Anna Maria Homes with Two Story Property Description

Anna Maria Homes with Two Story Property Description

Welcome to Anna Maria, a hidden gem nestled in the heart of Manatee County, Florida. This charming island city is renowned for its stunning white-sand beaches, crystal-clear waters, and a laid-back atmosphere that invites relaxation and rejuvenation. With a population of just over 1,500 residents, Anna Maria retains a quaint, small-town feel while offering a vibrant community spirit and an array of recreational activities. From delightful boutiques to delicious seafood restaurants, there’s something for everyone to enjoy.

One of the standout features of Anna Maria is its beautiful two-story homes. These properties not only provide ample space for families and guests but also offer breathtaking views of the surrounding landscape. Imagine sipping coffee on your balcony while watching the sunrise over the Gulf of Mexico or hosting a sunset barbecue on a spacious deck. The two-story designs often feature open floor plans, allowing for a seamless flow between living spaces, perfect for entertaining or simply enjoying quality time with loved ones.

Many of these homes are just a short stroll from the beach, giving residents easy access to sun-soaked days and tranquil evenings by the shore. With lush landscaping and charming architectural details, these properties reflect the coastal lifestyle that Anna Maria embodies. Whether you’re looking for a vacation retreat or a permanent residence, the two-story homes in Anna Maria offer the perfect blend of comfort, style, and coastal charm. Discover your dream home in this idyllic paradise and embrace the enchanting lifestyle that awaits you!

Newest Anna Maria Homes with Two Story Property Description

783 Jacaranda Road, Anna Maria
$1,999,000
3 Beds ⋅ 2 Baths ⋅ Shore Acres SubDv. ⋅ 34216 Zip Code
Paradise awaits on the coveted North End of Anna Maria Island! This 3 bedroom/2 bath pool home welcomes you with cathedral ceilings and family room open to the updated kitchen and dining room. Extend your relaxation to the screened porch with new Trex decking, overlooking your private, fenced backyard pool and covered dining area. Your guests will relax in their first floor bedrooms, while you will enjoy your upstairs primary en suite with peeks of the gulf, and an attached open loft. You’ll also love the second floor screened porch with great Gulf breezes! Downstairs there’s ample storage for beach toys and you’re only a hop, skip & a jump to your toes in the sand. With short term rentals allowed, this great space is an ideal investment property in the city of Anna Maria!

783 Jacaranda Road, Anna Maria
313 Magnolia Avenue, Anna Maria
$1,595,000
3 Beds ⋅ 2 Baths ⋅ Bimini Bay Colony Club Sub SubDv. ⋅ 34216 Zip Code
Welcome to Mangoes on Magnolia, a three-bedroom, two-bath vacation home with a private heated pool and hot tub, located less than a 10-minute walk from the white-sand beaches of Anna Maria Island. Nestled in a quiet neighborhood just two blocks from Pine Avenue’s shops and restaurants. This coastal retreat is perfect for families and friends. After sunny days on the beach, return to your lagoon-style heated pool and hot tub, the ultimate relaxation spot. Gather around the outdoor wood dining table by the pool to share meals in the fresh island air. With a bonus game room, Mangoes on Magnolia offers plenty of ways to keep everyone entertained. Step inside to a bright coastal living area ideal for relaxing after a day of island adventures. The fully equipped kitchen makes cooking simple, with two refrigerators, island seating, and all the essentials for preparing meals. Gather around the dining table for family dinners before heading to the bonus room for games and reading. The primary bedroom is a peaceful retreat, ample storage, and an ensuite bathroom with a step-in shower. The second bedroom also features a queen bed, while the third bedroom offers a full bed, making it perfect for kids or additional guests. The hallway bathroom includes a tub/shower combo and a spacious vanity. Guests love this home’s unbeatable location. Stroll to the boutiques and eateries on Pine Avenue, hop on the island trolley, or explore the natural beauty of Anna Maria Island by bike, kayak, or on foot. With spectacular sunsets just a short walk away, Mangoes on Magnolia makes it easy to enjoy the very best of island living.

