14401 MASTHEAD DRIVE, OSPREY, FL 34229 | MLS #MFRA4684834 | Berkshire Hathaway HomeServices Florida Network Realty
Maria Wilkes

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Listing provided courtesy of MICHAEL SAUNDERS & COMPANYas Distributed by MLSGrid- MLS# MFRA4684834MLS Provider

14401 MASTHEAD DRIVEOSPREY, FL 34229

Single Family · 3 Beds · 3 Full Baths · 1 Half Bath · 2,665 Sq. ft. | 0.44 Acres
$2,995,000 Active

14401 MASTHEAD DRIVE Overview

Time on Site:
117 days
Visits:
0

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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14401 MASTHEAD DRIVE Facts & Features

  • Type Single Family
  • Sq. ft. 2,665
  • Price/Sq.ft. $1,124
  • Lot 0.44 Acres

Details

General

Association/HOA

  • Association Amenities: Gated
  • Association Fee: 1928
  • Association Fee Frequency: Quarterly
  • Association Fee Includes: Common Area Taxes,Escrow Reserves Fund,Maintenance Grounds,Management,Private Road
  • Association Name: Bayside Community Association, Inc.
  • Association: Yes

School Information

  • Elementary School: Laurel Nokomis Elementary
  • Middle Or Junior School: Sarasota Middle
  • High School: Venice Senior High

Building Information

  • New Construction: No
  • Year Built: 2017

Location/Region

  • Country: US
  • County Or Parish: Sarasota
  • MLS Area Major: 34229 - Osprey
  • Subdivision Name: BAYSIDE
  • Township: 38S

Community/Development

  • Community Features: Buyer Approval Required,Deed Restrictions,Golf Carts OK,Sidewalks

Tax Information

  • Tax Annual Amount: 874.45
  • Tax Year: 2025

General Information

  • Furnished: Unfurnished
  • Listing Terms: Cash,Conventional
  • Ownership: Fee Simple
  • Parcel Number: 0148150048
  • Pets Allowed: Breed Restrictions,Yes
  • Property Condition: Completed
  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Senior Community: No
  • Special Listing Conditions: None
  • Zoning: RSF1

Interior

Parking Information

  • Garage Spaces: 2
  • Garage: Yes

Beds/Baths

  • Bathrooms Full: 3
  • Bathrooms Half: 1
  • Bathrooms Total: 4
  • Bedrooms Total: 3

Building Interior

  • Building Area Source: Public Records
  • Building Area Total: 3984
  • Building Area Units: Square Feet

General Information

  • 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
  • Cooling: Central Air
  • Fireplace Features: Electric,Living Room
  • Fireplace: Yes
  • Flooring: Marble,Tile
  • Foundation Details: Stem Wall
  • Heating: Electric
  • Interior Features: Built-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)
  • Laundry Features: Inside,Laundry Room
  • Levels: One
  • Living Area: 2665
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Other Equipment: Irrigation Equipment
  • Security Features: Closed Circuit Camera(s),Gated Community,Security System
  • Spa Features: Heated
  • Spa: Yes
  • Stories Total: 1
  • Window Features: Solar Screens

Exterior

Parking Information

  • Parking Features: Garage Door Opener

Lot Information

  • Additional Parcels: No
  • Lot Features: Cul-De-Sac,Flood Insurance Required,Paved
  • Lot Size Acres: 0.44
  • Lot Size Square Feet: 19235
  • Road Surface Type: Paved
  • Vegetation: Trees/Landscaped
  • Water Source: Public

Waterfront/View

  • View: Water
  • Water Body Name: LITTLE SARASOTA BAY
  • Waterfront Features: Bay/Harbor
  • Waterfront: Yes

Building Exterior/Construction

  • Attached Garage: Yes
  • Construction Materials: Block,Stucco
  • Direction Faces: East
  • Patio And Porch Features: Covered,Screened
  • Roof: Metal

General Information

  • Carport: No
  • Exterior Features: French Doors,Lighting,Outdoor Grill,Outdoor Kitchen,Outdoor Shower,Sidewalk,Sliding Doors
  • Pool Features: Deck,Heated,In Ground,Lap,Lighting,Outside Bath Access,Salt Water,Screen Enclosure,Solar Heat
  • Pool Private: Yes
  • Sewer: Public Sewer
  • Utilities: Cable Connected,Electricity Connected,Natural Gas Connected,Sewer Connected,Water Connected

Room Information

Room: Balcony/Porch/Lanai

  • Level: First
  • Dimensions: 19x30
  • Length: 30
  • Width: 19

Room: Bedroom 2

  • Level: First
  • Dimensions: 12x15
  • Length: 15
  • Width: 12
  • Features: En Suite Bathroom

Room: Bedroom 3

  • Level: First
  • Dimensions: 15x13
  • Length: 13
  • Width: 15
  • Features: En Suite Bathroom

Room: Den

  • Level: First
  • Dimensions: 11x12
  • Length: 12
  • Width: 11

Room: Dining Room

  • Level: First
  • Dimensions: 11x15
  • Length: 15
  • Width: 11

Room: Great Room

  • Level: First
  • Dimensions: 19x26
  • Length: 26
  • Width: 19
  • Features: Built-In Shelving

Room: Kitchen

  • Level: First
  • Dimensions: 15x16
  • Length: 16
  • Width: 15
  • Features: Kitchen Island,Walk-In Pantry

Room: Primary Bathroom

  • Level: First
  • Dimensions: 15x10
  • Length: 10
  • Width: 15
  • Features: Double Vanity

Room: Primary Bedroom

  • Level: First
  • Dimensions: 15x19
  • Length: 19
  • Width: 15

14401 MASTHEAD DRIVE Neighborhood

Community

34229 (OSPREY) Demographics

61
Median Age
972
Population Density (per sq. mile)
69%
College Educated
$88,542
Estimated Median Income
3,011
Estimated Total Home Owners
476
Estimated Total Renters
86% / 14%
Estimated Owner / Renter Divide
2
Estimated Average Household Size
Community data courtesy of LiveBy, Inc.

Schools

School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.

14401 MASTHEAD DRIVE Monthly Cost

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Dylan Leitman
* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

14401 MASTHEAD DRIVE Market Data

Based on the last 30 days in this zip code

$1,115,332
Average List Price
$460
Average Price per Square Foot
20
Properties Sold
160
Average Days on Market
148
Properties for Sale
Calculations provided by Reliance Network

14401 MASTHEAD DRIVE History

Date Event Value Agent
6/12/2026Source: My Florida Regional MLS Price Reduction
$2,995,000 -4.9%
5/1/2026Source: My Florida Regional MLS Price Reduction
$3,150,000 -3.1%
3/5/2026Source: My Florida Regional MLS Added to Database
March 05, 2026
10/14/2022Source: My Florida Regional MLS Added to Database
October 14, 2022