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$3,250,000
New Listing

14401 MASTHEAD DRIVE
OSPREY, FL 34229

For Sale|Single Family Residence|Active
3
Beds
4
Total Baths
3
Full Baths
1
Partial Bath
2,665
SqFt
$1,220
/SqFt
2017
Built
Subdivision:
BAYSIDE
County:
Sarasota
Call Now: 941-685-5565
Is this the listing for you? We can help make it yours.
941-685-5565
14401 MASTHEAD DRIVE14401 MASTHEAD DRIVE14401 MASTHEAD DRIVE14401 MASTHEAD DRIVE
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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.

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Listing Snapshot
Price 
$3,250,000
Days On Site 
0 Days
Bedrooms 
3
Inside Area (SqFt) 
2,665 sqft
Total Baths 
4
Full Baths 
3
Partial Baths 
1
Lot Size 
0.44 Acres
Year Built 
2017
MLS® Number 
A4684834
Status 
Active
Property Tax 
$874.45
HOA/Condo/Coop Fees 
$642.67 monthly
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
6 hours agoListing updated with changes from the MLS®
6 hours agoListing first seen on site
General Features
Acres 
0.44
Attached Garage 
Yes
Direction Faces 
East
Garage 
Yes
Garage Spaces 
2
Levels 
One
Number Of Stories 
1
Parking 
Garage Door OpenerAttached
Pets 
Breed RestrictionsYes
Property Sub Type 
Single Family Residence
Security 
Closed Circuit Camera(s)Gated CommunitySecurity System
Sewer 
Public Sewer
SqFt Total 
3984
Utilities 
Cable AvailableNatural Gas AvailableCable ConnectedElectricity ConnectedNatural Gas ConnectedSewer ConnectedWater Connected
Water Source 
Public
Zoning 
RSF1
Interior Features
Appliances 
Bar FridgeConvection OvenCooktopDishwasherDryerGas Water HeaterMicrowaveRange HoodRefrigeratorTankless Water HeaterWasherWater SoftenerWine Refrigerator
Cooling 
Central Air
Fireplace 
Yes
Fireplace Features 
ElectricLiving Room
Flooring 
MarbleTile
Furnished 
Unfurnished
Heating 
Electric
Interior 
Built-in FeaturesCrown MoldingEat-in KitchenHigh CeilingsOpen FloorplanTray Ceiling(s)Vaulted Ceiling(s)Walk-In Closet(s)
Laundry Features 
InsideLaundry Room
Spa 
Yes
Window Features 
Solar Screens
Balcony/Porch/Lanai 
Dimensions - 19x30Level - First
Bedroom 2 
Dimensions - 12x15Level - First
Bedroom 3 
Dimensions - 15x13Level - First
Den 
Dimensions - 11x12Level - First
Dining Room 
Dimensions - 11x15Level - First
Great Room 
Dimensions - 19x26Level - First
Kitchen 
Dimensions - 15x16Level - FirstFeatures - Kitchen Island
Master Bathroom 
Dimensions - 15x10Level - FirstFeatures - Double Vanity
Master Bedroom 
Dimensions - 15x19Level - First
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Exterior Features
Construction Details 
BlockStucco
Exterior 
LightingOutdoor GrillOutdoor KitchenOutdoor Shower
Lot Features 
Cul-De-SacPavedWaterfront
Patio And Porch 
CoveredScreened
Pool Features 
HeatedIn GroundLapSalt WaterScreen EnclosureSolar HeatPrivate
Private Pool 
Yes
Roof 
Metal
Spa 
Yes
Spa Features 
Heated
View 
Water
Waterfront 
Yes
Waterfront Features 
LITTLE SARASOTA BAY
Waterview 
Water
Windows/Doors 
Solar Screens
Community Features
Association Amenities 
Gated
Association Dues 
1928
Community Features 
GatedSidewalks
Financing Terms Available 
CashConventional
HOA Fee Frequency 
Quarterly
MLS Area 
34229 - Osprey
Roads 
Paved
Township 
38S
Schools
School District
Unknown
Elementary School
Laurel Nokomis Elementary
Middle School
Sarasota Middle
High School
Venice Senior High
Listing courtesy of MICHAEL SAUNDERS & COMPANY (941) 961-4023



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-03-05 11:14 PM EST

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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