• Buy
  • Rent
  • Sell
  • Agents
New DevelopmentWorld of Elliman
The latest in luxury property, lifestyle & culture, curated just for you.

Company

  • About Us
  • Leadership
  • Offices
  • Press & News
  • Elliman Cares
  • Join as an Agent
  • Careers
  • Elliman Global
  • Investors

Resources

  • World of Elliman
  • Elliman Insider
  • Magazines
  • Market Reports
  • Research Reports
  • Elliman Private Listings
  • New Elliman Exclusives
  • Featured Cities
  • Guides to Buying & Selling

Brand Portfolio

  • New Development
  • Commercial
  • Relocation
  • Sports & Entertainment
  • Farm & Ranch
  • Building Broker Specialists
  • Title Services
  • Estate, Trust & Probate

  • California
  • Colorado
  • Connecticut
  • Florida
  • Massachusetts
  • Mid-Atlantic
  • Nevada
  • New Jersey
  • New York
  • New York City
  • Texas
  • Vermont
  • Site Map
  • Terms
  • Privacy
  • Cookie Preferences
  • Do Not Sell or Share My Personal Information
  • NYS Housing Discrimination Disclosure Notice & Form
  • NYS Standard Operating Procedure
  • NYS Tenants' Rights to Reasonable Accommodations for persons with disabilities
  • California Consumer Privacy Act Notice
  • Texas Consumer Protection Notice
  • Texas Real Estate Commission Information About Brokerage Services
  • Text of NYC Human Rights Law
  • New York City Commission on Human Rights
  • NYC Source of Income Discrimination Information
  • NYC Source of Income Discrimination Tenant FAQs

THE SOURCE OF THE DISPLAYED DATA IS EITHER THE PROPERTY OWNER OR PUBLIC RECORD PROVIDED BY NON-GOVERNMENTAL THIRD PARTIES. IT IS BELIEVED TO BE RELIABLE BUT NOT GUARANTEED. FOR COLORADO VIEWERS, INFORMATION ABOUT NON-COMMERCIAL PROPERTIES IS PROVIDED EXCLUSIVELY FOR YOUR PERSONAL, NON-COMMERCIAL USE.

575 MADISON AVENUE, NEW YORK, NY 10022. 212.891.7000 © 2026 DOUGLAS ELLIMAN REAL ESTATE. EQUAL EMPLOYMENT OPPORTUNITY PROVIDER. ALL MATERIAL PRESENTED HEREIN IS INTENDED FOR INFORMATION PURPOSES ONLY. WHILE THIS INFORMATION IS BELIEVED TO BE CORRECT, IT IS REPRESENTED SUBJECT TO ERRORS, OMISSIONS, CHANGES, OR WITHDRAWAL WITHOUT NOTICE. ALL PROPERTY INFORMATION, INCLUDING, BUT NOT LIMITED TO SQUARE FOOTAGE, ROOM COUNT, NUMBER OF BEDROOMS, AND THE SCHOOL DISTRICT IN PROPERTY LISTINGS SHOULD BE VERIFIED BY YOUR OWN ATTORNEY, ARCHITECT, OR ZONING EXPERT. EQUAL HOUSING OPPORTUNITY. LISTING DATA REFRESHED ON APR 27 2026 AT 11:16 PM.

DOUGLAS ELLIMAN IS A LICENSED REAL ESTATE BROKER IN CALIFORNIA WITH LICENSE # 01947727, COLORADO WITH LICENSE # EC100053892, CONNECTICUT WITH LICENSE # REB.0314827, THE DISTRICT OF COLUMBIA WITH LICENSE # REO40000160, FLORIDA WITH LICENSE # CQ1020232, MARYLAND WITH LICENSE # 645270, MASSACHUSETTS WITH LICENSE # 422764, NEVADA WITH LICENSE # 1454643, NEW JERSEY WITH LICENSE # 0572105, NEW YORK WITH LICENSE # 10991211812, TEXAS WITH LICENSE # 9008706, AND VIRGINIA WITH LICENSE # 0226035659.

