$3,150,000
14401 Masthead Drive
Osprey, FL 34229
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 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.
Estimated monthly payment
$18,087/mo
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history64 days on market
- Status: ActiveMay 27, 2026
- Listed$3,250,000Mar 5, 2026
- Price reduced$3,150,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 64
- Subdivision
- Bayside
- County
- Sarasota
- Year built
- 2017
- Living area
- 2,665 sq ft
- Price/sq ft
- $1,182
- Building area
- 3,984 sq ft (Public Records)
- Lot size
- 19,235 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- VE, AE (12115C0236F)
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $874 (2025)
- Parcel #
- 0148150048
- Zoning
- RSF1
- MLS #
- A4684834
Interior Details
- Bedrooms
- 3
- Full bathrooms
- 3
- Half bathrooms
- 1
- Flooring
- Marble, Tile
- 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
- 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)
- Laundry
- Inside, Laundry Room
- Stories / Levels
- One
- Direction faces
- East
- Fireplace
- Yes
Heating & Cooling
- Heating
- Electric
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Garage Door Opener
HOA & Financial
- HOA fee
- $1,928 / Quarterly
- Monthly HOA
- $643/mo
- Total monthly fees
- $643/mo
- Total annual fees
- $7,712
- HOA name
- Bayside Community Association, Inc.
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 1 Month
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- Lease restrictions
- Approval process
- Approval required
Exterior & Construction
- Exterior features
- French Doors, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sidewalk, Sliding Doors
- Construction materials
- Block, Stucco
- Roof
- Metal
- Foundation
- Stem Wall
- Pool
- Private pool
- Waterfront
- Yes
- Water access
- Yes
- Water view
- Yes
- Road surface
- Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected
Community
- Pets allowed
- Breed Restrictions, Yes
Schools
School data from listing agent. Verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Great Room | First | 19x26 |
| Kitchen | First | 15x16 |
| Dining Room | First | 11x15 |
| Primary Bedroom | First | 15x19 |
| Primary Bathroom | First | 15x10 |
| Den | First | 11x12 |
| Bedroom 2 | First | 12x15 |
| Bedroom 3 | First | 15x13 |
| Balcony/Porch/Lanai | First | 19x30 |
Listing Details
- Listing date
- 2026-03-04
- On market date
- 2026-03-05
- Original list price
- $3,250,000
- Occupant type
- Owner
- MLS area
- 34229 - Osprey
- Listing AOR
- Sarasota - Manatee
- Status changed
- 2026-05-27
- 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
Location
- Flood zone
- VE, AE(12115C0236F)
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.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of May 27, 2026 at 1:06 PM ET. All data is obtained from various sources and may not have been verified by 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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