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OSPREY, FL 34229 14401 MASTHEAD DRIVE

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Presented By: MICHAEL SAUNDERS & COMPANY with 941-951-6660. - 941-951-6660
  • MLS# A4684834
  • 03/04/2026
  • Request Tour
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  • Beds • 3
  • Full/Half Baths • 3 / 1
  • SQFT • 2,665
  • Garage • 2

Home Details

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.
Presented By: MICHAEL SAUNDERS & COMPANY with 941-951-6660. - 941-951-6660

Interior Features for 14401 MASTHEAD DRIVE

Bedrooms

Total Bedrooms3

Bathrooms

Half Baths1
Total Baths4

Other Interior Features

LivingAreaSourcePublic Records
Air Conditioning Y/NYes
Fireplace FeaturesElectric, Living Room
Fireplace Y/NYes
FlooringMarble, Tile
Furnished Y/NUnfurnished
Heating Y/NYes
Interior AmenitiesBuilt-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)
Laundry FeaturesInside, Laundry Room
Total Stories1
Window FeaturesSolar Screens

General for 14401 MASTHEAD DRIVE

Additional Parcels Y/NNo
Additional RoomsDen/Library/Office
AppliancesBar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Dryer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
Assoc Fee Paid PerQuarterly
Association AmenitiesGated
Association Fee IncludesCommon Area Taxes, Escrow Reserves Fund, Maintenance Grounds, Manager, Private Road
Association NameBayside Community Association, Inc.
Attached Garage Yes
Body of WaterLITTLE SARASOTA BAY
Building Area UnitsSquare Feet
Carport Y/NNo
CityOSPREY
Community FeaturesDock, Water Access, Buyer Approval Required, Deed Restrictions, Golf Carts OK, Sidewalks
Construction MaterialsBlock, Stucco
CoolingCentral Air
CountySarasota
DirectionsFrom 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.
DockY/NNo
Elementary SchoolLaurel Nokomis Elementary
Facing DirectionEast
Flood Zone CodeVE, AE
Full Baths3
Garage Spaces2
Garage Y/NYes
HOA Fee$1928
HeatingElectric
High SchoolVenice Senior High
Home Warranty Y/NNo
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionLOT 38, BAYSIDE, PB 49 PG 41, SUBJ TO 92 C-SF CONSERVATION ESMT TO TIITF/STATE OF FLORIDA AS DESC IN ORI 2015156164
LevelsOne
Listing TermsCash, Conventional
Living Area UnitsSquare Feet
Lot Size Square Feet19235
Lot Size UnitsSquare Feet
MLS Area34229 - Osprey
Middle/Junior High SchoolSarasota Middle
Minimum Lease1 Month
Monthly HOA Amount642.67
New ConstructionNo
Occupancy TypeOwner
OwnershipFee Simple
Patio/Porch FeaturesCovered, Screened
Pet Size LimitExtra Large (101+ Lbs.)
Pets AllowedBreed Restrictions, Yes
Pool FeaturesDeck, Heated, In Ground, Lap, Lighting, Outside Bath Access, Salt Water, Screen Enclosure, Solar Heat
Property ConditionCompleted
Property SubtypeSingle Family Residence
Property TypeResidential
RoofMetal
STELLAR_InLawSuiteYNNo
Security FeaturesClosed Circuit Camera(s), Gated Community, Security System
Senior Community Y/NNo
SewerPublic Sewer
Spa FeaturesHeated
Standard StatusActive
StatusActive
Subdivision NameBAYSIDE
Tax Annual Amount874.45
Tax Lot38
Tax Year2025
Total Rooms9
UtilitiesCable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Solar, Water Connected
ViewWater
Water Access TypeBay/Harbor
Water Access Y/NYes
Water ViewBay/Harbor - Full
Water View Y/NYes
Waterfront FeaturesBay/Harbor
Year Built2017
ZoningRSF1

Exterior for 14401 MASTHEAD DRIVE

Building Area Total3984
Covered Spaces2
Exterior AmenitiesFrench Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sidewalk, Sliding Doors
Foundation DetailsStem Wall
Lot FeaturesCul-De-Sac, Flood Insurance Required
Lot Size Acres0.44
Lot Size Area19235
Parking FeaturesGarage Door Opener
Private PoolYes
Road Frontage TypeStreet Paved
Road Surface TypePaved
SpaYes
VegetationTrees/Landscaped
Water SourcePublic
Waterfront Y/NYes

Additional Details

Price History

Steven Silcock

Broker Owner
Price $3,250,000
MLS#A4684834
List Date 03/04/2026
Property Type Single Family
Phone 407.574.0218
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