convenience of an ensuite bathroom. Upstairs you will find three bedrooms and two bathrooms as well as a wetbar/coffee bar area. Step outside to the expansive area featuring an outdoor kitchen, dining area and turf area perfect for entertaining and hanging out. The roof top balcony offers breathtaking views of the Gulf, creating a serene setting for relaxation. The amount of outdoor living space in this home is truly one of a kind.The backyard of this home is your own private tropical oasis, complete with a heated pool and spa. Here, you can indulge in luxury living on Anna Maria Island and enjoy the tranquil surroundings. The finishes and attention to detail throughout the home are unmatched, ensuring an exceptional living experience. Whether you're in search of your forever home or a lucrative investment property, this is the one for you. With its prime location just a short distance to Pine Ave, where you'll find a variety of restaurants and shops, this home offers the perfect blend of convenience and tranquility. Don't miss out on the opportunity to own this incredible property. HOME IS CURRENTLY A SUCCESSFUL RENTAL PROPERTY. Schedule a showing today and secure your chance to own a piece of Anna Maria Island's luxury living.
154 CRESCENT DR, ANNA MARIA, FL 34216
$1,799,900144 Days on yellowkey MLS ID: A4675421
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1421 Built: 1959 Tax: $15,960 (2025)Community: Lake La Vista RepSpa: YesSingle Family
Taxes:$15,960
Remarks: Location! Location! Location! TRY BEFORE YOU BUY!!** Come Visit…Fall in Love with luxury beach living at it’s finest in this amazing, turnkey furnished, completely and beautifully remodeled 3 bedroom, 3 bathroom resort like pool home with lush island tropical landscaping. This exquisite cottage is nestled on a quiet palm tree lined street, just north of Pine Avenue, in the highly desirable city of Anna Maria, only three houses from the Bay Beach and City Pier!! This is a wonderful investment opportunity, currently showcased as a vacation rental, but could easily be enjoyed as a primary residence or secondary home for our welcomed “snow birds.” This open~ airy~ split floor plan effortlessly combines the seamless living areas of the kitchen, living room, and dining rooms. The updated, beautifully appointed kitchen is sure to impress even the most discerning chef, featuring coastal shaker wood cabinets, glass tile backsplash, stainless appliances, quartzite counter tops, and spacious island with ample seating and storage, illuminated by the beautiful glass pendant lighting above. The stunning formal dining room, with it’s gorgeous, expansive 21 ft sliding glass impact doors overlook the extremely spacious screened lanai and the breathtaking views of the spectacular resort-like pool~spa oasis. Enjoy abundant seating in the spacious living room with sleeper sofa, while watching your favorite movie on the large screen TV above the beautiful electric fireplace. After an enjoyable day at the beach or dinner at one of the many wonderful island restaurants, retreat to the serene primary king en-suite with walk-in shower. The second bedroom offers plenty of space with two twin beds. Impressive third bedroom presents a secondary king en-suite with vaulted ceilings, walk-in shower, private entrance, and is on the alternate side of the home for welcomed privacy. Indulge in the epitome of aquatic luxury with a meticulously crafted pool, complete with state-of-the-art heating and cooling systems, fiber optics, offering a symphony of color and ambiance. The tropical pool oasis is adorned by the captivating centerpiece, the hand crafted giant sea turtle sculpture that was painted by a local artist and previously hung in Mote Marine Aquarium in Sarasota. Enjoy peace of mind with new Hurricane Impact Windows (2022), new Hurricane Impact sliding glass doors (2025), new electrical wiring updated (2025), all new plumbing with new drain lines to the sewer as well as new supply lines (2022), newly built saltwater pool with pebble tech surface-heated and cooled with fiber optic lighting (2023), pool safety alarms (2023), new interior painting (2025), exterior painting (2022), outdoor shower, new landscaping (2023), new A/C (2025), new metal roof (2025)… too many updates to list! Extensive updates list available upon request. Enjoy all that Anna Maria has to provide with it’s nearby City Pier, beautiful world famous beaches, swimming, boating, fishing, abundant island boutiques and shops, plus wonderful island restaurants for your dining pleasure. Enjoy watching the enticing virtual tour and call today!! **If you book a stay as a guest and decide to buy, you will have your net rental refunded with an accepted contract at the Closing of Escrow. Subject to availability. Maximum rental 7 days. Based on NET rental rate. Cleaning, taxes & fees apply.
