Property Search/OSPREY/BAYSIDE

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Under contractPrice improved $400,000157 days on market

$2,850,000~~$3,250,000~~

14401 MASTHEAD DROSPREY, FL 34229BAYSIDE · Single Family Residence

3Beds

4Baths

2,665Sq ft

0.44 acLot

2-carGarage

2017Built

YesPool

YesWaterfront

About this home

Under contract-accepting backup offers. 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 millwo…

Description as provided by the listing brokerage.

Highlights

Heated saltwater pool
Water frontage — Bay/Harbor
2-car garage
Lighting
Outdoor Grill
Outdoor Kitchen
Outdoor Shower
Sidewalk
Built-in Features

Open houses

No open houses scheduled.

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The details

StatusUnder contract

MLS #MFRA4684834

Property typeSingle Family Residence

Year built2017

Lot size0.44 ac

Living area2,665 sq ft

Price per sq ft$1069

Baths4 + 1 half

HOA$1,928 / quarterly

CDDNo

Taxes$874 (2025)

Garage2-car

Stories1

Days on market157

CountySarasota

Flood zoneVE, AE (verify)

ListedMar 3, 2026

Features & property details

Interior

Full baths3

Half baths1

Rooms9

Additional roomsDen/Library/Office

FlooringMarble, Tile

AppliancesBar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Dryer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator

Interior featuresBuilt-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)

LaundryInside, Laundry Room

FireplaceYes

Fireplace featuresElectric, Living Room

WindowsSolar Screens

CoolingCentral Air

HeatingElectric

In-law suite0

Exterior & lot

Exterior featuresLighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sidewalk

Patio & porchCovered, Screened

ViewWater

Lot featuresCul-De-Sac, Flood Insurance Required, Paved

VegetationTrees/Landscaped

FacesEast

Road surfacePaved

Construction

ConstructionBlock, Stucco

FoundationStem Wall

RoofMetal

ConditionCompleted

Living area sourcePublic Records

Building area (sq ft)3,984

Parking

GarageYes

Attached garageYes

Garage dimensions21x20

CarportNo

Parking featuresGarage Door Opener

Pool & water

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

SpaYes

Spa featuresHeated

WaterfrontBay/Harbor

Water bodyLITTLE SARASOTA BAY

Water accessBay/Harbor

Water viewBay/Harbor - Full

Water extrasAssigned Boat Slip,Lift

Waterfront feet87

Dock0

Dock detailsDock w/Electric

Community & HOA

AssociationBayside Community Association, Inc.

HOA fee$1,928

HOA frequencyQuarterly

Fee includesCommon Area Taxes, Escrow Reserves Fund, Maintenance Grounds, Management, Private Road

AmenitiesGated

Fee requirementRequired

Approval required1

Total monthly fees$642.67

Total annual fees$7,712

Community featuresBuyer Approval Required, Deed Restrictions, Golf Carts OK, Sidewalks

55+ communityNo

PetsBreed Restrictions, Yes

Pet restrictions3 extra large pets

Pet sizeExtra Large (101+ Lbs.)

Max pet weight101

Number of pets3

Minimum lease1 Month

Lease restrictions1

Lease notesLease restrictions

SW communityBayside

Utilities & efficiency

UtilitiesCable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected

SewerPublic Sewer

Water sourcePublic

Financial & terms

CDD0

Tax year2,025

Homestead1

Listing termsCash, Conventional

OwnershipFee Simple

Special conditionsNone

Home warrantyNo

ZoningRSF1

OccupantOwner

MLS area34229 - Osprey

Where it sits

Open in Maps

Approximate location shown. Exact address available on request per listing brokerage.

Schools

ElementaryLaurel Nokomis ElementarySarasota County

MiddleSarasota MiddleSarasota County

HighVenice Senior HighSarasota County

School assignments change; verify with the district before relying on them.

Where you'd be

BAYSIDE, Florida

OSPREY · Sarasota County

Homes in OSPREY

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$2,850,00014401 MASTHEAD DR · OSPREY

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