14401 Masthead Drive, Osprey, FL 34229

Osprey
Local realty services provided by:Better Homes and Gardens Real Estate Synergy
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...

Contact an agent

contact an agent

Yes, I would like more information. Please use and/or share my information with a BHGRE®  affiliated agent to contact me about my real estate needs. By clicking Send message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a BHGRE®  affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (CENTURY 21® , Coldwell Banker® , Corcoran® , ERA® , Sotheby's International Realty® ). I acknowledge that I have read and agree to theTerms of useandPrivacy notice

Home facts

  • Year built:2017
  • Subdivision & Development:BAYSIDE
  • Listing ID #:A4684834
  • Added:199 day(s) ago
  • Updated:September 21, 2026 at 04:53 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
MLS LogoThe information being provided by Stellar Mls is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Stellar Mls. Better Homes and Gardens Real Estate Synergy is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Better Homes and Gardens Real Estate Synergy, a broker participant of Stellar Mls. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by Stellar Mls and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited. Properties in listings may have been sold or may no longer be available. Copyright 2026 Stellar Mls. All rights reserved.

New listings near 14401 Masthead Drive