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96 photos

$2,850,000

14401 MASTHEAD DR
OSPREY, FL 34229
Listed by MICHAEL SAUNDERS & COMPANY
Bedrooms
3
Bathrooms
3.1
Living area
2,665 sqft
Year built
2017

About this home

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.

Highlights

WaterfrontPrivate poolFireplace

Property details

MLS #
MFRA4684834
Property type
Single Family Residence
Subdivision
BAYSIDE
Status
Active
Days on market
153
On market date
March 5, 2026
Stories
N/A
Total bathrooms
4
Garage spaces
2
Parking spaces
N/A
Lot size
0.44 acres
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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
LAUREL NOKOMIS SCHOOL
5.18 mi away · Grades -1-8
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,342
Student:teacher ratio
14.7:1
District
SARASOTA
Middle
SARASOTA MIDDLE SCHOOL
6.41 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,217
Student:teacher ratio
17.9:1
District
SARASOTA
High
VENICE SENIOR HIGH SCHOOL
6.97 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
1.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
2,452
Student:teacher ratio
22.5:1
District
SARASOTA

Mortgage calculator

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Est. monthly payment
$17,313/mo
$570,000 down
$2,280,000 loan
Principal & interest$14,788
Property tax (est.)$2,375
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 5 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.