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14401 Masthead DriveOsprey, FL 34229Price: $3,150,000

  • Price: $3,150,000
  • Est. Mortgage of $/month
  • 92 Days on Market
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Federal 30-year interest rate: 6.48% last updated on Jun 4, 2026
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  • $3,150,000List Price
  • ActiveStatus
  • 96Number of Photos
  • 27.183671Latitude
  • 14401 Masthead DriveAddress
  • Masthead DriveStreet
  • OspreyTown
  • FLState
  • 34229Zip
  • SarasotaCounty
  • ResidentialProperty Type
  • A4684834MLS Number
  • 03/05/2026Date Listed
  • 93 DaysOnMarket Date
  • 3Bedrooms
  • 3Full Bath
  • 1Half Baths
  • 2,665Square Feet
  • 2017Year Built
  • 0.44Acreage
  • 93 DaysOnMarket Date

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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.

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LISTING COURTESY OF Mackenzie Longueuil of MICHAEL SAUNDERS & COMPANY (941-951-6660)

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of June 5, 2026 3:31 AM EDT. 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. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.

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