313 Magnolia Avenue, Anna Maria
511 South Drive, Anna Maria
$3,700,000
3 Beds ⋅ 3 Baths ⋅ Wells Bay Harbor SubDv. ⋅ 34216 Zip Code
Tucked away at the very end of a quiet street in Anna Maria, 511 South Drive is a truly distinctive waterfront retreat offering exceptional privacy and nearly 180 feet of water frontage along Bimini Bay. Once featured in SRQ Magazine, this three-bedroom, two-and-a-half-bath residence—known as The Morris House—captures the relaxed beauty of island living, with dolphins, manatees and coastal birdlife providing an ever-changing backdrop. Originally built by Ross Built, the home is rich in British Arts and Crafts character, yet has been beautifully updated for modern living. Throughout the home, remarkable details speak to its history and craftsmanship, from a William Morris stained-glass window to a mantel sourced from a mansion in Great Britain. Since 2024, the home has undergone an extensive collection of thoughtful improvements, blending its distinctive character with beautifully updated interiors, enhanced outdoor living and important mechanical upgrades. A private courtyard surrounded by mature tropical landscaping and a charming koi pond creates a memorable sense of arrival. Step inside, and oversized windows and French doors frame the waterfront setting, immediately drawing your eye toward sweeping water views. The main level was extensively refreshed in 2025 with new wood-grain tile flooring, custom wood trim and baseboards, and built-in living room bookshelves crafted by a master carpenter. The kitchen was reimagined with new cabinetry, quartz countertops and a suite of high-end appliances including a Fulgor Milano range, ASKO dishwasher and a GE Monogram refrigerator. A Blanco undermount sink features instant ultra-filtered hot water, while the adjoining pantry received additional cabinetry and electrical upgrades. The downstairs bath was also updated with new cabinetry, quartz countertops and a new sink. Designed for both gathering and everyday living, the expansive great room opens to the waterfront setting, while a separate media room and game room offer additional spaces for entertaining. Two guest bedrooms on the main level open directly to the courtyard and share a Jack-and-Jill bath. The entire upper level is dedicated to the primary suite, creating a private retreat surrounded by spectacular water views. Windows and French doors span three sides of the bedroom, while the expansive private deck provides an idyllic setting for sunrise coffee or an evening cocktail. The primary bath features an oversized walk-in shower and a clawfoot soaking tub. Outdoor living has also been beautifully enhanced. The wraparound porch was screened in 2024, creating a wonderful extension of the interior living space overlooking the water. A new hot tub was added in 2025, followed by an outdoor shower and new pavers along the front and side of the home in 2026. A new irrigation system was also installed. Along the nearly 180 feet of waterfront, two docks invite you to embrace the boating lifestyle, including a boat lift for easy access to fishing and sunset cruises and an enclosed boathouse for fishing gear and water toys. Additional recent improvements include a new downstairs AC system, new split AC unit, new hot water heater, floor outlets, updated lighting, and more. Just minutes from the beaches, Pine Avenue's shops and restaurants and the Anna Maria City Pier, The Morris House offers a rare combination of architectural character, exceptional privacy and substantial water frontage —all within a remarkable setting in Anna Maria.

511 South Drive, Anna Maria
103 Sunset Lane, Anna Maria
$2,295,000
3 Beds ⋅ 3 Baths ⋅ Sunset Cove At Holmes Beach SubDv. ⋅ 34216 Zip Code
A Rare Architectural Retreat in Sunset Cove, Steps from the Gulf! Gulf views, effortless beach access and a canvas of rare potential come together in this architectural gem in Sunset Cove, one of Anna Maria Island's most peaceful and private enclaves. The home sits at the end of a quiet cul-de-sac, just steps from dedicated beach access. Stroll out the door and within moments your feet are in sugar-white sand, with the turquoise Gulf stretching out before you. Monthly rental restrictions preserve the neighborhood's relaxed residential character. Designed by acclaimed architect H. Patterson Fletcher in the spirit of Frank Lloyd Wright, the custom-built residence embraces its natural surroundings with open, flowing spaces, abundant light and a seamless connection between indoors and out. Solidly constructed, the 3-bedroom, 2.5-bath home with bonus room rises three distinctive levels above an expansive walled lot, with ample room to create a private pool and a resort-style outdoor sanctuary. Inside, vaulted ceilings and walls of sliding glass bathe the living room in natural light and frame views of swaying palms and the shimmering Gulf beyond. The open kitchen and living area center on a kitchen island, custom solid-wood cabinetry and an oversized skylight that pours sunshine into the heart of the home. Step out to the generous elevated screened lanai for morning coffee, alfresco dining or a front-row seat as the evening sky turns to gold. The primary suite is a private escape, with a wall of sliders opening to its own balcony, a spacious ensuite bath and dual walk-in closets. Upstairs, two distinct sleeping areas and a full bath offer flexible accommodations for guests. The crown jewel is the rooftop deck. Along with the wraparound windows, it reveals sweeping treetop and Gulf views, an unforgettable setting for sunrise coffee, sunset cocktails and evenings under the stars. Below, an oversized garage provides exceptional storage for beach gear, bikes and island toys. This is a home ready for a new owner's vision. Architectural pedigree, privacy, Gulf views and beach access just steps away set the stage for an extraordinary, one-of-a-kind Anna Maria Island retreat.

