14401 MASTHEAD DRIVE at

14401 MASTHEAD DRIVE

For sale Days on market 157

$2,850,000

$1069/sq ft

$400,000
Price Decreased

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Overview

Bedroom

Bath

Year Built

2017

Garage

Sqft

2665

Property Type

Single Family Residence

Property Description

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.

Property Details

MLS#

A4684834

Garage

Total Floor in Bldg

Address

14401 MASTHEAD

City

OSPREY

State/county

Zip/Postal Code

34229

Area

Bayside

Country

United States

HOA

Yes

Assoc Fee

$1,928

Assoc Fee Pd

Quarterly

Tax Amount

$874

Maint Fee

$--

Tax Year

2025

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

Water

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