$2,850,000
Est. $14,637/mo principal and interest at 6.65% with 20% down
3 bd · 3.5 ba · 2,665 sqft · Single Family Residence
Active
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.
Monthly costs
- HOA
- $643/mo
- Includes
- Common Area Taxes, Escrow Reserves Fund, Maintenance Grounds, Manager, Private Road
- Est. monthly fees
- $643/mo
Bayside Community Association, Inc.
Estimated total including HOA and other monthly association fees
Key facts
- Type
- Single Family Residence
- Size
- 2,665 sqft
- Bedrooms
- 3
- Bathrooms
- 3.5
- Avg. price per sqft
- $1,069
- Days on market
- 172
- Year built
- 2017
- Lot size
- 0.44 acres
- Parking
- 2-car garage
- HOA
- $643/mo
- Annual taxes
- $874
- Flood zone
- AE
- Heating
- Electric
- Cooling
- Central Air
- Pets
- Breed Restrictions, Yes
- Waterfront
- Yes
- Furnished
- Unfurnished
- Subdivision
- BAYSIDE
- Financing
- Cash, Conventional
- Stories
- 1
- Levels
- One
- County
- Sarasota
- MLS number
- A4684834
- Status
- Active
- Property address
- 14401 Masthead Dr, Osprey, FL 34229
Features and extras
- 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
- Built-in Features
- Ceiling Fan(s)
- Crown Molding
- Eating Space In Kitchen
- High Ceilings
- Open Floorplan
- Primary Bedroom Main Floor
- Split Bedroom
- Thermostat
- Tray Ceiling(s)
- Vaulted Ceiling(s)
- Walk-In Closet(s)
- French Doors
- Irrigation System
- Lighting
- Outdoor Grill
- Outdoor Kitchen
- Outdoor Shower
- Sidewalk
- Sliding Doors
- Dock
- Water Access
- Buyer Approval Required
- Deed Restrictions
- Golf Carts OK
- Sidewalks
- Garage Door Opener
- Deck
- Heated
- In Ground
- Lap
- Outside Bath Access
- Salt Water
- Screen Enclosure
- Solar Heat
- Gated
- Inside
- Laundry Room
- Marble
- Tile
Property details
Interior
- Built-in Features
- Ceiling Fan(s)
- Crown Molding
- Eating Space In Kitchen
- High Ceilings
- Open Floorplan
- Primary Bedroom Main Floor
- Split Bedroom
- Thermostat
- Tray Ceiling(s)
- Vaulted Ceiling(s)
- Walk-In Closet(s)
- 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
- Marble
- Tile
- Inside
- Laundry Room
Exterior
- French Doors
- Irrigation System
- Lighting
- Outdoor Grill
- Outdoor Kitchen
- Outdoor Shower
- Sidewalk
- Sliding Doors
- Garage Door Opener
- Deck
- Heated
- In Ground
- Lap
- Outside Bath Access
- Salt Water
- Screen Enclosure
- Solar Heat
- Block
- Stucco
Community
- Dock
- Water Access
- Buyer Approval Required
- Deed Restrictions
- Golf Carts OK
- Sidewalks
- Gated
Schools
- District
- Sarasota County School District
- Elementary
- Laurel Nokomis Elementary
- Middle
- SARASOTA MIDDLE SCHOOL
- High
- VENICE SENIOR HIGH SCHOOL
School grades from FLDOE public records. District polygons and school points from NCES EDGE. Assignment is not a legal attendance guarantee. Composite scores, when present, are derived from public records and are not official FLDOE grades.
Where is this home?
Listed by
Mackenzie Longueuil · MICHAEL SAUNDERS & COMPANY
Listings courtesy of Stellar MLS
Common questions
How much is 14401 Masthead Dr, Osprey, FL 34229 listed for?
14401 Masthead Dr, Osprey, FL 34229 in Osprey, FL is listed at $2,850,000 (about $14,637/mo principal and interest at 6.65% with 20% down).
How many bedrooms and bathrooms does 14401 Masthead Dr, Osprey, FL 34229 have?
14401 Masthead Dr, Osprey, FL 34229 has 3 bedrooms, 3.5 bathrooms, and 2,665 square feet.
Who can show 14401 Masthead Dr, Osprey, FL 34229 in Osprey?
Jonathan Loescher is a Tampa Bay Realtor and Loan Originator. He can tour this home, compare nearby listings, and work the financing with you.
What do Tampa Bay clients say about Jonathan Loescher?
Verified reviews cover buying, selling, and refinancing, with the home search and the loan handled together. Reviews go live after staff approval.
Who should work with a Realtor who also originates the loan?
Buyers, sellers, and refinancers in Tampa Bay who want one person accountable for both the real estate timeline and the mortgage file. Loan approvals remain conditional on lender review.