USAFLOspreyBayside14401 Masthead Dr
14401 Masthead Dr | Image 1
New
14401 Masthead Dr | Image 2
14401 Masthead Dr | Image 3
14401 Masthead Dr | Image 4
14401 Masthead Dr | Image 5
14401 Masthead Dr | Image 6
14401 Masthead Dr | Image 7

$3,250,000

For Sale

17 hours ago

14401 Masthead Dr, Osprey, FL

House

MLS® A4684834

3 Bed

4 Bath

2665 sqft

--

  • Key Facts
  • Description
  • Rooms
  • Map

Key Facts

Type Single Family Residence
Levels Residential
Size 2665 sqft
Garage Yes
Taxes $874
Days Active 0
Lot Size 0.44 acres
Approx. Age 2017
Avg. Price Per Sqft $1,219
MLS® Number A4684834

Property Address: 14401 Masthead Dr, OSPREY, FL, 34229-2200

Average square foot calculated using Size range provided by listing agent.

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.
MLS® NumberA4684834
Laundry LevelInside, Laundry Room
Central VacNo
FireplaceNo
Acreage0.44
Exterior
GarageYes
Approx. Age2017
Basement
DrivewayGarage Door Opener
Garage Spaces2
Heat
A/C
Heating Fuel

Extras

Rooms

Change to metres

Other:First Floor15 × 10 ft
Other:First Floor19 × 30 ft
Den:First Floor11 × 12 ft
Bedroom 3:First Floor15 × 13 ft
Dining Room:First Floor11 × 15 ft
Kitchen:First Floor15 × 16 ft
Other:First Floor15 × 19 ft
Bedroom 2:First Floor12 × 15 ft
Great Room:First Floor19 × 26 ft

Price History

-End Date
Not Sold YetSold Price

For Sale

Mar 5, 2026List Date
$3,250,000List Price

Home Appraisal

This property is estimated to sell between: $1,333,000 and $4,209,000.
Similar properties in this area sold on average for: $1,333,928
Expected to sell in 92 days. Similar properties sold in 92 days. This home has been on eXp Realty for 0 days.

The estimated sale price does not take into account many variables such as recent renovations, type of appliances, school district etc. To get a more accurate estimate please contact agent.

Powered by Zoocasa
  • Commute

Commute

Starting Address
Destination Address
14401 Masthead Dr, OSPREY, FL

Like what you see?

Complete the form and we'll be in touch. No login necessary.

Add a Comment
Loading...

Similar Listings

Comparable Properties

Explore eXpFind an AgentJoin eXpInvestor RelationsCompany CareersHome Guides
eXp LifeZoocasaSUCCESS®SUCCESS® LendingeXp RevenoseXp CommercialeXp LuxuryeXp Land and RanchAccessibility
Terms and ConditionsPrivacy Rights RequestPrivacy PolicyCookie PolicyBrand GuidelinesHelpSitemap

2219 Rimland Drive, Suite 301, Bellingham, Washington, 98226

1 833-303-0610

[email protected]

eXp REALTY

© 2024 eXp Realty. eXp World Holdings, Inc. All Rights Reserved.

DMCA Notice

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply

Fair Housing and Reasonable Accommodations

MLS Compliance Statements

Karen Richards - Designated Managing Broker, Broker Operations - TX

Texas Real Estate Commission information about brokerage services

Texas Real Estate Commission Consumer Protection Notice

eXp Realty® is committed to adhering to the guidelines of The New York State Fair Housing Regulations.The Fair Housing Notice →

*Standardized Operating Procedure for Purchasers of Real Estate Pursuant to Real Property Law 442-H.Learn More →

eXp Realty of California, Inc. | CA DRE# 01878277 | Deborah Penny - Designated Broker

eXp Realty of Southern California, Inc. | CA DRE#01325837 | Jason Crawford – Designated Broker

eXp Realty of Greater Los Angeles, Inc. | CA DRE# 01240990 | Mike Mendibles - Designated Broker

eXp Realty of Northern California, Inc. | CA DRE# 01951343 | Ryan Rosas - Designated Broker

© 2026 eXp Realty. eXp World Holdings, Inc. All Rights Reserved