Date
Details
Price
Change
Source
3/05/2026
Listed
$3,250,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/96
$3,250,000 Just Listed
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Property Description
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.
Full Property Details
Full Property Details for 14401 Masthead Dr
General
- Price: $3,250,000
- HOA FEE: $643/month
- HOA FEE FREQ.: Quarterly
- Taxes: $874 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: A4684834
- Updated: 3/5/2026
- Added to Site: 2 day(s) ago
Rental Information
- Min. Lease: 1 Month
Interior
- Number of Rooms: 9
- Interior Features: 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)
- Fireplace: Yes
- Fireplace(s): Electric, Living Room
- 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
- Furnishings: Unfurnished
- Flooring: Marble, Tile
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Shared Amenities: Gated
- Pool: Yes
- Private Pool: Yes
- Pool Description: Deck, Heated, In Ground, Lap, Lighting, Outside Bath Access, Salt Water, Screen Enclosure, Solar Heat
- Spa: Yes
- Spa Description: Heated
- Security/Safety: Closed Circuit Camera(s), Gated Community, Security System
Exterior
- Exterior Features: French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sidewalk, Sliding Doors
- Deck/Patio: Covered, Screened
- Porch/Patio/Deck: Covered, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Garage Door Opener
Location
- Area: 34229 - Osprey
- County: Sarasota
- Development Name: 34229 - Osprey
- Subdivision: BAYSIDE
- 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.
- Direction Faces: East
School Information
- Elementary School: Laurel Nokomis Elementary
- Middle School: Sarasota Middle
- High School: Venice Senior High
Community
- Community Name: 34229 - Osprey
- Community Features: Dock, Water Access, Buyer Approval Required, Deed Restrictions, Golf Carts OK, Sidewalks
- Optional Amenities: Gated
- Association: Yes
- Assoc. Name: Bayside Community Association, Inc.
- Assoc. Fees Include: Common Area Taxes, Escrow Reserves Fund, Maintenance Grounds, Manager, Private Road
- Number of Pets: 3
- Pet Restrictions: 3 extra large pets, / 101lbs.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Electric
Utilities
- Sewer: Public Sewer
- Water District: LITTLE SARASOTA BAY
- Water: Public
- Utility Description: Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Solar, Water Connected
Structural Information
- Exterior Const.: Block, Stucco
- Roof: Metal
- Windows: Solar Screens
- Stories/Levels: One
- Square Feet: 2,665
- Sq. Ft. Source: Public Records
- Year Built: 2017
Lot Features
- Property View: Water
- Lot Size (Acres): 0.44
- Lot Size (Sq. Ft.): 19,235
- Lot Size: 19235
- Frontage: Street Paved
- Street/Road Desc.: Paved
Water Features
- Water Front: Yes
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Bay/Harbor
- Water Extras: Yes
- Water Front Name: LITTLE SARASOTA BAY
- Water Front Desc.: Bay/Harbor
Financial Considerations
- Association Fee: $1,928
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $874.45
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- 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
- Flood Zone Info: VE, AE
- APN: 148150048
- Property ID: 148150048
- Block/Lot/Section: 1
Listed by Michael Saunders & Company
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Listing agent
— 14401 Masthead Dr —
Michael Saunders & Company
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 14401 Masthead Dr
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Laurel Nokomis School 1900 Laurel Road East, Nokomis, FL 34275 | PK-8 | 5.2 mi |
Venice Senior High School 1 Indian Avenue, Venice, FL 34285 | 9-12 | 6.9 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 14401 Masthead Dr
Tax History
Tax History for 14401 Masthead Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$782
—
$1,295,472
3%
2024
$782
12%
$1,258,962
3%
2023
$697
5%
$1,222,293
3%
2022
$664
23%
$1,186,692
3%
2021
$541
—
$1,152,128
1%
2021
$541
12%
$1,136,221
2%
2019
$484
6%
$1,110,675
2%
2018
$455
-92%
$1,089,966
131%
2017
$6,030
-17%
$471,700
-15%
2016
$7,269
—
$558,200
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 14401 Masthead Dr
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14401 Masthead Drive, Osprey, FL 34229 (MLS# A4684834) is a Single Family property with 3 bedrooms, 3 full bathrooms and 1 partial bathroom. 14401 Masthead Drive is currently listed for $3,250,000 and was received on March 05, 2026. Want to learn more about 14401 Masthead Drive? Do you have questions about finding other Single Family real estate for sale in Osprey? You can browse all Osprey real estate or contact a Coldwell Banker agent to request more information.