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14401 Masthead Drive, Osprey, FL 34229

Osprey
Local realty services provided by:CENTURY 21 Circle
14401 Masthead Drive,Osprey, FL 34229
$2,850,000
  • 3 Beds
  • 4 Baths
  • 2,665 sq. ft.
  • Single family
  • Active
Listed by: mackenzie longueuil
Office: michael saunders & company
MLS#:A4684834
Source:MFRMLS

Price summary

  • Price:$2,850,000
  • Price per sq. ft.:$715.36
  • Monthly HOA dues:$642.67

About this home

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...

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Home facts

  • Year built:2017
  • Subdivision & Development:BAYSIDE
  • Listing ID #:A4684834
  • Added:193 day(s) ago
  • Updated:September 15, 2026 at 05:05 PM

Rooms and interior

  • Bedrooms:3
  • Total bathrooms:4
  • Full bathrooms:3
  • Half bathrooms:1
  • Flooring:Marble, Tile
  • Dining Description:Eat In Kitchen
  • Kitchen Description:Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Eat-in Kitchen, Microwave, Range Hood, Refrigerator, Water Softener, Wine Refrigerator
  • Bedroom Description:High Ceilings, Primary Bedroom Main Floor, Split Bedroom, Walk-In Closet(s)
  • Living area:2,665 sq. ft.

Heating and cooling

  • Cooling:Central Air
  • Heating:Electric
  • Central air:Yes

Structure and exterior

  • Roof:Metal
  • Year built:2017
  • Building area:2,665 sq. ft.
  • Lot area:0.44 Acres
  • Lot Features:Cul-de-sac, Paved
  • Construction Materials:Block, Stucco
  • Exterior Features:Covered Porch/Patio, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Screened, Sidewalk
  • Foundation Description:Stem Wall
  • Levels:1 Story

Schools

  • High school:Venice Senior High
  • Middle school:Sarasota Middle
  • Elementary school:Laurel Nokomis Elementary

Utilities

  • Water:Public, Water Connected
  • Sewer:Public Sewer, Sewer Connected

Finances and disclosures

  • Price:$2,850,000
  • Price per sq. ft.:$715.36
  • Tax amount:$874 (2025)

Features and amenities

  • Appliances:Bar Fridge, Built-in Oven, Convection Oven, Cooktop, Dishwasher, Dryer, Gas Water Heater, Irrigation Equipment, Microwave, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
  • Laundry features:Dryer, Inside, Laundry Room, Washer
  • Amenities:Built-In Features, Cable Connected, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, Gated, High Ceilings, Irrigation Equipment, Natural Gas Connected, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Thermostat, Tray Ceiling(s), Vaulted Ceiling(s), Walk-In Closet(s)
  • Pool features:Heated, In Ground, Lap, Outside Bath Access, Pool/Deck, Private Pool, Salt Water, Screen Enclosure, Solar Heat

Parking

  • Parking description:Attached Garage, Garage Door Opener
  • Garage:Yes
  • Garage spaces:2
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