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
See this Listing
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
- Address14401 MASTHEAD DRIVE OSPREY FL
- SubdivisionBAYSIDE
- CityOSPREY
- CountySarasota
- Zip Code34229
Subdivisions in OSPREY
- ACREAGE & UNREC
- ARBORS
- BAY ACRES – RESUB
- BAY OAKS ESTATES
- BAY OAKS ESTATES UNIT 1
- BAY STREET VILLAGE
- BAYPOINTE VISTA 1
- BAYPOINTE VISTA 2
- BAYSIDE
- BISHOPS COURT AT OAKS PRESERVE
- BISHOPSCOURT AT THE OAKS PRESERVE
- BISHOPSCOURT TOWNHOME ONE
- BLACKBURN HARBOR RESIDENCES
- BLACKBURN HARBOR WATERFRONT VILLAS
- BLACKBURN HARBOR WATERFRONT VILLAS PHASE 2
- BLACKBURN POINT WOODS
- CASEY KEY
- CORDES COVE
- DRY SLIPS AT BELLAGIO VILLAGE
- EDGEWATER/HIDDEN BAY PH 1 BLDG
- EDGEWATER/HIDDEN BAY PH 3
- EDGEWATER/HIDDEN BAY PH II BLD
- HARMS SUB
- HERON BAY CLUB SEC I
- HERON HOUSE
- HIDDEN BAY
- MERIDIAN AT THE OAKS
- MERIDIAN AT THE OAKS PRESERVE
- NORTH CREEK ESTATES
- OAKS
- OAKS 2 PH 1
- OAKS 2 PH 2
- OAKS 2 PH 4-A
- OAKS 2 PH 4-C PT 3
- OAKS 2 PHASE 2
- OAKS 3 PH 1
- OGBURNS T B ADD
- OSPREY EXECUTIVE PARK
- OSPREY HARBOR VILLAGE
- OSPREY PARK 2
- PALMS/CASEY KEY
- PARK TRACE ESTATES
- PHASE 1 OF BAY STREET
- PHASE 2 OF BAY STREET
- PINE RANCH
- PINE RANCH EAST
- PINE RUN I
- PINE RUN II
- PINE RUN III
- RIVENDELL
- RIVENDELL THE WOODLANDS
- RIVENDELL WOODLANDS
- SARABAY ACRES
- SAUNDERS V A RESUB
- SIESTA REV RESUB OF PT
- SORRENTO SHORES
- SOUTH CREEK
- SOUTHBAY YACHT & RACQUET CLUB
- THE OAKS
- THE OAKS BAYSIDE
- TOWNS-END SHORES
- VILLAS AT BELLAGIO HARBOR VILLAGE
- VILLAS/HARBOR VILLAGE
- WILLOWBEND PH 1
- WILLOWBEND PH 3
- WILLOWBEND PH 4
- WILLOWBEND PHASE 3
- WINDSOR LODGE AT THE OAKS
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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Courtesy of MICHAEL SAUNDERS & COMPANY. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 14401 MASTHEAD DRIVE
OSPREY, FL































































































