505 BAY BOULEVARD

Property Details

Description

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.

Facts & Costs

Property type

Single Family Residence

Year built

2014

Lot size

7,301 sq ft

Garage

2 spaces

Price per sq ft

$859

Days on market

286

Private pool

Yes

Waterfront

Yes

Community

Wells Bay Harbor

Subdivision

WELLS BAY HARBOR SEC A REP

County

Manatee

Flood zone

AE

Monthly & yearly costs

Property taxes

$35,732 / year (2025)

As reported by the listing agent. Verify with the HOA and county.

Construction & systems

Heating

Central, Electric

Cooling

Central Air

Flooring

Bamboo, Ceramic Tile, Tile

Roof

Metal

Construction

Block

Parking

Driveway, Garage Door Opener, Ground Level, Off Street, On Street, Parking Pad, Garage

View

Pool, Trees/Woods, Water, Gulf/Ocean - Partial, Gulf/Ocean to Bay

Payment Estimate

$16,883 / month

Principal & interest

$13,905

Property taxes

$2,978

HOA

$0

Home insurance

enter below

Estimate only, not a loan offer. Rate is a starting value; taxes and HOA are as reported by the listing agent. Florida insurance (including flood) varies widely. Ask George for a lender referral.

Location

Features & Amenities

• Built-In Oven
• Convection Oven
• Cooktop
• Dishwasher
• Disposal
• Dryer
• Range
• Range Hood
• Refrigerator
• Tankless Water Heater
• Washer
• Wine Refrigerator
• Ceiling Fans(s)
• Crown Molding
• Eat-in Kitchen
• Elevator
• L Dining
• Thermostat
• Walk-In Closet(s)
• Window Treatments
• Balcony
• Lighting
• Outdoor Shower
• Rain Barrel/Cistern(s)
• Rain Gutters
• Sidewalk
• Sprinkler Metered
• Storage
• Gunite
• Heated
• In Ground
• Salt Water
• Canal - Saltwater