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14401 Masthead Drive, 
Osprey, FL 34229

$3,250,000


3

Beds


4

Baths


2,665

Sq Ft


Single Family

Active

Listed by

Mackenzie Longueuil

Michael Saunders & Company

Last updated:

March 17, 2026, 02:54 PM

MLS#

A4684834

Source:

MFRMLS

About This Home

14401 Masthead Drive

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.

Home Facts

Single Family

4 Baths

3 Bedrooms

Built in 2017

Price Summary

3,250,000

$1,219 per Sq. Ft.

MLS #:

A4684834

Last Updated:

March 17, 2026, 02:54 PM

Added:

14 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

3

Interior

Living Area:

2,665 Sq. Ft.


Structure

Structure

Building Area:

3,984 Sq. Ft.

Year Built:

2017


Lot

Lot Size (Sq. Ft):

19,235


Finances & Disclosures

Finances

Price:

$3,250,000

Price per Sq. Ft:

$1,219 per Sq. Ft.

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Contact an Agent

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