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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

242 Oak Avenue, Anna Maria
$7,445,000
4 Beds ⋅ 4 Baths ⋅ Bimini Bay Estates SubDv. ⋅ 34216 Zip Code
Come sit on the lanai at this stunning property and you will realize just how different it is from anything else on Anna Maria Island. Set behind gates, tropically landscaped and surrounded by water on three sides, this very private property has only changed hands once in nearly 60 years. It is located on one of the most desirable beach access streets, yet feels remarkably removed from neighboring properties. This four-bedroom family home was constructed in 2020 and engineered to exceed the latest hurricane standards with the safety and security of a concrete elevated home. It was built as an upscale residence, for those who wish to live on Anna Maria, whether seasonally or full-time. It was not designed as a rental home, where the living space is sacrificed to multiple bedrooms. Instead the 3,850 square feet of air-conditioned living area is designed for effortless indoor/outdoor Florida living offering two primary bedrooms with ensuites, a formal dining room, family room and even a dedicated office for those who occasionally work from home. A guest house, connected by a bridge, has two more bedrooms, a full bath and kitchenette, giving family and guests total privacy. Separate utilities even allow this space to be easily closed off when not in use. Architecturally, the home blends Florida, Caribbean and South Pacific influences with custom imported cabinetry, vaulted wood ceilings and walls of glass that allow natural light to fill the interiors. Expansive glass doors disappear to open the great room completely to the covered waterfront lanai, where morning coffee may come with dolphins passing through Bimini Bay. Entertaining flows just as naturally. A Teppanyaki cooking island sits steps from the gourmet kitchen and on the same level, making it easy to move between indoor and outdoor spaces while enjoying the sweeping water views. Or gather around the fire pit, under the stars on your own sandy “beach” at the point of this extraordinary triangular waterfront parcel, surrounded by Bimini Bay. The grounds feel like a private resort, with a dramatic pool featuring fire and water elements, lush landscaping and multiple places to dine, gather or simply enjoy the view. The property is protected by more than 500 feet of new concrete seawall and for boaters offers direct access to the Gulf. A 60-foot dock with power and water accommodates a cruiser, while a separate 12,000-pound boat lift and additional dock provide space for smaller watercraft and toys. With more than 7,000 square feet of luxury covered living area on a one-of-a-kind waterfront parcel, perhaps the greatest luxury here is not something measured in square feet. It is the feeling of openness and privacy, with water in nearly every direction and the ability to enjoy everything you love about Anna Maria Island, then retreat to a place where, for a little while, the island feels entirely your own. Call now to experience this extraordinary waterfront retreat for yourself.

242 Oak 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

837 N Shore Drive, Anna Maria
$3,890,000
Wells Sub SubDv. ⋅ 34216 Zip Code
Presenting LOT 25 a rare opportunity to secure a beautiful buildable bayfront lot on the north end of Anna Maria Island, offering sweeping unobstructed water views, Skyway bridge views and an unparalleled coastal lifestyle. Located just moments from the pristine shores of Bean Point, this property provides coveted beach access to one of the island’s most peaceful stretches of sand. This exceptional lot is ready for your dream home, and the seller is offering a custom build-to-convey option, allowing you to enjoy a seamless design-and-build experience. Create a luxury coastal retreat tailored to your style—whether modern, elevated coastal, or classic island architecture. Perfectly positioned near the beach, shops, dining, and the island’s natural beauty, this property is ideal for a full-time residence, vacation home, or high-end investment with the property zoned for nightly rentals. You do also have the option to purchase both lots 24 and 25.

837 N Shore Drive, Anna Maria

839 N Shore Drive, Anna Maria
$3,890,000
Wells Sub SubDv. ⋅ 34216 Zip Code
Presenting LOT 24 a rare opportunity to secure a beautiful buildable bayfront lot on the north end of Anna Maria Island, offering sweeping unobstructed water views, Skyway bridge views and an unparalleled coastal lifestyle. Located just moments from the pristine shores of Bean Point, this property provides coveted beach access to one of the island’s most peaceful stretches of sand. This exceptional lot is ready for your dream home, and the seller is offering a custom build-to-convey option, allowing you to enjoy a seamless design-and-build experience. Create a luxury coastal retreat tailored to your style—whether modern, elevated coastal, or classic island architecture. Perfectly positioned near the beach, shops, dining, and the island’s natural beauty, this property is ideal for a full-time residence, vacation home, or high-end investment with the property zoned for nightly rentals. You do also have the option to purchase both lots 24 and 25.

839 N Shore Drive, Anna Maria