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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.

Can't make it? Request a private showing.

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

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

MLS# MFRA4684834Listing courtesy of MICHAEL SAUNDERS & COMPANYLast updated Aug 28, 2026, 4:44 PM
$2,850,00014401 MASTHEAD DR · OSPREY
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