Property Description

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.

Included Appliances

Bar FridgeBuilt-In OvenConvection OvenCooktopDishwasherDryerGas Water HeaterMicrowaveRange HoodRefrigeratorTankless Water HeaterWasherWater SoftenerWine Refrigerator

Property Details

Highlights

View

Yes

Waterfront

Yes

Interior

Additional Rooms

Den/Library/Office

Appliances

Bar FridgeBuilt-In OvenConvection OvenCooktopDishwasherDryerGas Water HeaterMicrowaveRange HoodRefrigeratorTankless Water HeaterWasherWater SoftenerWine Refrigerator

Bathrooms Total Decimal

3.5

Building Area Total

3984

Cooling

Central Air

Fireplace Features

ElectricLiving Room

Flooring

MarbleTile

Furnished

Unfurnished

Heating

Electric

Interior Features

Built-in FeaturesCeiling Fan(s)Crown MoldingEating Space In KitchenHigh CeilingsOpen FloorplanPrimary Bedroom Main FloorSplit BedroomThermostatTray Ceiling(s)Vaulted Ceiling(s)Walk-In Closet(s)

Laundry Features

InsideLaundry Room

Living Area

2665

Rooms Total

9

Security Features

Closed Circuit Camera(s)Gated CommunitySecurity System

Window Features

Solar Screens

Construction

Building Area Source

Public Records

Building Area Units

Square Feet

Construction Materials

BlockStucco

Direction Faces

East

Foundation Details

Stem Wall

Levels

One

Living Area Source

Public Records

Living Area Units

Square Feet

Num Timesper Year

4

Property Condition

Completed

Roof

Metal

Stories Total

Yes

Year Built

2017

Site & Exterior

Covered Spaces

2

Exterior Features

French DoorsIrrigation SystemLightingOutdoor GrillOutdoor KitchenOutdoor ShowerSidewalkSliding Doors

Flood Zone Code

VEAE

Garage Dimensions

21x20

Garage Spaces

2

I D X Participation

Yes

Lot Features

Cul-De-SacFlood Insurance Required

Lot Size Acres

0.44

Lot Size Area

19235

Lot Size Square Feet

19235

Lot Size Units

Square Feet

Parking Features

Garage Door Opener

Patio And Porch Features

CoveredScreened

Pool Features

DeckHeatedIn GroundLapLightingOutside Bath AccessSalt WaterScreen EnclosureSolar Heat

Public Survey Range

18E

Public Survey Section

10

Road Frontage Type

Street Paved

Road Surface Type

Paved

Sewer

Public Sewer

Spa Features

Heated

Total Acreage

1/4 to less than 1/2

Utilities

Cable ConnectedElectricity ConnectedNatural Gas ConnectedSewer ConnectedSolarWater Connected

Vegetation

Trees/Landscaped

View

Water

Water Access

Yes

Water Body Name

LITTLE SARASOTA BAY

Water Extras

Yes

Water Source

Public

Water View

Yes

Waterfront

Yes

Waterfront Features

Bay/Harbor

Waterfront Feet Total

87

Zoning

RSF1

Financials

Association Fee

1928

Association Fee Frequency

Quarterly

Association Fee Includes

Common Area TaxesEscrow Reserves FundMaintenance GroundsManagerPrivate Road

Calculated List Price By Calculated Sq Ft

1123.83

Contract Status Change Date

2026-03-05

Current Price

2995000

Feed Types

BBO

Lease Considered

Yes

Minimum Lease

1 Month

Monthly H O A Amount

642.67

Owner Name

ON RECORD

Ownership

Fee Simple

Parcel Number

0148150048

Public Survey Township

38S

Tax Annual Amount

874.45

Tax Block

Yes

Tax Book Number

49-41

Tax 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

Tax Lot

38

Tax Year

2025

Total Annual Fees

7712

Total Monthly Fees

642.67

Neighborhood & Lifestyle

Community & Association

Additional Lease Restrictions

Lease restrictions

Association Amenities

Gated

Association Approval Required

Yes

Association Email

robin@pinnaclecam.com

Association Fee Requirement

Required

Association Name

Bayside Community AssociationInc.

Association Phone

941-460-5560

Community Features

DockWater AccessBuyer Approval RequiredDeed RestrictionsGolf Carts OKSidewalks

Lease Restrictions

Yes

M L S Area Major

34229 - Osprey

Max Pet Weight

101

Number Of Pets

3

Pet Restrictions

3 extra large pets

Pet Size

Extra Large (101+ Lbs.)

Pets Allowed

Breed RestrictionsYes

S W Subdiv Community Name

Bayside

Subdivision Name

BAYSIDE

Schools

Ratings

Elementary

Laurel Nokomis Elementary

Middle

Sarasota Middle

High

Venice Senior High

Listing provided courtesy of STELLAR via IDX. Updated: Jun 27, 2026, 6:53pm.

14401 MASTHEAD DRIVE

14401 MASTHEAD DRIVE

Property Description

Property Details

Highlights

Interior

Construction

Site & Exterior

Financials

Neighborhood & Lifestyle

Community & Association

Schools

Mackenzie Longueuil

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14401 MASTHEAD DRIVE

14401 MASTHEAD DRIVE

Property Description

Property Details

Highlights

Interior

Construction

Site & Exterior

Financials

Neighborhood & Lifestyle

Community & Association

Schools

Mackenzie Longueuil