14401 MASTHEAD DRIVE
OSPREY, FL, 34229
Price$3,250,000
Beds3
Baths4
SqFt2,665
Baths4
SqFt2,665
Status:Active
Property Type:Residential
School:
Property Type:Residential
School:
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.
| Price | $3,250,000 | |
| Bedrooms | 3 | |
| Full Baths | 3 | |
| Half Baths | 1 | |
| Total Baths | 4 | |
| Lot Size Area | 19235 | |
| Lot Size Area Units | Square Feet | |
| Acres | 0.44 | |
| Property Type | Residential | |
| Sub type | Single Family Residence | |
| MLS Sub type | Single Family Residence | |
| 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) | |
| Exterior Features | French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sidewalk, Sliding Doors | |
| Year Built | 2017 | |
| Subdivision | BAYSIDE | |
| View | Water | |
| Roof | Metal | |
| Waterfront | LITTLE SARASOTA BAY | |
| Heating | Electric | |
| Foundation | Stem Wall | |
| Lot Description | Cul-De-Sac, Flood Insurance Required | |
| Laundry Features | Inside, Laundry Room | |
| Pool features | Deck, Heated, In Ground, Lap, Lighting, Outside Bath Access, Salt Water, Screen Enclosure, Solar Heat | |
| Parking Description | Garage Door Opener | |
| Garage spaces | 2 | |
| Association Name | Bayside Community Association, Inc. | |
| Association Fee | 1928 | |
| Association Amenities | Gated | |
| Directions | From US-41 South, west on Bay Avenue and immediately left onto Sarabay Road. Once through gate, take a right and then another right onto Masthead Drive. 14401 is the last home on the left, at the end of the cul-de-sac. | |
| County | Sarasota | |
| Latitude | 27.183671 | |
| Longitude | -82.491111 | |
| Market Area | 34229 – Osprey | |
| Address | 14401 MASTHEAD DRIVE, OSPREY, FL 34229 | |
| Postal Code | 34229 | |
| City | OSPREY | |
| State | FL | |
| Country | United States | |
| Listing Office | MICHAEL SAUNDERS & COMPANY | |
| Listing Office Phone | 941-951-6660 | |
| Listing Agent | Mackenzie Longueuil | |
| Listing Agent Phone | 941-961-4023 | |
| Special listing conditions | None | |
| Ownership | Fee Simple | |
| Terms | Cash, Conventional | |
| Elementary School | Laurel Nokomis Elementary | |
| Middle School | Sarasota Middle | |
| High School | Venice Senior High | |
| Days on market | 1 | |
| MLS Status | Active | |
| Listing Date | Mar 5, 2026 | |
| Listing Last Modified | Mar 6, 2026 | |
| Tax ID | 0148150048 | |
| Tax Year | 2025 | |
| Tax Annual Amount | 874 | |
| MLS Area | 34229 – Osprey | |
| MLS # | A4684834 | |
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