14401 Masthead Drive, Osprey, FL 34229
For Sale $3,150,000
Save Property
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.
Built-in Features
Ceiling Fans(s)
Crown Molding
Eat-in Kitchen
High Ceilings
Open Floorplan
Primary Bedroom Main Floor
Split Bedroom
Thermostat
Tray Ceiling(s)
Vaulted Ceiling(s)
Walk-In Closet(s)
Gated
Taxes: $874.45
Tax Year: 2025
Association Fee: $1,928.00
Association Fee Frequency: Quarterly
French Doors
Lighting
Outdoor Grill
Outdoor Kitchen
Outdoor Shower
Sidewalk
Sliding Doors
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
Water
Bay/Harbor
Assigned Boat Slip
Lift
Little Sarasota Bay
View: Bay/Harbor - Full
Elementary School: Laurel Nokomis Elementary
Middle School: Sarasota Middle
Junior High: Sarasota Middle
High School: Venice Senior High
MLS Area: 34229 - Osprey
Total Square Footage: 3,984
Price per Square Feet: $1,181.99
Total Floors: 1
Water: Public
Construction: Block, Stucco
Date Listed: 2026-03-05 00:00:00
Pool: Y
Pool Description: Deck, Heated, In Ground, Lap, Lighting, Outside Bath Access, Salt Water, Screen Enclosure, Solar Heat
Private Spa: Y
Furnished: Unfurnished
Windows: Solar Screens
Parking: Garage Door Opener
Garage Description: Y
Garage Spaces: 2
Attached Garage: Y
Flooring: Marble, Tile
Roof: Metal
Heating: Electric
Cooling: Central Air
Fireplace: Y
Security: Closed Circuit Camera(S), Gated Community, Security System
Laundry: Inside, Laundry Room
Pets: Breed Restrictions, Yes
Sewer: Public Sewer
Lot Desc.: Cul-De-Sac, Flood Insurance Required, Paved
Parcel ID: 0148150048
Amenities: Gated
Listing Courtesy Of: Michael Saunders & Company
mackenzielongueuil@michaelsaunders.com
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
Price: $3,150,000
Sq Ft: 2,665
($1,182 per
sqft)
Bedrooms: 3
Bathrooms: 3
Partial Baths: 1
City: Osprey
County: Sarasota
Type: Single Family
Development: Bayside
Acres: 0.4400
Year Built: 2017
Listing Number: A4684834
Status Code: A-Active
Taxes: $874.45
Tax Year: 2025
Garage:
2
/
Y
Furnishings: Unfurnished
Pets Allowed: Breed Restrictions, Yes
Total Recurring Fees: $643
Total Recurring Fee Frequency: 0.00
Interior Features:
Built-in Features
Ceiling Fans(s)
Crown Molding
Eat-in Kitchen
High Ceilings
Open Floorplan
Primary Bedroom Main Floor
Split Bedroom
Thermostat
Tray Ceiling(s)
Vaulted Ceiling(s)
Walk-In Closet(s)
Amenities:
Gated
Financial Information:
Taxes: $874.45
Tax Year: 2025
Association Fee: $1,928.00
Association Fee Frequency: Quarterly
Exterior Features:
French Doors
Lighting
Outdoor Grill
Outdoor Kitchen
Outdoor Shower
Sidewalk
Sliding Doors
Equipment:
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
View:
Water
Waterfront Description:
Bay/Harbor
Assigned Boat Slip
Lift
Little Sarasota Bay
View: Bay/Harbor - Full
School Information:
Elementary School: Laurel Nokomis Elementary
Middle School: Sarasota Middle
Junior High: Sarasota Middle
High School: Venice Senior High
Additional Information:
MLS Area: 34229 - Osprey
Total Square Footage: 3,984
Price per Square Feet: $1,181.99
Total Floors: 1
Water: Public
Construction: Block, Stucco
Date Listed: 2026-03-05 00:00:00
Pool: Y
Pool Description: Deck, Heated, In Ground, Lap, Lighting, Outside Bath Access, Salt Water, Screen Enclosure, Solar Heat
Private Spa: Y
Furnished: Unfurnished
Windows: Solar Screens
Parking: Garage Door Opener
Garage Description: Y
Garage Spaces: 2
Attached Garage: Y
Flooring: Marble, Tile
Roof: Metal
Heating: Electric
Cooling: Central Air
Fireplace: Y
Security: Closed Circuit Camera(S), Gated Community, Security System
Laundry: Inside, Laundry Room
Pets: Breed Restrictions, Yes
Sewer: Public Sewer
Lot Desc.: Cul-De-Sac, Flood Insurance Required, Paved
Parcel ID: 0148150048
Amenities: Gated
Map of 14401 Masthead Drive, Osprey, FL 34229
Listing Courtesy Of: Michael Saunders & Company
mackenzielongueuil@michaelsaunders.com