14401 MASTHEAD DRIVE
OSPREY, FL, 34229
$3,250,000
3 Beds
3.5 Baths
2,665 SqFt
0.44 Acres
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MLS #A4684834 image #0
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:
$3,250,000
MLS #:
A4684834
Status:
Active
Beds:
3
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
BAYSIDE
Neighborhood:
34229osprey
Listed Date:
Mar 5, 2026
Finished Sq Ft:
2,665
Total Sq Ft:
3,984
Lot Size:
19,235 sqft / 0.44 acres (approx)
Year Built:
2017
WaterfrontPoolPrimary Bedroom Main FloorCommunity Gated34229 – Osprey34229ospreyBaysideLaurel Nokomis ElementarySarasota MiddleVenice Senior HighLittle Sarasota BayWaterLease Restrictions1 MonthPets Allowed

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Schools

Elementary School:
Laurel Nokomis Elementary
Middle School:
Sarasota Middle
High School:
Venice Senior High

Interior

Appliances
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
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Marble, Tile
Heating
Electric
Laundry Features
Inside, Laundry Room

Exterior

Association Amenities
Gated
Community Features
Dock, Water Access, Buyer Approval Required, Deed Restrictions, Golf Carts OK, Sidewalks
Construction Materials
Block, Stucco
Exterior Features
French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sidewalk, Sliding Doors
Parking Features
Garage Door Opener
Roof
Metal
Security Features
Closed Circuit Camera(s), Gated Community, Security System

Financial

HOA Fee
$1,928
HOA Frequency
Quarterly
HOA Includes
Common Area Taxes, Escrow Reserves Fund, Maintenance Grounds, Manager, Private Road
HOA Name
Bayside Community Association, Inc.
Tax Year
2025
Taxes
$874

Map

Community

Market Summary

Current real estate data for Single Family in OSPREY as of Mar 13, 2026
115
Single Family Listed
121
Avg DOM
459
Avg $ / SqFt
$1,416,036
Avg List Price

Property Summary

    Located in the BAYSIDE subdivision, 14401 MASTHEAD DRIVE OSPREY FL is a Single Family for sale in OSPREY, FL, 34229. It is listed for $3,250,000 and features 3 beds, 4 baths, and has approximately 2,665 square feet of living space, and was originally constructed in 2017. The current price per square foot is $1,220. The average price per square foot for Single Family listings in OSPREY is $459. The average listing price for Single Family in OSPREY is $1,416,036. To schedule a showing of MLS#a4684834 at 14401 MASTHEAD DRIVE in OSPREY, FL, contact your CENTURY 21 Carioti agent at 2392986550.

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14401 MASTHEAD DRIVE
OSPREY, FL