Properties

Property Description

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.

Features
: Heated, In Ground, Deck, Lighting, Salt Water, Screen Enclosure, Outside Bath Access, Solar Heat, Lap
: Electric
: Central Air
: Water
: Yes, Breed Restrictions
: Covered, Screened
: Unfurnished
: Dishwasher, Dryer, Microwave, Refrigerator, Washer, Convection Oven, Cooktop, Range Hood, Tankless Water Heater, Water Softener, Built-In Oven, Gas Water Heater, Wine Refrigerator, Bar Fridge
: Buyer Approval Required, Deed Restrictions, Golf Carts OK, Sidewalks, Water Access, Dock
: Irrigation System, Sliding Doors, Outdoor Shower, Sidewalk, Lighting, French Doors, Outdoor Grill, Outdoor Kitchen
: Living Room, Electric
: Tile, Marble
2
: Eating Space In Kitchen, Open Floorplan, Walk-in Closet(s), Split Bedroom, Tray Ceiling(s), Thermostat, Vaulted Ceiling(s), Crown Molding, Ceiling Fan(s), Primary Bedroom Main Floor, Built-in Features, High Ceilings
: Laundry Room, Inside
: Flood Insurance Required, Cul-de-sac
: Garage Door Opener
: Metal
: Security System, Gated Community, Closed Circuit Camera(s)
: Public Sewer
: Heated
: Electricity Connected, Cable Connected, Sewer Connected, Water Connected, Natural Gas Connected, Solar
: Bay/harbor
Address Map
FL
Sarasota
OSPREY
34229
14401 MASTHEAD DRIVE
1
W83° 30' 32''
N27° 11' 1.2''
East
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.
BAYSIDE
MLS Addon
: Gated
$1,928
Quarterly
: Common Area Taxes, Maintenance Grounds, Manager, Private Road, Escrow Reserves Fund
: Block, Stucco
45
Laurel Nokomis Elementary
: Stem Wall
Venice Senior High
: One
281521991
281504998
: Cash, Conventional
Sarasota Middle
: Completed
: Street Paved
: No
1
$874
2025
: Public
RSF1

Residential For Sale

14401 MASTHEAD DRIVE, OSPREY, Florida 34229

3 Bedrooms
3 Bathrooms
2,665 Sqft
Visits : 47 in 50 days
$3,250,000
Listing ID #A4684834
Basic Details
Property Type : Residential
Listing Type : For Sale
Listing ID : A4684834
Status : Active
Brokerage Name : MICHAEL SAUNDERS & COMPANY
Agent Name : Mackenzie Longueuil
Bathrooms Total : 3.5
Price : $3,250,000
Bedrooms : 3
Rooms : 9
Bathrooms : 3
Half Bathrooms : 1
Square Footage : 2,665 Sqft
Year Built : 2017
Lot Size : 0.44 Acre
Building Area : 3,984 Sqft
Property SubType : Single Family Residence
Agent info
Gulf Sands Realty
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Gulf Sands Realtors

Steve Foster

Stevefosterhomes14@gmail.com

Magdalena Carr

Mcarr.FloridaHomes@hotmail.com

Kristen Silver

kristengulfsandsrealty@gmail.com

Karen Macdonald

Floridahousedream@gmail.com