103 Sunset Lane, Anna Maria
254 Gladiolus Street, Anna Maria
$1,845,000
3 Beds ⋅ 2 Baths ⋅ Luana Isles SubDv. ⋅ 34216 Zip Code
Located at the North End of Anna Maria Island 3 blocks from the beach and 1 block from the bay. Three bedrooms, 2 bathrooms with open living & dining floor plan that leads to a large screened porch for grilling, dinning and ping pong! Perfect for entertaining your friends and family. Freshly painted interior, natural light throughout, stainless steel appliances in the kitchen with a huge island. Downstairs has privacy landscaping, turf surrounding the heated pool and spa. Featuring an oversized 4-car garage with additional parking space available for a boat out front. Currently a vacation rental with a 1-7 day minimum. Schedule your private showing today.

254 Gladiolus Street, Anna Maria
109 Gull Drive, Anna Maria
$1,175,000
2 Beds ⋅ 2 Baths ⋅ Luana Isles SubDv. ⋅ 34216 Zip Code
Rare opportunity to own a canal-front lot in the heart of Anna Maria Island. Take your clean slate to design and build the coastal dream home you've been waiting for. Located on a quiet cul-de-sac street with access to the Bay and the Gulf of Mexico, boats to be able to fit under the 2 bridges. Anna Maria offers a laid-back, old-Florida lifestyle — walkable access to the island's white-sand beaches, local restaurants, and shops on Pine Ave. Whether you're envisioning a modern coastal retreat or a classic Florida cottage on stilts, this lot gives you the location and the water access to make it happen. Zoning allows for 1-7 day vacation rentals.

109 Gull Drive, Anna Maria
315 Hammock Circle, Anna Maria
$2,595,000
3 Beds ⋅ 4 Baths ⋅ Acreage SubDv. ⋅ 34216 Zip Code
Welcome to your private coastal retreat in the highly sought-after North End of Anna Maria Island. Completely remodeled from the studs out in 2017 by Gagne Construction, this elevated 3-bedroom, 3.5-bathroom home is situated on a spacious 0.21-acre lot, just a short stroll from the island’s famous white sand beaches and only a couple of minutes on foot from Pine Avenue, the heart of Anna Maria’s shops, restaurants, and island attractions. This superb location allows you and your guests to easily experience the best of the island without ever needing to get in the car. Offering the ideal combination of luxury, comfort, and laid-back island living, this fully furnished residence is perfect as a personal getaway, second home, or investment property with excellent rental potential. Inside, the thoughtfully designed open floor plan is filled with natural light and complemented by high-end finishes throughout. Hurricane impact windows and sliding glass doors provide added protection and peace of mind, while enhancing the home’s seamless connection to its tropical surroundings. The spacious living areas flow effortlessly into the modern kitchen, which features top-of-the-line appliances and plenty of room for gathering with family and friends. Each oversized bedroom offers its own private en-suite bathroom, while elegant, spa-inspired finishes contribute to the home’s relaxed yet refined coastal atmosphere. The outdoor living space is equally impressive and has recently been refreshed with new landscaping, new exterior paint, and new outdoor furniture. Lush tropical surroundings, a heated pool, and an oversized lanai create your own private island oasis. Spend the afternoon by the pool, enjoy dinner al fresco, or unwind outdoors after a day at the beach. The seamless indoor and outdoor layout is perfectly suited for entertaining, extended stays, and creating the type of vacation experience guests will want to enjoy again and again. Offered fully furnished and move-in ready, this home makes second-home ownership effortless while also providing the flexibility to generate rental income when you are away. Anna Maria Island is celebrated for its pristine beaches, tranquil waters, fresh local seafood, and charming small-town atmosphere. With Pine Avenue just moments away, this exceptional North End location places the very best of island living right outside your door. This is a rare opportunity to own a beautifully appointed island retreat where you can vacation, relax, entertain, and invest.

