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14401 MASTHEAD DRIVE OSPREY FL 34229

$3,250,000
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14401 MASTHEAD DRIVE, OSPREY, FL 34229 - MLS#MFRA4684834 14401 MASTHEAD DRIVE, OSPREY, FL 34229 - MLS#MFRA4684834 14401 MASTHEAD DRIVE, OSPREY, FL 34229 - MLS#MFRA4684834 14401 MASTHEAD DRIVE, OSPREY, FL 34229 - MLS#MFRA4684834

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
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Overview of 14401 Masthead Dr

3 Bedrooms
3/1 Bathrooms
2 Car Garage
3,984 Square Feet
2,665SF Living Area
Pool:
Yes
Water
Year Built 2017
Listed For 1 Days

Don't miss this home for sale in Bayside! 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.

This luxury single family home was built in 2017 and features 3 bedrooms, and 3 full bathrooms plus 1 half bath. This home for sale is 3,984 square feet, with 2,665 sq ft being air conditioned living space. The home has a 2 car garage and has a private swimming pool.

Directions to this property are as follows: 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.

Please contact your ZFC agent for more information about MLS# MFRA4684834 or any other homes for sale in Osprey or elsewhere in the Sarasota County area.

Features & Amenities

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

Other Equipment

Irrigation Equipment

Cooling

Central Air

Heating

Electric

Flooring

Marble, Tile

Parking

Garage Door Opener

Lot Size

19235

View

Water view

Construction Materials

Block, Stucco

Security Features

Closed Circuit Camera(s), Gated Community, Security System

Interior Features

Built-in Features, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Thermostat, Tray Ceiling(s), Vaulted Ceiling(s), Walk-In Closet(s)

Furnished

Unfurnished

Exterior Features

French Doors, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sidewalk, Sliding Doors

Lot Features

Cul-De-Sac, Flood Insurance Required, Paved

Property Condition

Completed

Patio And Porch Features

Covered, Screened

Pool Features

Deck, Heated, In Ground, Lap, Lighting, Outside Bath Access, Salt Water, Screen Enclosure, Solar Heat

Roof

Metal

Window Features

Solar Screens

Utilities

Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected

Waterfront Features

Bay/Harbor

Water Body Name

L I T T L E S A R A S O T A B A Y

Laundry

Inside, Laundry Room

Fireplace

Electric, Living Room

Spa Features

Heated

Zoning

R S F1

Year Built

2017

Pets Allowed

Breed Restrictions, Yes

Annual Real Estate Taxes

$874 (2025)

Legal Description

Lot 38, Bayside, Pb 49 Pg 41, Subj To 92 C-sf Conservation Esmt To Tiitf/state Of Florida As Desc In Ori 2015156164

Property Type

Single Family Home

HOA Fees

$1,928 /Quarterly

Association Fee Includes

Common Area Taxes, Escrow Reserves Fund, Maintenance Grounds, Management, Private Road

Association Amenities

Gated

Community Features

Buyer Approval Required, Deed Restrictions, Golf Carts O K, Sidewalks

Direction Faces

East

MLS Number

MFRA4684834

Universal Property Id

U S-12115-N-0148150048-R-N

Days On Market

1

Community Name

Bayside

Property Manager

Bayside Community Association, Inc. 941-460-5560

14401 Masthead Dr Price Calculator

Get Mortgage Quote For This Home

The payment calculator figures for 14401 Masthead Dr should be used as an estimate only. Loan terms including interest rate, and required downpayment will vary with each lender and/or individual. RE taxes for this home for sale are estimated based on the actual property taxes for this property for the tax year 2025 which are $874 but will likely change when this home sells. These estimations are calculated from a list price of $3,250,000 and a 25% down payment and do not include homeowners insurance which will vary greatly depending on the home characteristics and location.

Recent Home Sales near 14401 Masthead Dr

Address Sale Price Bed Bth Size Location Sale Date
No comps found for this property

MLS# MFRA4684834 Listing History

03/04/2026 Listed for sale by MICHAEL SAUNDERS & COMPANY with MLS# MFRA4684834 with a list price of $3,250,000.

Sarasota County Schools

High School

Public Transportation

Breeze Transit:

77 Siesta Islander

Breeze Transit:

Sarasota/US-41/Venice

Breeze Transit:

77 Siesta Islander

Breeze Transit:

77 Siesta Islander

Breeze Transit:

Sarasota/US-41/Venice

This listing of 14401 Masthead Dr Osprey FL 34229 was last updated on 2026-03-06 14:12:39. Listing courtesy of MICHAEL SAUNDERS & COMPANY.
MLS

Map of 14401 Masthead Dr Osprey FL 34229

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Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
Call Me
Text Me
Email Me
When clicking Submit Request, you are registering to this website and agreeing that ZFC Real Estate, its affiliates or associated third parties may contact you, including with calls or texts by automated means. You also agree to our Terms of Use and Privacy Policy

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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