Beds
5
Baths
5
Sq Ft
3,202 sq ft
Year Built
2014
Lot Size
0.17 acres
Garage
2
About This Property
Grandfathered to accommodate up to 12 guests—a rare and increasingly valuable advantage on Anna Maria Island—505 S Bay Boulevard offers an exceptional opportunity for investors seeking one of the island's highest-performing vacation rental properties. Unlike many homes subject to today's stricter occupancy regulations, this property retains its coveted higher occupancy allowance, creating significantly greater rental flexibility and income potential. The results speak for themselves: the property has already generated more than $163,000 in gross rental income by the end of June and is currently projected to exceed $210,000 in gross rental revenue by year-end, making this an incredible opportunity to own a luxury waterfront home with proven, substantial income-producing performance. Let the island breeze guide you home to 505 S Bay Boulevard, a waterfront haven where the world slows down and coastal living feels like poetry. Tucked along the tranquil north end of Anna Maria Island, this elevated five-bedroom, five-bath home invites you to experience a lifestyle wrapped in beauty, comfort, and pure island magic. Step inside and discover more than 3,200 square feet of thoughtfully designed living space, filled with natural light and framed by sweeping water views. The open-concept floor plan flows seamlessly, anchored by a gourmet kitchen featuring dual islands, high-end finishes, and a gas cooktop—perfect for everyday living and effortless entertaining. Multiple ensuite bedrooms, a versatile top-floor loft, and separate living areas provide privacy and flexibility for family, guests, or long-term stays. Four balconies extend the indoor living spaces outdoors, offering uninterrupted views of spectacular sunrises over the bay and peaceful evenings overlooking the water. Luxury amenities continue throughout the property, including a heated saltwater pool, private boat dock and lift on the canal, an eco-friendly rainwater cistern system, two tankless water heaters, an R38-rated metal roof with spray-foam insulated walls for exceptional energy efficiency, and a transferable 25-year termite warranty for added peace of mind. For boating enthusiasts, the home's 32 feet of saltwater canal frontage, deeded boat slip, and private lift provide direct access to the Intracoastal Waterway and the Gulf of Mexico. Durable coastal construction, impact-resistant features, and low-maintenance materials ensure lasting value while embracing the waterfront lifestyle. Beyond the home, Anna Maria Island offers one of Florida's most celebrated coastal experiences. A short stroll or bike ride leads to the charming boutiques, cafés, and galleries along Pine Avenue, while world-famous sugar-sand beaches and crystal-clear Gulf waters provide endless opportunities for boating, paddleboarding, fishing, shelling, and unforgettable sunsets. At 505 S Bay Boulevard, you're not simply purchasing a luxury waterfront residence—you're acquiring one of Anna Maria Island's rare investment opportunities, combining grandfathered high occupancy, exceptional proven rental performance, premier boating access, and the timeless island lifestyle that continues to make this one of Florida's most sought-after coastal destinations.
Property Overview
Interior Features
Exterior & Lot
Pool & Spa
Waterfront
Utilities
Parking
HOA & Community
Financial Details
Directions
On I-75, take Exit 220 for State Road 64 / Manatee Avenue toward Bradenton / Holmes Beach / Anna Maria Island. At the end of the exit, turn west onto State Road 64 (Manatee Ave W). Continue straight for about 10 miles on Manatee Avenue, heading toward the Gulf of Mexico. Cross the Anna Maria Island Bridge to enter the island. Continue on Manatee Ave until it ends at Gulf Drive. Turn right (north) onto Gulf Drive. Stay on Gulf Drive as it curves and continues north toward the City of Anna Maria. Turn right onto Magnolia Avenue. Turn right onto South Bay Boulevard. Continue along South Bay Blvd until you reach 505 S Bay Blvd — it will be on your right
Location
505 S BAY BOULEVARD, ANNA MARIA, FL 34216
Listing Information
Schedule a Showing
How to Buy This Home
Multiple financing options available for this $2,750,000 home in ANNA MARIA.
🏛️
FHA Loan
$96,250 Down
Government-backed, low down payment. Credit scores as low as 580.
🎖️
VA Loan
$0 Down
Zero down for eligible veterans, active duty, and military families.
🏦
Conventional
$137,500 Down
Traditional financing. As low as 3-5% down with good credit.
🌾
USDA Loan
$0 Down
Zero down for eligible rural areas. Income limits apply.
Florida Down Payment Assistance Programs
You may qualify for up to $35,000 in assistance to cover your down payment and closing costs.
Florida Hometown Heroes
Up to $35,000
First-time buyers working in FL
FL Assist
Up to $10,000
FHA, VA, or USDA borrowers
FL HLP Second Mortgage
Up to $10,000
First-time buyers, 0% deferred
Manatee County SHIP
Varies
Income-qualifying Manatee residents
Can You Afford This Home?
Quick check based on the 28% debt-to-income rule. Not a guarantee — just a starting point.
Listing information is deemed reliable but not guaranteed. All measurements and data should be independently verified. This information is provided by the Stellar MLS. The listing broker's offer of compensation is made only to participants of the MLS where the listing is filed. IDX information is provided exclusively for consumers' personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated: July 1, 2026.