FL
Sarasota
OSPREY
34229
14401 MASTHEAD DRIVE
14401 MASTHEAD DRIVE, OSPREY, FL 34229
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Listing Type
Single Family
Listing Status
Active
96
$3,250,000

Home Details for 14401 MASTHEAD DRIVE

Price
$3,250,000
Type
Residential
Bedrooms
3
Bathrooms
4.0
Square feet
2665
Year built
2017
Lot size acres
0.44
County
Sarasota
Total rooms
9
Garage
2
Days on site
0
MLS Listing#
A4684834
Hoa
1928
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 Features
  • House Interior
    • Built-in Features
    • Crown Molding
    • Eat-in Kitchen
    • High Ceilings
    • Open Floorplan
    • Tray Ceiling(s)
    • Vaulted Ceiling(s)
    • Walk-In Closet(s)
  • Utilities
    • Cable Available
    • Natural Gas Available
    • Cable Connected
    • Electricity Connected
    • Natural Gas Connected
    • Sewer Connected
    • Water Connected
  • Parking
    • Garage Door Opener
    • Attached
  • Fire Place
    • Electric
    • Living Room
  • Cooling Information
    • Central Air
  • Heating Information
    • Electric
  • Water Features
    • Public
  • Garage
    • 1
School Information
School Information for 14401 MASTHEAD DRIVE, OSPREY, FL 34229
Elementary School
Laurel Nokomis Elementary
Middle School
Sarasota Middle
High School
Venice Senior High
Listing Courtesy: MICHAEL SAUNDERS & COMPANY - 941-951-6660
Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright ©2026 MLS GRID. All Rights Reserved.
Last Updated: 2026-03-06 13:40:24
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EXIT KING REALTY
1800 S. Tamiami Trail, Venice, FL 34293
Dwayne Summers
License #: 3645659
Sales Representative
Office
941 497 6060
Agent
941 204 9828
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