14401 MASTHEAD DRIVE

Property Details

Description

Under contract-accepting backup offers. Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom-built in 2017 by Rob Allegra and ideally positioned on a private cul-de-sac between Sarasota and Venice, this home offers a rare opportunity to experience the best of Florida’s Gulf Coast lifestyle. Sweeping views of the Bay and Intracoastal Waterway greet you upon entry, while the dramatic great room features a striking cupola with soaring 22-foot ceilings, wraparound windows, architectural beams, and detailed millwork that beautifully frame the waterfront setting. Pocketing impact sliders seamlessly open the living space to an expansive covered lanai where breathtaking sunsets, dolphins, and gentle coastal breezes create an unforgettable everyday backdrop. The open chef’s kitchen is designed for both entertaining and daily living, offering high end stainless appliances, a gas cooktop with pot filler, wine cooler, abundant cabinetry, and an oversized quartz island. Outdoor living shines with wood-paneled ceilings, crema pro leathered marble flooring, a gas fire pit, and a fully equipped outdoor kitchen with grill and beverage refrigerator. The solar and heat pump-heated saltwater lap pool and spa, outdoor shower, and private dock with lift complete the ultimate waterfront retreat. The primary suite enjoys beautiful water views and features a sitting area, double tray ceiling, dual custom walk-in closets, and a luxurious bath with double vanities and walk-in shower. Two additional en-suite bedrooms, a den or office, and a powder room provide comfort and flexibility. Wood-look tile flooring runs throughout, complemented by impact windows and doors, a smart-enabled security system, whole-home generator, and water conditioning system. Located just minutes from Casey Key, Nokomis Beach, Oscar Scherer State Park, and the Legacy Trail, this home offers effortless access to beaches, boating, dining, and recreation. An extraordinary waterfront residence where luxury, comfort, and coastal beauty come together, offering the lifestyle you’ve always imagined.

Facts & Costs

Property type

Single Family Residence

Year built

2017

Lot size

0.44 acres

Stories

1

Garage

2 spaces

Half baths

1

Price per sq ft

$1,069

Days on market

209

Private pool

Yes

Waterfront

Yes

Community

Bayside

Subdivision

BAYSIDE

County

Sarasota

Flood zone

VE, AE

Monthly & yearly costs

HOA fee

$1,928 / quarterly

Property taxes

$874 / year (2025)

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

Construction & systems

Heating

Electric

Cooling

Central Air

Flooring

Marble, Tile

Roof

Metal

Construction

Block, Stucco

Parking

Garage Door Opener

View

Water

Payment Estimate

$15,127 / month

Principal & interest

$14,411

Property taxes

$73

HOA

$643

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

• Bar Fridge
• Built-In Oven
• Convection Oven
• Cooktop
• Dishwasher
• Dryer
• Gas Water Heater
• Microwave
• Range Hood
• Refrigerator
• Tankless Water Heater
• Washer
• Water Softener
• Wine Refrigerator
• Built-in Features
• Ceiling Fans(s)
• Crown Molding
• Eat-in Kitchen
• High Ceilings
• Open Floorplan
• Primary Bedroom Main Floor
• Split Bedroom
• Thermostat
• Tray Ceiling(s)
• Vaulted Ceiling(s)
• Walk-In Closet(s)
• Lighting
• Outdoor Grill
• Outdoor Kitchen
• Outdoor Shower
• Sidewalk
• Deck
• Heated
• In Ground
• Lap
• Outside Bath Access
• Salt Water
• Screen Enclosure
• Solar Heat
• Bay/Harbor