- Lori Ann Bugliaro P.A., PA,REALTOR ®
- Tropic Shores Realty
- Helping My Clients Make the Right Move!
- Mobile: 352.585.0041
- Fax: 888.519.7102
- Mobile: 352.585.0041
- loribugliaro.realtor@gmail.com
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- 14401 Masthead Drive, OSPREY, FL 34229
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- MLS#: A4684834 ( Residential )
- Street Address: 14401 Masthead Drive
- Viewed: 8
- Price: $3,250,000
- Price sqft: $816
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Bay/Harbor
- Year Built: 2017
- Bldg sqft: 3984
- Bedrooms: 3
- Total Baths: 4
- Full Baths: 3
- 1/2 Baths: 1
- Garage / Parking Spaces: 2
- Days On Market: 24
- Additional Information
- Geolocation: 27.1837 / -82.4911
- County: SARASOTA
- City: OSPREY
- Zipcode: 34229
- Subdivision: Bayside
- Elementary School: Laurel Nokomis
- Middle School: Sarasota
- High School: Venice Senior
- Provided by: MICHAEL SAUNDERS & COMPANY
- Contact: Mackenzie Longueuil
- 941-951-6660

- DMCA Notice
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DescriptionUnobstructed 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 Floridas 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 chefs 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 youve always imagined.
Property Location and Similar Properties
All
Similar
Features
Waterfront Description
- Bay/Harbor
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
Association Amenities
- Gated
Home Owners Association Fee
- 1928.00
Home Owners Association Fee Includes
- Common Area Taxes
- Escrow Reserves Fund
- Maintenance Grounds
- Management
- Private Road
Association Name
- Bayside Community Association
- Inc.
Association Phone
- 941-460-5560
Carport Spaces
- 0.00
Close Date
- 0000-00-00
Cooling
- Central Air
Country
- US
Covered Spaces
- 0.00
Exterior Features
- French Doors
- Lighting
- Outdoor Grill
- Outdoor Kitchen
- Outdoor Shower
- Sidewalk
- Sliding Doors
Flooring
- Marble
- Tile
Furnished
- Unfurnished
Garage Spaces
- 2.00
Heating
- Electric
High School
- Venice Senior High
Insurance Expense
- 0.00
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)
Legal Description
- LOT 38
- BAYSIDE
- PB 49 PG 41
- SUBJ TO 92 C-SF CONSERVATION ESMT TO TIITF/STATE OF FLORIDA AS DESC IN ORI 2015156164
Levels
- One
Living Area
- 2665.00
Lot Features
- Cul-De-Sac
- Flood Insurance Required
- Paved
Middle School
- Sarasota Middle
Area Major
- 34229 - Osprey
Net Operating Income
- 0.00
Occupant Type
- Owner
Open Parking Spaces
- 0.00
Other Expense
- 0.00
Parcel Number
- 0148150048
Parking Features
- Garage Door Opener
Pets Allowed
- Breed Restrictions
- Yes
Pool Features
- Deck
- Heated
- In Ground
- Lap
- Lighting
- Outside Bath Access
- Salt Water
- Screen Enclosure
- Solar Heat
Property Condition
- Completed
Property Type
- Residential
Roof
- Metal
School Elementary
- Laurel Nokomis Elementary
Sewer
- Public Sewer
Tax Year
- 2025
Township
- 38S
Utilities
- Cable Connected
- Electricity Connected
- Natural Gas Connected
- Sewer Connected
- Water Connected
View
- Water
Water Source
- Public
Year Built
- 2017
Zoning Code
- RSF1
Disclaimer: All information provided is deemed to be reliable but not guaranteed.
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Listings provided courtesy of The Hernando County Association of Realtors MLS.
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The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Display of MLS data is usually deemed reliable but is NOT guaranteed accurate.
Datafeed Last updated on March 30, 2026 @ 12:00 am
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