315 Hammock Circle, Anna Maria
215 Sycamore Avenue, Anna Maria
$5,895,000
4 Beds ⋅ 5 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code
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.

215 Sycamore Avenue, Anna Maria
103 Park Avenue, Anna Maria
$5,195,000
5 Beds ⋅ 5 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code
HUGE PRICE IMPROVEMENT! LUXURY COASTAL LIVING AT IT’S FINEST! This one-of-a-kind residence, designed by Emily Anne Smith, stands on one of the most sought-after streets in Anna Maria, just one home from the Gulf and a short walk to the charm of Pine Avenue. The location offers an exceptional combination of beach proximity, walkability, and privacy. Thoughtfully designed for both entertaining and multi-generational living, the home offers over 4,500 square feet of curated living space with distinct gathering areas throughout. The main living room opens to a front verandah and features a fireplace, with an additional fireplace located in the primary suite. The kitchen, designed for both function and presentation, featuring marble countertops and backsplash, custom cabinetry, a butler’s pantry, and dual sinks is well-suited for both everyday use and larger gatherings. Emily Anne Smith is known for her mindful and timeless coastal design, and this home reflects that level of craftsmanship throughout. The property includes a main residence and a separate cottage, providing flexibility and privacy with a total of 5 bedrooms and 4.5 bathrooms. Additional features include multiple verandahs, two dedicated study spaces, and a well-designed outdoor living area with a pool, shower, and lounge space. The private guest quarters with separate entrance offers an ideal setup for extended family, guests, or private accommodation. This is a rare opportunity to own a thoughtfully designed home in a premier Anna Maria location, with Gulf views and exceptional sunset exposure.

103 Park Avenue, Anna Maria
889 N Shore Drive, Anna Maria
$4,200,000
3 Beds ⋅ 3 Baths ⋅ Shore Acres SubDv. ⋅ 34216 Zip Code
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!

889 N Shore Drive, Anna Maria
103 Palm Avenue, Anna Maria
$5,450,000
4 Beds ⋅ 4 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code
Welcome to 103 Palm Avenue on Anna Maria Island, home to some of the best beaches in Florida. This exceptional beachfront property features not one, but two direct Gulf-front residences, offering a rare opportunity for multi-generational living, rental income, or a private coastal compound. The property includes 4 bedrooms and 4 bathrooms and was completely remodeled in 2020, with a brand-new roof installed in 2025. An elevator provides convenient access between levels, enhancing both comfort and accessibility. Enjoy breathtaking beach views, unforgettable sunsets, and the relaxed island lifestyle Anna Maria Island is known for. Ideally located close to shopping, dining, and local attractions, this is true beachfront living at its finest.

103 Palm Avenue, Anna Maria
403 N Bay Boulevard, Anna Maria
$2,185,000
4 Beds ⋅ 3 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code
JUST IN - HUGE $115,OOO PRICE REDUCTION - INVESTOR OPPORTUNITY - YTD Gross Income is $153,177 - Florida is all about LOCATION, LOCATION, LOCATION - DIRECT BAY & SKYWAY BRIDGE VIEWS - Pool - Excellent Rental Income - Being Sold Turnkey - Welcome to exceptional island living on the highly sought-after north end of Anna Maria Island, where luxury 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. This property is now one of the Best Priced investment or vaction home opportunites 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 Bay. 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 waterview 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!

403 N Bay Boulevard, Anna Maria
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