14401 MASTHEAD DRIVE
Osprey, FL, 34229
Active Under Contract$2,850,000
14401 MASTHEAD DRIVE
Osprey, FL, 34229
Active Under Contract$2,850,000
3
Bedrooms
4
Bathrooms
2,665 sqft
Living Area
2017
Year Built
19,235
Lot Size (sqft)
$1,928
HOA / Quarterly
157
Days on Market
Dock Score™
DockOnlyWhat shaped this score
DockOnly.com rating, not provided by the MLS or listing broker.
Dock & Water AccessMLS
AI Aerial Imagery Detection
Detected by AI from open-source aerial mapping imagery and may not reflect current conditions. This information was not provided by the MLS or listing broker. Always verify dock infrastructure with the listing agent.
Open WaterDockOnly
This dock fronts open water — a bay, harbor or marina basin rather than a canal.
There is no across-the-canal bank here, so no canal width applies and boat length is not limited by room to turn around. Check depth, beam and slip dimensions with the listing agent.
Navigation RouteDockOnly
Data sources: SFWMD AHED waterway polygons · FHWA National Bridge Inventory 2024 · Not provided by the MLS or listing broker.
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.
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Location
Osprey, FL, 34229
Displayed by Blue Mar Real Estate Group Inc., Licensed Florida Real Estate Broker (DBPR CQ1018554) · [email protected]
Listing courtesy of MICHAEL SAUNDERS & COMPANY via Stellar MLS
Last checked: 5 hours ago
Listing updated: August 28, 2026
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Dock Score™
DockOnlyWhat shaped this score
DockOnly.com rating, not provided by the MLS or listing broker.
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