14401 MASTHEAD DRIVE, OSPREY, FL 34229

Description of 14401 MASTHEAD DRIVE, OSPREY, FL 34229

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 for 14401 MASTHEAD DRIVE, OSPREY, FL 34229

Bathrooms Full

3

Bathrooms Half

1

Interior Features

Built-in Features, Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Thermostat, Tray Ceiling(s), Vaulted Ceiling(s), Walk-In Closet(s)

Appliances

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

Flooring

Marble, Tile

Heating

Electric

Cooling

Central Air

Furnished

Unfurnished

Garage Spaces

2

Attached Garage

Yes

Parking Features

Garage Door Opener

Pool Features

Deck, Heated, In Ground, Lap, Lighting, Outside Bath Access, Salt Water, Screen Enclosure, Solar Heat

Pool Private

Yes

Property Condition

Completed

Direction Faces

East

Building Information for 14401 MASTHEAD DRIVE, OSPREY, FL 34229

Building Area Total

3984

Building Area Units

Square Feet

Stories Total

1

Association

Yes

Association Fee

$1,928

Association Fee Frequency

Quarterly

Association Amenities

Gated

Pets Allowed

Breed Restrictions, Yes

Security Features

Closed Circuit Camera(s), Gated Community, Security System

Property Information for 14401 MASTHEAD DRIVE, OSPREY, FL 34229

Lot Features

Cul-De-Sac, Flood Insurance Required

Lot Size Square Feet

19,235

Waterfront

Yes

Waterfront Features

Bay/Harbor

View

Water

Construction Materials

Block, Stucco

Roof

Metal

Exterior Features

French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sidewalk, Sliding Doors

Sewer

Public Sewer

Water Source

Public

New Construction

No

Public Records for 14401 MASTHEAD DRIVE, OSPREY, FL 34229

Parcel Number

0148150048

Tax Annual Amount

$874

Tax Year

2025

Tax Legal Description

LOT 38, BAYSIDE, PB 49 PG 41, SUBJ TO 92 C-SF CONSERVATION ESMT TO TIITF/STATE OF FLORIDA AS DESC IN ORI 2015156164

Zoning

RSF1

County Or Parish

Sarasota

Schools Near 14401 MASTHEAD DRIVE, OSPREY, FL 34229

Elementary School

Laurel Nokomis Elementary

Middle School

Sarasota Middle

High School

Venice Senior High

School assignments are provided by the listing and should be independently verified.

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