14401 MASTHEAD DRIVE

House For Sale

$3,150,000

BTC: 49.21875000

ETH: 1,804.12371134

-$100K (2026/05/01)

90 days

Waterfront

For Sale

House

3 bds •

3 ba •

2,665 sqft

Overview

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.

Location

Florida • OSPREY • 34229 • House • For Sale • Waterfront

Details

Type:

Residential

Parking:

Garage Door Opener

Year Built:

2017

Lot:

0.44 Acres

Heating:

Electric

Price/sqft:

$1,182

Cooling:

Central Air

HOA:

$1,928

Type:

Residential

Parking:

Garage Door Opener

Year Built:

2017

Lot:

0.44 Acres

Heating:

Electric

Price/sqft:

$1,182

Cooling:

Central Air

HOA:

$1,928

Private inquiry

Talk to the advisor on this listing.

Floor plans, HOA docs, off-market comparables, scheduling a private showing — one message, direct to the local specialist.

Valuation

Our model vs. what's actually selling nearby.

Estimate

$1,197,500

$762K – $2.4M

Confidence Low

List vs. estimate

$2.0M above estimate

List $3,150,000 · +163.0%

Our model says this listing is priced above recent comparable activity. Room to negotiate.

Price per sq ft

$1,181

+195.9% vs. city median $399

Based on

6 MLS comparables

Median of recent comparable listings. Sold comps use closing price, active listings use list price.

Highlights

Annual tax

$874

2025

HOA

$1,928/qtr

Common Area Taxes, Escrow Reserves Fund, Maintenance Grounds

Pool

Deck

View

Water

Waterfront

Bay/Harbor

Garage

2 car garage

Pets

Allowed

All facts and features

Flooring

• Marble

• Tile

Heating

• Electric

Cooling

• Central Air

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 interior features

• Built-in Features

• Ceiling Fan(s)

• Crown Molding

• Eating Space In Kitchen

• High Ceilings

• Open Floorplan

• Primary Bedroom Main Floor

• Split Bedroom

• Thermostat

• Tray Ceiling(s)

• Vaulted Ceiling(s)

• Walk-In Closet(s)

Bedrooms and bathrooms

• Bedrooms: 3

• Bathrooms: 1

• Full bathrooms: 3
Parking

• Garage Door Opener

Property

• Levels: One

• Pool Private: Yes

• Exterior Features: French Doors / Irrigation System / Lighting / Outdoor Grill / Outdoor Kitchen / Outdoor Shower / Sidewalk / Sliding Doors

Lot

• Lot: 0.44 Acres

Other Property Information

• Parcel Number: 0148150048

• Zoning: RSF1
Type and style

• Property Type: Residential

• Property Sub Type: Single Family Residence
Utility

• Cable Connected

• Electricity Connected

• Natural Gas Connected

• Sewer Connected

• Solar

• Water Connected
Other financial information

• HOA: $1,928

• HOA Frequency: Quarterly

• Annual tax amount: $874
Source details

• MLS ID: A4684834

Other facts

• Construction Materials: Block / Stucco

• Foundation Details: Stem Wall

• Fireplace Features: Electric / Living Room

• Laundry Features: Inside / Laundry Room

• Lot Features: Cul-De-Sac / Flood Insurance Required

• Patio And Porch Features: Covered / Screened

• Pool Features: Deck / Heated / In Ground / Lap / Lighting / Outside Bath Access / Salt Water / Screen Enclosure / Solar Heat

• Window Features: Solar Screens

• Direction Faces: East

• Waterfront: Yes

• Fireplace: Yes

• Water Body Name: LITTLE SARASOTA BAY

• Garage Spaces: 2

• Attached Garage: Yes

• Garage: Yes

• Living Area: 2665

• Water Source: Public

• Subdivision Name: BAYSIDE

Private inquiry

Talk to the advisor on this listing.

Floor plans, HOA docs, off-market comparables, scheduling a private showing — one message, direct to the local specialist.

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Market around this address

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The multiple listing information is provided by the Stellar MLS from a copyrighted compilation of listings. The compilation of listings and each individual listing are ©2026-present Stellar MLS. All Rights Reserved. The information provided is for consumers' personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Listing courtesy of: MICHAEL SAUNDERS & COMPANY

14401 MASTHEAD DRIVE

Overview

Location

Details

Valuation

Highlights

Interior details

Property details

Construction details

Utilities / Green Energy Details

HOA and Financial Details

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