14401 MASTHEAD DRIVE, Osprey, FL 34229

• 3 beds |
• 4 baths |
• 2,665 sqft

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.

Listing Status:

Active

Date Added:

March 5, 2026

Data Last Updated:

March 15, 2026 at 5:23PM

Listing Office:

MICHAEL SAUNDERS & COMPANY : 941-951-6660

Listing Agent:

Mackenzie Longueuil : 941-961-4023

MLS ID:

A4684834

Interior

• General: Built-in FeaturesCeiling Fans(s)Crown MoldingEat-in KitchenHigh CeilingsOpen FloorplanPrimary Bedroom Main FloorSplit BedroomThermostatTray Ceiling(s)Vaulted Ceiling(s)Walk-In Closet(s)
• Rooms: Den/Library/Office
• Appliances: Bar FridgeBuilt-In OvenConvection OvenCooktopDishwasherDryerGas Water HeaterMicrowaveRange HoodRefrigeratorTankless Water HeaterWasherWater SoftenerWine Refrigerator
• Laundry: InsideLaundry Room
• Flooring: MarbleTile
• A/C: Central Air
• Heating: Electric
• Fireplace: ElectricLiving RoomFireplace

Exterior

• General: French DoorsLightingOutdoor GrillOutdoor KitchenOutdoor ShowerSidewalkSliding DoorsHeated
• Other Structures: ScreenedCovered
• Pool: DeckHeatedIn GroundLapLightingOutside Bath AccessSalt WaterScreen EnclosureSolar Heat
• Parking: Garage Door Opener

Construction

• Roofing: Metal
• Windows: Solar Screens
• General: BlockStuccoOneStem Wall

Location

• Road/Access: Paved
• HOA Amenities: GatedCommon Area TaxesEscrow Reserves FundMaintenance GroundsManagementPrivate Road1928.0Quarterly
• Originating MLS: Stellar MLS
• County: Sarasota

Lot

• Zoning: RSF1LOT 38BAYSIDEPB 49 PG 41SUBJ TO 92 C-SF CONSERVATION ESMT TO TIITF/STATE OF FLORIDA AS DESC IN ORI 20151561640148150048
• View: Water

Utilities

• Utilities: Cable ConnectedElectricity ConnectedNatural Gas ConnectedSewer ConnectedWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple