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14401 Masthead Drive
Osprey, FL
Listing Details
- $3,150,000
- MLS# A4684834
- Type Residential - Single Family
- Status Active
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... Read more
Key Features
- French Doors
- Lighting
- Outdoor Grill
- Outdoor Kitchen
- Outdoor Shower
- Sidewalk
- Sliding Doors
- 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)
- Buyer Approval Required
- Deed Restrictions
- Golf Carts OK
- Sidewalks
Gallery
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Luxury Homes Specialist
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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 05/28/2026. The listing information on this page last changed on 05/28/2026. 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 05/28/2026 12:02:43 AM EST) or Miami MLS (last updated Wed 05/27/2026 11:59:02 PM EST) or Stellar MLS (last updated Wed 05/27/2026 11:45:12 PM EST) or SPC MLS (last updated Wed 05/27/2026 11:21:00 PM EST) or Martin MLS (last updated Wed 05/27/2026 11:38:13 PM EST) or Indian River MLS (last updated Wed 05/27/2026 11:30:18 PM EST) or Northeast Florida MLS (last updated Wed 05/27/2026 11:58:58 PM EST) or Beaches MLS (last updated Wed 05/27/2026 11:58:59 PM EST) or Naples MLS (last updated Wed 05/27/2026 11:40:32 PM EST) or PBI MLS (last updated Wed 05/27/2026 11:21:26 PM EST) or Florida Keys MLS (last updated Wed 05/27/2026 8:29:45 PM EST). Real estate listings held by brokerage firms other than Illustrated Properties 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.
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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.
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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 05/28/2026. The listing information on this page last changed on 05/28/2026. 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 05/28/2026 12:02:43 AM EST) or Miami MLS (last updated Wed 05/27/2026 11:59:02 PM EST) or Stellar MLS (last updated Wed 05/27/2026 11:45:12 PM EST) or SPC MLS (last updated Wed 05/27/2026 11:21:00 PM EST) or Martin MLS (last updated Wed 05/27/2026 11:38:13 PM EST) or Indian River MLS (last updated Wed 05/27/2026 11:30:18 PM EST) or Northeast Florida MLS (last updated Wed 05/27/2026 11:58:58 PM EST) or Beaches MLS (last updated Wed 05/27/2026 11:58:59 PM EST) or Naples MLS (last updated Wed 05/27/2026 11:40:32 PM EST) or PBI MLS (last updated Wed 05/27/2026 11:21:26 PM EST) or Florida Keys MLS (last updated Wed 05/27/2026 8:29:45 PM EST). Real estate listings held by brokerage firms other than Illustrated Properties 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.
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
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All Property Features
- Property Type: Residential - Single Family
- 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
- Cooling: Central Air
- Days on Site: 83
- 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
- Exterior Features: French Doors, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sidewalk, Sliding Doors
- Fireplace: Electric, Living Room
- Fireplace Y/N: Yes
- Flood Zone Code: VE, AE
- Flooring: Marble, Tile
- Foundation: Stem Wall
- Frontage Bay Harbor: 87
- Garage: 2 car attached
- Garage Dimensions: 21x20
- Heating: Electric
- HOA Fee: 1928/ Quarterly
- HOA Y/N: Yes
- Home Warranty Y/N: No
- 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)
- Listing Terms: Cash, Conventional
- Lot Description: Cul-De-Sac, Flood Insurance Required, Paved
- Lot Dimensions: 0.44
- Lot Size: 0.44 Acres
- 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
- Roof Type: Metal
- 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
- Stories: 1.0
- Swimming Pool: Yes
- Taxes: $874
- 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
- Year Built: 2017
- Zoning: RSF1