14401 MASTHEAD DRIVE, Osprey, FL, 34229 | $3,250,000

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.

Features

  • Amenities: Gated
  • Rooms: 9
  • Bedrooms: 3
  • Baths: 3 full / 1 half
  • Laundry: Inside, Laundry Room
  • Year Built: 2017
  • Garage: 2-car Garage Door Opener
  • Heating: Electric
  • Cooling: Central Air
  • Approx Sq. Feet: 2,665
  • Acreage: 0.44
  • Est. Taxes: $874
  • HOA Fee: $1,928 Quarterly
  • Lot Desc: Cul-De-Sac, Flood Insurance Required
  • View: Water
  • Elem. School: Laurel Nokomis Elementary
  • Middle School: Sarasota Middle
  • High School: Venice Senior High
  • Pool: Deck, Heated, In Ground, Lap, Lighting, Outside Bath Access, Salt Water, Screen Enclosure, Solar Heat
  • Pet Policy: Breed Restrictions, Yes
  • 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
  • MLS#: A4684834
  • Days on Market: 19 days
  • Website: https://www.raveis.com
    /eprop/A4684834/14401mastheaddrive_osprey_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is 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. (last updated 4/5/2026 1:17:07 PM)

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Jeff KaplanVP of Investment Sales

203.505.3375

Jeff.Kaplan@raveis.com

Our family of companies offer our clients a new level of full-service real estate. We shall:

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To learn more about our credentials, visit raveis.com today.

Francine SilbermanVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 69244

914.260.2006

Francine.Silberman@raveis.com

Our Executive Mortgage Banker:

  • Is available to meet with you in our office, your home or office, evenings or weekends
  • Offers you pre-approval in minutes!
  • Provides a guaranteed closing date that meets your needs
  • Has access to hundreds of loan programs, all at competitive rates
  • Is in constant contact with a full processing, underwriting, and closing staff to ensure an efficient transaction

Mace L. RattetVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 69957

914.260.5535

Mace.Rattet@raveis.com

Our Executive Mortgage Banker:

  • Is available to meet with you in our office, your home or office, evenings or weekends
  • Offers you pre-approval in minutes!
  • Provides a guaranteed closing date that meets your needs
  • Has access to hundreds of loan programs, all at competitive rates
  • Is in constant contact with a full processing, underwriting, and closing staff to ensure an efficient transaction

Gene RahillyInsurance Sales Director, William Raveis Insurance

917.494.9386

Gene.Rahilly@raveis.com

Our Insurance Division:

  • Will Provide a home insurance quote within 24 hours
  • Offers full-service coverage such as Homeowner's, Auto, Life, Renter's, Flood and Valuable Items
  • Partners with major insurance companies including Chubb, Kemper Unitrin, The Hartford, Progressive,
    Encompass, Travelers, Fireman's Fund, Middleoak Mutual, One Beacon and American Reliable

14401 MASTHEAD DRIVE, Osprey, FL, 34229

$3,250,000

Jeff Kaplan

VP of Investment Sales

William Raveis Real Estate

Phone: 203.505.3375

Jeff.Kaplan@raveis.com

Francine Silberman

VP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 914.260.2006

Francine.Silberman@raveis.com

NMLS Mortgage Loan Originator ID 69244

Mace L. Rattet

VP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 914.260.5535

Mace.Rattet@raveis.com

NMLS Mortgage Loan Originator ID 69957

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $2,600,000 $2,600,000 $2,600,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.750% 6.125% 6.000%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.263% 6.259% 6.223%
Monthly Tax Payment $73 $73 $73
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $15,173 $15,798 $21,940
Total Monthly Payment $15,371 $15,996 $22,138

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.  The Total Monthly Payment does not include the estimated HOA/Common Charge payment.