SCAMMERS ARE IMPERSONATING REAL ESTATE AGENTS AND USING ACTIVE LISTINGS TO REQUEST FAKE DEPOSITS. SHOULD YOU HAVE A QUESTION ABOUT THE LEGITIMACY OF A DOUGLAS ELLIMAN AGENT OR LISTING, PLEASE CONTACT THE AGENT DIRECTLY VIA THE “AGENTS” LINK IN THE TOP MENU. DOUGLAS ELLIMAN WILL NEVER ASK FOR ANY PAYMENT TO RESERVE, HOLD, OR VIEW A PROPERTY. THESE CHARGES ARE PROHIBITED UNDER NEW YORK LAW. IF YOU RECEIVE A SUSPICIOUS REQUEST FOR MONEY, DO NOT SEND FUNDS. REPORT IT TO THE NYS DEPARTMENT OF STATE AND NOTIFY DOUGLAS ELLIMAN. YOU CAN READ THE NEW YORK STATE DEPARTMENT OF STATE'S CONSUMER ALERT HERE.

This website has been translated using automated software for convenience. While reasonable efforts have been made to ensure accuracy, machine translation may contain errors and is not a substitute for human translation. Translations are provided “as is,” without any express or implied warranty regarding their accuracy, reliability, or completeness. Some content (including images or videos) may not be translated accurately. The official version of this website is the English version. Any discrepancies in translation are not binding and have no legal effect; the English version controls.

POWERED BY PURLIN.AI

14401 MASTHEAD Dr

osprey, FL 34229

$3,250,000

  • 3 BR
    3 BA, 1 HALF BA
    approx. 2,665 SF

Interested? Let's Connect

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.

Details

2,665 Sq Ft

0.44 Private Acres Lot Size

single family home

$1,928 Quarterly Maintenance/CC

$874 Annual Tax

Built in 2017

MLS/Listing ID A4684834

1 Stories

Amenities & Features

Outdoor Shower

Outdoor Kitchen

Outdoor Grill

Lighting

Living Room Fireplace

Electric Fireplace

Tile

Marble

Unfurnished

Heating - Electric

Walk-in Closets

Vaulted Ceilings

Tray Ceilings

Wine Refrigerator

Water Softener

Washer

Tankless Water Heater

Refrigerator

Range Hood

Microwave

Gas Water Heater

Dryer

Dishwasher

Public Water

Split Bedrooms

Open Floor Plan

Sidewalk

Irrigation System

French Doors

Community - Golf Carts OK

Community - Deed Restrictions

Community - Buyer Approval Required

Water View

Pool - Heated

Pool - Inground

Pool - Lap

Pool - Outside Bath Access

Pool - Salt Water

Pool - Screen Enclosure

Pool - Solar Heated

Covered

Screened

Parking - Garage Door Opener

Lot - Cul-de-sac

Inside

Laundry Room

Built-in Features

Crown Molding

Eat-in Kitchen

High Ceilings

Sliding Doors

Stem Wall

Ceiling Fans

Thermostat

Lot - Flood Insurance Required

Pool - Deck

Pool - Lighting

Metal

Bay/Harbor

Solar Screens

Public Sewer

Cooktop

Convection Oven

Built-in Oven

Bar Fridge

Association - Gated

Community - Water Access

Community - Sidewalks

Community - Dock

Construction - Stucco

Construction - Block

Cooling - Central Air

Pets Allowed

Estimate my mortgage

TOTAL MONTHLY COST

$0

  • PRINCIPAL & INTEREST

    $0

  • PROPERTY TAXES

    $0

  • Common Charges

    $0

HOME PRICE
DOWN PAYMENT
TERM
INTEREST

Interested In 14401 MASTHEAD Dr?