Refine Search

14401 Masthead Drive, Osprey, FL 34229

$3,250,000

96 Total Photos [Click to View All]

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.

14401 Masthead Drive | MLS# A4684834

This single family home located at 14401 Masthead Drive, Osprey, FL 34229 is currently listed for sale with an asking price of $3,250,000. This property was built in 2017 and has 3 bedrooms and 3 full and 1 partial baths with 2665 sq. ft. Masthead Drive is located in the BAYSIDE subdivision. Search BAYSIDE real estate on rstein.watsonrealtycorp.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air
Garage: 2 car attached
Heating: Electric
Lot Size: 0.44 Acres
Roof Type: Metal
Stories: 1.0
Taxes: $874
Year Built: 2017
Square Feet: 2,665

Amenities

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)
French Doors
Lighting
Outdoor Grill
Outdoor Kitchen
Outdoor Shower
Sidewalk
Sliding Doors

Feature Descriptions

Additional Rooms: Den/Library/Office
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
Association Amenities: Gated
Body of Water: LITTLE SARASOTA BAY
Community Features: Buyer Approval Required, Deed Restrictions, Golf Carts OK, Sidewalks
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.
Exterior: Block, Stucco
Fireplace: Electric, Living Room
Fireplace Y/N: Yes
Flood Zone Code: VE, AE
Flooring: Marble, Tile
Foundation: Stem Wall
Frontage Bay Harbor: 87
Garage Dimensions: 21x20
HOA Fee: 1928/ Quarterly
HOA Y/N: Yes
Home Warranty Y/N: No
Listing Terms: Cash, Conventional
Lot: Cul-De-Sac, Flood Insurance Required, Paved
Lot Dimensions: 0.44
Number of Pets: 3
Other Equipment: Irrigation Equipment
Ownership: Fee Simple
Parking: Garage Door Opener
Parking Notes: Garage Door Opener
Patio/Porch: Covered, Screened
Pets Allowed: Breed Restrictions, Yes
Pets Restrictions: 3 extra large pets
Pets Size: Extra Large (101+ Lbs.)
Pets Weight (Max): 101
Pool: Deck, Heated, In Ground, Lap, Lighting, Outside Bath Access, Salt Water, Screen Enclosure, Solar Heat
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Security: Closed Circuit Camera(s), Gated Community, Security System
Sewer: Public Sewer
Showing Instructions: Listing Agent Must Accompany
Spa: Heated
Special Sale Provisions: None
Special View Info: Water
Swimming Pool: Yes
Utilities: Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected
Vegetation: Trees/Landscaped
Water: Public
Water Access: Bay/Harbor
Water Access Y/N: Yes
Waterfront Features: Bay/Harbor, Assigned Boat Slip, Lift
Water View: Bay/Harbor - Full
Windows: Solar Screens
Zoning: RSF1

Room Sizes

Great Room: 19x26
Kitchen: 15x16
Dining Room: 11x15
Primary Bedroom: 15x19
Primary Bathroom: 15x10
Den: 11x12
Bedroom 2: 12x15
Bedroom 3: 15x13
Balcony/Porch/Lanai: 19x30

Local Schools

High School: Venice Senior High
Middle School: Sarasota Middle
Elementary School: Laurel Nokomis Elementary

Listed By / Shown By

Listed By

Agency Name: MICHAEL SAUNDERS & COMPANY
Agency Contact: 941-951-6660

Shown By

Agent Name: Bob Stein
Agent Phone: (386) 843-3304
Agency Title: Watson Realty Corp., REALTORS ®

IDX logo

Estimate Your Payment

Estimated Payment

$ 16,692.74 per month $15,671.99 Principal & Interest $72.83 Property Tax $947.92 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)
Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 03/05/2026. The listing information on this page last changed on 03/05/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 03/05/2026 3:07:08 AM EST) or GAMLS (last updated Wed 03/04/2026 11:15:00 PM EST) or Stellar MLS (last updated Thu 03/05/2026 1:58:49 AM EST) or SPC MLS (last updated Wed 03/04/2026 11:20:38 PM EST) or Martin MLS (last updated Wed 03/04/2026 11:38:12 PM EST) or Indian River MLS (last updated Wed 03/04/2026 11:30:24 PM EST) or Daytona MLS (last updated Wed 03/04/2026 11:36:48 PM EST) or Northeast Florida MLS (last updated Thu 03/05/2026 12:18:40 AM EST) or Beaches MLS (last updated Thu 03/05/2026 2:35:52 AM EST) or BORMLS (last updated Wed 03/04/2026 11:15:45 PM EST) or Golden Isles MLS (last updated Wed 03/04/2026 11:26:34 PM EST) or Amelia/Nassau MLS (last updated Wed 03/04/2026 11:25:17 PM EST) or Dixie Gilchrist Levy MLS (last updated Wed 03/04/2026 11:42:25 PM EST). Real estate listings held by brokerage firms other than Watson Realty Corp., REALTORS ® may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data and photos distributed by MLSGRID
Member Participants (and their affiliated licensees, if applicable) shall indicate on their websites that IDX information is provided exclusively for consumers’ personal non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time. MLS GRID may, at its discretion, require use of other disclaimers as necessary to protect Member Participant, and/or their MLS from liability.
Based on information submitted to the MLS GRID. 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.



Privacy Policy / DMCA Notice / ADA Accessibility

Login to My Homefinder

Pixel