Listing is courtesy of: WAGNER REALTY (941-761-3100)
Listing Agent: Rennie Evans (310-437-9336)
771 JACARANDA RD, ANNA MARIA, FL 34216
$1,799,000274 Days on yellowkey MLS ID: A4660805
0 Days Off yellowkey (back on 5/3/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1447 Built: 1979 Tax: $22,639 (2024)Community: Shore Acres Second AddSingle Family
Taxes:$22,639
Remarks: An easy 5-minute walk to the Gulf on the coveted north end of Anna Maria Island, Limelight is a fully furnished, nightly-rental-friendly pool home offering privacy, charm, and exceptional island value. Located just a few short blocks from direct beach access, this 3-bedroom, 2-bath single-family residence is ideal as a second home, full-time residence, or income-producing investment. Inside, vaulted white wood-plank ceilings, custom millwork, and rich wood flooring create a bright, welcoming coastal atmosphere throughout the open living and dining spaces. The kitchen flows seamlessly into the main living area and features stainless steel appliances, granite countertops, a custom tile backsplash, breakfast bar seating, and a reverse osmosis drinking water system. The primary suite offers a walk-in closet and en-suite bath with a walk-in shower, while guest bedrooms feature crown molding, custom wood trim, and warm wood floors — a timeless north-end aesthetic buyers seek. Outdoor living is where Limelight truly shines. A heated freeform pool is surrounded by lush tropical landscaping for complete privacy, complemented by a covered patio, outdoor shower, and an expansive open-air ground-level living area perfect for lounging, dining, or creating a poolside bar. Electric roll-down screens and hurricane shutters allow for year-round enjoyment. Notable upgrades include a new roof 2024, impact-rated doors and windows, 2-car tandem garage with impact door, interior laundry with storage, tankless hot water heater, app-controlled HVAC with AirKnight air purification, water softener with chlorine removal, 2020 stair and railing updates, and a new 2024 TV in the cabana area. Nightly rentals are permitted, and 2025 rental history reflects just under $100,000 in gross income, despite downtime related to hurricane impacts and owner use, highlighting strong income potential alongside personal enjoyment. The home is offered fully furnished and move-in ready, making this a rare opportunity to own a private pool home within walking distance of the beach on the north end of Anna Maria Island.
Listing Agent: Mary Anne Muniz (651-470-7020)
519 SOUTH DR, ANNA MARIA, FL 34216
$1,598,000145 Days on yellowkey MLS ID: A4675370
REDUCED by $97,000 (5.7%) on 04/01/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2131 Built: 1972 Tax: $26,805 (2024)Community: Wells Bay Harbor Sec ASpa: YesSingle Family
Taxes:$26,805
Remarks: “Anna Maria Oasis” is a Bimini Bay Coastal Classic, perfectly positioned on the coveted north end in the City of Anna Maria. With deep-water access directly from your backyard, no bridges to the bay or the Gulf of Mexico, and a 50’ dock with pilings already in place for lift installation, this property is truly a boater’s and fisherman’s paradise. Originally built in 1972, the home was completely transformed in a top-to-bottom remodel in 2025, blending modern luxury with timeless island charm. No detail was overlooked. Highlights include imported Filipino shell stone flooring throughout, all-new drywall, insulation, plumbing, electrical, paint, fixtures, kitchen, and fresh landscaping. The living space was thoughtfully expanded with energy-efficient mini-split systems, increasing the under-air square footage from 1,582 sq ft to approximately 2,131 sq ft, offering enhanced comfort and flexibility. Additional upgrades include a new pool (2019), new AC unit 2025 and new roof (2020). Designed for effortless indoor-outdoor living, this home is ideal for entertaining, launching a sunset cruise, or unwinding while taking in tranquil water views. This one-of-a-kind island property delivers the ultimate coastal lifestyle. Don’t miss this rare opportunity to own waterfront luxury in the heart of Anna Maria—where elegant design meets laid-back island living. Currently an active vacation rental please see remarks for link to the site.
