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3 Beds
4 Baths
2,665 sqft

$2,850,000

14401 MASTHEAD DR, OSPREY FL, 34229

Price per sqft$1,069.42
Built in2017
Property size2,665 sqft
Property typeResidential
Courtesy of MICHAEL SAUNDERS & COMPANY, Mackenzie Longueuil  Listing Contact: 941-951-6660

Overview

Under contract

Pending

Listed Mar 5, 2026

Updated 2 weeks ago

Under contract-accepting backup offers. 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.

$18,961/mo

Est. mortgage payment based on a $2,850,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
A4684834

Interior Features

Bedrooms
3
Bathrooms
4
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
0.44 Acres

Other Property Details

Taxes
$874
Tax Frequency
Annually
Association Fee Frequency
Monthly
Garage
Yes
View
Yes
Pets Allowed
Yes
Pool
Yes
Waterfront
Yes
55+/Senior Community
No

Listings courtesy of Stellar MLS as distributed by MLS GRID

All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) nor Chris Carpenter shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Properties displayed may be listed or sold by various participants in the MLS. 

Based on information submitted to the MLS GRID as of 9:00 AM UTC on 9/17/2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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