$3,250,000
14401 Masthead Drive Osprey, FL 34229 - LITTLE SARASOTA BAY
For Sale MLS# A4684834
3 beds 4 baths 2,665 sq ft Single Family
OPEN HOUSE: Sunday, 5/3 01:00 PM - 03:00 PM
Details for 14401 Masthead Drive
MLS# A4684834
Description for 14401 Masthead Drive, Osprey, FL, 34229 - LITTLE SARASOTA BAY
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.
Listing Information
Property Type: Residential, Single Family Residence
Status: Active
Bedrooms: 3
Bathrooms: 4
Lot Size: 0.44 Acres
Square Feet: 2,665 sq ft
Year Built: 2017
Garage: Yes
Stories: 1 Story
Construction: Block,Stucco
Construction Display: New Construction
Subdivision: Bayside
Foundation: Stem Wall
County: Sarasota
Construction Status: New Construction
School Information
Elementary: Laurel Nokomis Elementary
Middle: Sarasota Middle
High: Venice Senior High
Room Information
Main Floor
Porch: 30x19
Bedroom 3: 13x15
Bedroom 2: 15x12
Den: 12x11
Primary Bathroom: 10x15
Primary Bedroom: 19x15
Dining Room: 15x11
Kitchen: 16x15
Great Room: 26x19
Bathrooms
Full Baths: 3
1/2 Baths: 1
Additonal Room Information
Laundry: Laundry Room, Inside
Interior Features
Appliances: Built-In Oven, Wine Refrigerator, Convection Oven, Bar Fridge, Dishwasher, Microwave, Refrigerator, Dryer, Cooktop, Water Softener, Range Hood, Tankless Water Heater, Gas Water Heater, Washer
Flooring: Marble,Tile
Doors/Windows: Solar Screens
Fireplaces: Electric, Living Room
Additional Interior Features: Eat-In Kitchen, Split Bedrooms, Tray Ceiling(s), Walk-In Closet(s), Ceiling Fan(s), Vaulted Ceiling(s), High Ceilings, Crown Molding, Open Floorplan, Built-in Features, Main Level Primary
Utilities
Water: Public
Sewer: Public Sewer
Other Utilities: Cable Connected,Electricity Connected,Natural Gas Connected,Sewer Connected,Water Connected
Cooling: Ceiling Fan(s), Central Air
Heating: Electric
Exterior / Lot Features
Attached Garage: Attached Garage
Garage Spaces: 2
Parking Description: Garage, Garage Door Opener
Roof: Metal
Pool: Heated, In Ground, Outside Bath Access, Salt Water, Screen Enclosure, Solar Heat, Lap
Lot View: Bay,Water
Additional Exterior/Lot Features: Sprinkler/Irrigation, French Patio Doors, Outdoor Grill, Outdoor Shower, Outdoor Kitchen, Lighting, Screened, Covered, Cul-de-Sac, Landscaped, Buyer Approval Required
Waterfront Details
Standard Water Body: LITTLE SARASOTA BAY
Water Front Features: Bay Access, Bayfront
Community Features
Community Features: Golf Carts OK, Water Access, Gated, Dock, Sidewalks
Security Features: Security System, Closed Circuit Camera(s), Gated Community
Association Amenities: Gated
HOA Dues Include: Association Management, Maintenance Grounds, Reserve Fund, Road Maintenance, Common Areas, Taxes
Homeowners Association: Yes
HOA Dues: $1,928 / Quarterly
Driving Directions
From US-41 South, west on Bay Avenue and immediately left onto Sarabay Road. Once through gate, take a right and then another right onto Masthead Drive. 14401 is the last home on the left, at the end of the cul-de-sac.
Financial Considerations
Terms: Cash,Conventional
Tax/Property ID: 0148150048
Tax Amount: 874.45
Tax Year: 2025
A broker reciprocity listing courtesy: MICHAEL SAUNDERS & COMPANY
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Interest rate and annual percentage rate (APR) are based on current market conditions, are for informational purposes only, are subject to change without notice and may be subject to pricing add-ons related to property type, loan amount, loan-to-value, credit score and other variables. Estimated closing costs used in the APR calculation are assumed to be paid by the borrower at closing. If the closing costs are financed, the loan, APR and payment amounts will be higher. If the down payment is less than 20%, mortgage insurance may be required and could increase the monthly payment and APR. Contact us for details. Additional loan programs may be available. Accuracy is not guaranteed, and all products may not be available in all borrower's geographical areas and are based on their individual situation. This is not a credit decision or a commitment to lend.
Sales History & Tax Summary for 14401 Masthead Drive
Sales History
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Tax Summary
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
Schools
Schools nearby 14401 Masthead Drive
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The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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