Listing Agent: Jessica Batten (941-962-3380)
801 N SHORE DR, ANNA MARIA, FL 34216
$9,850,000121 Days on yellowkey MLS ID: A4676858
REDUCED by $1,000,000 (9.2%) on 05/02/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4728 Built: 2005 Tax: $64,344 (2024)Community: Shore Acres First AddSpa: NoSingle Family
Taxes:$64,344
Remarks: Rising gracefully on the sugar-white sands of Bean Point, The Golden Dolphin is a timeless Gulf-front residence that blends enduring craftsmanship with inspired artistry. Thoughtfully curated and offered turnkey furnished, this extraordinary home is appointed with bespoke furnishings and window treatments by Italian artisans, complemented by world-renowned works of art that elevate every space. The main living level unfolds into a grand living and dining area, where a full wall of sliders frame endless Gulf views and spectacular sunsets. The expansive balcony is an entertainer’s dream, featuring a fully equipped Lynx outdoor kitchen and a beautifully carved fireplace—an inviting setting for al fresco dining or evenings by the fire. Inside, the chef’s kitchen is outfitted with Sub-Zero, Viking, and Miele appliances, seamlessly combining performance and elegance. A refined library retreat, complete with a fireplace and exquisitely carved bookcases, offers a quiet haven for reading or reflection. The third floor is devoted to luxurious private living. The palatial primary ensuite is a serene sanctuary with spa-like amenities and opens to its own Gulf-facing balcony. Here, a soaking tub, rain shower, and an additional fireplace create an indulgent, resort-style experience. Also on this level are a gracious guest suite, a whimsical children’s ensuite bedroom, and a conveniently located laundry room. The first floor welcomes you with a dramatic foyer featuring soaring ceilings and an elevator. Just beyond lies the imaginative Captain’s Quarters, a fantastical space designed to replicate the galley of a pirate’s lair—both playful and unforgettable. An expansive office follows, showcasing granite countertops and intricately carved walls with integrated drawers and shelving, offering both beauty and function. Outdoors, the home transforms into a private oasis. The grotto-style pool provides shaded comfort and is adorned with multiple water features, while a surrounding fireplace and dining area create an intimate setting for gathering. Beyond the pool, a sun-drenched private patio invites leisurely afternoons of relaxation and sunbathing. Built to stand the test of time, The Golden Dolphin is constructed with concrete and rebar throughout and engineered with advanced drainage systems designed to reroute floodwaters. This exceptional residence has sustained no damage from past hurricanes, offering peace of mind alongside its unparalleled beauty. A rare offering on Anna Maria Island, The Golden Dolphin is a masterful expression of luxury, resilience, and coastal elegance—where art, architecture, and the Gulf converge in perfect harmony.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Becky Sirigotis (941-201-8000)
228 GLADIOLUS ST, ANNA MARIA, FL 34216
$1,995,00021 Days on yellowkey MLS ID: A4690821
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1458 Built: 1979 Tax: $22,184 (2025)Community: Luana IslesSpa: YesSingle Family
Taxes:$22,184
Remarks: Anna Maria Island Income-Producing Beach Retreat | 3BR/2BA | Oversized Pool + Spa Exceptional opportunity to own an elevated 3-bedroom, 2-bath home on Anna Maria Island, just a short walk to the beach. Whether you’re looking for a personal island getaway, full-time residence, or a successful vacation rental investment, this property offers the perfect combination of lifestyle and income potential. Designed for coastal living, the home features a bright and open floor plan with spacious living and dining areas, ideal for entertaining guests or relaxing after a day in the sun. The elevated design offers added peace of mind and classic island charm. Step outside to your own private tropical oasis featuring an oversized heated pool and spa, with plenty of room for lounging, outdoor dining, and enjoying the Florida sunshine year-round. This outdoor space is a major highlight for both homeowners and vacation renters. Located in one of the most desirable areas on the North end Anna Maria Island, the home is within easy walking distance to the beach, shops, dining, and everything that makes island living so special. Property Highlights: • 3 bedrooms, 2 bathrooms • Elevated home • Oversized private pool with spa • Short walk to beach access • Proven vacation rental / income-producing property • Excellent investment potential
Listing is courtesy of: PINEYWOODS REALTY LLC (813-225-1890)
Listing Agent: Amanda Cornett (941-807-2811)
527 MAGNOLIA AVE, ANNA MARIA, FL 34216
$2,095,000442 Days on yellowkey MLS ID: A4640924
0 Days Off yellowkey (back on 5/2/2026)
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!
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.