14401 Masthead Drive
OSPREY, FL 34229
3
Bed
4
Bath
2,665Sqft
0.44Acre(Lot)
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 back
Property Details
Map
Map
What's Nearby
Nearby Areas
Features
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Bedroom Information
Total Bedroom: 3Bathroom Information
Total Baths: 4 Full Baths: 3 Half Baths: 1Interior 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) Roof: Metal 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 Laundry Features: Inside, Laundry RoomRoofing Information
Metal -
Flooring Information
Flooring: Marble, Tile Construction Materials: Block, Stucco -
Heating & Cooling
Heating: Electric Cooling: Central Air Water front: 1 WaterSource: Public
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Building Information
Year Built: 2017 -
Exterior Features
French Doors, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sidewalk, Sliding Doors Construction Materials: Block, Stucco Foundation Details: Stem Wall -
Pool Features
Private Pool: 1 Deck, Heated, In Ground, Lap, Lighting, Outside Bath Access, Salt Water, Screen Enclosure, Solar Heat
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Lot Information
Lot Description: Cul-De-Sac, Flood Insurance Required, Paved Lot Square Feet: 19235 Lot Acres: 0.44 Lot Size (SqMt): 1787Property Information
Property Type: Residential Sub Type: Single Family Residence
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Listing Price Information
Original List Price:$3250000
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Tax Information
Tax Block: 1 Tax Book Number: 49-41, Tax Lot: 38 Tax 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 Annual Tax: $874.45 Tax Year: 2025 Parcel Number: 0148150048
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Parking Information
Garage Door OpenerGarage Information
Has Garage: Yes Garage Space: 2 Garage Dimensions: 21x20Homeowners Association Information
Included Fees: Common Area Taxes, Escrow Reserves Fund, Maintenance Grounds, Management, Private Road Included Amenities: Gated HOA: $1,928.00 Quarterly
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School Information
Elementary School: Laurel Nokomis Elementary Junior High School: Sarasota Middle Senior High School: Venice Senior High -
Utility Information
Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected Sewer: Public Sewer Water Source: Public -
Location Information
Subdivision: BAYSIDE City: OSPREY Direction: 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.
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Nearby Home Value
| Address | Estimate | Bed | Bath | Sq. Ft | Lot Size |
|---|---|---|---|---|---|
| Undisclosed Address, Osprey, FL, 34229 | $799,000 | 4 | 3 | 2,607 | 2,607 SqFt |
| 408 Park Trace Boulevard, Osprey, FL, 34229 | $595,000 | 3 | 3 | 1,840 | 1,840 SqFt |
| 472 Park Trace Boulevard, Osprey, FL, 34229 | $599,000 | 4 | 2 | 2,217 | 2,217 SqFt |
| 619 Oak River Court, Osprey, FL, 34229 | $609,900 | 3 | 2 | 2,047 | 2,047 SqFt |
| 448 E Macewen Drive, Osprey, FL, 34229 | $2,100,000 | 4 | 4 | 3,768 | 3,768 SqFt |
| 1361 New Forest Lane, Osprey, FL, 34229 | $535,000 | 3 | 2 | 2,074 | 2,074 SqFt |
| 759 Fordingbridge Way, Osprey, FL, 34229 | $715,000 | 4 | 4 | 2,950 | 2,950 SqFt |
| 403 Longbow Trail, Osprey, FL, 34229 | $1,095,000 | 4 | 3 | 2,770 | 2,770 SqFt |
| 816 Shadow Bay Way, Osprey, FL, 34229 | $655,000 | 3 | 3 | 2,251 | 2,251 SqFt |
| 538 Dove Pointe Drive, Osprey, FL, 34229 | $1,950,000 | 4 | 6 | 4,346 | 4,346 SqFt |
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Based on information submitted to the MLS GRID as of 07/19/2026 @ 18:20. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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ByOwner last updated this listing 07/19/2026 @ 18:20
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