Beds
3
Baths
4
Sq Ft
2,665 sq ft
Year Built
2017
Lot Size
0.44 acres
Garage
2
About This 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.
Property Overview
Interior Features
Exterior & Lot
Pool & Spa
Waterfront
Utilities
Parking
HOA & Community
Financial Details
Schools
Directions
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.
Location
14401 MASTHEAD DRIVE, OSPREY, FL 34229
Listing Information
Schedule a Showing
How to Buy This Home
Multiple financing options available for this $2,995,000 home in OSPREY.
🏛️
FHA Loan
$104,825 Down
Government-backed, low down payment. Credit scores as low as 580.
🎖️
VA Loan
$0 Down
Zero down for eligible veterans, active duty, and military families.
🏦
Conventional
$149,750 Down
Traditional financing. As low as 3-5% down with good credit.
🌾
USDA Loan
$0 Down
Zero down for eligible rural areas. Income limits apply.
Florida Down Payment Assistance Programs
You may qualify for up to $35,000 in assistance to cover your down payment and closing costs.
Florida Hometown Heroes
Up to $35,000
First-time buyers working in FL
FL Assist
Up to $10,000
FHA, VA, or USDA borrowers
FL HLP Second Mortgage
Up to $10,000
First-time buyers, 0% deferred
Sarasota County SHIP
Varies
Income-qualifying Sarasota residents
Can You Afford This Home?
Quick check based on the 28% debt-to-income rule. Not a guarantee — just a starting point.
Listing information is deemed reliable but not guaranteed. All measurements and data should be independently verified. This information is provided by the Stellar MLS. The listing broker's offer of compensation is made only to participants of the MLS where the listing is filed. IDX information is provided exclusively for consumers' personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated: June 27, 2026.